Oh, my God,” the local kids shouted and giggled. One by one, they jumped into the water from the side of a concrete boat ramp and came to the surface, repeating what they had just heard us say as we did the same thing to cool off after a long afternoon of chart and boat briefings at The Moorings charter base on Raiatea, a gem of a destination in the Leeward Islands of French Polynesia. 

From the water, I watched their mothers chatting the late Sunday afternoon away in the shade of a stand of trees. To the north, I took in the unfamiliar shapes of the daymarks lining the channels, and the coral between our harbor swimming hole and the island of Taha’a, a couple of miles away. It was all but impossible to keep my eyes off the iconic rocky peak of Mount Otemanu, shrouded in tropical haze on Bora Bora, some 20 miles to the northwest. I’d seen it in pictures hundreds of times as I read South Pacific adventure tales. 

But now, oh, my God, indeed: Here we were. We were going sailing. In Tahiti.

It took three days to get there from ­wintry Boston, with an evening stopover in Los Angeles and a second night spent in a hotel in French Polynesia’s capital city, Papeete. From there, photographer Jon Whittle and I, along with the trip’s organizer, Josie Tucci from Sunsail, and one her friends from Florida took a morning flight on a small commuter plane to Uturoa, Raiatea’s main commune. Our travels ended with a short cab ride to the Sunsail docks nearby. For the next few hours, eight more sailing and golfing friends of Tucci’s wandered in, ready to help celebrate her big 5-0 aboard two roomy cruising cats: a Sunsail 505 for the birthday girl, and Magic Dancer II, a Sunsail 454, for Whittle, me and overflow guests.

Most of the sailing we’d be doing for the next 10 days would be around the large islands that sit inside extensive coral barrier reefs, so the chart briefing was quite detailed. A local skipper went over aids to navigation, points of interest, anchorages and the like. He stressed to us North American sailors that Lateral System A is used in this part of the world, with red marks left to port, not starboard, when entering passes from the open water. Inside the lagoons, square red daymarks designate dangers toward land; green triangles show hazards along the reef; and various configurations of triangles atop poles indicate whether to leave obstructions to the north, south, east or west. We took detailed notes on large paper charts and downloaded a cruising guide PDF that would be consulted frequently throughout the trip.

There are four main islands within the group. Two of them, Raiatea and Taha’a, are quite close and within the same barrier reef. Between them lie well-marked shallows and coral beds, so sailing back and forth is fairly simple. 

Bora Bora and Huahine are another story. To reach them, open-water passages of about 20 miles are required, with a long slog upwind either going or returning, depending on the island. Early-morning departures are required so that upon arrival, passes can be navigated while the sun is high. An eye on the weather is also recommended because conditions can get boisterous.

Midafternoon, the briefing formalities were put on hold for nearly an hour when a troupe of local musicians and dancers came to welcome us. They handed out leis and headbands made from colorful local flowers, including tiare apetahi blossoms, which grow only high in Raiatea’s mountainous interior. The men sat with their instruments and played Polynesian tunes while the dancers, a mix of women and children, twirled and shimmied their grass skirts in lively routines handed down from their ancestors.

It being a Sunday, all stores had closed at noon, so provisioning had to wait until Monday. Early in the day, a couple of us from each boat took a taxi to the Champion market in downtown Uturoa, a bustling urban area where the cruise ships dock. Though all of the islands in the group have grocery stores of some sort, we were advised to get the bulk of our provisions here. The market was well-stocked, but with all goods needing to be shipped in across the vast Pacific, prices were steep.

Back at the boats, we loaded supplies and topped off water tanks. By late morning, it was time for the adventures to begin. First stop: Passe Rautoanui, an opening through the reef on the northwest side of the island. 

As we approached, we picked out the cardinal marks indicating the opening. White waves crashed on the coral reefs to either side, but the water between them was dark blue and deep. Outside, we rounded up into an offshore breeze gusting to 20 knots or so. We went with a single reef in the main, unfurled the genoa, and settled in for an easy reach south to Passe Punaeroa, about 8 nautical miles away.

Ashore, the mountaintops disappeared into the haze and clouds. The colors—blue sky, green jungle, white breakers on the reef—were spectacular and everything I’d imagined French Polynesia would be.

Back inside the lagoon, Tucci’s boat led the way along a narrow channel around the southern end of the island to a tiny anchorage behind Motu Nao Nao. We’d been told during the briefing that there’s room for only three or so boats, and there was already a large monohull there, so we aboard Magic Dancer II opted for a mooring a mile or so away in deep water off another small motu, or island. We took the inflatable across to join the festivities underway aboard what already had become the party boat. Nao Nao was the perfect place to spend a hot afternoon with a cold beverage and snacks. A few of us took off snorkeling over the nearby coral heads. It was an excellent transition to island time. 

With evening approaching and the sky clouding over, I hopped into the dinghy alone, figuring I’d make better time motoring solo back to Magic Dancer. I didn’t make it far from the swimming hole, though, before the sky turned black. Time to turn back to the cat that stayed at anchor to ride it out? Nah. I pressed on and almost at once got gobbled up in a white squall that came rolling through with ferocious gusts, stinging rain, and lots of lightning. That was a dinghy ride to remember.

Tuesday, we continued the counterclockwise tour of Raiatea, the largest island in the Leeward Group. Late morning, we anchored in about 30 feet of water, deep in Baie De Fa’aroa, a fjord located about halfway up the island’s eastern side. From there, several of us took two inflatables up the Apoomau River. We were told that it’s the only river trip in all of French Polynesia, and we soon discovered spectacular glimpses of Mount Tefatuaiti with its towering rock walls and deep valleys shrouded with mist. Our destination was the botanical garden near the headwaters. 

It was slow-going, with many sunken trees and shallow spots to dodge. Along the way, we met a local man who, for a modest fee, paddled his faded orange kayak ahead of us and gave us a guided tour of the gardens. On the way back, we stopped at his camp, where his wife and daughter wielded machetes to cut up coconuts, red papayas, grapefruits and bananas for us. We ate so much fruit that we almost didn’t need the lunch of shrimp curry and rice that Tucci’s sailing mate, Paula, had cooked while we were gone.

Later that afternoon, we tried to visit the small village of Marae, home to an ancient Polynesian temple, but the holding was poor and evening was coming, so instead we found a sandy spot to anchor on the reef off Pointe Tamapua. The crew voted to go ashore for dinner at the Opoa Beach Restaurant, where the ginger tiger shrimp were indeed a delicacy, as ­promised on the menu.

Early Wednesday morning, the big-boat crew set off for the airport in Uturoa to pick up a late-arriving guest. We lingered a bit for a swim and breakfast before hoisting sails and reaching across flat water along the shore. At the top of the island, we found the marks for a channel skirting Grand Banc Central shallows, which lie between Raiatea and Taha’a, and crossed for a lunchtime rendezvous with the big boat in Baie Apu, an anchorage on the southern end of Taha’a. 

From there, we motored up the west side of the island until we spotted the Motu Tautau and a cluster of luxury bungalows built out over the water, the La Taha’a by Pearl Resorts. We anchored just south of them in a sandy spot with about 7 feet of water. The breeze was brisk, so I stayed behind to watch the boats while the rest of the crew took the tenders and motored past the resort to a channel between a pair of small motus. Once they secured the boats, they walked up-current along the shore of one of the islets, and then jumped in for a fast snorkel back to where they’d started. Everyone returned raving about the ride.

For me, the highlight of the trip came the next day, when our little armada set off for Bora Bora. After a brief motorsail south to clear the reef through Passe Papai, we killed the engines and started off on what would be our longest day of sailing. 

Out of the lee of Taha’a, Magic Dancer lived up to its name, slicing and surfing through big trade-wind swells. According to the chart, our desired heading was 293 degrees, but trying to steer that in a blustery southeast breeze of 15 to 20 knots proved nearly impossible because of the constant threat of an accidental jibe and the jib being blanketed. Instead, we crisscrossed the rhumb line on a series of broad reaches—each one bringing the towering peak of Mount Temanu more clearly into focus—until we finally spotted the iconic light that marks Pointe Te Turi Roa on the southeast corner of the reef surrounding Bora Bora.

Along the way, we spotted flocks of birds diving for baitballs roiled up by tuna and other big fish. Occasionally, an interisland freighter or fishing boat came into view, but for the most part, we were on our own, out on a great big sea, surrounded by whitecaps and having a ball. Or at least some of us were. The others, well, they spent the time nursing cases of mal de mer.

The birthday boat was ahead of us at the light, but by radio we called them back so that Whittle could launch a drone and get photos of the two cats sailing along the edge of the reef. It was a surreal scene: the boats side by side on a deep blue ocean, a long line of frothy white surf where the swells piled up on the coral, the tranquil lagoon just beyond with the lush green island in its center. Overhead, the white clouds had greenish-blue bottoms because of the sunlight reflecting upward off the water. It was a lot to take in.

There is only one way in and out of Bora Bora: Passe De Teavanui, which is about halfway up the island’s western shore. It was midafternoon when we arrived, and once through it, we had a straight shot to the mooring field at the Bora Bora Yacht Club. We went ashore to the club for dinner and topped off the evening playing Boule, a bowling game, on sand courts near the bar.

Friday morning, a few of us walked the shore road to an ATV trail cut into the jungle-covered hillside. It was a steep climb to the top, but the reward was a stunning view of the lagoon below and a couple of cruise ships that had just arrived.

That afternoon, we got underway and followed a twisting channel inside the reef across the top of the island and down the eastern side. Though it was windy, the breeze was, for the most part, on the nose, so we motored. To be honest, it was a nerve-racking trip through shallow water teeming with coral heads. Off to port, numerous resorts were built on stilts over the water and reef. They were well-marked on the chart and helpful as we tried to keep our bearings straight. 

Anchoring is not allowed within the reef at Bora Bora, but mooring balls are plentiful all around the island. We grabbed ones off a sandy beach at the southeast corner of the lagoon and settled in for an afternoon of swimming that slowly faded into star-filled night. Overhead, the Southern Cross and Orion kept us company.

In the morning, a few of us jumped into the inflatables with snorkels and fins and went exploring in a marine park by two small islets a mile or so away. There were a couple of tour boats from nearby resorts when we arrived, but soon they cleared out and we had the place to ourselves. We found fish and coral aplenty in 10 to 12 feet of water.

That afternoon, the trip back around the island was simple: All we had to do was follow the track we’d laid down on the chart plotter the day before. Near the north end of the island, a kayaker fell in behind us as we motored by at 6 knots. He hitched a ride on Magic Dancer’s wake for 2 or 3 miles. It was an impressive paddling demonstration that the fellow put on.

For lunch, we made a stop at Bloody Mary’s, a popular shoreside bar and restaurant. As we ate, a band appeared on stage and locals started to wander in for what seemed to be turning into a Saturday-afternoon ripper. We took it in for a while, then headed back to the boats and went to find a mooring out near the reef on the western edge of the lagoon.

The original plan was to head back to Raiatea on Sunday morning, and from there, sail to Huahine for a day. To pull it off, we’d need to keep moving, and personally, I was looking forward to three more long open-water crossings. But some of the others who’d suffered on the way up weren’t so keen. On any charter, and especially one with a large contingent of nonsailors, keeping the crew happy is ­paramount. So, it only made sense to scrap the plan. Instead of spending Sunday at sea, we’d play. Hard.

The next morning, we explored ­nearby sandy motus. In the shallow waters around them, we swam with small blacktip sharks and searched for rays. After lunch, we all kicked back on the big cat, where a couple of techs from the charter company appeared with a motorboat and wakeboard. The scene only became more festive as more powerboats filled with locals zipped by, many of them pulling tubes loaded with screaming kids.

Along toward sunset, as a dinner of chicken curry simmered on the stove, Tucci’s friends decorated the boat for the birthday bash that turned into a ­laugh-filled night of music and revelry.

Monday started slow. We motored back to the mooring field by Bloody Mary’s and made a provisioning run for supplies to last us to the end of the trip. Then we took the tenders across the shallows at the southern tip of Bora Bora that keep big boats at bay. Besides seeing the southern tip of the island, we wanted to check out the good snorkeling area we’d visited earlier. It was a long, wet ride in the small boats, but well worth it once we got there. Visibility was better, and the fish were easier to spot and more plentiful.

The sea was glassy and the wind was initially calm for our return to Taha’a on Tuesday. As we passed the lighthouse on the corner of the reef, a breeze began to stir, so we raised the main and motorsailed closehauled, pointing as high as we could. Then, with 6 miles to go, the wind suddenly kicked up to near 20 knots on the nose and brought with it waves that made it a slow slog the rest of way to the pass back through the reef at Taha’a.

Inside, we motored north again along the island’s west coast and picked up a mooring in Baie Tapuamu, across from where we’d anchored a week earlier. The big cat arrived soon after, and following lunch, we headed ashore for a tour of Domaine Pari Pari, a local rum distillery. The white rum had a raw taste to it, not anything like the Caribbean rums most of us were used to. But it was ­drinkable enough, poured over ice on a hot afternoon.

Wednesday was our last full day aboard the boats. In the morning, we took our snorkeling gear and went by inflatable a short way up the coast, where we were told we might find rays. Just when I thought we’d been skunked, I watched a single manta ray come up from the depths. It had about a 6-foot wingspan and wild-looking markings on its back. Most everyone got a glimpse of it gliding along the shallows before it disappeared back into the deep.

Back in the tenders, we pushed a bit farther north until we spotted a dock and buildings where we thought we might find a spot for lunch. Instead, we’d landed at the Iaorana Pearl Farm, said to be the largest in French Polynesia. The farm manages some 2 million oysters in the waters surrounding the island. 

We were introduced to a man whose job it is to sit at a desk and implant small pebbles taken from the Mississippi River and sent to Taha’a via Japan into some 300 oysters a day. The oysters are then affixed to strings and returned to the water for 18 months, when the pearls are ready to be harvested. Several of the crew purchased necklaces and such. It was hard to pass up such unique souvenirs from an unexpected stopover.

Midafternoon and back at the boat, it was time for one last motorsail, so we set off for Raiatea, where we dropped anchor on the reef, not far from the charter base. There was still swimming to be done and merriment to be had, but I could feel my sense of island time slipping away as we checked plane reservations and packed. That evening, we went ashore to the Fish & Blue restaurant for a last team dinner. And of course, we sat up a little too late for a last glimpse of the Southern Hemisphere’s night sky. What else would anyone do on their last night in the Society Islands?

Mark Pillsbury is a CW editor at large. 

If You Go

Our flights to Papeete, Tahiti, were booked on Air Tahiti Nui, which has regular flights from Los Angeles. From the US East Coast, it was easiest to plan an overnight at a Los Angeles hotel. Our flight across the Pacific was aboard a clean and comfortable plane, decorated in soothing tropical pastels. It’s a long flight but endurable.

From Papeete to Raiatea, we flew Air Tahiti. Flight time is just under two hours; a four and a half-hour ferry ride is a cheaper alternative.

Provisioning at the base in Raiatea is straightforward but expensive. Eating out is even more so: A $50 bill for lunch per person was common for our group, and a hamburger cost $15 to $18.

Most charter boats come equipped with chart plotters. Still, I found that having an iPad loaded with Navionics cartography was a great help within the reefs. It allowed us to have one chart zoomed out and the other zoomed in for details. When the onboard chart plotter stopped functioning one morning as we traveled along the south coast of Raiatea, we were able to carry on by iPad until I could reset the recalcitrant equipment. —MP

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Apparently, we want it all—and bareboat charter companies are trying to give it all to us. If you haven’t checked out the bareboating scene in recent years, then you might find a fair bit of it unrecognizable. Yes, personal freedom and natural beauty are still part of the package with island and river cruising alike, but in many cases, everything from the booking process to the boats has undergone a serious upgrade. 

Wet heads? A lot of today’s bareboaters won’t book boats that have them. No air conditioning? That’s a deal-breaker now too. Squeezing like sardines into itty-bitty berths? Forget about it. Life is too short.

“The boats are going more luxury,” says Lisa Mclean, ­marketing manager at Le Boat, who adds that especially since the pandemic, bareboaters are insisting on comfort. “It doesn’t have to be luxury, but people are more discerning—and people value spending money on experiences. They’re willing to spend a little bit more to have the boat customized the way they want it.” 

That includes having enough room to move. Numerous ­companies are investing in fleets with bigger boats because ­bareboaters are demanding them. This is especially true of catamarans, says Tina Huewe, US senior marketing executive at Dream Yacht Charter.

“Modern vessels are built with comfort and convenience in mind, featuring spacious cabins, fully equipped galleys and high-quality furnishings,” Huewe says. “Innovations like air conditioning, watermakers and improved refrigeration ­systems have become standard on many charter boats, ensuring a ­comfortable living environment regardless of the destination.” 

Ian Pedersen, senior marketing manager for The Moorings in North America, says that his company is experiencing the same trend, with today’s bareboaters preferring large-volume ­catamarans to smaller-volume monohulls. 

“The modern-day charter experience is very much about large catamarans,” Pedersen says. “Both sailing catamarans and power catamarans have become the norm in the charter space as guests crave space, comfort, and all the amenities of home.”

At Voyage Charters, broker Peter Jones says that he has noticed this significant change in bareboaters’ expectations in a relatively short time span. Even five years ago, Voyage Charters was booking boats with manual pump toilets and no air conditioning. Today, the new boat is the Voyage 590, which won Best Charter Boat in Cruising World’s 2022 Boat of the Year competition. 

“That boat has six equal guest cabins with walkaround beds and en suites, plus crew quarters,” Jones says. “Everything’s electric and inverts off batteries from generators that start when they’re programmed to. It’s a massive change.”

From his vantage point on Tortola, Jones says, he sees all the boats that other companies are offering for charter. The entire market, he says, has “trended radically” toward bigger boats with more amenities, including a major shift into power ­catamarans. 

In some cases, transformations are ­happening ashore as well. The British Virgin Islands remains the top destination for The Moorings, Pedersen says, and the company recently completed extensive renovations to the marina property, hotel, on-site restaurants, gift shops and on-site supermarket. 

“If you haven’t chartered with The Moorings in the BVI recently, we welcome you to join us again and see for yourself what a difference a few years can make,” Pedersen says. 

In terms of new destinations, The Moorings recently announced its first one in years, in La Paz, Mexico. It’s expected to be up and running in time for the 2025 season. 

To the north, Le Boat recently added a route along Canada’s Trent-Severn Waterway, based on the popularity of the Rideau Canal route. Bareboaters from the United States are choosing to drive to the boats instead of hopping on a plane—about 15 to 20 percent of them with their pets in tow, for an additional $180 cleaning fee, Mclean says.

“It doesn’t have to be luxury, but people are more discerning—andpeople value spending money on experiences.”

—Lisa Mclean, Le Boat

“We’ve seen big English sheepdogs, tons of golden retrievers, and of course, the purse puppies,” she says. “We’re also seeing a lot more multigenerational travel. Pre-COVID, our smaller boats were more popular. Now, it’s the four- and five-cabin boats. I think people are appreciating being on vacation with their families, or celebrating special occasions like a wedding anniversary or a 50th birthday that they didn’t get to celebrate during COVID.”

Le Boat is also seeing a sizable increase in inquiries for Holland and the United Kingdom, particularly along rivers such as the Thames. Mclean adds, “People are more appreciative of getting on the smaller waterways and getting out of the big cities.”

Huewe says that Dream Yacht Charter is seeing a similar trend with bareboaters in Europe. Demand is increasing for destinations that just a few years ago, many people didn’t even consider.

“While Croatia has long been a favorite for sailing enthusiasts, some of its lesser-known islands are now gaining popularity,” Huewe says. “Areas such as the Kornati archipelago, in easy reach from our base in Šibenik, and the Elaphiti Islands close to Dubrovnik offer tranquil waters, picturesque landscapes, and a growing number of modern marinas.”

Technology too has become a must-have while bareboating. Today’s cruisers are not willing to settle for access to Wi-Fi once a week at an internet cafe onshore. They want USB ports to charge their devices, and the ability to work or attend school from on board. 

That profile fits at least 20 percent of Le Boat’s customers today, Mclean says. “People aren’t just traveling for vacation now. They’re working from wherever they are now. You’re on vacation, but you’re still checking email and calling in for a weekly Zoom meeting. Instead of doing it from your kitchen table, you’re doing it from the table on the boat.”

Demand has also increased for tech-focused booking processes, Pedersen says. The Moorings audience is more youthful than in decades past, with more clients in the 35- to 45-year-old range. They’d rather click on a screen than talk to a person.

“As such, much of our planning processes have become mostly digital, allowing guests to complete almost the entirety of the pre-departure journey online before they arrive to pick up the boat,” he says.

Demand for modern tech also extends to the helm and engine room in some of today’s fleets. Bareboaters don’t just want to be online, Huewe says; they also want top-notch weather forecasting apps and eco-friendly propulsion systems.

“Modern catamarans and monohulls are now equipped with state-of-the-art navigation systems, including GPS chart plotters, AIS, and advanced autopilot systems,” Huewe says, adding that Dream Yacht Charter has partnered with Fountaine Pajot on electric-propulsion options. “The Aura 51 Smart Electric yachts have been part of the Dream Yacht fleet since spring of last year, and meanwhile have been joined by the electric Fountaine Pajot Elba 45 and various electric Dufour 530 Smart Electric models.”

Going forward, these companies say that bareboaters should expect even more creature comforts as new models join the fleets. Jones says that Voyage Charters has a 51 in the early stages of production and coming to charter next year with four en suite staterooms plus two cabins for crew. Le Boat also has plans in the works for a more luxurious option for bareboaters who want even more amenities.

“I think that as soon as one charter company is offering something to try to entice charter guests, it becomes an expectation,” Jones says. “It’s raising the bar for everyone a little bit. The result of that is that we’ve got these super-equipped charter boats with all the bells and whistles.”

The post More, Bigger, Better: The Modern Charter Experience appeared first on Cruising World.

I woke up with the sun and climbed into the cockpit with a blanket and a hot mug of coffee, breath steaming in the crisp morning air. The shoreline was luminous in the soft light, the empty beach alluring. The boat rocked gently in the breeze as an eagle called out from high above. I had to pinch myself; I was not in the San Juan Islands near Seattle or in the Gulf Islands of Canada. I was on Lake Superior in Wisconsin, a lake that both looked and acted very much like an ocean.

I am an ocean sailor. I learned to sail in the Pacific Northwest and left to go cruising from there, my sights pointed south and west. I had never been sailing on fresh water. When travel restrictions in response to the COVID-19 outbreak kept us from returning to our boat waiting for us in a boatyard in French Polynesia, my husband, John, and I looked around to get our sailing fix locally. We found it in the unlikeliest of places: right in the middle of the country.

The Apostle Islands is a grouping of 22 protected islands nestled in the corner of one of the biggest lakes in the world. “Lake” is a bit of a misnomer; “inland sea” is a more accurate description. This particular inland sea is the size of Austria and at places is over 1,200 feet deep. It has the largest surface area of any freshwater lake on Earth, over 31,000 square miles, and holds 10 percent of the entire planet’s fresh water. That’s crazy! It’s also hard to conceptualize because the entire sea is situated 600 feet above sea level. To reach the ocean, boats must sail 2,400 miles across three lakes and navigate 16 locks to descend those 600 feet.

I simply couldn’t imagine it: a lake like an ocean, a contained body of water capable of throwing challenging weather conditions to test even the most seasoned sailors. Unpredictable wind, sudden pea-soup fog, navigational hazards and steep wind waves are all common conditions. The rewards are just as sweet too. Secluded anchorages, stunning sunsets, vibrant contrasting colors of red sandstone, verdant green trees and clear blue water. I just had to see it for myself.

Superior Charters & Yacht Sales in Bayfield arranged for us to sail a Jeanneau 349, aptly named Bliss, for a four-day cruise through the Apostle Islands. These islands, along with the nearby mainland coast, make up a 70,000-acre National Lakeshore area. Only one of the islands is inhabited; the rest are home only to healthy populations of black bears, deer, eagles, otters and more. It was the beginning of September and the start of their shoulder season, which meant quiet anchorages, fewer bugs, cool crisp nights and unpredictable weather.

Bliss was well-appointed with a full galley, plenty of water and diesel, good sails, an anchor windlass and an autopilot. One of the benefits of chartering from Superior Charters & Yacht Sales is that they encourage guests to board the boat the night before the official start of the vacation. We picked up an envelope at 7 p.m. with a map of the marina, codes for the bathrooms and a checklist of items we should verify on the boat. That evening we introduced ourselves to Bliss, unpacked and settled in. It was a wonderful, stress-free way to start the vacation.

The next morning, checkout was a breeze. Mike, a captain with Superior Charters, arrived promptly at 0800 to review the checklist and answer questions. He ensured that we knew where everything was, what safety equipment we had and how to use the systems on board. He then revealed his love for this unique place as he bragged about the beauty of the islands and shared with us some of his favorite secluded spots.

By midmorning, we waved goodbye to Mike, slipped our dock lines and hoisted the sails in a sporty 15 to 20 knots from the southwest. The weather forecast kept us conservative in distance and anchorage choice that first night. The wind was predicted to make a 135-degree shift in the evening and blow a gale from the north all night. There are no all-weather anchorages in the Apostles, so one thing Capt. Mike coached us on was to always have a backup plan in case the winds decide to buck the forecaster’s predictions. We chose the southeast hook of Stockton Island, a popular choice judging by the six other boats in the bay, all nestled into the northern corner.

The forecast was not joking. Just as the sun dipped below the horizon, the wind made an about-face and started blowing from the north without lessening in intensity. A new boat in a new place in 35 to 40 knots of wind overnight is never a recipe for a good night’s sleep, but Bliss handled the weather like a champ. We got up to confirm our position and check the anchor rode for chafing a few times, all without incident. She held well in the sticky sand, the wind whistling harmlessly through the rigging.

A gale was an exciting way to start the trip, and a good reminder that shoulder-season sailing means being prepared for a variety of conditions. It was just like cruising in the San Juan Islands in September, when summer and winter collide overhead. A fresh breeze turns cheeks red; puffy jackets and beanies appear from the depths of lockers. It was so similar to sailing in the San Juans, in fact, that I kept watching for whale spouts in the distance!

We fell into a familiar routine. Our days started with an unhurried cup of coffee in the cockpit while listening to the weather forecast on the VHF. We would then haul the anchor and hoist the sails for a few hours of exploration. By late afternoon, we would set the hook in a new anchorage, with plenty of time to explore the shore by kayak or foot before happy hour. A glass of wine, a beautiful sunset, a big hearty dinner and a quiet evening with a good book. It felt so good to be back on the water.

The Apostle Islands are bunched together, which makes them easy and accessible for fun daysailing. While our conditions were not always (well, ever) a perfect 15 knots on the aft quarter, we never felt exposed or in danger. In fact, most of our time under sail was fully voluntary. We were never far from our next anchorage and would often take the meandering way, easily turning a 10-mile passage into a 30-mile sail that laced us through rocky outcroppings and along sandy shorelines.

Each island in the Apostles has its own personality. Stockton has an intriguing mix of lakes, forests and wetlands. Wonderful hiking trails crisscross the island, often on raised boardwalks above the delicate grasses and swampland.

Oak Island is the tallest at 1,000 feet above sea level (and 400 feet above this sea’s level). It was the first Apostle island, emerging about 10,000 years ago as the level began to drop in a giant lake that had formed between the retreating glacier edge to the north and high ground to the south. Today Oak Island has steep cliffs that rise abruptly out of the sea and a very active black bear population.

Outer Island is the guardian, a sentinel standing tall in the northeast corner, with the other islands huddled behind it. It is this island that gets pummeled by the most vicious northeasterly gales. As evidence of its protective responsibility, the rugged coastline is dramatically pocked with sea caves where waves have battered the sandstone for thousands of years.

Madeline is the only populated island, with 302 full-time residents. The main street through town is dotted with a handful of tourist shops and restaurants, served by a quaint car ferry from Bayfield. It was particularly quiet when we arrived midweek and out of season, following an unstable and worrying summer. Only one restaurant was open, offering burgers and sandwiches for takeout only. The impact of the pandemic is most apparent in places like this, where the whole town relies on summer tourism. With a high season only 90 days long, even in a good year it is hard to stay sustained through the slow winter. This year, some shops and restaurants never opened at all.

Too soon it was time to sail back to the marina. Or rather, motorsail; by then we had a wispy 6 knots from the northeast. The cruise had been just the antidote to my landlocked blues: a wonderful wilderness escape with no cell service or Wi-Fi, and few other people. It was four days of communing with the wind and waves, punctuated with visits to picturesque havens of sandstone and verdant conifers.

We only just got a taste. The crystal-clear water beckoned me for a swim, but the cold north wind dampened my enthusiasm to jump in. The leaves started to change while we were there, taunting me to come back and see the islands when they explode in color. And in winter, when conditions are just right, it’s possible to walk to some of the sea caves instead of sail. Icicles protrude from the caves, the whole scene still and quiet as if frozen in time. That is something I simply cannot imagine, and so I know I’ll be back.

Cruising the Apostle Islands

Bayfield, Wisconsin, is the home of Superior Charters and the Gateway to the Apostle Islands. The small town is located on the coast of Lake Superior and is about a 90-minute drive east from Duluth, Minnesota, which has an international airport.

Charter season: Late May through September, with the summer months being in greatest demand.

Guide Books: Superior Way by Bonnie Dahl and Sailing Adventures in the Apostle Islands by Lawrence W. Newman.

Provisioning: Grocery stores are available in Bayfield and nearby Washburn.

Fleet: Superior Charters’ current ­bareboat fleet comprises 26 monohulls and two catamarans.

Becca Guillote is a freelance writer and full-time sailor aboard Halcyon, a Valiant 40.

The post Apostle Islands Sailing Charter appeared first on Cruising World.

Effortless broad reaching, a dip in refreshing waters, cocktails in the cockpit, reunions with family and friends, a chance to learn a new onboard skill — those are the reasons vacation sailors say they return year after year to their bareboat company of choice.

But why do the owners and operators of these companies do it? Aside from the obvious reason — it’s a way to earn a living — running a charter company isn’t magic. It’s work. Or, “a labor of love,” as one put it.

A roundup of a dozen successful small bareboat charter companies, some of them family-owned and in business for decades, reveals why they got in and how they stay in the game. Companies also explain how their approach helps them shape and ­prioritize their business goals, and what the challenges are, as well as the opportunities — from operating in the virtual sphere of digital technology to minding the fleet in the flesh by walking the docks and sending sailors out in divergent, if gorgeous, ­cruising grounds.

Origins/Motives/Genesis

Fresh from careers in hotel management and banking, Cindy Chestnut and Brian Gandey knew what they sought when they started Conch Charters at Fort Burt Marina on the island of Tortola, in the British Virgin Islands, in 1987.

“We always wanted to be a small company,” Chestnut says. “And it was also a conscious choice to locate Conch Charters at a sailor’s marina rather than a fancy marina. We went for a location that allowed us to pass the savings on to our customers. And our customers seem to appreciate that more than having a swimming pool.”

What Gandey and Chestnut carried out, parlaying skills learned in one industry to do well in another, also worked for others.

Merion and Jennifer Martin run a mixed fleet of 25 power- and sailboats at Desolation Sound Yacht Charters in Comox, British Columbia, Canada. “Having worked in the superyacht industry in Europe and the Caribbean charter circuit for years has given us the experience to know what people expect and how to exceed their expectations,” Jennifer says.

Dave Conrad, of Great Lakes Sailing Co. in Traverse City, Michigan, says he and his wife, Kristen, met while he was managing a charter base in the Caribbean. Together, the couple worked aboard crewed yachts before buying the Traverse City 20-strong fleet of sail- and powerboats.

“Our success is a direct result of our hands-on approach to running the company,” Conrad says. “In the early days, we had little to no staff. We commissioned over 20 boats every year. We painted every bottom, did all the rigging, repairs and maintenance, and answered every phone call ourselves. We worked boat shows together even when Kristen was eight months pregnant.”

Some sailors got into the business so they could immerse themselves in a beloved pastime. “We started 40 years ago with one boat, as a way to help pay for it,” says Roger Van Dyken, of San Juan Sailing in Bellingham, Washington. “It turned into a hobby, then a pleasurable activity, and then, when we formed the business, it became an enjoyable enterprise.”

As Patti Gonsalves, of Cruise Abaco in the Bahamas, puts it, “We started the company with our own personal boat, grew to three, and just kept growing.”

For Brian Blank, of Newport, Rhode Island, this “labor of love” arose from a brush with America’s Cup fame. “I was working a summer job in 1977 at Bannister’s Wharf and became part of the dock crew for Ted Turner and Courageous,” Blank recalls. “Most fun I’ve ever had! I guess I just fell into the boating lifestyle and adventures. I ended up buying my first 38-foot sailboat for charter in 1985 and have never looked back!” His Bareboat Sailing Charters 15-member fleet floats on moorings in Brenton Cove, in Newport Harbor.

Know Your Niche, and Set Priorities

Serendipity didn’t play a major role in Kurt Jerman’s business plans when he opened the charter portion of West Coast Multihulls in 2011 in San Diego, but ­understanding the market did.

“There have always been plenty of schools and charter locations in the Southeastern United States, the Bahamas and the Caribbean,” he says. “The key for us has been to fill a void in the market here on the West Coast with catamaran ­instruction and charters.”

A few local sailing clubs dabbled in catamarans, Jerman says, “but none really knew that much about the boats, or the catamaran business as a whole. As a retail outlet for multiple catamaran manufacturers, my company had been importing cats to the West Coast since 1999.”

With an emphasis on teaching and ­certifying aspiring cat sailors, the business has gone from a two-boat, one-base center to a 10-boat, two-base concern, with a fleet of 10 privately owned cats from 35 to 58 feet in length. The new base, opened in high season 2018, is at Puerto Escondido, in the city of Loreto, Baja California Sur, Mexico, off the Sea of Cortez.

If charter is the “try before you buy” gateway to informed ownership, West Coast Multihulls has a fraternal East Coast twin. Over 25 years in existence, Maine Cat, of Bremen, Maine, has built 140 of its fast, light sail and power catamaran models in a range of lengths to an enthusiastic clientele. Its focus is on boatbuilding and direct sales to customers.

“When people say, ‘Let’s go charter a boat,’ Maine Cat is not the first company that comes to mind,” says owner Dick Vermeulen. “If you want to go sailing, we’re not the typical charter boat — our cats are performance cruisers.

“Our focus is not chartering. Having said that, our base in the Bahamas allows people to try one of our models and see if they like it.” The company’s base in Abaco, Bahamas, and its one-cat charter availability from Rockland, Maine, are live showrooms, and typically fully booked.

While charter is a valid means for sailors and aspiring sailors to transition to ownership, the critical stage of instruction can’t be overlooked, and that too has long been an ingredient of the recipe for success for West Coast Multihulls, Maine Cat and countless other charter outfits. Schools offer certification through custom curriculums or through organizations such as the American Sailing Association and US Sailing.

“We have been an ASA school since 1985 — one of the oldest still around,” says Barb Hansen, of Southwest Florida Yachts. “We see even more of a need for instruction now as the baby boomers get close to retirement. They now have the means to buy a boat, but might not have the skills.”

And Hansen, faced with countless aspiring owners, feels obligated to assess their needs. “When people come and ask me to help them find a boat to buy, I ask them what their experience is,” she says. “If they have none, I strongly suggest they go through our classes first. I tell them, ‘I would be happy to sell you a boat, but you would be buying a boat without the proper knowledge or experience.’ As with anything else, an informed buyer is going to be a better owner.”

Other companies, such as South Coast Sailing Adventures in Kemah, Texas, near Galveston Bay, remain dedicated and focused on instruction. “Our sailing school is the core of our business,” says owner Lucy Newman. “We strive to train competent and knowledgeable sailors, with a focus on safety and courtesy, while still having fun. We strongly believe that safe boating is achieved through education.”

With a view to longevity, Cindy Kalow, of Superior Charters in Bayfield, Wisconsin, adds, “Instruction is now paramount to our ability to maintain a fresh customer base and create future sailors. We would not still be in business if we didn’t have a training/certification arm to our business.”

Challenges and Opportunities

Fleet maturity is a challenge that some smaller charter companies have had to deal with, and some have had an unprecedented hurricane season transform their business plan.

“The image of us having older boats is one we’ve been working hard to alter; our oldest boats are now 7 or 8 years old,” says Chestnut, of Conch Charters, of a fleet that grew to 56 a few years back. “Of course, hurricanes Irma and Maria in September 2017 affected that.”

As Conch rallied to get under way in time for charters in high season 2018 with a dozen boats, Chestnut says, “We never anticipated that we’d be at this juncture at this point. We want to continue to rebuild — it’s Conch Charters. It’s our baby. We don’t want to see it go poof! We’re coming back.”

Mother Nature isn’t the only force at play. “The market has changed,” says Kalow. “People no longer participate in just a few hobbies or activities. In the past, people would label themselves a sailor or a golfer. Our younger customer base is very active and has a lot of interests. We continually work to tap into new markets and customers who are looking for new and different experiences. You have to keep your product fresh, understand what you offer and stay sharp on how you present that offering.”

Then there’s the effort you put out.

“We have worked our tails off for nearly 35 years,” says Hansen. “I’m still here seven days (and nights) a week, with the occasional day off. If you don’t have that passion for your business, then you won’t succeed. You have to believe in what you do and then try to do the best job you can do.”

Rapid advances in digital technology have also had a major impact, and present new possibilities. “The sharing economy has opened up people’s eyes to unique lodging opportunities, and being based in San Diego makes it easy for us to offer Cruise-N-Snooze charter stays on the boat, like Airbnb on the water with a sunset cruise thrown in,” Jerman says. “That might have been hard to explain before, but now people just get it.”

Adds Chestnut, “People are more easily reached and found. Our reservation system is online. We put an e-tablet on each boat with the chart briefing and all charts and a nav system, as well as fun facts like plants and fish they might encounter. We have a checklist of each yacht’s systems. If charterers have a problem while they’re out, they can take a picture and send it to us via a text or email.”

It’s Magic — or Is It?

Company owners enjoy describing the ineffable twist to attracting repeat clientele.

“We retrieve lost luggage and deliver it, grab the bag of ice they forgot, pick up their trash on the water if they missed the drop-off in a settlement,” says Gonsalves, of Cruise Abaco. “When the owner of the company is the one who you see on the dock and on the water, you know you’re being taken care of. No request is impossible!”

“We make sure the client gets what he or she paid for — a fantastic time on the ­water,” Jerman says. “There’s a risk in making things overcomplicated.”

Resilience in the face of setbacks such as hurricanes also scores big with sailors. “At the end of the day, it’s all about attention to detail and giving people a little bit more than they expect — a beach bag, a bottle of rum,” says Chestnut. “One client has been chartering with us for 27 years for two weeks a year. They ask us if they can bring anything down. They’ve brought us starter motors for cars, maple syrup. That’s what makes our company nice. It’s like a family.”

It helps that, by and large, a charter trip is a happy experience. “Our customers are on vacation!” Hansen says. “It’s not like they are going in for a root canal. We love that we are often fulfilling a dream for someone or we are helping them plan the trip of a lifetime!”

It works at San Juan Sailing too. “Our staff derives sheer joy from helping people have joy — period,” Van Dyken says. “Nothing beats passionate, selfless service.”

Blank, of Bareboat Sailing, sticks to this philosophy: “Keep your customers happy, and they will always come back.”

Elaine Lembo is a CW editor at large.

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