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Caribbean sailing destination

Catamaran Charter Caribbean

Hurricane season June-November. Trade winds reliable December-April. Peak season Christmas-March.

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At a Glance

Best Months Dec, Jan, Feb, Mar, Apr
Shoulder Months Nov, May
Off Season Jun, Jul, Aug, Sep, Oct
Wind (Winter / Summer) 18 / 14 knots
Hurricane Risk Aug, Sep, Oct
Currency / Language USD (most islands) / English (most), Spanish, French, Dutch
Sailing Difficulty easy to moderate
Recommended Level beginner friendly
7-Day Charter Price Range $3,500 – $35,000+

Charter Destinations in Caribbean

British Virgin Islands

Peak: Dec, Jan, Feb, Mar, Apr · From $3,500/wk · beginner friendly

US Virgin Islands

Peak: Dec, Jan, Feb, Mar, Apr · From $3,500/wk · beginner friendly

Bahamas

Peak: Dec, Jan, Feb, Mar, Apr · From $4,000/wk · intermediate

St Martin / St Maarten

Peak: Dec, Jan, Feb, Mar, Apr · From $3,800/wk · beginner friendly

Antigua

Peak: Dec, Jan, Feb, Mar, Apr · From $4,200/wk · intermediate

Saint Lucia

Peak: Dec, Jan, Feb, Mar, Apr · From $3,800/wk · intermediate

Grenada & the Grenadines

Peak: Dec, Jan, Feb, Mar, Apr · From $4,000/wk · intermediate

Saint Barthélemy

Peak: Dec, Jan, Feb, Mar, Apr · From $8,000/wk · intermediate

Anguilla

Peak: Dec, Jan, Feb, Mar, Apr · From $4,500/wk · beginner friendly

Martinique

Peak: Dec, Jan, Feb, Mar, Apr · From $3,800/wk · intermediate

Recommended Catamarans

Lagoon
Lagoon 50

4 cabins · 8 guests · 50 ft
Lagoon
Lagoon 46

4 cabins · 8 guests · 46 ft
Bali
Bali 4.6

4 cabins · 8 guests · 48 ft
Fountaine Pajot
Astrea 51

4 cabins · 8 guests · 51 ft

Frequently Asked Questions

When is the best time to charter in Caribbean? ▾
Peak season in Caribbean is Dec, Jan, Feb, Mar, Apr. During these months you'll get the most reliable weather and the most charter fleet options, but also the highest prices and most crowds. Shoulder months (Nov, May) are often the sweet spot — good weather, fewer crowds, lower prices. Avoid Jun, Jul, Aug, Sep, Oct unless you specifically want low-season rates.
How much does a catamaran charter cost in Caribbean? ▾
A 7-day catamaran charter in Caribbean typically runs from $3,500 (low season, smaller boat) to $35,000+ (high season, large crewed catamaran). A mid-range 45-50ft catamaran in shoulder season averages around $9,000/week. Prices exclude fuel, provisioning, mooring fees, and gratuity.
Do I need a visa for Caribbean? ▾
Visa requirements for Caribbean vary by passport: US: varies by island; EU: visa free most; CA: visa free most; CN: visa required most. Most Western passport holders can enter visa-free or with visa-on-arrival. Check with your country's travel advisory before booking.
Is Caribbean good for first-time charterers? ▾
Yes — Caribbean is one of the best places in the world for a first catamaran charter. The sailing is easy to moderate, anchorages are well-protected, and charter fleets are abundant with crew training included. Many operators offer a checkout sail before departure.
How many days do I need in Caribbean? ▾
A 7-day charter is the most popular booking length and lets you see the highlights. With 10–14 days you can slow down, weather-proof your itinerary, and reach more remote anchorages. 5 days is doable but rushed. Anything less than 5 days usually doesn't justify the travel cost for most international visitors.
What are the must-visit places in Caribbean? ▾
Ask your charter captain or broker for the local favorites — every destination has anchorages the guidebooks don't cover.
Is Caribbean safe for families with children? ▾
Yes — Caribbean is one of the most family-friendly sailing destinations in the world. Sheltered anchorages, calm seas, and warm water make it ideal for kids. Most charter operators provide child-size life jackets, and many allow infants on board. Bareboat with children: plan shorter passages (2-4 hours), pick beaches with easy swim access.
What sailing experience do I need for Caribbean? ▾
For bareboat charter in Caribbean, most operators accept sailors with basic keelboat experience plus an ICC (International Certificate of Competence). You'll typically do a 2-3 hour checkout sail at the base before departure. If you're new to sailing, opt for crewed charter — captain and hostess are affordable insurance for a great vacation.

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