What It’s Like to Go on an American Sailing Vacation Trip

When you step aboard an American Sailing Vacations journey, you quickly realize it’s not just about where you sail—it’s about the way you experience it. Whether you’re cruising the rugged beauty of New England on the majestic Arabella, exploring ancient coastal towns in Croatia aboard Cataleya, drifting along the Amalfi Coast on the sleek Chronos, or joining a flotilla in the Caribbean, these trips offer more than a vacation. They create a community, a rhythm, and a sense of wonder that lingers long after you’ve stepped back onto shore.

Life Aboard: Relaxation Without Responsibility

For many travelers, the true joy of these voyages is the freedom from decision-making. As one passenger put it, sailing on the Arabella meant “the worry-free sailing—just being a passenger and enjoying the relaxation.” Unlike bareboat charters, where guests manage the sails, cooking, and logistics, these vacations are fully crewed. You’re free to sip coffee at sunrise, read on deck, or strike up conversations with fellow travelers while the crew handles the details.

Flotillas add another layer to this experience. Picture a dozen yachts sailing in tandem through the turquoise waters of the British Virgin Islands, each boat a floating micro-community, yet all converging for beachside gatherings, group excursions, and impromptu parties under the stars.

Destinations That Surprise You

One of the charms of sailing with American Sailing Vacations is discovering destinations you might not have considered on your own. “I hadn’t even thought of sailing New England until we experienced it,” said one traveler after cruising around Martha’s Vineyard and Newport aboard the Arabella.

Another guest sailing through Croatia recalled walking through ancient cities, joining excursions, and even dancing with new friends to ABBA—an experience she laughingly called “life changing.” In Italy, passengers aboard the Chronos savored the Amalfi Coast, where time in port was balanced perfectly: “adequate time to tour and shop, but not too much.”

And in the Caribbean, flotillas like the Lenny Shabes Sailing Festival BVI Flotilla deliver an entirely different kind of adventure.

A Floating Festival in the BVI

If the crewed yachts of Europe and New England feel like boutique hotels at sea, then the BVI flotillas are a traveling festival of sailing culture. During the Lenny Shabes Sailing Festival, mornings often begin with a splash—guests diving off sterns into warm turquoise water before breakfast. By mid-morning, the flotilla is under sail, white canvas stretched across the steady trade winds as a loose caravan of yachts makes its way toward the next island.

Afternoons bring exploration—snorkeling at The Indians, wandering barefoot through the sands of Jost Van Dyke, or hiking to a hilltop bar where the rum flows as freely as the music. But the flotilla truly comes alive when boats raft together, decks transform into dance floors, and laughter carries from one yacht to the next. Onshore, the activities range from small regattas to lobster feasts to a little dancing by a bonfire.

Unlike the quieter pace of Arabella or Chronos, flotilla life is about energy, variety, and the joy of knowing your adventure is shared across a fleet of kindred spirits. It’s as much about the people as the place.

The Crew Makes the Difference

Across all the ships, one thing stands out: the crews. Guests consistently describe them as upbeat, attentive, and committed to creating a memorable trip. From providing dairy-free meals in Italy to keeping spirits high in New England, the crews’ dedication shines through. “The crew was amazing—full stop!” wrote one Arabella guest. Even when the wind didn’t cooperate for sailing, or when dinghy rides became a challenge for those with bad knees, travelers noted that the crew made the experience smooth and enjoyable.

On flotillas, the leadership plays a similar role. Experienced captains and flotilla leaders chart the course, handle logistics, and set the tone for the adventure, allowing participants to focus on sailing, exploring, and building lasting friendships.

Food, Fun, and Small Touches

Meals are another highlight. On the Chronos, one traveler called the food “outstanding quality and variety.” In Croatia, guests praised the options but wished for a little more variety at breakfast—proof that while the meals are good, travelers aren’t shy about suggesting improvements. Still, the joy of dining together—whether on board or ashore—often becomes part of the adventure. Some guests even recall following their trip leader into hidden restaurants that became unforgettable dining experiences.

Flotilla dining has its own charm: some nights, crews gather for barbecues on deck or potluck-style meals shared across boats, while other evenings everyone heads ashore for a lively group dinner at a beachside restaurant.

Entertainment comes naturally, too. From sunset cruises around Newport Harbor to impromptu dance parties on deck, the combination of setting, company, and atmosphere sparks moments of pure fun. In the Caribbean, that might mean steel drums on a beach, live bands during the festival, or music drifting from one rafted boat to the next as the flotilla becomes one big floating party.

Not Without Its Imperfections

Of course, no vacation is perfect. Some travelers noted practical challenges—cabins that were smaller than expected, long tender rides to shore, or air conditioning that didn’t quite keep up with the Mediterranean heat. And while everyone loves the idea of sailing, sometimes Mother Nature doesn’t deliver the wind. Yet, even when things weren’t perfect, travelers overwhelmingly said they’d recommend the trips to friends—and most have already booked their next adventure.

Why People Keep Coming Back

Perhaps the best measure of these vacations’ impact is how many guests return. “Absolutely! And have done so,” wrote one repeat Arabella traveler. Another said simply, “Please offer it again.” For some, the trips offer relaxation. For others, they deliver connection—with new friends, with family, or with themselves.

Whether it’s the elegance of Arabella in New England, the culture-rich coasts of the Mediterranean, or the high-energy fun of a flotilla in the Caribbean, the thread is always the same: community, discovery, and the freedom of the sea.

And that’s the secret of an American Sailing Vacation: it isn’t just about where you sail, but with whom and how. It’s the laughter echoing off a harbor wall in Croatia, the taste of limoncello on a hot afternoon in Amalfi, the hush of a New England sunset. It’s the way the sea takes you out of your life, just long enough to show you a new one.