At the 50,000 euro per week level, the Leeward Islands chain offers private charter access through a carefully selected group of crewed vessels that make the Caribbean island-hopping experience achievable without the operating costs of a larger yacht. These yachts in the 30 to 35 metre range carry a professional captain and two to three crew who know the passages between the islands and the best anchorages for each season.
The Leeward Islands at this price point reward an itinerary focused on the central islands: St Barts, St Kitts and Nevis, with the passages covered comfortably at a relaxed cruising speed. Gustavia in St Barts provides the social and provisioning hub, with the famous beach restaurants at Shell Beach and the weekly boat parade offering a festive atmosphere. Nevis Pinney Beach makes an excellent overnight anchorage with the Four Seasons resort providing dinner ashore as an option.
The advance provisioning allowance at this price adds approximately 15,000 euros, covering fuel for inter-island passages, marina fees at the key stops and daily provisioning from local markets. The crew handles all logistics, leaving guests free to focus entirely on the islands and the water.
Booking two to four months ahead is sufficient for this price level outside of the Christmas and New Year peak, when six months ahead is more prudent. The best vessels at this level are popular and fill their peak calendars early.
