The Leeward Islands are to the east of Puerto Rico in the Lesser Antilles of the Caribbean. They are some of the most beautiful yachting destinations in the world…offering something for everyone…from pristine, private beaches to chic shops and restaurants. The most notable islands in the Leeward Chain are Anguilla and St Barts - winter favourites for the Jet Set worldwide.

If you are looking for quiet and relaxation, we know where to find it. If you are looking for Caribbean versions of San Tropez packed with activities and other people, the Leewards offer that as well!
More information on the Leeward Islands

Sort through the boats below or use these handy links to quickly find the boats that best fit your needs:
Super and Mega Yachts:   Motor  |  Sail
Motor Boats:   Crewed
Monohull Sailboats:   Bareboat  |  Crewed
Catamarans:   Bareboat  |  Crewed
Yachts for Special Events:   Motor  |  Sail

190 boats found: Currently displaying 0 to 30.           Next 30 >>>

Sort: All Countries and Ports Aland Islands    -- Scandinavia --          Mariehamn Anguilla    -- Leeward Islands --          Anguilla Antigua          English Harbour Argentina    -- Patagonia --          Punta Arenas Australia    -- South Pacific --          Port Douglas         Sydney         Whitsunday Islands Bahamas    -- Bahamas --          Abaco - Marsh Harbor         Freeport         Georgetown         Green Turtle Cay         Marsh Harbour         Nassau         Paradise Island         Stroud Cay Barbados    -- Barbados --          Bridgetown Belgium    -- North Sea --          Antwerp         Ostend Belize    -- Central America --          Belize City         Placencia         San Pedro Bora Bora    -- South Pacific --          Huahine         Raiatea         Taha`a Brazil    -- South America --          Angra dos Reis         Sao Paulo British Virgin Islan    -- Virgin Islands --          Tortola         Virgin Gorda - Spani Canada    -- North America --          Quebec   -- Pacific Northwest --          Prince Rupert, BC         Vancouver         Victoria, BC Caribbean    -- Virgin Islands --          Caribbean Christmas Croatia    -- Adriatic Sea --          Baska Voda         Biograd         Brijuni         Dubrovnik         Hvar         Kastela         Korcula         Kremik-Primosten         Mali Losinj         Marina Dalmacija, Za         Murter         Primosten         Pula         Rovinj         Sibenik         Split         Trogir         Vinisce         Zadar Dominica    -- Leeward Islands --          Dominica Ecuador    -- South Pacific --          Galapagos Fiji          Fiji Finland    -- Scandinavia --          Taalintehdas France    -- Corsica --          Ajaccio         Bonifacio         Calvi         Corsica         Macinaggio         Porto Vecchio         Propriano   -- French Riviera --          Antibes         Bandol         Beaulieu sur Mer         Bormes les Mimosas         Cannes         Eze sur Mer         Golfe Juan         Hyeres les Palmiers         Juan les Pins         Lavandou         Marseille         Nice         Porquerolles         Port Cogolin         Port Grimaud         Saint Jean Cap Ferra         St Mandrier         St Maxime         St Tropez         Toulon Hyeres         Villefranche Germany    -- North Sea --          Hamburg Greece    -- Aegean Sea - Greece --          Athens   -- Cyclades Islands --          Mykonos         Paros   -- Dodecanese Islands --          Kefalos, Kos         Kos         Rhodes   -- Ionian Sea --          Lefkas   -- Northern Ionian Sea --          Corfu   -- Northern Sporades Is --          Skiathos   -- Southern Ionian Sea --          Kalamata Grenada    -- Windward Islands --          St Georges         True Blue Bay Guadeloupe    -- Leeward Islands --          Point a Pitre Holland    -- North Sea --          Amsterdam India    -- Andaman Sea --          Andaman Islands Indonesia    -- Lesser Sunda Islands --          Bali   -- South China Sea --          Anambas Islands Italy    -- Adriatic Sea --          Venice   -- Aeolian Islands --          Aeolian Islands         Lipari   -- Amalfi Coast --          Capri         Gaeta         Marina Grande         Ostia         Salerno         Sant’Agata   -- Gulf of Naples --          Naples         Procida   -- Italian Riviera --          Civitavecchia         Genoa         Porto Ercole         Porto Santo Stefano         Portoferraio, Elba         Portofino         San Remo         Santa Margherita Lig   -- Rome --          Fiumicino         Marina Porto Di Roma   -- Sardinia --          Alghero         Cagliari         Cannigione         Carloforte         Maddalena         Olbia         Palau         Poltu Quatu         Portisco         Porto Cervo         Porto Rotondo         Punt Aldia         Santa Teresa Gallura         Stintino   -- Sicily --          Eolie Island         Marsala         Milazzo         Palermo         Portorosa         Riposto   -- Southern Italy --          Agropoli         Reggio Calabria   -- The Italian Lakes --          Lake Garda   -- Tuscany --          Cala Galera         Elba         Etrusca Marina         Piombino         Scarlino         Viareggio Kiribati    -- South Pacific --          Kiritimati Madagascar    -- Madagascar --          Madagascar         Nosy Be Malaysia    -- Andaman Sea --          Langkawi   -- South China Sea --          Tioman Maldives    -- Maldives --          Male Malta    -- Maltese Islands --          Gzira Martinique    -- Leeward Islands --          Martinique   -- Windward Islands --          Baie du Marin         Bassin Tortue         Le Marin Mauritius    -- Mauritius --          Bain Boeuf         Mauritius         Pointe Jerome         Port Louis         Trou aux Biches Mexico    -- Central America --          Acapulco         Cabo San Lucas         La Paz         Loreta         Manzanillo         Puerto Vallarta Monaco    -- French Riviera --          Monaco Monserrat    -- Leeward Islands --          Monserrat Montenegro    -- Adriatic Sea --          Kotor Mozambique    -- --          Bazaruto         Quirimbas Archipelag Myanmar (Burma)    -- Andaman Sea --          Mergui Archipelago Nevis    -- Leeward Islands --          Nevis New Caledonia    -- South Pacific --          New Caledonia New Zealand          Auckland Norway    -- Scandinavia --          Norwegian Fjords Panama    -- Central America --          Bocos Del Toro         Panama Portugal    -- Algarve --          Faro         Lagos         Portimao   -- Madeira --          Calheta         Funchal Puerto Rico    -- Spanish Virgin Islan --          Culebra         Fajardo         Vieques Samoa    -- South Pacific --          Samoa Seychelles    -- Seychelles --          La Digue         Mahe         Praslin Singapore    -- South China Sea --          Singapore         Singapore Grand Prix Slovenia    -- Adriatic Sea --          Izola South Pacific    -- South Pacific --          South Pacific Spain    -- Barcelona --          Barcelona   -- Canaries --          Gran Canaria         Lanzarote         Tenerife   -- Costa Brava --          L` Escala         L`Estartit         Palamos         Roses         Sant Feliu de Guixol   -- Costa de Valencia --          Valencia   -- Costa del Sol --          Estepona         Marbella         Puerto Banus         Puerto Sotogrande   -- Ibiza --          Ibiza Port         San Antonio   -- Mallorca --          Andratx         Palma         Puerto Pollensa         Puerto Portals   -- Menorca --          Mahon St Barts    -- Leeward Islands --          Gustavia St Kitts          St Kitts St Lucia    -- Windward Islands --          Marigot Bay         Rodney Bay St Thomas    -- Virgin Islands --          St Thomas St Vincent and the G    -- Windward Islands --          Blue Lagoon St. Maarten    -- Leeward Islands --          Simpson Bay Sweden    -- Scandinavia --          Gothenberg         Stockholm Tahiti    -- South Pacific --          Moorea         Tahiti Thailand    -- Andaman Sea --          Koh Lanta         Koh Racha         Koh Rok         Krabi         Phang Nga Bay         Phi Phi Islands         Phuket         Similan Islands         Surin Islands   -- Gulf of Thailand --          Koh Chang         Koh Kut         Koh Phangan         Koh Samet         Koh Samui         Koh Tao         Pattaya         Trat Tonga    -- South Pacific --          Tonga Trinidad    -- Central America --          Trinidad Turkey    -- Aegean Sea - Turkey --          Bodrum         Fethiye         Gocek         Gocek         Marmaris         Turgutreis United Kingdom    -- Solent --          Cowes         Hamble         Lymington         Poole         Portsmouth         Southampton   -- South Coast England --          Brighton   -- Thames --          London         London - St Katharin US Virgin Islands    -- Virgin Islands --          St Thomas USA    -- California --          Marina del Rey         San Diego   -- Cape Cod and Islands --          Falmouth         Hyannis         Marthas Vineyard         Nantucket   -- Connecticut --          Old Saybrook, CT   -- Florida --          Daytona 500         Ft Lauderdale         Miami         Palm Beach         St. Pete Grand Prix         Super Bowl, Tampa   -- Florida Keys --          Islamorada         Key Largo         Key West   -- Hawaii --          Honolulu   -- Maine --          Bar Harbor         Boothbay Harbor         Harpswell         Kennebunk         Portland, Maine   -- Mid Atlantic --          Annapolis         Beaufort         Charleston, SC         Wilmington   -- New York --          Brooklyn NY   -- Pacific Northwest --          Anacortes, WA         Astoria, OR         Juneau, Alaska         Ketchikan, Alaska         Seattle   -- Rhode Island --          Newport Vanuatu    -- South Pacific --          Vanuatu Venezuela    -- Isla Margarita --          Los Roques   -- South America --          Puerto La Cruz Vietnam    -- South China Sea --          Nha Trang Zimbabwe    -- Northern Zimbabwe --          Lake Kariba Cabins 1 Cabins 2 Cabins 3 Cabins 4 Cabins 5 Cabins Boat Type MotorSailCatamaran Price Price Up Price Down CurrencyEUR USD GBP SGD THB MUR
LADY ANGELE - 72ft Custom - Caribbean - Virgin Islands Berths: 8 Cabins: 4 Crew: Crewed Type: Sail From $ 19250 per week Add to “My Yachts”
AKASHA - 76ft Custom - Caribbean Berths: 10 Cabins: 5 Crew: Crewed Type: Catamaran Year: 2005 From $ 45800 per week Boatbookings.com Preferred Add to “My Yachts”
MIRACLE - 115 Monte Fino - USA - Bahamas - British Virgin Islands Berths: 8 Cabins: 4 Crew: Crewed Type: Motor Year: 2000 From $ 42000 per week Add to “My Yachts”
SILENT WORLD II - 120ft Christensen - Caribbean - Bahamas - New England Berths: 8 Cabins: 3 Crew: Crewed Type: Motor Year: 1991/2007 refit From $ 42500 per week Boatbookings.com Preferred Add to “My Yachts”
GRAUNYA - 51 Beneteau - Caribbean Berths: 6 Cabins: 3 Crew: Crewed Type: Sail Year: 1985/2005 refit From $ 10000 per week Add to “My Yachts”
BRAVEHEART - Simonis 54 - Virgin Islands - Leeward Islands Berths: 9 Cabins: 7 Crew: Crewed Type: Catamaran Year: 1999/2004 From $ 18000 per week Boatbookings.com Preferred Add to “My Yachts”
ARGYLL - 153ft North American - Caribbean - Bahamas - New England Berths: 10 Cabins: 5 Crew: Crewed Type: Motor Year: 2002 From $ 150000 per week Add to “My Yachts”
DIAMOND GIRL II - 62ft Sunreef - Bahamas - Caribbean Berths: 6 Cabins: 3 Crew: Crewed Type: Catamaran Year: 2006/2007 From € 20000 per week Add to “My Yachts”
AQUASITION - 147 Intermarine - New England - Caribbean Berths: 10 Cabins: 5 Crew: Crewed Type: Motor Year: 2002/2007 refit From $ 127000 per week Boatbookings.com Preferred Add to “My Yachts”
ZIG ZAG - Oyster 82 - Caribbean Berths: 6 Cabins: 3 Crew: Crewed Type: Sail Year: 2007 From £ 16000 per week Boatbookings.com Preferred Add to “My Yachts”
CLASSHIP I - 92 ft - Mediterranean - Virgin Islands - Caribbean Berths: 12 Cabins: 6 Crew: Crewed Type: Sail Year: 2000/2005 From $ 35000 per week Add to “My Yachts”
NEW MOON II - 112ft Westport - Great Lakes - Florida - Bahamas - Caribbean Berths: 8 Cabins: 4 Crew: Crewed Type: Motor Year: 2005 From $ 46000 per week Add to “My Yachts”
GO FREE - Custom 58ft - Bahamas - Caribbean Berths: 8 Cabins: 4 Crew: Crewed Type: Catamaran Year: 2004 From € 20000 per week Add to “My Yachts”
SASSY - 94ft Hargrave - Caribbean - Virgin Islands Berths: 8 Cabins: 4 Crew: Crewed Type: Motor Year: 2004 From $ 40000 per week Add to “My Yachts”
WATERCOLOURS - 115ft Trinity - Caribbean - Bahamas Berths: 8 Cabins: 4 Crew: Crewed Type: Motor Year: 1990/2007 refit From $ 49500 per week Add to “My Yachts”
DREAM SEEKER - 139 Feadship - Florida - Bahamas Berths: 10 Cabins: 5 Crew: Crewed Type: Motor Year: 1984/1998 From $ 80000 per week Boatbookings.com Preferred Add to “My Yachts”
MOSAIQUE Proteksan - 6 Cabins - Mediterranean - Caribbean Berths: 12 Cabins: 6 Crew: Crewed Type: Motor Year: 2002 From € 200000 per week Add to “My Yachts”
LOHENGRIN - Trinity 161 - Caribbean - Florida - Bahamas Berths: 10 Cabins: 5 Crew: Crewed Type: Motor Year: 2006 From $ 217000 per week Add to “My Yachts”
TAHUATA - Privilege 58 - Caribbean Berths: 8 Cabins: 4 Crew: Crewed Type: Catamaran Year: 2004/2005 refit From € 20000 per week Add to “My Yachts”
TIPUTA - Privilege 58ft - Caribbean Berths: 8 Cabins: 4 Crew: Crewed Type: Catamaran Year: 2004 From € 20000 per week Add to “My Yachts”
SURYA - 85ft Pacific Mariner - Virgin Islands - Bahamas Berths: 8 Cabins: 4 Crew: Crewed Type: Motor Year: 2005 From $ 36000 per week Add to “My Yachts”
TRUE NORTH - 65ft Privilege - Caribbean Berths: 8 Cabins: 4 Crew: Crewed Type: Catamaran Year: 1996/2004 refit From $ 36225 per week Add to “My Yachts”
LA VIDA - 97ft Hargrave - Caribbean - Bahamas - Florida Berths: 8 Cabins: 4 Crew: Crewed Type: Motor From $ 40000 per week Add to “My Yachts”
COCKTAILS - 100 Hargrave - Bahamas - Caribbean Berths: 8 Cabins: 4 Crew: Crewed Type: Motor Year: 2006 From $ 49500 per week Add to “My Yachts”
ARIETA - 112ft Westport - New England - Caribbean Berths: 8 Cabins: 4 Crew: Crewed Type: Motor Year: 2002 From $ 52000 per week Add to “My Yachts”
SHALIMAR - Benetti 118 - Caribbean Berths: 10 Cabins: 5 Crew: Crewed Type: Motor Year: 1996/2006 refit From $ 75000 per week Add to “My Yachts”
SACAJAWEA - 130 Hatteras - New England - Caribbean Berths: 10 Cabins: 5 Crew: Crewed Type: Motor Year: 1995/1999 refit From $ 85000 per week Boatbookings.com Preferred Add to “My Yachts”
ATLANTICA - Christensen 135 - Bahamas - Florida Berths: 10 Cabins: 5 Crew: Crewed Type: Motor Year: 2000/2001 refit From $ 110000 per week Add to “My Yachts”
DRUMBEAT 1 - Irwin 72 - Virgin Islands Berths: 8 Cabins: 4 Crew: Crewed Type: Sail Year: 1985/1996 refit From $ 17000 per week Add to “My Yachts”
QUIXOTE - 87ft Cheoy Lee - Caribbean Berths: 6 Cabins: 3 Crew: Crewed Type: Sail Year: 1989/2004 refit From $ 18500 per week Add to “My Yachts”

190 boats found: Currently displaying 0 to 30.           Next 30 >>>

If you cannot find the charter yacht you are looking for or would like more information about chartering, boats or destinations, please contact us. We can organize any charter boat that is available worldwide through our global network of charter representatives and suppliers. Our service is free to you.

Charter Yacht Disclaimer: The yacht specifications, prices, images and availability above are displayed in good faith to help you find the right yacht for your next charter. Although we strive for accuracy, this information is not guaranteed. All information is subject to change without notice and is offered without warranty. A Boatbookings.com yacht charter consultant will confirm each charter and all pricing details during your charter selection process, and there is no formal commitment until a contract is signed by the charterer and the boat owner or operator. Full terms of service can be found here.

We look forward to working with you on your next charter, and welcome all enquiries. Click here for more information about boatbookings.com or here to learn how to use this site