Your Caribbean - All Results
Your Caribbean - All Results
Sail Date | Cruise Line | Ship | Destination | Departs | Length | Price | You Save | Discounts | ||||
---|---|---|---|---|---|---|---|---|---|---|---|---|
24 reviews ![]() | 8 night Caribbean (In the Wake of the Spanish Armadas 8D ORJ-ONX (Feb 1 2026)) | Feb 01, 2026 | Windstar | Wind Surf | Oranjestad | Colon | 8 Nights | Bocas del Toro | Cartagena | Colón | Oranjestad | Santa Marta | $3,199 Up To $500 Onboard Credit | Onboard Credit! | View Itinerary | Get FREE Quote |
24 reviews ![]() | 16 night Star Collector Voyages (Natural History Meets Ancient Mystery: Latin America & Beyond 16D ORJ-CZM (Feb 1 2026)) | Feb 01, 2026 | Windstar | Wind Surf | Oranjestad | Cozumel | 16 Nights | Belize City | Bocas del Toro | Cartagena | Colón | Costa Maya | Cozumel | Isla San Andres | Oranjestad | Roatan | Santa Marta | $5,099 Up To $750 Onboard Credit | Onboard Credit! | View Itinerary | Get FREE Quote |
11 reviews ![]() | 14 night Star Collector Voyages (Caribbean Explorations 14D PH1-PH1 (Feb 7 2026)) | Feb 07, 2026 | Windstar | Wind Spirit | Philipsburg | Philipsburg | 14 Nights | Basseterre | Charlestown | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Pigeon Island | Road Bay | Roseau | Soper's Hole | St. Maarten | Virgin Gorda / Prickly Pear | $4,099 Up To $500 Onboard Credit | Onboard Credit! | View Itinerary | Get FREE Quote |
11 reviews ![]() | 7 night Caribbean (Classic Caribbean 7D PH1-PH1 (Feb 7 2026)) | Feb 07, 2026 | Windstar | Wind Spirit | Philipsburg | Philipsburg | 7 Nights | Basseterre | Charlestown | Gustavia | Les Saintes | Pigeon Island | Roseau | St. Maarten | $2,599 Up To $300 Onboard Credit | Onboard Credit! | View Itinerary | Get FREE Quote |
24 reviews ![]() | 8 night Mexico (Mayan Legacies 8D ONX-CZM (Feb 9 2026)) | Feb 09, 2026 | Windstar | Wind Surf | Colon | Cozumel | 8 Nights | Belize City | Bocas del Toro | Colón | Costa Maya | Cozumel | Isla San Andres | Roatan | $3,199 Up To $500 Onboard Credit | Onboard Credit! | View Itinerary | Get FREE Quote |
24 reviews ![]() | 19 night Star Collector Voyages (Caribbean Cultures: Latin America & the Greater Antilles 19D ONX-PH1 (Feb 9 2026)) | Feb 09, 2026 | Windstar | Wind Surf | Colon | Philipsburg | 19 Nights | Belize City | Bocas del Toro | Cayman Brac | Colón | Costa Maya | Cozumel | Grand Cayman | Isla San Andres | Jost Van Dyke, Great Harbour | La Romana | Port Antonio | Roatan | Santo Domingo | St. Maarten | Virgin Gorda / Prickly Pear | $5,599 Up To $750 Onboard Credit | View Itinerary | Get FREE Quote | |
5 reviews ![]() | 24 night Star Collector Voyages (*NEW Winter Mediterranean Adventure 24D VCE-BCN (Feb 12 2026)) | Feb 12, 2026 | Windstar | Star Legend | Venice | Barcelona | 24 Nights | Barcelona | Cartagena | Dubrovnik | Genoa, Italy | Gibraltar | Livorno | Málaga | Messina (Taormina) | Naples | Nice | Palma de Mallorca | Rome | Valencia | Venice | Zadar | $7,999 Up To $1000 Onboard Credit | View Itinerary | Get FREE Quote | |
11 reviews ![]() | 7 night Caribbean (Beach Fun & Sun: A Remote Caribbean Getaway 7D PH1-PH1 (Feb 14 2026)) | Feb 14, 2026 | Windstar | Wind Spirit | Philipsburg | Philipsburg | 7 Nights | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Road Bay | Soper's Hole | St. Maarten | Virgin Gorda / Prickly Pear | $2,599 Up To $300 Onboard Credit | View Itinerary | Get FREE Quote | |
15 reviews ![]() | 7 night Costa Rica & Panama Canal (Costa Rica & Panama Canal 7D PTC-ONX (Feb 16 2026)) | Feb 16, 2026 | Windstar | Star Pride | Puerto Caldera | Colon | 7 Nights | Balboa / Fuerte Amador | Colón | Golfo Dulce | Isla Parida | Panama Canal | Puerto Caldera | Quepos | $3,099 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) | View Itinerary | Get FREE Quote |
24 reviews ![]() | 11 night Caribbean (Stars of the Greater Antilles 11D CZM-PH1 (Feb 17 2026)) | Feb 17, 2026 | Windstar | Wind Surf | Cozumel | Philipsburg | 11 Nights | Cayman Brac | Cozumel | Grand Cayman | Jost Van Dyke, Great Harbour | La Romana | Port Antonio | Santo Domingo | St. Maarten | Virgin Gorda / Prickly Pear | $3,799 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) | View Itinerary | Get FREE Quote |
24 reviews ![]() | 18 night Star Collector Voyages (Deep Dive into the Blue: Underwater Worlds of the Caribbean 18D CZM-PH1 (Feb 17 2026)) | Feb 17, 2026 | Windstar | Wind Surf | Cozumel | Philipsburg | 18 Nights | Basseterre | Cayman Brac | Charlestown | Cozumel | Grand Cayman | Gustavia | Jost Van Dyke, Great Harbour | La Romana | Les Saintes | Pigeon Island | Port Antonio | Roseau | Santo Domingo | St. Maarten | Virgin Gorda / Prickly Pear | $4,799 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) | View Itinerary | Get FREE Quote |
5 reviews ![]() | 16 night Star Collector Voyages (*NEW Winter & Spain & Rivieras 16D CVV-BCN (Feb 20 2026)) | Feb 20, 2026 | Windstar | Star Legend | Rome | Barcelona | 16 Nights | Barcelona | Cartagena | Genoa, Italy | Gibraltar | Livorno | Málaga | Nice | Palma de Mallorca | Rome | Valencia | $5,299 Up To $750 Onboard Credit | View Itinerary | Get FREE Quote | |
11 reviews ![]() | 14 night Star Collector Voyages (Leeward & Windward Caribbean Havens 14D PH1-BGI (Feb 21 2026)) | Feb 21, 2026 | Windstar | Wind Spirit | Philipsburg | Bridgetown | 14 Nights | Basseterre | Bridgetown | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Little Bay | Pigeon Island | Road Bay | Roseau | Soper's Hole | St. Maarten | Virgin Gorda / Prickly Pear | $3,999 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) | View Itinerary | Get FREE Quote |
11 reviews ![]() | 7 night Caribbean (Beach Fun & Sun: A Remote Caribbean Getaway 7D PH1-PH1 (Feb 21 2026)) | Feb 21, 2026 | Windstar | Wind Spirit | Philipsburg | Philipsburg | 7 Nights | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Road Bay | Soper's Hole | St. Maarten | Virgin Gorda / Prickly Pear | $2,599 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) | View Itinerary | Get FREE Quote |
11 reviews ![]() | 21 night Star Collector Voyages (A Lesser Antilles Odyssey 21D PH1-BGI (Feb 21 2026)) | Feb 21, 2026 | Windstar | Wind Spirit | Philipsburg | Bridgetown | 21 Nights | Anse Mitan | Basseterre | Bridgetown | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Little Bay | Pigeon Island | Road Bay | Roseau | Soper's Hole | St. Maarten | Virgin Gorda / Prickly Pear | $6,099 Up To $750 Onboard Credit | View Itinerary | Get FREE Quote | |
5 reviews ![]() | 9 night Mediterranean (Southern Spains Winter Escapes (Feb 27 2026)) | Feb 27, 2026 | Windstar | Star Legend | Barcelona | Barcelona | 9 Nights | Barcelona | Cartagena | Gibraltar | Málaga | Palma de Mallorca | Valencia | $3,499 Up To $500 Onboard Credit | Suite! | View Itinerary | Get FREE Quote |
5 reviews ![]() | 16 night Star Collector Voyages (*NEW Winter & Spain & Rivieras 16D BCN-CVV (Feb 27 2026)) | Feb 27, 2026 | Windstar | Star Legend | Barcelona | Rome | 16 Nights | Barcelona | Cartagena | Genoa, Italy | Gibraltar | Livorno | Málaga | Nice | Palma de Mallorca | Rome | Valencia | $5,299 Up To $750 Onboard Credit | Suite! | View Itinerary | Get FREE Quote |
5 reviews ![]() | 24 night Star Collector Voyages (*NEW Winter Mediterranean Adventure 24D BCN-VCE (Feb 27 2026)) | Feb 27, 2026 | Windstar | Star Legend | Barcelona | Venice | 24 Nights | Barcelona | Cartagena | Dubrovnik | Genoa, Italy | Gibraltar | Livorno | Málaga | Messina (Taormina) | Naples | Nice | Palma de Mallorca | Rome | Valencia | Venice | Zadar | $7,999 Up To $1000 Onboard Credit | View Itinerary | Get FREE Quote | |
11 reviews ![]() | 7 night Caribbean (Lush & Lovely Islands of the Lesser Antilles 7D PH1-BGI (Feb 28 2026)) | Feb 28, 2026 | Windstar | Wind Spirit | Philipsburg | Bridgetown | 7 Nights | Basseterre | Bridgetown | Gustavia | Les Saintes | Little Bay | Pigeon Island | Roseau | St. Maarten | $2,399 Up To $250 Onboard Credit | Onboard Credit! | View Itinerary | Get FREE Quote |
11 reviews ![]() | 14 night Star Collector Voyages (Antilles Adventures 14D PH1-BGI (Feb 28 2026)) | Feb 28, 2026 | Windstar | Wind Spirit | Philipsburg | Bridgetown | 14 Nights | Anse Mitan | Basseterre | Bridgetown | Gustavia | Les Saintes | Little Bay | Pigeon Island | Roseau | St. Maarten | $3,999 Up To $500 Onboard Credit | Onboard Credit! | View Itinerary | Get FREE Quote |
How It Works
Vacationing has never been easier or cheaper with the help of a dedicated travel consultant from AffordableTours.com
1. Free Quote
Find your perfect trip on our website and simply request a free quote. Need to speak to a live person? Call us 7 days a week at 1-800-627-3753. No robots here!
2. Dedicated Travel Consultant
Your personal travel consultant will reach out and be your point of contact for your entire travel experience from start to finish. Did we mention you'll be working with an award winning team? Sweet!
3. Low Price Guaranteed
Because we're one of the largest sellers of travel, we're able to give you a discount on your vacation package. No one beats our prices!
4. Stress Free Travel
Knowing you got the great deal, all that's left is for you to pack your bags and enjoy your vacation!