The Cruise Web

Our expert consultants and customer service teams are standing by to help with all of your cruising needs.

Explore with us

FacebookTwitterInstagramPinterestyoutube

Follow us for the latest cruise and travel news, including our best vacation deals.

Subscribe

Cruise Deals - delivered to your inbox

Cruise Deals

Destinations

Alaska

Asia

Australia/New Zealand

Canada/New England

Caribbean

Europe

Hawaii

Bahamas

All Destinations

Departure Ports

Baltimore

Galveston

New Orleans

Miami

Port Canaveral

All Departure Ports

Cruise Lines

Carnival Cruise Line

Celebrity Cruises

Holland America Line

Norwegian Cruise Line

Princess Cruises

Royal Caribbean Int'l

All Cruise Lines

Deals

Family Deals

Holiday Deals

Military Deals

Last Minute Deals

2026 Deals

Land Vacations

Cosmos Tours

Globus Tours

All Land Tours

All About Cruising

Articles

Experiences

All Ports

Contact Us

About Us

Already Booked

Gift Certificates

Future Cruise Credits

The Cruise Web, Inc.

8614 Westwood Center Drive
 Suite 800
 Tysons, VA 22182

Phone: 1-800-377-9383

International: +1 240-487-0155

Fax: 1-240-487-0154

BBB LogoCruise Lines International Association logo

© 1994 – 2025 The Cruise Web, Inc.

Terms and Conditions

Privacy Policy

Do Not Sell or Share My Personal Information

4.9/5 ⭐Google 600+ Reviews | A+ Better Business Bureau

The Cruise Web
DestinationsDeparture PortsCruise LinesDealsLand ToursFind Cruises
1-800-377-9383
The Cruise Web
1-800-377-9383

Call

27 Results

Taxes and fees included in all prices shown

Sort

Loading...

Offramp

    • Showing results 1 - 24 of 27

*Rates and offers are per person, in US Dollars, based on double occupancy, capacity controlled, subject to availability and confirmation, and may change without notice. Government taxes and fees are included. Rates and offers are available for select dates and categories only. Additional restrictions may apply. Call 1-800-377-9383 for full terms and conditions.

Rocky beach and palm trees in Barbados.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

7-night Jewels of the Windward Islands Cruise

Bridgetown (Barbados)
Little Bay
Iles des Saintes
Roseau
Anse Mitan
+2 more

Aboard

Wind Spirit

From

Bridgetown, Barbados

1 Sailing

Mar 21, 2026

1 Sailing

Mar 21, 2026

Cupecoy Beach with white resort buildings, St. Maarten.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

7-night Classic Caribbean Cruise

St. Maarten (Philipsburg)
Charlestown
Roseau
Pigeon Island
Iles des Saintes
+2 more

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

11 Sailings

Dec 7, 2025 - Mar 20, 2027

11 Sailings

Dec 7, 2025 - Mar 20, 2027

Rocky beach and palm trees in Barbados.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

14-night Star Collector: Leeward & Windward Caribbean Havens Cruise

St. Maarten (Philipsburg)
Sopers Hole
Jost Van Dyke
Virgin Gorda
Gustavia
+8 more

Aboard

Wind Spirit

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Feb 21, 2026

1 Sailing

Feb 21, 2026

Colorful colonial balconies in Cartagena.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

17-night Star Collector: Seeking The Antilles Cruise

San Juan
Cruz Bay
St. John's
Iles des Saintes
Pigeon Island
+10 more

Aboard

Star Seeker

From

San Juan, Puerto Rico

1 Sailing

Mar 27, 2026

1 Sailing

Mar 27, 2026

Rocky beach and palm trees in Barbados.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

14-night Star Collector: Captivating Caribbean Cruise

Bridgetown (Barbados)
Little Bay
Iles des Saintes
Roseau
Anse Mitan
+8 more

Aboard

Wind Spirit

From

Bridgetown, Barbados

1 Sailing

Mar 7, 2026

1 Sailing

Mar 7, 2026

Rocky beach and palm trees in Barbados.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

22-night Star Collector: Caribbean Beats & Transatlantic Treats Cruise

Bridgetown (Barbados)
Basseterre
Iles des Saintes
Roseau
Anse Mitan
+3 more

Aboard

Wind Spirit

From

Bridgetown, Barbados

1 Sailing

Mar 21, 2026

1 Sailing

Mar 21, 2026

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

7-night Windward Islands Surf & Sunsets Cruise

San Juan
Bequia
Mayreau
Soufriere
Iles des Saintes
+2 more

Aboard

Star Seeker

From

San Juan, Puerto Rico

4 Sailings

Jan 30 - Mar 13, 2026

4 Sailings

Jan 30 - Mar 13, 2026

A picturesque view of a small town nestled at the base of a lush, green mountain on Iles des Saintes, Guadeloupe, with boats moored in the deep blue water and fluffy clouds in the sky.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

7-night Classic Caribbean Cruise

St. Maarten (Philipsburg)
Charleston
Roseau
Pigeon Island
Iles des Saintes
+2 more

Aboard

Wind Spirit

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Feb 7, 2026

1 Sailing

Feb 7, 2026

An idyllic white-sand beach with turquoise water and palm trees on Jost Van Dyke, with a lush green hill in the background.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

12-night Star Collector: Ivory Beaches & Sapphire Seas of the Caribbean Cruise

St. Maarten (Philipsburg)
Sopers Hole
Jost Van Dyke
Virgin Gorda
Gustavia
+5 more

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Dec 2, 2025

1 Sailing

Dec 2, 2025

A panoramic view of Gustavia, Saint Barthélemy, featuring a bay filled with luxury yachts and sailboats, framed by lush, green hillsides dotted with houses.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

28-night Star Collector: Grand Caribbean & Panamanian Adventure Cruise

St. Maarten (Philipsburg)
St. John's
Road Bay
Virgin Gorda
Sopers Hole
+14 more

Aboard

Wind Spirit

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Feb 21, 2026

1 Sailing

Feb 21, 2026

An idyllic white-sand beach with turquoise water and palm trees on Jost Van Dyke, with a lush green hill in the background.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

14-night Star Collector: Lovely Leewards Cruise

San Juan
Cruz Bay
Basseterre
Gustavia
St. Maarten (Philipsburg)
+8 more

Aboard

Star Pride

From

San Juan, Puerto Rico

13 Sailings

Nov 2, 2025 - Jan 3, 2027

13 Sailings

Nov 2, 2025 - Jan 3, 2027

A snorkeler swims in the turquoise waters of the Baths National Park on Virgin Gorda, surrounded by massive granite boulders and palm trees.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

14-night Star Collector: Caribbean Explorations Cruise

St. Maarten (Philipsburg)
Charlestown
Roseau
Pigeon Island
Iles des Saintes
+7 more

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

19 Sailings

Dec 7, 2025 - Mar 13, 2027

19 Sailings

Dec 7, 2025 - Mar 13, 2027

A view of Pigeon Island National Landmark, St. Lucia, showing a lush, green peninsula jutting out into the ocean with waves crashing on the rocks.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

7-night Lush & Lovely Islands of the Lesser Antilles Cruise

St. Maarten (Philipsburg)
Basseterre
Gustavia
Little Bay
Iles des Saintes
+3 more

Aboard

Wind Spirit

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Feb 28, 2026

1 Sailing

Feb 28, 2026

A scenic view of a pristine beach on the San Blas Islands, Panama, with a line of tall palm trees casting shadows on the white sand and clear turquoise water.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

49-night Star Collector: Grand Caribbean & Americas Explorer Cruise

San Juan
Cruz Bay
St. John's
Iles des Saintes
Pigeon Island
+30 more

Aboard

Star Seeker

From

San Juan, Puerto Rico

1 Sailing

Mar 27, 2026

1 Sailing

Mar 27, 2026

An aerial view of Road Bay, Anguilla, showing a pristine white sand beach, lush green vegetation, and the stunningly clear turquoise water of the Caribbean Sea.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

14-night Star Collector: Caribbean Explorations Cruise

St. Maarten (Philipsburg)
Sopers Hole
Jost Van Dyke
Virgin Gorda
Gustavia
+7 more

Aboard

Wind Spirit

From

Philipsburg, St. Maarten, The Netherlands

2 Sailings

Jan 31 - Feb 7, 2026

2 Sailings

Jan 31 - Feb 7, 2026

A scenic shot of the stunning Seven Mile Beach in Grand Cayman, with a wide, sandy beach, calm turquoise water, and resorts with palm trees under a beautiful blue sky.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

18-night Star Collector: Deep Dive Into the Blue: Underwater Worlds of the Caribbean Cruise

Cozumel
Grand Cayman (George Town)
Cayman Brac
Port Antonio
Santo Domingo
+11 more

Aboard

Wind Surf

From

Cozumel, Mexico

1 Sailing

Feb 17, 2026

1 Sailing

Feb 17, 2026

A snorkeler swims in the turquoise waters of the Baths National Park on Virgin Gorda, surrounded by massive granite boulders and palm trees.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

17-night Star Collector: Hidden Gems of the Caribbean Cruise

St. Maarten (Philipsburg)
Little Bay
Roseau
Castries
Mayreau
+10 more

Aboard

Wind Spirit

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Jan 14, 2026

1 Sailing

Jan 14, 2026

An aerial view of the colorful waterfront of St. George's, Grenada, with the town's buildings nestled on a hillside and a long, rocky breakwater extending into the calm, turquoise water.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

10-night Gems Of The Leeward Islands Cruise

San Juan
Cruz Bay
St. John's
Iles des Saintes
Pigeon Island
+5 more

Aboard

Star Seeker

From

San Juan, Puerto Rico

1 Sailing

Mar 27, 2026

1 Sailing

Mar 27, 2026

An aerial view of the colorful waterfront of St. John's, Antigua, with a long pier extending into the calm, blue sea and the town's charming buildings and marina in the background.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

7-night Jewels of the Windward Islands Cruise

Bridgetown (Barbados)
Basseterre
St. John's
Iles des Saintes
Roseau
+3 more

Aboard

Wind Spirit

From

Bridgetown, Barbados

1 Sailing

Mar 7, 2026

1 Sailing

Mar 7, 2026

A panoramic view of Gustavia, Saint Barthélemy, featuring a bay filled with luxury yachts and sailboats, framed by lush, green hillsides dotted with houses.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

24-night Star Collector: Historic Caribbean: Legendary Islands, Colombia And Panama Cruise

San Juan
Cruz Bay
St. John's
Iles des Saintes
Pigeon Island
+16 more

Aboard

Star Seeker

From

San Juan, Puerto Rico

1 Sailing

Mar 27, 2026

1 Sailing

Mar 27, 2026

A scenic landscape view of Admiralty Bay in Bequia, St. Vincent and the Grenadines, with dozens of sailboats moored on the vibrant turquoise water, surrounded by lush green hills.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

10-night Blue Waters Of The Leeward Islands Cruise

St. Maarten (Philipsburg)
Little Bay
Roseau
Castries
Mayreau
+5 more

Aboard

Wind Spirit

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Jan 14, 2026

1 Sailing

Jan 14, 2026

An aerial view of the colorful waterfront of St. John's, Antigua, with a long pier extending into the calm, blue sea and the town's charming buildings and marina in the background.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

22-night Star Collector: A Lesser Antilles Odyssey Cruise

St. Maarten (Philipsburg)
St. John's
Road Bay
Virgin Gorda
Sopers Hole
+9 more

Aboard

Wind Spirit

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Feb 21, 2026

1 Sailing

Feb 21, 2026

A panoramic view of Gustavia, Saint Barthélemy, featuring a bay filled with luxury yachts and sailboats, framed by lush, green hillsides dotted with houses.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

15-night Star Collector: Antilles Adventure Cruise

St. Maarten (Philipsburg)
Basseterre
Gustavia
St. John's
Iles des Saintes
+5 more

Aboard

Wind Spirit

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Feb 28, 2026

1 Sailing

Feb 28, 2026

Rocky beach and palm trees in Barbados.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

7-night Windward Island Delights Cruise

Bridgetown (Barbados)
Basseterre
Iles des Saintes
Roseau
Mayreau
+2 more

Aboard

Wind Spirit

From

Bridgetown, Barbados

1 Sailing

Dec 28, 2025

1 Sailing

Dec 28, 2025

A beautiful panoramic view of Roseau, Dominica, with a colorful town nestled between the deep blue Caribbean Sea and a backdrop of lush green, volcanic mountains.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

15-night Star Collector: Merry Christmas & Happy New Years From The Caribbean Cruise

Oranjestad
Willemstad
Kralendijk
St. George's
Mayreau
+7 more

Aboard

Wind Spirit

From

Oranjestad, Aruba, Caribbean

1 Sailing

Dec 20, 2025

1 Sailing

Dec 20, 2025