Price Per Night:$148.22 (USD) (based on double occupancy, for comparison only)
Dec 23, 2026through Jan 04, 2027
Itinerary:
Miami, Fl, Great Stirrup Cay, Bahamas, CABO ROJO, DOMINICAN REPUBLIC, Oranjestad, Aruba, Willemstad, Netherland Antilles, PHILIPSBURG ST MAARTEN, NETHERLAND ANTILLES, ST THOMAS, VI, Tortola, British Virgin Islands, PUERTO PLATA, DOMINICAN REPUBLIC, Miami, Fl
Unveil the vibrant beauty of the Caribbean on a sun-soaked 12-day vacation. Grab a frozen drink and lounge in your private beachfront cabana on Great Stirrup Cay, our tropical paradise that’s just for you. In Oranjestad, Aruba, embrace European-Caribbean charm along vibrant avenues or seek out the calm of secluded coves. Stroll the colorful streets of Willemstad, Curacao, admiring Dutch-inspired architecture and lively markets brimming with local treasures.
Price Per Night:$667.50 (USD) (based on double occupancy, for comparison only)
Dec 27, 2026through Jan 04, 2027
Itinerary:
Miami, Puerto Plata, Dominican Republic, Isla Catalina, New Year Fireworks SJU, Saint John/Cruz Bay, Jost van Dyke, New Year Fireworks SJU, Basseterre, Charlotte Amalie (Saint Thomas), San Juan
Price Per Night:$805.00 (USD) (based on double occupancy, for comparison only)
Jan 28, 2026through Feb 07, 2026
Itinerary:
St. John's, Antigua, Gustavia, St. Barts, Sailing Sir Francis Drake Channel, The Bight - Norman Island, British Virgin Islands, White Bay, Jost van Dyke (B.V.I.), Sopers Hole - Tortola, British Virgin Islands (BVI, Spanish Town - Virgin Gorda, British Virgin Island, Beach, Captain's Best, British Virgin Islands (B.V, Basseterre, St. Kitts (morning), South Friars Bay - Beach, St. Kitts (afternoon)...
Price Per Night:$281.43 (USD) (based on double occupancy, for comparison only)
Dec 06, 2025through Dec 13, 2025
Itinerary:
Philipsburg, St. Maarten, Road Bay, Anguilla, White Bay, Jost van Dyke (B.V.I.), Sopers Hole - Tortola, British Virgin Islands (BVI, Sailing Sir Francis Drake Channel, The Bight - Norman Island, British Virgin Islands, Spanish Town - Virgin Gorda, British Virgin Island, Beach, Captain's Best, British Virgin Islands (B.V, Basseterre, St. Kitts (morning), South Friars Bay - Beach, St. Kitts (afternoon)...
Price Per Night:$181.36 (USD) (based on double occupancy, for comparison only)
Nov 21, 2026through Dec 05, 2026
Itinerary:
San Juan, Virgin Gorda, St. John's, Antigua, Saint- Pierre, Port Elizabeth, Bequia, Saint George's, Scarborough, Tobago, Bridgetown, Castries, Roseau...
Price Per Night:$132.81 (USD) (based on double occupancy, for comparison only)
Feb 16, 2027through Mar 09, 2027
Itinerary:
Miami, FL, USA, Grand Cayman, Cayman Islands, Montego Bay, Jamaica, Roatan, Honduras, Costa Maya, Mexico, Cozumel, Mexico, Miami, FL, USA, San Juan, Puerto Rico, Antigua, Dominica, Dominica...
Take each day as slowly as you like on this 21-night sailing in the Caribbean that includes captivating ports like Montego Bay in Jamaica, San Juan in Puerto Rico, and Philipsburg in St. Maarten.
Price Per Night:$189.42 (USD) (based on double occupancy, for comparison only)
Nov 18, 2025through Dec 07, 2025
Itinerary:
Lisbon, St. John's, 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
Caribbean beaches, vibrant tropical fish, and savory West Indies cuisine during this 19-day transatlantic crossing. Relax, unwind and refocus with back-to-back spa days throughout your ocean crossing and dine on award-winning meals paired with the company of your new Windstar family. Relive history while sailing aboard a former America's Cup competition sailboat or cook up delicious French meals with a certified chef in Grand Case outside Philipsburg, St. Maarten.
Price Per Night:$132.55 (USD) (based on double occupancy, for comparison only)
Dec 27, 2025through Jan 05, 2026
Itinerary:
Fort Lauderdale, Florida, Puerto Plata, Dominican Rep, San Juan, Puerto Rico, Philipsburg, St. Maarten, Tortola, B.V.I., St. Croix, U.S.V.I., Fort Lauderdale, Florida
Price Per Night:$182.72 (USD) (based on double occupancy, for comparison only)
Dec 18, 2026through Jan 05, 2027
Itinerary:
San Juan, Charlotte Amalie, St. Thomas, Virgin Gorda, St. John's, Antigua, Gustavia, Saint- Pierre, Port Elizabeth, Bequia, Scarborough, Tobago, Mayreau, Grenadines, Bridgetown...
Price Per Night:$145.12 (USD) (based on double occupancy, for comparison only)
Feb 07, 2027through Feb 14, 2027
Itinerary:
San Juan, Pr, PHILIPSBURG ST MAARTEN, NETHERLAND ANTILLES, Basseterre, Saint Kitts - Nevis, Bridgetown, Barbados, ST LUCIA, SAINT LUCIA, ST THOMAS, VI, Tortola, British Virgin Islands, San Juan, Pr
Sail away from San Juan for seven days of pure island enchantment, where each port beckons with promise and charm. Start in Road Town, Tortola, where lush hills and secret coves await - dive into crystal waters where you might see a gentle sea turtle or journey inland to the mystical Baths, where giant granite boulders create hidden grottos.
Price Per Night:$404.40 (USD) (based on double occupancy, for comparison only)
Sep 29, 2025through Oct 09, 2025
Itinerary:
Fort Lauderdale, Florida, Tortola, B.V.I., St. Johns, Antigua, Bridgetown, Barbados, Castries, St. Lucia, Basseterre, St Kitts & Nevis, Fort Lauderdale, Florida
Price Per Night:$185.57 (USD) (based on double occupancy, for comparison only)
Nov 07, 2026through Nov 14, 2026
Itinerary:
San Juan, Puerto Rico, Virgin Gorda, St. John's, Antigua, St. Pierre, Port Elizabeth, Bequia, Saint George's, Scarborough, Tobago, Bridgetown
Price Per Night:$499.93 (USD) (based on double occupancy, for comparison only)
Dec 06, 2026through Dec 20, 2026
Itinerary:
Miami, San Juan, Virgin Gorda, Carambola Beach, Roseau, Martinique, Terre-De-Haut, Montserrat, Road Bay, Great Harbour, Jost Van Dyke...
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:$167.37 (USD) (based on double occupancy, for comparison only)
Dec 26, 2026through Jan 02, 2027
Itinerary:
San Juan, Puerto Rico, Tortola, B.V.I., Philipsburg, St. Maarten, St. Johns, Antigua, Basseterre, St Kitts & Nevis, St. Croix, U.S.V.I., Cruising, San Juan, Puerto Rico
