British and US Virgin Islands
Consider the Virgin Islands when you want protected anchorages, compact island-hopping and a choice of embarkation points around Tortola or St Thomas. Cross-border routes require the right clearance plan.
Private crewed yacht charter
Caribbean Yacht Charter
Compare crewed yachts for the Virgin Islands, St Barts, Antigua, the Bahamas and the wider Caribbean, then request live availability for your dates and route.
Photo: VentureSail Holidays
Principal seasonNovember to April
Cruising stylesMotor, sailing and catamaran
Planning focusYacht, route and dates together
Explore the fleet
Find a Caribbean charter yacht
Start with the whole Caribbean and Bahamas region, or narrow the search to a specific island group. Results use published cruising areas and rates. Live position and availability are confirmed separately.
3,500+ Crewed Luxury Yachts for Charter
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A guide by an industry leaderComplimentary planning guide
Plan the Caribbean before you choose the yacht
Download the MY OCEAN guide to comparing the Virgin Islands, Leewards, Bahamas and Windwards, with practical sections on seasonality, yacht fit, embarkation and charter costs.
- ✓Cruising-ground comparison
- ✓US and BVI travel planning
- ✓Yacht-selection checklist
- ✓Budget and broker-brief template
Choose your Caribbean
Match the island group to the way you want to travel
St Barts, St Martin and Antigua
Choose the Leewards for a balance of beaches, dining and more varied passages. Antigua and St Martin can be practical gateways, while St Barts is often a focal point for time ashore.
The Bahamas
The Bahamas suits guests drawn to cays, clear water and unhurried island-hopping. Yacht draft matters, so the vessel and route should be considered together.
Explore the BahamasWindward Islands
St Lucia, St Vincent and the Grenadines, and Grenada suit a more passage-led itinerary with dramatic landscapes. A longer charter can reduce the need to rush between stops.
When to go
Plan around the region, not a single forecast
The principal Caribbean charter season generally runs from November to April. The region is broad, so conditions and route logic still vary between the Bahamas, the Virgin Islands, the Leewards and the Windwards. Industry guidance supports treating the yacht and island group as one planning decision. [3]
NOAA defines the Atlantic hurricane season as running from 1 June to 30 November and identifies the climatological peak as 10 September. That does not predict the conditions for a specific voyage. Dates near the official season require careful review of yacht positioning, forecasts, insurance and cancellation terms. [1]
How planning works
Turn a broad region into a workable charter plan
MY OCEAN can help clarify your requirements, request live availability, compare suitable yachts and coordinate questions with the yacht’s representative.
- 01
Choose the island group
Start with flight access, preferred pace and the balance between time at anchor and time ashore.
- 02
Match the yacht
Compare guest layout, draft, range, tender access, stabilisers and the equipment that matters to your group.
- 03
Check live position
Ask for current availability, delivery fees, operating area, taxes and any constraints on the intended route.
- 04
Confirm the agreement
Review the charter fee, APA, cancellation terms, insurance expectations and local clearance requirements.
Caribbean charter FAQ
Questions to settle before you choose a yacht
Plan the next step
Start your Caribbean charter search
Share your dates, guest count, preferred island group and weekly budget so the available options can be checked against your plan.