Sailing the Caribbean combines steady trade winds, short island hops, and a wide range of anchorages—from lively beach towns to quiet marine parks. There is a remarkable diversity of Caribbean destinations available for yacht charters, each offering unique attractions and itineraries. It’s written for first-time crews and returning skippers planning either bareboat charter Caribbean or catamaran charter Caribbean, with clear seasonal, regulatory, and planning notes. All of these experiences take place within the stunning expanse of the Caribbean Sea, known for its extensive archipelagos and world-class yachting opportunities.

Yacht Charter Caribbean: When to Go & What to Expect

• Sailing season. Peak months are December–May: warm temperatures, consistent trade winds (often 10–20 knots), and relatively dry weather.

• Hurricane season. June–November is the wet season, bringing higher humidity, increased rainfall, and the possibility of tropical systems (most likely Aug–Oct). If you sail then, build flexibility into your plan and monitor forecasts closely.

• Sea state & navigation. The Leeward Islands (BVI/USVI/Saint Martin/Antigua) offer shorter legs and more line-of-sight navigation; the Windward Islands (Martinique to Grenada) deliver stronger breeze and livelier channels between islands.

• Moorings & marinas. Expect public mooring fields in popular bays, marine-park buoys in protected zones, and full-service marinas on larger islands (fuel, water, provisions).

Bareboat Charter Caribbean: Skills, Paperwork, and Planning

A bareboat charter Caribbean gives you full control of the route and daily rhythm. At least one skipper should have recent experience handling similar size/rig, plus comfort with anchoring, picking up moorings, and coastal navigation. Some bases ask for a sailing resume or recognized certificate; others are experience-based. Whether you are a novice or an experienced sailor, there are chartering options in the Caribbean to suit your skill level and preferences.

Checklist before you book:

• Understand the chartering process, including confirming any cruising permits, park fees, and customs/immigration steps for island crossings.

• Review safety gear, dinghy/outboard, and ground tackle on the boat’s listing.

• Plan realistic legs (arrive early at popular mooring fields), and keep a fallback anchorage each day.

• Download offline charts and local notices; bring a paper chart as backup.

If you’d rather not skipper, add a licensed captain — see yacht charters Caribbean crewed.

Catamaran Charter Caribbean: Why Many Crews Choose Two Hulls

A catamaran charter in Caribbean offers:

• Stability & space. Minimal heel under sail, wide decks, and roomy salons—ideal for large families and mixed-ability groups who need extra room and comfort.

• Shallow draft. Access to reef-fringed anchorages and sandy shelves closer to shore.

• Ventilation. Cross-breezes and generous outdoor living areas suit the tropical climate.

• Well equipped. Catamarans are often well equipped with amenities for comfort and convenience, making them suitable for a variety of activities and guest needs.

Trade-off: higher charter and mooring fees versus same-length monohulls, and slightly reduced upwind performance. For easy living and short hops among islands, cats are a strong fit.

Yacht Charter BVI : Line-of-Sight Island Hopping

The British Virgin Islands are the Caribbean’s most approachable cruising ground for first-time charterers and relaxing family trips. Distances are short, anchorages are well charted, and the vibe ranges from quiet coves to casual beach bars. Many of the islands, such as The Baths on Virgin Gorda and White Bay on Jost Van Dyke, are charter favorites among visitors for their stunning scenery and excellent amenities.

A wide variety of charter yachts are available in the BVI, from bareboat monohulls BVI and catamarans to fully crewed luxury vessels, making it easy to find the perfect option for your group and preferred style of adventure.

Yacht Charter US Virgin Islands (St. Thomas & St. John): Easy Access, Quiet Coves

The US Virgin Islands combine straightforward travel (especially for US guests) with classic Caribbean anchorages. Charter guests appreciate the convenience and services available in the USVI, making it an ideal destination for a hassle-free charter experience.

• Yacht charter St. Thomas offers provisioning, marinas, and charter bases.

• St. John is largely national park: secluded bays, clear water, and designated moorings that protect coral reefs. For those seeking more seclusion, remote anchorages are also available, providing calm waters and a peaceful setting.

• Sample plan: Start in St. Thomas, spend a couple of nights around St. John’s north shore (Hawksnest/Francis), then loop to quieter south-shore bays before returning.

Many itineraries combine USVI + BVI (check current customs procedures and timing for cross-border hops).

Yacht Charter Saint Martin (St. Martin / Sint Maarten): Culture Hub & Day-Sail Spokes

Saint Martin blends French and Dutch influences, lively dining scenes, and strong yachting services.

• Marigot (French side) for markets and bakeries; Simpson Bay (Dutch side) for chandleries and nightlife.

• Day-sail spokes to the surrounding island group—Anguilla (calm beaches), St. Barts (boutiques, dining), and Saba (diving)—each with unique characteristics and appeal.

• Channels can be brisk in a strong trade wind—time your crossings and reef early when needed.

This base suits crews seeking a comprehensive yachting experience from Saint Martin, with a mix of short sails, multiple countries, and shore-side variety.

Yacht Charter Martinique (Windward Islands Gateway): French Flair & Open-Water Legs

Martinique is a practical hub for Windward itineraries, with European-standard marinas (e.g., Le Marin), French-Caribbean cuisine, and scenic west-coast anchorages. Most charter yachts relocate to the Caribbean during the peak season, increasing availability for travelers.

• Typical routes: Martinique ↔ St. Lucia (Marigot Bay, Soufrière/Pitons) or south into St. Vincent & the Grenadines (Bequia, Mayreau, Tobago Cays).

• Both standard and luxury yacht charters are available from Martinique, offering a range of high-end amenities and personalized services.

• Expect livelier channels and swell between islands than in the Virgin Islands—rewarding sailing for crews comfortable with longer legs.

Affordable Yacht Charter Caribbean: Keeping Costs Predictable

• Seasonality. Shoulder months (late spring/early winter) often mean lower rates and easier mooring availability than peak holidays.

• Boat type. Older monohulls are generally the most budget-friendly; catamarans cost more but can reduce per-person pricing for larger groups.

• Base fees vs. extras. Clarify what the charter fee includes (cleaning, linens, water toys) and what is extra (fuel, marinas/moorings, park fees, skipper/chef gratuities).

• Provisioning. Pre-order basics at the base or shop locally; many crews mix a few dinners ashore with simple meals on board to manage spend.

Sailing in the Caribbean: Activities & Shore Time

• Scuba diving & snorkelling. Coral gardens and wrecks abound (e.g., BVIs’ RMS Rhone, Grenada’s underwater sculpture park, Grenadines’ turtle-rich shallows).

• Hikes & viewpoints. From Antigua’s Shirley Heights to St. Lucia’s Pitons and coastal forts scattered throughout the islands.

• Beach bars & markets. Casual food, local music, and fresh produce add variety between sailing days.

After a day of adventure, unwind by witnessing sensational sunsets over the Caribbean and soaking in the breathtaking views of turquoise water that make this region truly unforgettable.

Bring reef-safe sunscreen, respect buoyed swimming areas, and follow local guidance to protect coral reefs and seagrass.

Provisioning and Supplies: Stocking Up for Your Charter

A successful Caribbean yacht charter starts with thoughtful provisioning. Before you set sail, it’s essential to ensure your yacht is fully stocked with everything you’ll need for a comfortable and carefree journey. This means planning ahead for food, beverages, toiletries, and any special items that will make your caribbean sailing vacation truly enjoyable.

Your charter broker is a valuable resource in this process, helping you create a provisioning list tailored to your tastes, dietary needs, and the length of your sailing vacation. Many caribbean yacht charter companies offer convenient provisioning services, so you can arrive to a yacht already loaded with fresh produce, snacks, and your favorite drinks. This allows you to maximize your time exploring the islands, swimming in turquoise waters, and relaxing on deck, rather than making last-minute trips to shore.

Whether you prefer to cook onboard or sample local cuisine at island restaurants, a well-provisioned caribbean yacht ensures you have the flexibility to enjoy your charter your way. With the right supplies on hand, you can focus on the adventure, the scenery, and the unforgettable moments that make a caribbean yacht charter so special.

Charter Logistics: Permits, Formalities & Safety

• Cruising permits & check-ins. Some islands require cruising permits or marine-park fees; inter-island routes may involve customs/immigration. Carry passports and boat papers, and plan your port of entry/exit days.

• Moorings & anchoring. Use secluded anchorages with sand patches where permitted; pick up park moorings when available.

• Weather. Review forecasts each morning and set conservative departure times in peak trade-wind periods.

• Insurance & deposits. Expect a refundable security deposit or damage waiver on bareboats; crewed yachts outline inclusions in the contract. Many charter agreements follow standardized templates provided by the Charter Yacht Brokers Association to ensure professionalism and clarity.

• Safety. Confirm lifejackets, VHF, flares, and dinghy/oars; brief the crew on MOB procedures and night-time deck policy.

Other Charter Destinations to Consider

• Antigua & Barbuda (Leewards). Many anchorages, historic Falmouth Harbour and English Harbour, and good windward/leeward options.

• St. Vincent & the Grenadines (Windwards). Classic island hopping and protected reefs in the Tobago Cays; better for crews happy with channel crossings.

• Grenada. “Spice Island” base with protected southern bays, day sails to Carriacou/PSV, and accessible diving/snorkelling.

• Bahamas (Abacos & Exumas). Shallow, crystal clear waters, sandbars, and line-of-sight routes; cats and shallow-draft monohulls excel here.

• St. Martin hub to Anguilla/St. Barts/Saba. Short spokes for varied culture, dining, and diving.

Charter Boat Caribbean: Choosing the Right Setup

• Sailboat charter Caribbean (monohull). Engaging helm, lower costs, traditional sailing feel.

• Catamaran charter Caribbean. Stability, space, shallow-draft access, popular for families/groups.

• Motor yacht. Faster repositioning and elevated comfort, with higher fuel budgets.

• Private yacht charter Caribbean. Whether bareboat or crewed, match layout (cabins/heads) and equipment (solar, watermaker, A/C) to group size and itinerary.

Book Your Caribbean Yacht Rental with Boataround

When you’re ready to charter in the Caribbean, compare verified listings, live availability, and transparent pricing on Boataround. Filter by destination (BVI, USVI, Saint Martin, Martinique), boat type (catamaran charter Caribbean, monohull, motor yacht), and crewed vs. bareboat. You can review equipment, read guest feedback, and tailor your trip—whether you’re planning an affordable yacht charter Caribbean, an all-inclusive yacht charters Caribbean experience, or a special-occasion getaway.

Start here: Caribbean yacht charters on Boataround — set your dates, choose your yacht, and set sail.

Set Sail for Your Caribbean Adventure

A caribbean yacht charter is the ultimate way to experience the region’s natural beauty, vibrant culture, and endless possibilities for adventure. From the secluded white sand beaches of the Virgin Islands to the colorful coral reefs of the British Virgin Islands, every day brings new discoveries and unforgettable moments.

With the guidance of an experienced charter broker, you can craft a sailing vacation that’s perfectly tailored to your dreams—whether you crave relaxation, excitement, or a bit of both. Set sail on a caribbean yacht and immerse yourself in the turquoise waters, explore hidden islands, and savor the freedom that only a yacht charter can offer.

Do you want more information? Check our Sailing in the Caribbean guide.

Yacht rental in Caribbean

Charter a yacht and explore Caribbean! Prices start from 174 € per day. Choose from the largest selection of catamarans, sailing yachts, power catamarans, motor boats and motor yachts.

Boats are available in many of the country's most popular regions, including Caribbean Islands, BVI, British Virgin Islands, Martinique, Saint Martin, Saint Thomas, U.S. Virgin Islands and USVI.