Windward Islands Charter Yachts and Sailing Vacations

The Windward Islands are so named because they were more windward to sailing ships arriving in the New World than the Leeward Islands, given that the prevailing trade winds in the West Indies blow east to west.

The Windward Islands are renowned for sailing vacations and yacht charters because they offer all the best of that which is Caribbean - sun, beach, marine life, beautiful water, and of course, great island to island sailing! The main islands in the Windwards are: Martinique, Saint Lucia, Saint Vincent and the Grenadines, Grenada, Dominica, Trinidad and Tobago and Barbados.

We can find you the perfect charter yacht in the Windward Islands, and recommend itineraries that suit your needs. Just check through the boats below or simply contact us and we will recommend the perfect boat for you!

If you`re interested in an Ecological Charter, see our Grenada Eco Tourism Guide.
See our Windward islands Yacht Charter Guide

275 charter yachts found: Currently displaying 0 to 30.           Next 30 >>>

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All Countries and Ports Anguilla    -- Leeward Islands --          Anguilla Antigua          English Harbour         Falmouth Harbour         Jolly Harbour Australia    -- South Pacific --          Airlee Beach Whitsu         Great Barrier Reef         Hamilton Island Whi         Port Douglas         Sydney         Whitsunday Islands Bahamas    -- Bahamas --          Bahamas         Freeport         Georgetown         Green Turtle Cay         Marsh Harbor - Abaco         Nassau         Paradise Island         Shroud Cay         Staniel Cay Barbados    -- Barbados --          Bridgetown Belgium    -- North Sea --          Antwerp         Ostend Belize    -- Central America --          Belize City         Placencia         San Pedro Brazil    -- Amazon --          Amazon River British Virgin Islan    -- Virgin Islands --          Tortola         Virgin Gorda - Spani Canada    -- Nova Scotia --          Nova Scotia   -- Pacific Northwest --          Desolation Sound         Ladner - 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South America --          Galapagos Fiji    -- South Pacific --          Fiji Finland    -- Scandinavia --          Mariehamn Aland Isla         Taalintehdas France    -- Corsica --          Ajaccio         Bastia         Bonifacio         Calvi         Corsica         Macinaggio         Porto Vecchio         Propriano         Solenzara   -- French Riviera --          Antibes         Bandol         Beaulieu sur Mer         Bormes les Mimosas         Cagne-sur-Mer         Cannes         Cap d`Ail         Cap Ferrat         Cavalier sur Mer         Cogolin         Eze sur Mer         Frejus Port         Golfe Juan         Hyeres les Palmiers         Iles de Lerins         Juan les Pins         La Napoule Mandelieu         Lavandou         Marseille         Nice         Pin Rolland Toulon H         Porquerolles         Port Grimaud         Saint Jean Cap Ferra         St Mandrier         St Maxime         St Raphael         St Tropez         St-Laurent-du-Var         Theoule sur Mer         Toulon Hyeres         Villefranche         Villeneuve Loubet Germany    -- North Sea --          Hamburg Gibraltar    -- Costa del Sol --          Gibraltar Greece    -- Aegean Sea - Greece --          Alimos         Athens         Lavrio         Samos   -- Cyclades Islands --          Aegina         Mykonos         Paros         Santorini         Syros   -- Dodecanese Islands --          Kefalos - Kos         Kos         Rhodes   -- Ionian Sea --          Corfu         Kalamata         Lefkas         Zakynthos   -- Northern Sporades Is --          Skiathos Grenada    -- Windward Islands --          St Georges         True Blue Bay Guadeloupe    -- Leeward Islands --          Point a Pitre Guernsey    -- South Coast England --          St Peter Port Holland    -- North Sea --          Amsterdam India    -- Andaman Sea --          Andaman Islands Indonesia    -- Banda Sea --          Banda Islands         Raja Ampat   -- Lesser Sunda Islands --          Bali         Flores         Komodo   -- South China Sea --          Anambas Islands         Bintan Italy          Riva di Traiano   -- Adriatic Sea --          Grado         Pescara         San Rocco - Trieste         Trieste         Venice   -- Aeolian Islands --          Aeolian Islands         Lipari   -- Amalfi Coast --          Amalfi         Amalfi Coast         Capri         Castellammare di Sta         Gaeta         Marina di Stabia         Ostia         Positano         Salerno         Sorrento   -- Gulf of Naples --          Naples         Pozzuoli         Procida   -- Italian Riviera --          Civitavecchia         Genoa         La Spezia         Porto Ercole         Porto Santo Stefano         Portofino         Rapallo         San Remo         Santa Margherita Lig         Savona   -- Rome --          Marina Porto Di Roma         Nettuno   -- Sardinia --          Alghero         Cagliari         Cannigione         Carloforte         La Maddalena         Olbia         Palau         Poltu Quatu         Portisco         Porto Cervo         Porto Rotondo         Punt Aldia         Santa Teresa Gallura         Sardinia   -- Sicily --          Cefalu         Eolie Island         Marsala         Milazzo         Palermo         Portorosa         Riposto         Sant Agata di Milite         Sicily         Trapani   -- Southern Italy --          Agropoli         Reggio Calabria         Tropea         Vibo Valentia   -- The Italian Lakes --          Lake Garda   -- Tuscany --          Cala Galera         Elba         Etrusca Marina         Livorno         Piombino         Portoferraio Elba         Punta Ala         Puntone         Scarlino         Viareggio Jersey    -- Channel Islands --          St Helier Malaysia    -- Andaman Sea --          Langkawi         Penang   -- South China Sea --          Kota Kinabalu         Sabah         Tioman Maldives    -- Maldives --          Male Malta    -- Maltese Islands --          Gzira         Malta         Valetta Martinique    -- Windward Islands --          Baie du Marin         Bassin Tortue         Le Marin         Martinique Mexico    -- Central America --          Cabo San Lucas         Cancun         Cozumel         La Paz         Mexico         Puerto Vallarta Monaco    -- French Riviera --          Monaco Montenegro    -- Adriatic Sea --          Budva         Kotor         Tivat Myanmar (Burma)    -- Andaman Sea --          Mergui Archipelago New Caledonia    -- South Pacific --          New Caledonia New Zealand          Auckland         New Zealand Oman    -- Middle East --          Masqat Pacific Northwest    -- Pacific Northwest --          Pacific Northwest Panama    -- Central America --          Bocos Del Toro         Panama Portugal    -- Algarve --          Faro         Lagos   -- Madeira --          Calheta         Funchal Puerto Rico    -- Spanish Virgin Islan --          Culebra         Fajardo         Humacao         Vieques Scotland    -- Orkney --          Kirkwall   -- Scotland West Coast --          Armadale         Oban Seychelles    -- Seychelles --          Mahe         Praslin Singapore    -- South China Sea --          Singapore Slovenia    -- Adriatic Sea --          Izola South Pacific    -- South Pacific --          Cook Islands         Samoa         South Pacific         Tonga Spain    -- Almeria --          Almeria   -- Balearic Islands --          Mallorca   -- Barcelona --          Barcelona   -- Canaries --          Gran Canaria         Lanzarote         Tenerife   -- Costa Blanca --          Alicante   -- Costa Brava --          L` Escala         L`Estartit         Palamos         Roses         Sant Feliu de Guixol   -- Costa Calidas --          Aguilas   -- Costa de Alicante --          Denia   -- Costa de Valencia --          Valencia   -- Costa del Sol --          Estepona         Marbella         Puerto Banus         Puerto Sotogrande   -- Ibiza --          Formentera         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         Marstrand         Stockholm Tahiti    -- South Pacific --          Bora Bora         Moorea         Raiatea         Tahiti Thailand    -- Andaman Sea --          Krabi         Phang Nga Bay         Phi Phi Islands         Phuket         Phuket Kings Cup         Similan Islands   -- Gulf of Thailand --          Koh Chang         Koh Kut         Koh Phangan         Koh Samui         Koh Tao Tonga    -- South Pacific --          Tonga Trinidad    -- Central America --          Trinidad Turkey    -- Aegean Sea - Turkey --          Antalya         Bodrum         Fethiye         Gocek         Kas         Kusadasi         Marmaris         Turgutreis   -- Istanbul - Bosporus --          Bosporus and Istanbu Turks and Caicos    -- Bahamas --          Turks and Caicos UAE    -- Middle East --          Dubai Ukraine    -- Eastern Europe --          Balaklava         Kiev         Odessa United Kingdom    -- Solent --          Cowes         Hamble         Lymington         Poole         Portsmouth         Southampton   -- South Coast England --          Brighton         Torquay   -- Thames --          London         London - St Katharin US Virgin Islands    -- Virgin Islands --          St Thomas         St. John USA    -- Hawaii --          Honolulu   -- Mid Atlantic --          Annapolis MD         Charleston SC         Georgetown         Manteo NC         Outer Banks - OBX -          Virginia Beach VA   -- New England - NY - N --          Bar Harbor Maine         Boothbay Harbor ME         Boston MA         Brooklyn NY         Camden ME         Cape Cod and Islands         Gloucester         Hyannis MA         Jersey City         Kennebunkport ME         Marthas Vineyard MA         Nantucket MA         Newport RI         Penobscot Bay Maine         Portland Maine         Sag Harbor NY         Searsport Maine   -- Pacific Northwest --          Anacortes WA         Bellingham WA         Juneau AK         Juneau AK         Ketchikan AK         Kodiak AK         Petersburg AK         San Juan Islands         Seattle WA         Seward         Sitka AK   -- SouthEast US - Flori --          Boca Grande FL         Clearwater FL         Fort Myers FL         Ft Lauderdale FL         Islamorada FL         Jacksonville FL         Key Largo         Key West FL         Kissimmee FL         Miami FL         Naples FL         Palm Beach FL         Port Canaveral FL         Sanbel Island FL         Sarasota FL         Tampa FL   -- West Coast US - Cali --          Marina del Rey Calif         Newport Beach Califo         San Diego California         San Francisco Califo Vanuatu    -- South Pacific --          Vanuatu Venezuela    -- Isla Margarita --          Los Roques   -- South America --          Puerto La Cruz Cabins 1 Cabins 2 Cabins 3 Cabins 4 Cabins 5+ Cabins Type MotorSailCatamaran Crew Bareboat Crewed Lengthbelow 10m/32ft10-13m/32-40ft13-16m/40-50ft16-23m/50-75ft23-30m/75-100ft30-40m/100-130ft40-50m/130-165ft50+m/165+ft
IN THE WIND - Sunreef 62 - 4 Cabins - French Riviera - Monaco - Turkey - Croatia - Greece - Virgin Islands - Leeward Islands - Windward Islands Berths: 8 Cabins: 4 Crew: Crewed Length: 18.9 m (62'0") Type: Catamaran Year: 2011 Boatbookings.com says: "A high performance luxury sailing catamaran - guaranteed to exceed expectations" From $ 22000 to 24000 per week Add to “My Yachts”
SEAZEN II - Sunreef 70 - 4 Cabins - Mediterranean - Caribbean Berths: 10 Cabins: 4 Crew: Crewed Length: 21.33 m (70'0") Type: Catamaran Year: 2008 From $ 35550 per week Boatbookings.com Preferred Add to “My Yachts”
WHISPER - 116 Holland Jachtbouw - 3 Staterooms - New England - Caribbean - Virgin Islands Berths: 6 Cabins: 3 Crew: Crewed Length: 35 m (114'10") Type: Sail Year: 2003 From $ 69000 to 75000 per week Add to “My Yachts”
NEXUS - Nexus 58 - 3 Cabins - Virgin Islands - Leeward Islands - Windward Islands - Bahamas Berths: 6 Cabins: 3 Crew: Crewed Length: 18.28 m (60'0") Type: Catamaran Year: 2009 From $ 14000 to 20000 per week Add to “My Yachts”
PICNIC - Monte Fino 100 - 4 Staterooms - Caribbean - Bahamas - Virgin Islands Berths: 8 Cabins: 4 Crew: Crewed Length: 30.48 m (100'0") Type: Motor Year: 2010 Boatbookings.com says: "Ideal for elite charter clientele who demand the utmost in service and seaworthiness." From $ 39500 to 43500 per week Boatbookings.com Preferred Add to “My Yachts”
ELLE - 151 Tacoma - 5 Cabins - Bahamas - Virgin Islands - Leeward Islands - Windward Islands Berths: 10 Cabins: 5 Crew: Crewed Length: 151 m (495'5") Type: Motor Year: 1993 - refitted 2008 From $ 135000 per week Add to “My Yachts”
MAUNI - 62ft Sunreef - 3 Cabins - Caribbean - Venezuela - Central America Berths: 6 Cabins: 3 Crew: Crewed Length: 18.23 m (59'10") Type: Catamaran Year: 2006 From $ 24000 to 26000 per week Add to “My Yachts”
SUBLIME - 72ft Irwin - 4 Cabins - Virgin Islands - Leeward Islands - Windward Islands Berths: 8 Cabins: 4 Crew: Crewed Length: 21.17 m (69'5") Type: Sail From $ 14000 to 18000 per week Add to “My Yachts”
FORTUNA - Custom Build - 5 Cabins - Spain - Balearic Islands - Leeward Islands - Windward Islands Berths: 10 Cabins: 5 Crew: Crewed Length: 25.2 m (82'8") Type: Sail Year: 1995 - refitted 2005 Boatbookings.com says: "One of a kind! a truly spectacular experience!" From € 12480 to 33350 per week Add to “My Yachts”
TACHYON - 47 Robertson and Caine - 3 Cabins - WIndward Islands - St Vincent - Grenada Berths: 6 Cabins: 3 Crew: Crewed Length: 14.33 m (47'0") Type: Catamaran Year: 2001 From $ 5500 to 13000 per week Add to “My Yachts”
HANALEI BAY - 72ft Custom Build - 3 Cabins - Virgin Islands - Leeward Islands - Windward Islands Berths: 6 Cabins: 3 Crew: Crewed Length: 21.95 m (72'0") Type: Sail Year: 1990 - refitted 2003 and annual ongoing From $ 7800 to 12600 per week Add to “My Yachts”
GOOD MEDICINE - Fontaine Pajot 46 - 3 Cabins - Virgin Islands - Leeward Islands - Windward Islands Berths: 6 Cabins: 3 Crew: Crewed Length: 14.02 m (46'0") Type: Catamaran Year: 2004 Boatbookings.com says: "SAILING IS GOOD MEDICINE" From $ 10000 to 12400 per week Sleep aboard/half board special this summer aboard the luxury GOOD MEDICINE Special ends on 24-08-2012 Add to “My Yachts”
ALDEBARAN - Lagoon 57 - 3 Cabins - Virgin Islands - Grenadines - Windward Islands Berths: 7 Cabins: 3 Crew: Crewed Length: 16.76 m (55'0") Type: Catamaran Year: 2001 Boatbookings.com says: "Lovely well taken care of cat, light and airy inside." From $ 17495 to 21000 per week Add to “My Yachts”
PACIFIC WAVE - Giorgretti & Magrini 72 - 3 Cabins - Virgin Islands - Windward Islands Berths: 6 Cabins: 3 Crew: Crewed Length: 21.95 m (72'0") Type: Sail Year: 1986 - refitted 2008 From $ 14500 to 18000 per week Add to “My Yachts”
ZINGARA - Silhouette 76 - 5 Cabins - Virgin Islands - Leeward Islands - Windward Islands Berths: 10 Cabins: 5 Crew: Crewed Length: 22.34 m (73'4") Type: Catamaran Year: 2006 From $ 46800 to 49900 per week Add to “My Yachts”
EAGLE`S NEST - MCP 98 - 4 Cabins - Caribbean - Bahamas Berths: 8 Cabins: 4 Crew: Crewed Length: 29.9 m (98'1") Type: Motor Year: 2007 Boatbookings.com says: "A luxury crewed open plan fun boat, very family orientated" Enquire for prices Add to “My Yachts”
NORTHERN LIGHTS - Westship 132 - 5 Staterooms - Bahamas - Caribbean - Virgin Islands Berths: 10 Cabins: 5 Crew: Crewed Length: 40.23 m (132'0") Type: Motor Year: 2000/refit 2005, 2008 Boatbookings.com says: "Crew is particularly wonderful with kids!" From $ 75000 to 90000 per week Add to “My Yachts”
THIS IS US - 141 ft Holland Jachtbouw - 4 Cabins - Caribbean - Monaco - Corsica - French Riviera - Italy - Sardinia - Croatia Berths: 8 Cabins: 4 Crew: Crewed Length: 42.98 m (141'0") Type: Sail Year: 2005 - refreshed 2010 Boatbookings.com says: "A beautiful high performance and luxury sailing yacht." From € 64000 to 70000 per week Add to “My Yachts”
LADY BEE - Christensen 142 - 6 Cabins - Bahamas - St Maarten - Virgin Islands - Leeward Islands Berths: 12 Cabins: 6 Crew: Crewed Length: 43.28 m (142'0") Type: Motor Year: 1995 - refitted 2010 From $ 110000 per week Add to “My Yachts”
LADY JOY - Christensen 157 - 7 Cabins - Caribbean - Mediterranean Berths: 12 Cabins: 7 Crew: Crewed Length: 47.85 m (157'0") Type: Motor Year: 2007 Enquire for prices Boatbookings.com Preferred Add to “My Yachts”
TRUE NORTH - 65ft Privilege - 4 Cabins - Belize - Virgin Islands - Leeward Islands - Windward Islands Berths: 8 Cabins: 4 Crew: Crewed Length: 19.11 m (62'8") Type: Catamaran Year: 1996 - refitted 2009 Boatbookings.com says: "Lavishly appointed with a great crew" From $ 24500 to 36225 per week Add to “My Yachts”
ANTILLEAN - 50 Beneteau - 3 Cabins - Virgin Islands - Leeward Islands - Windward Islands Berths: 6 Cabins: 3 Crew: Crewed Length: 14.7 m (48'3") Type: Sail Year: 1997 From $ 6000 to 9500 per week Add to “My Yachts”
MUSCADE - 56 Fontaine Pajot - 4 Cabins - British Virgin Islands - Leeward Islands - Windward Islands Berths: 8 Cabins: 4 Crew: Crewed Length: 16.46 m (54'0") Type: Catamaran Year: 1996 From $ 15500 to 20350 per week Add to “My Yachts”
ROCKETEER - 55 Chris White - 3 Cabins - St. Maarten - Virgin Islands - Windward Islands - Leeward Islands Berths: 6 Cabins: 3 Crew: Crewed Length: 16.76 m (55'0") Type: Catamaran Year: 2002 From $ 10000 to 16500 per week Add to “My Yachts”
YES DEAR - Simonis Voyage 58 - 5 Cabins - Virgin Islands - Grenadines - Leeward Islands - Windward Islands Berths: 10 Cabins: 5 Crew: Crewed Length: 17.05 m (55'11") Type: Catamaran Year: 2007 From $ 21000 to 25300 per week Add to “My Yachts”
SOON COME - 62 Sunreef - Bahamas - Caribbean Berths: 8 Cabins: 4 Crew: Crewed Length: 18.23 m (59'10") Type: Catamaran Year: 2006 From $ 23000 to 27000 per week Add to “My Yachts”
LADY ANGELE - 72ft Custom Ketch - 3 Cabins - New England - Virgin Islands - Leeward Islands - Windward Islands Berths: 6 Cabins: 3 Crew: Crewed Length: 21.17 m (69'5") Type: Sail Year: 1991 - refitted 2010 Boatbookings.com says: "Perfect for exploring the Caribbean and New England" From $ 15000 to 18500 per week Add to “My Yachts”
DRUMBEAT 1 - Irwin 72 - 4 Cabins - Virgin Islands - Leeward Islands - Windward Islands Berths: 8 Cabins: 4 Crew: Crewed Length: 21.95 m (72'0") Type: Sail Year: 1985 refitted 1996 From $ 14000 to 18000 per week Add to “My Yachts”
RENA - 145 Hargrave - 5 Staterooms - New England - Newport RI - Great Lakes - Caribbean - Bahamas Berths: 10 Cabins: 5 Crew: Crewed Length: 42.63 m (139'10") Type: Motor Year: 1989/2005 From $ 95000 to 105000 per week Add to “My Yachts”
BALAJU - Intermarine 146 - 5 Staterooms - French Riviera - Caribbean Sea Berths: 10 Cabins: 5 Crew: Crewed Length: 44.5 m (146'0") Type: Motor Year: 2002/refit 2007 Boatbookings.com says: "For those who enjoy the finer things in life, insist on Balaju" Enquire for prices Boatbookings.com Preferred Add to “My Yachts”

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

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