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Travel to the Caribbean by yacht

Lush rainforests, ancient sites, and vibrant coastlines connect diverse cultures along two dazzling seaboards.

Find yachts in the Caribbean
Highlights

A world-famous geological wonder, The Baths on Virgin Gorda features massive granite boulders forming striking sea pools and grottoes.

A restored Georgian naval base and UNESCO site, Nelson’s Dockyard in Antigua lets you sip cocktails beside historic stone warehouses once used by the British Royal Navy.

A volcanic summit draped in rainforest trails, Nevis Peak offers sweeping coastal views across Saint Kitts and Nevis.

Unlike resorts, where luxury can feel curated, the Caribbean offers an effortless blend of upscale comfort and untamed natural beauty. One night, you might dock alongside superyachts in Gustavia; the next, anchor in a remote bay off Dominica, where rainforest meets black sand and hot springs bubble just inland.

Unlike Mediterranean resorts, where luxury can feel curated, the Caribbean offers an effortless blend of upscale comfort and untamed natural beauty. One night, you might dock alongside superyachts in Gustavia; the next, anchor in a remote bay off Dominica, where rainforest meets black sand and hot springs bubble just inland.

Moving between these extremes is surprisingly seamless. While short inter-island flights are available, many travelers prefer to charter a yacht. The region’s maritime infrastructure is built for this, with professional marinas and smooth, discreet customs processes tailored to the expectations of luxury travelers. Each island offers a fresh cultural perspective. French, Dutch, British, and Afro-Caribbean influences mix uniquely across the region. One day, you might watch a cricket match in Antigua; the next, stroll through Saint Martin practicing your French.

From colonial architecture to calypso rhythms and spicy goat curry, no two landfalls are alike. Best of all, travel here bends to your rhythm. Caribbean yacht charters deliver comfort without the constraints—inviting you to explore, linger, or simply enjoy the view, entirely on your terms.

Local Tips

Some of the best beaches have no road access. Ask your captain about anchor-only spots like Petite Saline or Sandy Island.

In-demand beach clubs like Nikki Beach in St. Barths or Scilly Cay in Anguilla often book out during the high season. To secure seats at a specific spot, make reservations well before departure.

High-season marina berths can disappear weeks out. If dockage isn’t available, anchor nearby and tender ashore. It’s often the more scenic option, anyway.

Many cultural sites, such as churches or local markets, prefer modest dress—even in beach towns. Pack a lightweight cover-up for shore visits.

Cellular service varies widely between islands. If you’re sailing between less developed areas, consider a satellite hotspot or regional SIM for stable coverage.

Reasons to charter a yacht to the Caribbean versus staying in a hotel

The day begins in stillness—trade winds rustle the rigging as the sun rises over limestone cliffs and mangrove shores. In the distance, emerald peaks come into view—perhaps Saint Lucia’s Pitons or Bequia’s hills. A few catamarans float nearby, serene and silent. There’s no check-in, no reception desk—just a calm bay ahead and the luxury of time.

The day begins in stillness—trade winds rustle the rigging as the sun rises over limestone cliffs and mangrove shores. In the distance, emerald peaks come into view—perhaps Saint Lucia’s Pitons or Bequia’s hills. A few catamarans float nearby, serene and silent. There’s no check-in, no reception desk—just a calm bay ahead and the luxury of time. Unlike even the finest hotels, a Caribbean yacht charter offers unmatched freedom. While others wait in customs lines or for the next island hopper, your morning begins with fresh fruit on deck and a view of paradise.

Your private crew can chart a course to Mustique, where a picnic awaits on a private beach, or to Terre-de-Haut, where café au lait and croissants are served in a charming village square. And when night falls, there’s no last call. The evening unfolds at your pace, far from the crowds. You’ll drift to sleep in quiet comfort, knowing a new destination awaits just over the horizon.

Why sail with us?

Exceptional yachts and effortless journeys.

Carefully curated

A selection of quality yachts to suit any adventure

Global collection

Options for every corner of the world

Experienced crew

All charters include a chef, captain, and housekeeping

Premium protection

Up to $1B in insurance coverage

Things to do in the Caribbean

An image of Fort George

Fort George

18th-century hilltop fort in Grenada with commanding views over St. George’s Harbor. Ideal for a photo stop before drinks ashore.

An image of Blackwell Rum Bar

Blackwell Rum Bar

Dramatic oceanfront bar set inside a limestone cavern.

An image of Cartanza Senora Wreck

Cartanza Senora Wreck

A 190-foot WWII-era freighter turned dive site, now home to coral, turtles, and reef fish just off Buck Island’s coast.

An image of Carambola Golf Club

Carambola Golf Club

Set inland on the island’s lush northwest side, this Robert Trent Jones Sr. course runs through thick rainforest and presents a challenging layout.

An image of Port Lucaya Marketplace

Port Lucaya Marketplace

Upscale, open-air shopping destination near Freeport. Visit for luxury duty-free shopping and classy cocktails. Perfect for provisioning after docking in Freeport.

An image of Wilhelmina Park

Wilhelmina Park

A quiet, palm-lined waterfront promenade in Oranjestad’s historic quarter. Tropical gardens and shaded paths contrast the Dutch colonial architecture.

An image of Mount Scenery Trail

Mount Scenery Trail

Climb 1,015 stone steps through rainforest and into cloud forest on the highest peak in the Dutch Caribbean.

Places to eat and drink in the Caribbean

eat Da Conch Shack

Oceanfront staple serving fresh conch every way imaginable, from curry to chowder, with live music and toes-in-the-sand dining

Eat Morgan’s Mango

Colorful, open-air spot celebrating neo-Caribbean and Latin flavors with island-inspired dishes and an impressive selection of rum, steps from Cruz Bay

Eat The Cliff

An elegant clifftop restaurant with panoramic sea views. Expect artfully plated seafood delivered from its open kitchen.

eat Ms. Piper’s Kitchen + Garden

Retro-chic garden setting offering fresh cuisine and craft cocktails in a quiet residential corner of Seven Mile Beach

Drink Capella Marigot Bay

Yacht-friendly hideaway known for its locally sourced sushi and midday rum tastings served straight from a floating barrel.

eat Le Petibonum

Volcanic black-sand dining experience—part rum bar, part bistro, but always something fun happening.

eat The Landing

Seasonal Bahamian dining inside a colonial-era building with a wine list tailored for serious collectors

When to visit

Choosing when to take your yacht charter to the Caribbean depends on many factors, including the weather and anticipated crowds. Consider these key factors as you plan your Caribbean getaway.

Summer Season

May – September

Spring

One of the most reliable seasons for yacht travel. The weather is dry across most of the region, with average temperatures in the mid-70s to mid-80s Fahrenheit. Trade winds remain steady, making this a strong season for sailing. Major events such as Antigua Sailing Week and the St. Lucia Jazz Festival draw visitors, but crowd levels stay manageable compared to winter. Marina space is still competitive but easier to secure.

Summer

Fewer crowds and more flexibility make this a good time for travelers looking to avoid the high season. Temperatures climb into the high 80s, and short afternoon rains are common. Some islands—like Barbados, Grenada, and Curaçao—remain active with festivals and open ports throughout the summer. Charter pricing tends to drop, and berth availability increases, though hurricane planning becomes a consideration starting in June.

Winter Season

October – April

Fall

The lowest traffic season of the year. Many charters undergo maintenance, and some marinas operate at reduced capacity. However, destinations like Aruba and the Grenadines sit outside the main hurricane belt and continue to welcome yacht traffic. Rates are typically at their lowest, and most shore-based services are more accessible without reservation pressure. For those prioritizing privacy over events, this is a practical and economical time to travel.

Winter

This is the peak season for good reason. Conditions are stable across the region—temperatures range from the low 70s to mid-80s with minimal rainfall. Charter demand spikes sharply from mid-December through February, so many islands host private events and high-profile gatherings then.

Festivals/events in the Caribbean

Bahamas Junkanoo

Costumed parades and brass bands take over Nassau’s streets before dawn. Skip the bleachers—locals head to Rawson Square for the best view.

Carnival in Trinidad & Tobago

The most beloved celebration in the region. Visitors join masquerade bands, watch pan performances, or attend sunrise parties that run for hours.

Heineken Regatta, St. Maarten

The largest regatta in the Caribbean takes place over four days and attracts upwards of 20,000 sailing enthusiasts.

Antigua Sailing Week

A cornerstone of Caribbean yachting culture, with competitive racing by day and social events throughout English Harbour in the evenings.

Crop Over Festival

A cultural season with colorful celebrations, including the Cohobblopot show and art exhibitions. Grand Kadooment closes the celebration with a full-costume procession through Bridgetown.

Curaçao North Sea Jazz Festival

International acts take the waterfront stage in Willemstad.

An image of a yacht sailing in sea.

How to get to the Caribbean

Plane

Most major islands host international airports for commercial flights and FBOs for private jets. Inter-island flights on carriers like Tradewind Aviation and interCaribbean Airways offer reliable service to smaller destinations such as Anguilla and Dominica, often landing at short-runway airports inaccessible to commercial jets.

Boat

Yachting remains the most flexible way to travel between islands. Full-service marinas in St. Barths, the BVI, Antigua, the U.S. Virgin Islands, and many other islands accommodate vessels for overnight anchorage. Inter-island ferry routes also connect places like St. Martin to Anguilla or Guadeloupe to Les Saintes, offering fast access for guests joining charters mid-itinerary.

All Yachts for Charter in Caribbean

FAQ about the Caribbean

What is it like to charter a luxury yacht to the Caribbean?

A luxury yacht charter in the Caribbean feels less like a destination vacation and more like accessing a private network of tropical paradises. The routes are flexible to your desires, and you can island-hop between countries in a matter of hours.

When is the best time of the year to charter a luxury yacht to the Caribbean?

The prime season runs from mid-December through April, when the weather is driest and demand for top-tier marinas is at its highest. Spring shoulder months offer better flexibility and fewer crowds. Summer and early fall are less popular due to storm risk, though select islands outside the hurricane belt—such as Aruba, Curaçao, and Grenada—remain attractive for off-season charters.

How complicated is it to cross between different countries while chartering in the Caribbean?

Visiting several nations on a single charter is common, especially in the Leeward or Windward Islands. Still, each has its own customs and immigration process—even when the distance between ports is just a few nautical miles. Your captain will typically handle entry documents and coordinate with local agents to clear the vessel and passengers efficiently. That said, clearance hours can vary, and may be closed on holidays or weekends, so itineraries often need to account for processing windows when crossing borders.

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