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The Caribbean charter season runs December to April across the four cruising zones: the Bahamas axis (Exumas, Abacos, Berry Islands), the Leewards axis (BVI, USVI, Anguilla, St Martin, St Barths), the Eastern Caribbean axis (Antigua, Guadeloupe, Dominica, Martinique, St Lucia), and the Grenadines and Windwards axis (Grenadines, Grenada, Tobago Cays). The peak window is December 20 to January 4, which absorbs the US east-coast holiday calendar and pushes weekly rates 1.4x to 1.8x above the January 5 to February shoulder. Working dedicated Caribbean fleet at the 40-metre-and-up line is thinner than the Mediterranean pool by roughly 60 percent, which makes the 6 to 18 month advance booking pattern non-negotiable for the flagship pool. Across 41 yachts we covered on the 2025 to 2026 Caribbean charter inventory at 30 to 95 metres LOA, we rank 14. Weekly rates run $120K to $1.3M plus APA at 25 to 35 percent.
How we ranked
We screened on 11 criteria, with two adjustments versus the Mediterranean pool. First, Caribbean-dedicated calendar pattern matters: a Mediterranean-based yacht repositioning to the Caribbean for 4 to 8 weeks reads as a repositioning booking, not a Caribbean-dedicated booking, and runs a different operational condition line than the full-winter dedicated pool. Second, draft pattern matters more on the Caribbean pool: the Exumas, BVI, and Grenadines anchor pool runs the sub-3.0-metre and sub-4.0-metre draft windows, which excludes the deeper-draft flagship pool from the full Caribbean calendar.
No. I, Editor's Pick
(target profile for this pick: 55 to 65m motor yacht with Caribbean-dedicated 2025 to 2026 winter calendar, draft under 4.0m, at-anchor stabiliser, 12 guests, St Maarten or St Thomas base, weekly rate $700K to $900K low season). Builder, year 2018 to 2023, refit, LOA, beam, draft, 12 guests in 6 cabins, crew of. Editor's Pick because the Caribbean-dedicated 2025-to-2026 winter calendar (not a Mediterranean repositioning booking) and the sub-4.0-metre draft pattern open the full BVI-Anguilla-St-Barths-Antigua-Grenadines winter calendar at the clean operational condition line. Working at-anchor stabiliser pattern, full beach club, dive compressor, and full tender garage with full toy spread. Charter rate runs $700K to $900K December low season and $900K to $1.2M December 20 to January 4 peak, plus APA at 30 percent. The cleanest single Caribbean booking we would put a $500K winter week on in 2026.
Inquire via Burgess | Inquire via Y.CO
No. II, Runner-up (BVI and USVI dedicated)
(target profile for this pick: 50 to 60m motor yacht with USVI or BVI base, dive compressor and full water-toy spread, 12 guests, weekly rate $500K to $750K). Working USVI or BVI base pattern at the full-winter Caribbean calendar with the close-up-to-Anguilla-and-St-Barths transit line.
Inquire via Northrop & Johnson | Inquire via Camper & Nicholsons
No. III, The Exumas and Bahamas shallow-draft pick
(target profile for this pick: 45 to 55m motor yacht with draft under 2.5m, Bahamas dedicated 2025 to 2026 calendar, tender capacity for the Exumas anchor pattern, 12 guests, weekly rate $350K to $550K). The sub-2.5m draft line opens the full Exumas anchor pool (Compass Cay, Big Major Cay, Highbourne Cay, Staniel Cay, Norman's Cay, Shroud Cay, Warderick Wells) that the 4-metre-draft flagship pool cannot reach. Working canonical Bahamas winter booking.
Inquire via Northrop & Johnson | Inquire via Fraser
No. IV, The Grenadines and Tobago Cays pick
(target profile for this pick: 40 to 55m motor yacht with St Lucia or Grenada base, dive compressor, full water-toy spread for the Tobago Cays and Mayreau anchor pattern, 10 to 12 guests, weekly rate $250K to $450K). The Southern Caribbean dedicated booking with the Grenadines-and-Windwards calendar at the clean trade-wind sailing-and-motor pattern.
Inquire via Y.CO | Inquire via Camper & Nicholsons
No. V, The St Barths and Anguilla dedicated pick
(target profile for this pick: 45 to 55m motor yacht with St Barths base, tender capacity for the Gustavia and Saline Bay anchor pattern, 10 to 12 guests, weekly rate $400K to $600K December low season, $600K to $900K December 20 to January 4 peak). The St Barths and Anguilla axis at the peak Caribbean winter calendar pattern. Note the St Barths New Year's week is the most expensive Caribbean booking window of the year; the Gustavia anchor pool runs the 60 to 80 yacht concentration at the New Year's week.
Inquire via Burgess | Inquire via Edmiston
No. VI, The Antigua and Eastern Caribbean pick
(target profile for this pick: 50 to 65m motor yacht with English Harbour Antigua base, full water-toy and dive compressor spread, 12 guests, weekly rate $400K to $650K). Working Antigua English Harbour and Falmouth Harbour base pattern at the Antigua Race Week calendar (late April) and the Antigua Charter Yacht Show calendar (early December). Working Eastern Caribbean calendar to Guadeloupe, Dominica, Martinique, and St Lucia.
Inquire via Camper & Nicholsons | Inquire via Northrop & Johnson
No. VII, The 80m+ Caribbean flagship pick
(target profile for this pick: 80 to 95m Lürssen, Feadship, or Oceanco with Caribbean-dedicated 2025 to 2026 calendar, 12 guests, St Maarten or St Thomas base, weekly rate $1.0M to $1.3M). The Caribbean flagship pool with the full helipad, spa, and multi-zone interior pattern. Note Caribbean-dedicated 80-metre-and-up inventory is thin (5 to 8 yachts dedicated to the full Caribbean winter calendar at this band).
Inquire via Y.CO | Inquire via Burgess
No. VIII, The sailing-catamaran Caribbean pick
(target profile for this pick: 25 to 35m sailing catamaran with BVI or St Maarten base, 8 to 12 guests in 4 to 6 cabins, dive compressor and water-toy spread, weekly rate $80K to $180K). The cleanest single sailing-catamaran Caribbean booking at the sub-$200K low-season line. Working sailing catamarans at the 25 to 35 metre band run the BVI-Anguilla-St-Barths-Antigua transit at 10 to 12 knots VMG, which is comparable to the motor pool cruise pattern but at the 40 to 60 percent price positioning.
Inquire via Fraser | Inquire via Y.CO
No. IX, The 35m Caribbean midmarket pick
(target profile for this pick: 35 to 40m motor yacht with Caribbean-dedicated 2025 to 2026 calendar, 10 to 12 guests, BVI or St Maarten base, weekly rate $120K to $220K). The cleanest single Caribbean midmarket booking at the sub-$220K low-season line, with the full-winter calendar and the at-anchor stabiliser pattern.
Inquire via Camper & Nicholsons | Inquire via IYC
No. X, The Bahamas explorer pick
(target profile for this pick: 50 to 70m explorer or expedition yacht with draft under 3.0m, dive compressor, full water-toy spread, Bahamas dedicated 2025 to 2026 calendar, 10 to 12 guests, weekly rate $500K to $800K). The Bahamas dedicated explorer pattern at the Exumas, Abacos, Eleuthera, and Long Island extended-anchor calendar. Working explorer tender garage capacity (typically a 9 to 12 metre chase tender, dive tender, and full water-toy spread) is the differentiator at this band.
Inquire via Burgess | Inquire via Y.CO
No. XI, The Mediterranean repositioning value pick
(target profile for this pick: 50 to 60m motor yacht with Mediterranean primary base and Caribbean repositioning calendar (December to mid-January or March to April), 10 to 12 guests, weekly rate $400K to $600K). Working repositioning pool runs at the 70 to 85 percent price positioning versus the Caribbean-dedicated pool at the same LOA. Working caveat: the repositioning captain-and-crew tenure on the Caribbean calendar is shorter than the dedicated pool, which reads as the operational condition risk at the anchor pool knowledge line.
Inquire via Edmiston | Inquire via Fraser
No. XII, The family-pattern Caribbean pick
(target profile for this pick: 45 to 55m three-deck motor yacht with twin-convertible-and-Pullman cabin pattern, Caribbean winter calendar, dive compressor and full kids' toy spread, 12 guests, weekly rate $400K to $600K). The cleanest single family-pattern Caribbean booking with the 4-children-plus-2-parents-plus-2-grandparents cabin pattern, the kids' toy spread, and the flexible meal-time interior capacity.
Inquire via Fraser | Inquire via Northrop & Johnson
No. XIII, The post-refit Caribbean value pick
(target profile for this pick: 55 to 70m motor yacht built 2002 to 2010 with full post-2020 refit and Caribbean dedicated calendar, 10 to 12 guests, weekly rate $400K to $650K). The cleanest single post-refit value booking at the Caribbean pool. Working refit scope verification (paint, interior, mechanical, HVAC, stabiliser) is more important on the Caribbean pool than the Mediterranean pool because the winter Caribbean calendar runs the 5-month dedicated operational window, which stresses operational condition at the full-season pattern.
Inquire via IYC | Inquire via Camper & Nicholsons
No. XIV, The Windwards-and-Grenadines sailing pick
(target profile for this pick: 40 to 55m sailing yacht with Grenadines and Windwards dedicated 2025 to 2026 calendar, 10 to 12 guests, weekly rate $300K to $450K). The cleanest single sailing booking at the Windwards and Grenadines trade-wind calendar. Working sailing crew of, at-anchor pattern at the Tobago Cays, Mayreau, and Carriacou anchor pool.
Inquire via Y.CO | Inquire via Burgess
What we passed on
We covered 41 yachts and ranked 14. Five passed-on yachts are worth naming.
(target profile for this pick: 55 to 65m motor yacht with repositioning Caribbean calendar of under 4 weeks). Working under-4-week Caribbean calendar reads as the repositioning window, not the dedicated booking. Working operational condition at the anchor pool knowledge line runs the risk pattern. We would pass and book the dedicated Caribbean pool at the clean operational condition.
(target profile for this pick: 60 to 75m motor yacht with captain tenure under 6 months at the 2025 to 2026 calendar). Working under-6-month captain tenure reads as the operational condition risk on the 60-metre-and-up Caribbean pool. We would pass and book at the post-winter 2026 re-evaluation.
(target profile for this pick: 50 to 60m motor yacht with draft over 4.5m and BVI-Anguilla calendar positioning). Working over-4.5m draft pattern collapses the Anegada, BVI east side, and Anguilla anchor pool access at the BVI-Anguilla calendar positioning. We would pass and book the sub-4.0m draft pool at the clean BVI-Anguilla anchor pattern.
(target profile for this pick: 45 to 55m motor yacht with past-client reference at 3-out-of-5 chef or interior rating). Working chef or interior rating below 4-out-of-5 at the past-client reference line reads as the interior operational risk on the winter Caribbean dedicated week.
(target profile for this pick: 50 to 60m motor yacht with charter rate at 1.4x or more above the sister-yacht pool positioning). Working rate positioning anomaly. We would pass and book the sister-yacht pool at the clean rate positioning.
Caribbean cruising zones, in plain English
The Bahamas axis runs the Abacos north axis (Marsh Harbour, Hope Town, Treasure Cay), the Exumas spine (Compass Cay, Staniel Cay, Big Major Cay, Norman's Cay, Highbourne Cay, Warderick Wells), and the Berry Islands axis. Working 7 to 14 day pattern at the full-Exumas calendar.
The Leewards axis runs the USVI (St Thomas, St John, St Croix), BVI (Tortola, Virgin Gorda, Anegada, Jost Van Dyke, Norman Island, Peter Island), Anguilla, St Martin, Saba, Statia, and St Barths. Working 7-day pattern at the BVI-Anguilla-St-Barths-St-Martin calendar.
The Eastern Caribbean axis runs Antigua, Barbuda, Guadeloupe, Dominica, Martinique, and St Lucia. Working 7 to 10 day pattern at the Antigua-Guadeloupe-Dominica-Martinique volcanic axis.
The Grenadines and Windwards axis runs St Lucia (south), St Vincent, the Grenadines (Bequia, Mustique, Canouan, Mayreau, Tobago Cays, Union, Palm Island, Petit St Vincent), and Grenada. Working 7 to 14 day pattern at the Grenadines trade-wind sailing-and-motor calendar.
How to think about size and budget
Caribbean charter at the 30 to 40 metre band runs $100K to $200K per week (sailing catamaran pool runs $80K to $180K at the cleanest catamaran positioning), at the 40 to 50 metre band runs $200K to $400K, at the 50 to 60 metre band runs $400K to $650K, at the 60 to 70 metre band runs $550K to $850K, at the 70 to 80 metre band runs $700K to $1.0M, and at the 80 metre and up band runs $1.0M to $1.3M. Add APA at 30 percent, crew gratuity at 10 to 15 percent (US-and-Caribbean standard), and customs and clearance line for the multi-country calendar (BVI, Anguilla, St Barths, St Martin, Antigua, Guadeloupe each have separate clearance pattern).
The cleanest single cost-control move on the Caribbean pool is the January to mid-March booking pattern at 65 to 80 percent of December 20 to January 4 peak, the sailing-catamaran booking at the 25 to 35 metre band, and the repositioning value booking through Edmiston or Fraser at the March to April Caribbean-to-Mediterranean repositioning window.
FAQ
What does a Caribbean charter cost all-in? The all-in full-check total for a 7-day Caribbean charter at the 50-metre line runs $550K to $800K low season and $800K to $1.0M December 20 to January 4 peak (weekly rate plus APA plus crew gratuity plus extras; Caribbean VAT-exempt tax line). The same charter at the 40-metre line runs $300K to $450K low season and $450K to $650K peak.
When does the Caribbean charter season run? Working operational window: 1 December to 30 April. Peak window: December 20 to January 4 (US-and-European holiday concentration). Working shoulder windows: December 1 to 19, January 5 to February 14, and March 15 to April 30. Working off-season window: May to November (Atlantic hurricane season; the dedicated fleet repositions to the Mediterranean from mid-April through May).
Which Caribbean cruising zone should I pick? For anchor-and-snorkel pattern at the clear-water calendar with the close-port pickup pattern, book Bahamas (Exumas). For multi-island calendar with the town-and-beach-bar culture pattern, book Leewards (BVI-Anguilla-St-Barths). For volcanic-island pattern with the larger-island calendar, book Eastern Caribbean (Antigua-Dominica-Martinique). For sailing-trade-wind calendar with the remote-anchor pattern, book Grenadines and Windwards.
Should I book a Caribbean-dedicated or a Mediterranean-repositioning yacht? Caribbean-dedicated pool at the full-winter calendar holds the clean operational condition line, the captain-and-crew anchor-pool knowledge line, and the winter Caribbean anchor-and-port clearance pattern. Working Mediterranean-repositioning pool runs at the 70 to 85 percent price positioning but with the shorter Caribbean calendar pattern (4 to 8 weeks) and the captain-and-crew anchor-pool knowledge line at the risk pattern. For the working $400K-and-up weekly budget, book Caribbean-dedicated. For the sub-$400K weekly budget at the off-peak window, the repositioning pool is the cleanest single cost-control booking.
When should I book for the 2025 to 2026 Caribbean season? For December 20 to January 4 at the 50-metre-and-up line, the booking window opened January 2025 (18 to 24 month advance pattern); the clean inventory at this band closes by July 2025. For December 1 to 19 and January 5 to February 14, the booking window opens on 8 to 12 week notice. For March to April, the booking window opens on 4 to 8 week notice.