New to chartering? Start with our complete guide to how to charter a boat in the Caribbean — bareboat vs. crewed, costs, and what to expect.
Choosing the right Caribbean charter itinerary depends on your experience level, preferred sailing conditions, and the time of year. Whether you’re planning your first bareboat charter in the British Virgin Islands or an adventurous island-hopping cruise through the Grenadines, this guide helps you find the route that best matches your sailing style.
Planning a Caribbean charter? You’re in the right place. ALL AT SEA has covered Caribbean sailing since 1993, and this is our complete library of day-by-day charter itineraries — real routes through the islands we sail, write about, and call home. Each guide breaks a destination down leg by leg: where to start, the anchorages and mooring fields worth your night, the distances between them, and where to clear customs. Whether you’re after the line-of-sight ease of the BVI or the turquoise solitude of the Grenadines, start with the region that fits your experience and the season, then follow the route ashore.
How to Choose Your Caribbean Charter Route
Not sure where to point the bow? A few ways to narrow it down:
- By experience. First bareboat? The BVI and the Grenadines offer short, sheltered, line-of-sight hops with plentiful moorings. Confident crews after open-water passages will prefer Antigua, Martinique, or the St. Maarten–St. Barths–Anguilla circuit.
- By conditions. The Grenadines, BVI, and Abacos are protected and forgiving; the outer islands and inter-island legs (Antigua–Barbuda, St. Lucia–Grenada) mean bigger trade-wind sailing.
- By region. The Eastern Caribbean clusters tight island groups; the Southern Caribbean (St. Lucia down to Grenada) trades a little more distance for fewer crowds; the Western Caribbean and Bahamas mean shallow, reef-fringed cruising.
- By season. Peak season is December–April for steady trades and dry weather; hurricane season (June–November) narrows the field — see below.
Caribbean Sailing Itineraries by Region
(Sections map 1:1 onto the regions taxonomy — Eastern / Southern / Western — for clean cross-linking with the region hubs.)
Eastern Caribbean
- British Virgin Islands (7 days) — The Caribbean’s charter capital: line-of-sight hops from The Baths to Jost Van Dyke, with a run out to Anegada. Easy mooring-ball sailing, ideal for a first bareboat.
- US Virgin Islands (7 days) — St. Thomas and St. John’s protected bays — Christmas Cove, Caneel Bay, Cruz Bay — a short, sheltered week with an optional hop into the BVI.
- Puerto Rico & the Spanish Virgin Islands (7 days) — Fajardo out to Culebra and Vieques: Flamenco Beach, bioluminescent bays, and quiet anchorages off the usual charter track.
- St. Maarten, St. Barths & Anguilla (7 days) — Three flags in a week: Simpson Bay, glamorous Gustavia, and Anguilla’s empty beaches. A reach-heavy circuit for confident crews.
- Antigua & Barbuda (7 days) — 365 beaches, English Harbour and Nelson’s Dockyard, plus an offshore leg to Barbuda’s pink sands. Open-water sailing with big trades.
- Martinique (7 days) — French flair from Fort-de-France to Sainte-Anne: Les Anses-d’Arlet, St. Pierre beneath Mont Pelée, and some of the arc’s best provisioning.
Southern Caribbean
- St. Lucia (7 days) — Rodney Bay to the Pitons: Marigot Bay, Soufrière’s volcanic backdrop, and Sulphur Springs ashore. Short hops, dramatic scenery.
- St. Vincent & the Grenadines (7 days) — The classic Grenadines loop: Bequia, Mustique, the Tobago Cays, and Mayreau. Turquoise, turtle-filled, and sheltered.
- St. Vincent to Grenada (10 days) — The full Grenadines run, one-way via the Tobago Cays, Union Island, and Carriacou, with the international clearance handled day by day.
- Grenada (7 days) — Spice-island sailing from Prickly Bay to Carriacou and Sandy Island, past the underwater sculpture park. Calm southern-Caribbean conditions.
Western Caribbean
- The Abacos, Bahamas (7 days) — Hope Town’s candy-striped lighthouse, Green Turtle Cay, and Nipper’s on Great Guana — shallow, gin-clear Sea of Abaco cruising.
- Belize (7 days) — Bareboat behind the world’s second-largest barrier reef: the cayes, Turneffe Atoll, and world-class diving and snorkeling.
- Cayman Islands (7 days) — North Sound, Stingray City, and Rum Point — a relaxed, reef-fringed week in famously clear water.
Best Time to Sail the Caribbean
The Caribbean charter season runs December through April, when the northeast trade winds blow a steady 15–20 knots and rainfall is lowest — prime conditions across every region here. May and late November are quieter shoulder months with good sailing and lower rates. Hurricane season officially spans June 1 to November 30; charters still run, but storms are most likely August–October, and the southernmost islands (Grenada, Trinidad, the ABCs) sit largely below the traditional hurricane belt if you want to sail through summer. Always check the forecast and your charter company’s weather policy before you book.
Bareboat vs. Crewed Charter
A bareboat charter puts you in command — you skipper, you provision, you choose each anchorage. It’s the most affordable and flexible way to sail the Caribbean, and most companies require a sailing résumé or certification (ASA, RYA, or IYT) plus a checkout sail. A crewed charter comes with a captain — and often a chef — handling navigation, cooking, and local know-how while you relax, ideal for first-timers, larger groups, or anyone who’d rather not stand watch. Most routes here work either way; the itineraries assume you’re at the helm, but a captain will happily follow the same legs.
Frequently Asked Questions About Caribbean Charter Itineraries
What is the best Caribbean charter destination for beginners?
The British Virgin Islands and St. Vincent & the Grenadines are often considered the best destinations for first-time bareboat charterers. Both offer:
- Short sailing distances
- Line-of-sight navigation
- Protected anchorages
- Plenty of moorings and services
Which Caribbean islands are best for experienced sailors?
More experienced crews often enjoy:
- Antigua & Barbuda
- St. Martin, St. Barths & Anguilla
- Martinique
- Belize
- The Cayman Islands
These destinations feature longer passages, more open-water sailing, and fewer sheltered anchorages.
How long should a Caribbean charter be?
Most Caribbean charters last between seven and ten days. A week is enough to explore a single island group, while 10 to 14 days allows for more ambitious itineraries and multi-country routes.
What is the most popular charter destination in the Caribbean?
British Virgin Islands remains the Caribbean’s most popular charter destination thanks to its protected waters, easy navigation, and abundance of anchorages.
When is the best time to sail in the Caribbean?
The prime sailing season runs from December through April when trade winds are steady and rainfall is generally lower. May and November offer good shoulder-season opportunities with fewer crowds and often lower charter rates.
Can you charter a yacht during hurricane season?
Yes, although extra caution is required. Hurricane season officially runs from June through November, with the highest storm activity typically occurring between August and October.
Southern destinations such as:
- Grenada
- Trinidad
- Aruba
- Bonaire
- Curaçao
often experience lower hurricane risk than islands farther north.
Do you need a sailing license to bareboat charter in the Caribbean?
Requirements vary by charter company and destination. Most operators require either:
- A sailing résumé showing sufficient experience
- ASA certification
- RYA certification
- IYT certification
Many companies also conduct a checkout sail before departure.
What is the difference between a bareboat and crewed charter?
A bareboat charter places you in charge of the yacht, navigation, and itinerary.
A crewed charter includes a professional captain and often a chef who handle sailing, navigation, meals, and local logistics.
Which Caribbean charter destination has the clearest water?
Several destinations are known for exceptional visibility:
- The Bahamas
- The Exumas
- Belize
- The Cayman Islands
- Tobago Cays in St. Vincent & the Grenadines
Which Caribbean charter destination offers the most variety?
For diversity of islands, cultures, and experiences, many sailors favor:
- St. Martin, St. Barths & Anguilla
- Puerto Rico and the Spanish Virgin Islands
- St. Vincent & the Grenadines
Each combines multiple islands with distinctly different personalities.