Price Per Night:$399.80 (USD) (based on double occupancy, for comparison only)
Dec 02, 2025through Dec 07, 2025
Itinerary:
Philipsburg, St. Maarten, Jost Van Dyke, Great Harbour, Soper's Hole, Jost Van Dyke, Great Harbour, Virgin Gorda / Prickly Pear, British Virgin Islands, Gustavia, Philipsburg, St. Maarten
The British Virgin Islands is known as the yachting capital of the Caribbean and this five-day escape shows you why. Come with us to charming islands with a laid-back attitude, places where you can still find incredible natural beauty, and colonial towns that effortlessly blend Dutch, French, and Caribbean cultures. Explore 17th century forts and duty-free shopping on St. Maarten and St. Bart. Go snorkeling or take a Jeep off-roading on mountainous Tortola.
Price Per Night:$621.00 (USD) (based on double occupancy, for comparison only)
Dec 21, 2024through Jan 04, 2025
Itinerary:
Bridgetown, Barbados, Rodney Bay, St. Lucia, Pointe-a-pitre, , Carambola Beach, Great Harbour, Jost Van Dyke, San Juan, Puerto Rico, Willemstad, Curacao, Kralendijk, Bonaire, Oranjestad, Aruba...
Aboard The Yachts of Seabourn, the world is more intimate and more enchanting. Here, you’ll explore ports rarely visited by larger ships and meet people who are happy to show you around their hidden corner of the globe. With their unmatched sense of style, elegance and grace, The Yachts of Seabourn beckon you to travel beyond the bounds of the imagination. Aboard Seabourn, every desire is met promptly and with a welcoming smile. Whether it's a warm blanket and a cup of gourmet hot chocolate as you drift along the Norwegian Fjords or a relaxing neck massage poolside, you'll feel that you're a member of a very exclusive club.
Price Per Night:$342.71 (USD) (based on double occupancy, for comparison only)
Dec 14, 2025through Dec 21, 2025
Itinerary:
Philipsburg, St. Maarten, Falmouth Harbour, Road Bay, Jost Van Dyke, Great Harbour, Soper's Hole, Jost Van Dyke, Great Harbour, Virgin Gorda / Prickly Pear, British Virgin Islands, Gustavia, Philipsburg, St. Maarten
Bask on remote beaches resplendent in natural beauty during this relaxing, unrushed, and uncrowded 7-day getaway to secluded Caribbean destinations Windstar specializes in. Board a private speedboat bound for Little Bay, Anguilla’s smallest and most private beach, then snorkel among flitting grunts, wrasses and snappers. Guide your own rigid inflatable boat (RIB) through Sir Francis Drake Waterway bays and isles around Jost Van Dyke.
Price Per Night:$453.14 (USD) (based on double occupancy, for comparison only)
Jan 24, 2026through Feb 07, 2026
Itinerary:
Bridgetown, Barbados, Castries, Saint Lucia, Montserrat, St. Johns, Antigua and Barbuda, Carambola Beach, Great Harbour, Jost Van Dyke, Philipsburg, Sint Maarten, Frenchmans Cay, Carambola Beach, ...
Aboard The Yachts of Seabourn, the world is more intimate and more enchanting. Here, you’ll explore ports rarely visited by larger ships and meet people who are happy to show you around their hidden corner of the globe. With their unmatched sense of style, elegance and grace, The Yachts of Seabourn beckon you to travel beyond the bounds of the imagination. Aboard Seabourn, every desire is met promptly and with a welcoming smile. Whether it's a warm blanket and a cup of gourmet hot chocolate as you drift along the Norwegian Fjords or a relaxing neck massage poolside, you'll feel that you're a member of a very exclusive club.
Price Per Night:$108.55 (USD) (based on double occupancy, for comparison only)
Dec 06, 2025through Dec 19, 2025
Itinerary:
San Juan, Puerto Rico, Virgin Gorda, St. John's, Antigua, St. Pierre, Port Elizabeth, Bequia, Saint George's, Scarborough, Tobago, Bridgetown, Castries, Roseau...
Price Per Night:$639.90 (USD) (based on double occupancy, for comparison only)
Nov 14, 2024through Nov 24, 2024
Itinerary:
Miami, Cruising The Atlantic Ocean, Puerto Plata, San Juan, Gustavia, Roseau, St. John's, Tortola, Cruising The Atlantic Ocean, Cruising The Bahamian Waters...
Price Per Night:$335.64 (USD) (based on double occupancy, for comparison only)
Feb 08, 2025through Feb 22, 2025
Itinerary:
Philipsburg, St. Maarten, Roseau, Pigeon Island, Les Saintes, Basseterre, Gustavia, Philipsburg, St. Maarten, Falmouth Harbour, Jost Van Dyke, Great Harbour, Virgin Gorda / Prickly Pear, British Virgin Islands...
Skip the usual Caribbean cruise stops and discover the small harbors, overlooked havens and most remote secrets among the Leeward Islands. Whether you’re looking for hidden shops, sampling new cuisine or seeking a local place to sip rum cocktails over the melodic beat of steel drums, this highly personalized adventure is an intimate opportunity to familiarize yourself with the lesser-known charms of Les Saintes, Anse Mitan, Pigeon Island and much more.
Price Per Night:$558.86 (USD) (based on double occupancy, for comparison only)
Feb 15, 2025through Mar 01, 2025
Itinerary:
Bridgetown, Barbados, Castries, Saint Lucia, Terre-de-Haut, Iles des Saintes, Guadeloupe, St. Johns, Antigua and Barbuda, Great Harbour, Jost Van Dyke, Carambola Beach, Philipsburg, Sint Maarten, Frenchmans Cay, Carambola Beach, Fort-De-France, Martinique...
Aboard The Yachts of Seabourn, the world is more intimate and more enchanting. Here, you’ll explore ports rarely visited by larger ships and meet people who are happy to show you around their hidden corner of the globe. With their unmatched sense of style, elegance and grace, The Yachts of Seabourn beckon you to travel beyond the bounds of the imagination. Aboard Seabourn, every desire is met promptly and with a welcoming smile. Whether it's a warm blanket and a cup of gourmet hot chocolate as you drift along the Norwegian Fjords or a relaxing neck massage poolside, you'll feel that you're a member of a very exclusive club.
Price Per Night:$102.33 (USD) (based on double occupancy, for comparison only)
Oct 16, 2025through Nov 06, 2025
Itinerary:
Miami, Florida, San Juan, Puerto Rico, Antigua, St Lucia, Saint Lucia, Barbados, Barbados, St. Maarten, Netherlands Antilles, Tortola, B.V.I., Miami, Florida, Amber Cove,Dominican Republic, Montego Bay, Jamaica...
The shores of Central America and the Caribbean await on this voyage. From tree-lined beaches in Montego Bay to Mayan ruins in Belize, you’ll find a little slice of paradise in every port you visit.
Price Per Night:$285.67 (USD) (based on double occupancy, for comparison only)
Jan 04, 2026through Jan 25, 2026
Itinerary:
Philipsburg, St. Maarten, Falmouth Harbour, Road Bay, Jost Van Dyke, Great Harbour, Soper's Hole, Jost Van Dyke, Great Harbour, Virgin Gorda / Prickly Pear, British Virgin Islands, Gustavia, Philipsburg, St. Maarten, Basseterre...
Embrace extraordinary experiences exclusive to small ship cruising during this three-week exploration of the Caribbean’s Lesser Antilles island chain. Swim with dolphins during an extended overnight stay in Jost Van Dyke in the British Virgin Islands. Savor African, European, and Indian ingredients and influences in popular Caribbean dishes as you sample spicy regional cuisine in the Fairview Great House on St. Kitts.
Price Per Night:$89.21 (USD) (based on double occupancy, for comparison only)
Mar 15, 2025through Mar 29, 2025
Itinerary:
New York, New York, St. Thomas, Virgin Islands, U.S.A., St. Maarten, Netherlands Antilles, St Lucia, Saint Lucia, Barbados, Barbados, Dominica, Dominica, St. Kitts, ST Kitts/Nevis, Tortola, B.V.I., New York, New York
Sail round trip from New York to the palm-fringed beaches of the Caribbean on this 14-night voyage on Queen Mary 2. On board, fill your days with various activities, or perhaps do nothing at all.
Price Per Night:$199.95 (USD) (based on double occupancy, for comparison only)
Dec 13, 2026through Jan 03, 2027
Itinerary:
London (Southampton), England, New York, New York, Amber Cove,Dominican Republic, Tortola, B.V.I., Dominica, Dominica, Barbados, Barbados, St Lucia, Saint Lucia, St. Kitts, ST Kitts/Nevis, New York, New York
What could be better than Christmas spent in the Caribbean sunshine? This festive voyage offers days ashore to explore the likes of Dominica and Barbados, with plenty of festive cheer on board.
Price Per Night:$209.05 (USD) (based on double occupancy, for comparison only)
Dec 20, 2026through Jan 11, 2027
Itinerary:
New York, New York, Amber Cove,Dominican Republic, Tortola, B.V.I., Dominica, Dominica, Barbados, Barbados, St Lucia, Saint Lucia, St. Kitts, ST Kitts/Nevis, New York, New York, London (Southampton), England
Join in the festive fun and games on board as you celebrate Christmas in the Caribbean sunshine. Then, enjoy a New Year’s Eve to remember, counting down to midnight as you sail toward New York.