⛵Sept '26: One Extraordinary Week in French Polynesia ⛵ Jan '27: Legendary Caribbean Sailing in BVI

Exciting Liveaboard Destinations

Trade Your Cold Weather Blues for a Better Kind of Winter Blues!

So often, our guests tell us it's their dream to spend a week living aboard, sailing during the day, lounging by the sea and enjoying a tropical cocktail. We may be a little biased, but we can't think of a better way to spend some vacation days! We can help you check off your bucket list and not only sail anywhere in the world, we can act as your travel agent and help you arrange every detail of your dream vacation. Warm days, cool nights and cold cocktails...what could be more perfect?

Our multi-day liveaboard sailing vacations are offered between November and April. Learn more about our destination sails below or just contact us to reserve your destination sail.

Photo of boats at anchor on a Caribbean destination sail

Picture yourself here, aboard your own liveaboard sailing vacation.

Sailing Vacations and Learning to Sail

Sailing Vacations

Learn to Sail in Tropical Places

Sailboat and seaplane on a destination sail in the Caribbean.

Dreaming of getting away from it all, sailing from one island to another, and waking in a new cove each morning? Captain Wendy's expertise in monohull and catamaran sailing offers you an opportunity to spend your vacation time living aboard a sailboat without the worry of how to sail it. In addition to being dual-licensed with both the US Coast Guard and Royal Yachting Association, Captain Wendy has 25 years of travel planning expertise and a wealth of knowledge about many island destinations, Captain Wendy can offer you a vacation you'll remember for years to come.

Some of Captain Wendy's favorite destinations include the British Virgin Islands (BVIs), the Grenadines, St. Martin, The Society Islands of Tahiti, Moorea & Bora Bora, and The Whitsunday Islands of Australia. Have another destination in mind? Let us know and we'll set it up for you!

In addition, if you prefer to completely relax, Captain Wendy has a network of sailing chefs who can prepare your onboard meals and drinks for you!

Multi-day live aboard sailing vacations for 2-10 guests.

Learn to Sail in Tropical Places

A student learning to sail using a winch on a sailboat in the Caribbean.

Learn to sail in some of the world's best sailing destinations!

Captain Wendy is the only American Sailing Association Certified Instructor on Martha's Vineyard. She is certified and qualified to teach basic sailing as well as coastal cruising, bareboat chartering and catamaran sailing. Her calm demeanor and patience make learning easy and fun. She can offer you and your friends sailing instruction during any of our sailing charters or during a sailing charter vacation to any destination of your choice

Read more about Captain Wendy's experience and credentials on our About Us page.

September 2026: One Extraordinary Week in French Polynesia

Some dreams live on bucket lists for years. This is the one that finally turns a dream into reality.

Join Captain Wendy, beloved by her Vineyard guests for her warm hospitality and confident seamanship, for an unforgettable seven-night sailing adventure through the Society Islands.

Aboard an elegant sailing catamaran with three guest cabins for up to six guests, you’ll explore the legendary lagoons of Bora Bora, Raiatea, and Taha'a—where emerald mountains rise from impossibly clear turquoise water.

Each day brings a new anchorage and new experiences:

Snorkeling vibrant coral gardens and an unforgettable drift snorkel through a reef pass
Swimming with graceful stingrays in warm, crystal-clear lagoons
Visiting a traditional Tahitian pearl farm
Hiking lush volcanic islands with sweeping lagoon views
Experiencing Polynesian music and dance beneath the stars
Paddleboarding, swimming, and sunset sailing in secluded anchorages

Life aboard moves at the perfect island rhythm—morning swims straight from the boat, afternoons exploring hidden coves, and evenings beneath the brilliant South Pacific sky.

Seven nights. Three extraordinary islands. One unforgettable voyage.

Includes the yacht, Captain Wendy's professional services, and provisions for meals aboard.

Meals are self-catered, allowing your group to cook together and enjoy the relaxed pace of life at sea. Prefer a fully indulgent experience? A private onboard chef can be arranged for an additional fee.

Private sailing experience — from $5,000 per person
Limited to six guests.

Our multi-day liveaboard sailing vacations are offered between November and April. Learn more about our destination sails below or just contact us to reserve your destination sail.

Jan 2027: Sail The British Virgin Islands with Captain Wendy

Legendary Caribbean Sailing — Easy to Reach, Impossible to Forget

The British Virgin Islands are widely considered the sailing capital of the Caribbean—and once you arrive, it’s easy to see why. Steady trade winds, protected passages, and islands just a short sail apart create the perfect setting for an unforgettable week at sea with Captain Wendy at the helm.

Days are spent sailing crystal-clear waters, snorkeling vibrant reefs, and dropping anchor at legendary beaches. Evenings bring a different rhythm—barefoot dinners ashore, live music drifting from beach bars, and sunsets that seem designed to keep you lingering just a little longer.

Your week in the BVIs may include:

Sailing through the island chain with steady Caribbean trade winds
Exploring the famous granite boulders and hidden pools of The Baths
Anchoring off the legendary white sands of Jost Van Dyke and visiting the iconic Soggy Dollar Bar
Snorkeling coral reefs and swimming in warm turquoise coves
Paddleboarding quiet anchorages and learning the art of sailing along the way
Beachside dinners, live island music, and relaxed Caribbean nightlife

Your charter includes the yacht, Captain Wendy’s professional services, onboard provisions for self-catered breakfasts and lunches, and all cruising permits, national park fees, taxes, and moorings. Evenings are typically spent enjoying the islands ashore, where the BVIs’ vibrant beach bars and restaurants come alive after sunset.

An easy escape. A legendary sailing destination. A week in the Caribbean you’ll wish lasted longer.

Private sailing adventure — from $3,500 per person
Based on six guests aboard a luxury sailing catamaran. Gratuity not included. Larger groups may be accommodated upon request.

Our multi-day liveaboard sailing vacations are offered between November and April. Learn more about our destination sails or just contact us to reserve your destination sail.

⛵Sept '26: One Extraordinary Week in French Polynesia ⛵ Jan '27: Legendary Caribbean Sailing in BVI