When invited to take part in Sunsail’s 50th anniversary flotilla in the British Virgin Islands, I admit I hesitated. Flotillas, I thought, smacked of follow-the-leader boating and constraints. But I could not have been more wrong. Our week was fluid and stress-free, a medley of parties, activities and friendly competitions on the water and off, and I disembarked with a new attitude and appreciation of sailing en masse.  

Flotillas are in Sunsail’s DNA. The genesis of the company was a fledgling vacation sailing business in Greece’s Saronic Gulf in 1974. In North America “Blazing Saddles” was No. 1 at the box office, “The Way We Were” was the top tune, and Watergate dominated the news when on the other side of the planet a small flotilla of sailboats heralded the launch of what would evolve into the Sunsail company. And here I was, half of a century later, flotilla sailing with what has become one of the leading vacation charter companies in the world. Because who doesn’t love a trip to the BVI?

Our event kicked off at the Tortola base shared by Sunsail and its sister company The Moorings. Although everyone seemed to arrive tired and overheated, the spacious depot, icy bottles of water, complimentary showers, heads and pool quickly cooled tempers. From the time your taxi pulls up and you’re greeted by the staff, to boat check out and send-off, it’s a first-class operation.

Welcome drinks and a reception greeted the flotilla goers, followed by a generous breakfast and briefing the next morning where we got T-shirts, 50th anniversary battle flags, and an opportunity to meet our cohorts. Scott and Rick are longtime friends and self-described adventurers from Arizona. They and their spouses have chartered before, but the two couples joining them were complete newbies. 

“We’re pretty much the only experienced sailors on the boat, so opted for the flotilla,” Scott said.

“For people who are new to chartering, a flotilla is a fantastic way to start,” said Melissa Johnson, part of Sunsail’s vacation planning and marketing team. “You have a lead boat providing on-the-water support and local knowledge, which is like having a local tour guide. It’s a great way to introduce yourself to a new destination with this safety net in place. You get assistance with moorings, reservations and the itinerary and don’t have to worry about a lot of things: it’s kind of a set-it-and-forget-it vacation! But it’s not like little ducklings in a row. You definitely have a lot of freedom, but you have a lot of fun together too.”

Which is how I found myself judging rum concoctions on the beach at Norman Island on a balmy evening in July. It was a terrific icebreaker for the dozen-plus boats, hosting crews from four different nations on a weeklong adventure. 

The itinerary had taken us from Tortola to Norman Island the first day, an easy 7-nautical-mile passage and shakedown for the fleet. Destinations in the BVI are bite-sized with plenty of options for passages of different lengths and challenges to suit your conditions, skillset and whims, each ending in a stunning destination.

Day Two saw us off to Virgin Gorda and our crew was eager to sail. We hoisted the main, unfurled the jib and stretched our legs in the brisk easterly breeze. The Sunsail 454L was kind to weather, handling well particularly considering the 45-foot long, 24-foot beam catamaran has four roomy en suite cabins and tons of communal living space.

We tacked heartily across the Sir Francis Drake channel for several hours until, with the promise of cold drinks at Leverick Bay Bar calling, we furled up the jib and motorsailed the rest of the way.

Sunsail hosted a superb spread that night including a whole roasted pig, entrees and dishes for every palate, washed down with drinks from Jumbies. The hosted DJ spun tunes into the wee hours with several crews rocking the night away. With a 9 a.m. start to the informal race to Anegada though, we snuck back to our cat for a leisurely nightcap on the top deck, watching the stars come out.

But there is no such thing as an informal race if you’re a serious sailor. So we set off promptly on the bracing 13-mile reach to Anegada. Summer squalls sprinkled across the horizon, but we could see them in plenty of time to trim and take cover. Hitting a light patch we contemplated shaking out the reef but thankfully didn’t. 

As we approached the narrow channel into Setting Point a thick haze of white swept the sky. About face! We turned back and stood off as rain engulfed the anchorage. The wind gusted to 30 knots and hail pummeled the boat, while we roared with glee, feeling safe and snug aboard the boat until the squall passed.

Sunsail had arranged for trucks to transport us across the rugged isle to Tipsy’s bar where we met up for games and libations, then returned for delicious lobster dinners at Potters, where organizers had more fun up their sleeves with dancing and a limbo contest.

The departure from Anegada was much calmer, as we wriggled through the winding channel into the expanse of Caribbean Sea. It was a leisurely reach to Jost Van Dyke in modest breeze, dodging sprinkles and we all got in a nap. 

That night at Foxy’s our swashbuckling group gathered for drinks dressed in pirate costumes. Winning that competition were Sue and Steve from Sussex, England, who have enjoyed scores of flotillas over the past 40 years. 

“Flotillas are more of a European thing,” they said, adding they appreciate meeting participants of different ages and backgrounds. 

“Sometimes it’s difficult to find just the right cruising companions and coordinate dates,” Sue said. “And a flotilla provides the desired amount of camaraderie and fun, with the option to retreat to their boat when the time comes.”

“And I’m on holiday!” Steve continued. “I don’t want to have to navigate and plan where to go and all that stuff. I just want to get here and have the lead skipper tell me where to go and when.” 

He noted the added advantage of having an engineer or handyman on the lead boat, saying, “If the head gets stuffed up a man just comes over and fixes it.” 

Or in this case, a gal. Flotilla leaders Melissa and Imogen were Janey-on-the-spot with any presented question or challenge, any time of day or night. Their guidance and presence were a clear benefit of flotilla sailing and made it a joy.

On our free day we opted to stay at Great Harbour, swim, snorkel and hang out on the boat. This newest version of the Sunsail 454L catamaran is an absolute party machine. Four refrigerator/freezers, including a dedicated beverage fridge in the main cockpit, made it nearly impossible to run out of ice, and the massive water tanks meant we never needed to try out the new watermaker.

There’s a forward cockpit, accessed through a door in the galley, refreshed with the prevailing breeze when at anchor or on a mooring. And lo and behold, the 454L has an upper deck, cabintop lounge with seating, a table and cushioned day beds. This is where we would end each day, relaxing until the rain (inevitable in the summer nights) would start to fall and we’d retreat to our sumptuously air-conditioned cabins. 

The final night was a lively poolside party and prizegiving back at the base in Tortola, where Sunsail first established its BVI fleet in 1991. Everyone, it seems, got a prize for costumes, décor, drinks, races or something, and exchanged stories and numbers. 

“Flotillas are so popular in the Mediterranean, where it all started, and are becoming more popular in the Caribbean,” Melissa said. “From a price standpoint there’s a nominal difference (to bareboating) but that covers the support boat, schwag like T-shirts and hats, some hosted meals, parties, drinks, games and prizes. Plus you get the chance to meet new people who are like-minded and enjoy the same sport.”

A new advocate of flotilla sailing, I realized it offers no-brainer planning and preparation, with built in community, support and fun, and a real chance to let loose and “go with the flo(tilla).” 

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Two hulls, twice the fun

The cat is out of the bag. Chartering a catamaran for a bareboat vacation is twice the fun, with spacious, stable boats that double as a party platform when anchored or moored. 

While it’s true that multihulls don’t go to weather as smartly as monohulls, they do reach well. Reaching will be more comfortable and successful than attempting a destination directly to weather or dead downwind. Picking your itinerary and course to maximize your best sailing angle in the given breeze ensures fun sailing.

A catamaran’s minimal heel is an ideal introduction to guests who are new to sailing and might be put off by a monohull. Although a cat isn’t as tippy, it will heel some, so put away the toaster, blender and anything else that might fly before you get underway. Be aware that the minimal heel might not tip you off to wind velocity, so remember to take a reef when the breeze hits the double-digits.

Twin-engines make catamarans incredibly maneuverable and easy to get on and off the dock or mooring. And they handle tight quarters with confidence.

Spacious cabins and interior are another bonus along with the roomy, covered main cockpit. Some models enjoy a forward cockpit too, which offers a breezy escape once you’re anchored. Just don’t try sitting there while sailing.

Generous swim steps aft make it easy to take a dip and board from the tender, especially if there’s snorkel or diving gear to contend with. Be sure to pull up the swim ladder and close the gates before you get under sail to keep everyone safe.

Whenever chartering plan to arrive early to get your chart briefing and boat-check out of the way so you can get off the dock as quickly as possible. Review your boat inventory ahead of time so any missing or broken items can be replaced promptly. 

Plan your menu and provisioning ahead of time and feel free to get plenty of drinks and chow: capacious catamarans translate to large refrigerators plus extra stowage space under the floorboards. The expansive beam may also allow for bigger water tanks, plus room for a generator and air conditioner. Be sure to check all the available amenities before you finalize your booking. 

“Cats are connoisseurs of comfort,” wrote famed author James Herriot. Aptly put.--B.S.

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For more information visit sunsail.com