Tag: caribbean sailing

Crewed catamaran crossing between the Windward and Leeward Islands

Destinations

Windward vs. Leeward Islands: Which Chain Should You Sail?

Windward vs leeward islands: which islands are in each chain, why the names look backwards, and why Aruba, some 550 miles away, belongs to neither of them.
Aft deck and cockpit of the crewed catamaran Ohana, set for lunch under shade in the Virgin Islands

Destinations

BVI vs USVI Catamaran Charter 2026: Which Is Right for You?

174 of 277 Virgin Islands crewed catamarans work both territories, and the median week is about $32,000 whichever flag you pick. The real BVI vs USVI difference is the passport rule.
charter_costs

Charter Guides

How to Plan a Caribbean Yacht Charter: A Broker’s Complete Guide

How to plan a yacht charter in the Caribbean: $20K-$100K/week costs, destination picks, booking timelines, and what's actually included.
A sailing vessel moves through bright turquoise Caribbean sea water under a clear blue sky

Charter Guides

BVI Crewed Yacht Charter: Complete Insider Guide 2026

A BVI crewed yacht charter lists a $32,000 median week for 8 guests, all-inclusive. See what the rate covers, the size bands, and the one line that never does.
A white sailing catamaran gliding across clear turquoise Caribbean water under a bright blue sky

Destinations

Ultimate Guide to Caribbean Crewed Charter Destinations

The Caribbean's top crewed charter destinations compared side-by-side, with pricing, best-fit traveler profiles, and insider picks for first-timers and repeat guests.
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