Your Caribbean - All Results

Showing 41 - 60 Cruises

Filter Cruises

Destination Date Cruise Line Length Departure Port

Round-trip Repositioning Cruisetour Only

Specialty Resident

Senior (55+) Military Airline Employee Civil Service Employee

Showing 41 - 60 Cruises

Sort By

Sail Date	Cruise Line	Ship	Destination	Departs	Length	Price	You Save	Discounts
24 reviews	7 night Caribbean (Beach Fun & Sun: A Remote Caribbean Getaway 7D PH1-PH1 (Jan 4 2026))	Jan 04, 2026	Windstar	Wind Surf	Caribbean	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) View Cruise Get FREE Quote	Shipboard Credit Per Person ($100)	View Itinerary	Get FREE Quote
24 reviews	14 night Star Collector Voyages (Leeward & Windward Caribbean Havens 14D PH1-BGI (Jan 4 2026))	Jan 04, 2026	Windstar	Wind Surf	Caribbean	Philipsburg	Bridgetown	14 Nights	Basseterre \| Bridgetown \| Deshaies \| Falmouth Harbour \| Gustavia \| Jost Van Dyke, Great Harbour \| Little Bay \| Pigeon Island \| Road Bay \| Roseau \| Soper's Hole \| St. Maarten \| Virgin Gorda / Prickly Pear	$4,099 Shipboard Credit Per Person ($100) View Cruise Get FREE Quote	Shipboard Credit Per Person ($100)	View Itinerary	Get FREE Quote
24 reviews	21 night Star Collector Voyages (A Lesser Antilles Odyssey 21D PH1-BGI (Jan 4 2026))	Jan 04, 2026	Windstar	Wind Surf	Caribbean	Philipsburg	Bridgetown	21 Nights	Anse Mitan \| Basseterre \| Bequia \| Bridgetown \| Castries \| Deshaies \| Falmouth Harbour \| Gustavia \| Jost Van Dyke, Great Harbour \| Little Bay \| Mayreau \| Pigeon Island \| Road Bay \| Roseau \| Soper's Hole \| St. George's \| St. Maarten \| Virgin Gorda / Prickly Pear	$6,299 Up To $750 Onboard Credit View Cruise Get FREE Quote	Onboard Credit!	View Itinerary	Get FREE Quote
24 reviews	55 night Star Collector Voyages (Grand Caribbean Adventure 55D PH1-PH1 (Jan 4 2026))	Jan 04, 2026	Windstar	Wind Surf	Caribbean	Philipsburg	Philipsburg	55 Nights	Anse Mitan \| Basseterre \| Belize City \| Bequia \| Bocas del Toro \| Bridgetown \| Cartagena \| Castries \| Cayman Brac \| Colón \| Costa Maya \| Cozumel \| Deshaies \| Falmouth Harbour \| Grand Cayman \| Gustavia \| Isla San Andres \| Jost Van Dyke, Great Harbour \| Kralendijk \| La Romana \| Little Bay \| Man-O-War Bay \| Mayreau \| Oranjestad \| Pigeon Island \| Port Antonio \| Road Bay \| Roatan \| Roseau \| Santa Marta \| Santo Domingo \| Soper's Hole \| Soufriere \| St. George's \| St. Maarten \| Virgin Gorda / Prickly Pear \| Willemstad	$16,699 Up To $1000 Onboard Credit View Cruise Get FREE Quote	Onboard Credit!	View Itinerary	Get FREE Quote
Need Help Planning A Cruise? Our cruise experts can help you: Find the best discounts Hold a cabin for 24 hours for free Receive personalized recommendations Book handicap accessible cabins Call 1-800-627-3753
24 reviews	28 night Star Collector Voyages (The Best of the Windward & Leeward Isles 28D PH1-ORJ (Jan 4 2026))	Jan 04, 2026	Windstar	Wind Surf	Caribbean	Philipsburg	Oranjestad	28 Nights	Anse Mitan \| Basseterre \| Bequia \| Bridgetown \| Castries \| Deshaies \| Falmouth Harbour \| Gustavia \| Jost Van Dyke, Great Harbour \| Kralendijk \| Little Bay \| Man-O-War Bay \| Mayreau \| Oranjestad \| Pigeon Island \| Road Bay \| Roseau \| Soper's Hole \| Soufriere \| St. George's \| St. Maarten \| Virgin Gorda / Prickly Pear \| Willemstad	$8,399 Up To $1000 Onboard Credit View Cruise Get FREE Quote	Onboard Credit!	View Itinerary	Get FREE Quote
24 reviews	7 night Caribbean (Lush & Lovely Islands of the Lesser Antilles 7D PH1-BGI (Jan 11 2026))	Jan 11, 2026	Windstar	Wind Surf	Caribbean	Philipsburg	Bridgetown	7 Nights	Basseterre \| Bridgetown \| Deshaies \| Gustavia \| Little Bay \| Pigeon Island \| Roseau \| St. Maarten	$2,599 Shipboard Credit Per Person ($100) View Cruise Get FREE Quote	Shipboard Credit Per Person ($100)	View Itinerary	Get FREE Quote
24 reviews	14 night Star Collector Voyages (Antilles Adventures 14D PH1-BGI (Jan 11 2026))	Jan 11, 2026	Windstar	Wind Surf	Caribbean	Philipsburg	Bridgetown	14 Nights	Anse Mitan \| Basseterre \| Bequia \| Bridgetown \| Castries \| Deshaies \| Gustavia \| Little Bay \| Mayreau \| Pigeon Island \| Roseau \| St. George's \| St. Maarten	$4,199 Shipboard Credit Per Person ($100) View Cruise Get FREE Quote	Shipboard Credit Per Person ($100)	View Itinerary	Get FREE Quote
24 reviews	7 night Caribbean (Jewels of Windward Islands 7D BGI-BGI (Jan 18 2026))	Jan 18, 2026	Windstar	Wind Surf	Caribbean	Bridgetown	Bridgetown	7 Nights	Anse Mitan \| Bequia \| Bridgetown \| Castries \| Mayreau \| Pigeon Island \| St. George's	$2,699 Up To $300 Onboard Credit View Cruise Get FREE Quote		View Itinerary	Get FREE Quote
24 reviews	14 night Star Collector Voyages (Captivating Caribbean 14D BGI-ORJ (Jan 18 2026))	Jan 18, 2026	Windstar	Wind Surf	Caribbean	Bridgetown	Oranjestad	14 Nights	Anse Mitan \| Bequia \| Bridgetown \| Castries \| Kralendijk \| Man-O-War Bay \| Mayreau \| Oranjestad \| Pigeon Island \| Soufriere \| St. George's \| Willemstad	$4,299 Up To $500 Onboard Credit View Cruise Get FREE Quote	Onboard Credit!	View Itinerary	Get FREE Quote
24 reviews	15 night Star Collector Voyages (Windward Islands & Spanish New World 15D BGI-ONX (Jan 25 2026))	Jan 25, 2026	Windstar	Wind Surf	World Cruise	Bridgetown	Colon	15 Nights	Bocas del Toro \| Bridgetown \| Cartagena \| Colón \| Kralendijk \| Man-O-War Bay \| Mayreau \| Oranjestad \| Santa Marta \| Soufriere \| Willemstad	$4,699 Up To $500 Onboard Credit View Cruise Get FREE Quote		View Itinerary	Get FREE Quote
24 reviews	7 night Caribbean (Windward Ways & Tobago Cays 7D BGI-ORJ (Jan 25 2026))	Jan 25, 2026	Windstar	Wind Surf	Caribbean	Bridgetown	Oranjestad	7 Nights	Bridgetown \| Kralendijk \| Man-O-War Bay \| Mayreau \| Oranjestad \| Soufriere \| Willemstad	$2,699 Up To $300 Onboard Credit View Cruise Get FREE Quote		View Itinerary	Get FREE Quote
24 reviews	8 night Caribbean (In the Wake of the Spanish Armadas 8D ORJ-ONX (Feb 1 2026))	Feb 01, 2026	Windstar	Wind Surf	Caribbean	Oranjestad	Colon	8 Nights	Bocas del Toro \| Cartagena \| Colón \| Oranjestad \| Santa Marta	$3,199 Up To $500 Onboard Credit View Cruise Get FREE Quote		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	Caribbean	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 View Cruise Get FREE Quote		View Itinerary	Get FREE Quote
24 reviews	8 night Mexico (Mayan Legacies 8D ONX-CZM (Feb 9 2026))	Feb 09, 2026	Windstar	Wind Surf	Mexico	Colon	Cozumel	8 Nights	Belize City \| Bocas del Toro \| Colón \| Costa Maya \| Cozumel \| Isla San Andres \| Roatan	$3,199 Up To $500 Onboard Credit View Cruise Get FREE Quote		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	Caribbean	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 Cruise Get FREE Quote		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	Caribbean	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) View Cruise Get FREE Quote	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	Caribbean	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) View Cruise Get FREE Quote	Shipboard Credit Per Person ($100)	View Itinerary	Get FREE Quote
24 reviews	7 night Caribbean (Classic Caribbean 7D PH1-PH1 (Feb 28 2026))	Feb 28, 2026	Windstar	Wind Surf	Caribbean	Philipsburg	Philipsburg	7 Nights	Basseterre \| Charlestown \| Gustavia \| Les Saintes \| Pigeon Island \| Roseau \| St. Maarten	$2,299 Shipboard Credit Per Person ($100) View Cruise Get FREE Quote	Shipboard Credit Per Person ($100)	View Itinerary	Get FREE Quote
24 reviews	14 night Star Collector Voyages (Caribbean Explorations 14D PH1-PH1 (Feb 28 2026))	Feb 28, 2026	Windstar	Wind Surf	Caribbean	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	$3,699 Shipboard Credit Per Person ($100) View Cruise Get FREE Quote	Shipboard Credit Per Person ($100)	View Itinerary	Get FREE Quote
24 reviews	7 night Caribbean (Beach Fun & Sun: A Remote Caribbean Getaway 7D PH1-PH1 (Mar 7 2026))	Mar 07, 2026	Windstar	Wind Surf	Caribbean	Philipsburg	Philipsburg	7 Nights	Falmouth Harbour \| Gustavia \| Jost Van Dyke, Great Harbour \| Road Bay \| Soper's Hole \| St. Maarten \| Virgin Gorda / Prickly Pear	$999,999 Up To $1000 Onboard Credit View Cruise Get FREE Quote	Onboard Credit!	View Itinerary	Get FREE Quote

Sort By

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!

We Are Committed To:

Better Business Bureau

AffordableTours.com is a proud recipient of the Better Business Bureau (BBB) awards 2006-2024 with A+ Rating.

It Pays To Refer! Earn Up To $200!

It's simple: Sign up your friends, family, and anyone to us and when they book you will receive an American Express gift card worth up to $200 in the mail for simply referring.

Your Caribbean - All Results