from
$2,359.00
(USD)
Per Person
Dec 05, 2026
through Dec 18, 2026
through Dec 18, 2026
Nights:
13
Ship:
Azamara Journey
Price Per Night:$181.46 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Dec 05, 2026
through Dec 18, 2026
Itinerary:
San Juan, Puerto Rico, Virgin Gorda, St. John's, Antigua, St. Pierre, Port Elizabeth, Bequia, Saint George's, Scarborough, Tobago, Bridgetown, Castries, Roseau...
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$4,760.00
(USD)
Per Person
Feb 10, 2027
through Feb 17, 2027
through Feb 17, 2027
Nights:
7
Ship:
Le Bougainville
Price Per Night:$680.00 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Feb 10, 2027
through Feb 17, 2027
Itinerary:
Fort-de-France, Antigua, Virgin Gorda, Jost Van Dyke, Basseterre, Saint Kitts, Deshaies, Marie-Galante, Fort-de-France
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$1,381.00
(USD)
Per Person
Feb 01, 2026
through Feb 15, 2026
through Feb 15, 2026
Nights:
14
Ship:
Grand Princess
Price Per Night:$98.64 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Feb 01, 2026
through Feb 15, 2026
Itinerary:
San Juan, Tortola, St Kitts, Antigua, Dominica, Barbados, San Juan, St Thomas, St Maarten, Antigua...
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$1,495.00
(USD)
Per Person
Oct 19, 2025
through Nov 02, 2025
through Nov 02, 2025
Nights:
14
Ship:
Grand Princess
Price Per Night:$106.79 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Oct 19, 2025
through Nov 02, 2025
Itinerary:
San Juan, St Thomas, St Maarten, Antigua, St Lucia, Barbados, San Juan, Tortola, St Kitts, Dominica...
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$6,659.00
(USD)
Per Person
+ $21,306.00 taxes/fees
Sep 17, 2026
through Oct 27, 2026
through Oct 27, 2026
Nights:
40
Ship:
Queen Elizabeth
Price Per Night:$166.48 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Sep 17, 2026
through Oct 27, 2026
Itinerary:
Seattle, Washington, Ketchikan, Alaska, Juneau, Alaska, Tracy Arm, Alaska, Victoria, BC, Canada, Seattle, Washington, Los Angeles, California, Cabo San Lucas, Mexico, Puerto Quetzal, Guatemala, Fuerte Amador (tours to PanamaCity), Panama...
Spend 40 nights on Queen Elizabeth enjoying all the experiences on board when you’re not exploring the sights and sounds that await in Alaska, North America, Central America, and the Caribbean.
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$3,944.00
(USD)
Per Person
+ $7,329.00 taxes/fees
Dec 15, 2025
through Jan 11, 2026
through Jan 11, 2026
Nights:
27
Ship:
Queen Mary 2
Price Per Night:$146.07 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Dec 15, 2025
through Jan 11, 2026
Itinerary:
London (Southampton), England, New York, New York, St. Thomas, Virgin Islands, U.S.A., St. Kitts, ST Kitts/Nevis, English Harbour, Antigua, St. Maarten, Netherlands Antilles, Tortola, B.V.I., New York, New York, London (Southampton), England
Enjoy a Christmas and New Year like no other on this Caribbean voyage. Be swept away in the festive spirit on board and spend time however you please, exploring the likes of Basseterre and Tortola.
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$1,009.00
(USD)
Per Person
Nov 13, 2025
through Nov 23, 2025
through Nov 23, 2025
Nights:
10
Ship:
Enchanted Princess
Price Per Night:$100.90 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Nov 13, 2025
through Nov 23, 2025
Itinerary:
Fort Lauderdale, Princess Cays, St Thomas, St Maarten, Antigua, St Kitts, Tortola, Fort Lauderdale
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$3,599.00
(USD)
Per Person
+ $81.00 taxes/fees
Nov 18, 2025
through Dec 07, 2025
through Dec 07, 2025
Nights:
19
Ship:
Wind Surf
Price Per Night:$189.42 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Nov 18, 2025
through 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.
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$2,099.00
(USD)
Per Person
+ $51.00 taxes/fees
Dec 02, 2025
through Dec 07, 2025
through Dec 07, 2025
Nights:
5
Ship:
Wind Surf
Price Per Night:$419.80 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Dec 02, 2025
through 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.
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$5,300.00
(USD)
Per Person
Jan 10, 2027
through Jan 20, 2027
through Jan 20, 2027
Nights:
10
Ship:
Silver Shadow
Price Per Night:$530.00 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Jan 10, 2027
through Jan 20, 2027
Itinerary:
San Juan, Jost Van Dyke (British Virgin Islands), Gustavia, St Barthelemy, St. John's, Little Bay, Montserrat, Les Saintes, Basseterre, St. Kitts, Trois Ilets, Castries, St George's...
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$991.17
(USD)
Per Person
Mar 01, 2026
through Mar 08, 2026
through Mar 08, 2026
Nights:
7
Ship:
Brilliance of the Seas
Price Per Night:$141.60 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Mar 01, 2026
through Mar 08, 2026
Itinerary:
San Juan, Puerto Rico, Cruising, Willemstad, Curacao, Oranjestad, Aruba, Cruising, Tortola, B.V.I., San Juan, Puerto Rico
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$1,171.60
(USD)
Per Person
Dec 26, 2026
through Jan 02, 2027
through Jan 02, 2027
Nights:
7
Ship:
Radiance of the Seas
Price Per Night:$167.37 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Dec 26, 2026
through 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
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$2,471.00
(USD)
Per Person
Dec 21, 2025
through Jan 04, 2026
through Jan 04, 2026
Nights:
14
Ship:
Grand Princess
Price Per Night:$176.50 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Dec 21, 2025
through Jan 04, 2026
Itinerary:
San Juan, Tortola, Guadeloupe (Pointe-A-Pitre), Dominica, Grenada, Barbados, San Juan, St Thomas, St Maarten, Antigua...
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$1,390.00
(USD)
Per Person
+ $251.00 taxes/fees
Nov 15, 2026
through Nov 25, 2026
through Nov 25, 2026
Nights:
10
Ship:
Brilliant Lady
Price Per Night:$139.00 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Nov 15, 2026
through Nov 25, 2026
Itinerary:
Miami, Florida, Sailing, Philipsburg, St. Maarten, Tortola, Basseterre, St. John's, Sailing, Beach Club at Bimini, Miami, Florida
Depart Miami and sail 2 days to the beautiful beaches of Saint Maarten, Philipsburg, followed by the ancient ruins and glowing lagoons of Tortola, British Virgin Islands. The next day you'll awake in Basseterre, St. Kitts followed by the epitome of paradise with top-of-the-line everything - St. John's, Antigua. Finally, sail 2 days to the private Beach Club at Bimini before returning to Miami.
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$5,019.25
(USD)
Per Person
Mar 11, 2026
through Mar 26, 2026
through Mar 26, 2026
Nights:
15
Ship:
Explora II
Price Per Night:$334.62 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Mar 11, 2026
through Mar 26, 2026
Itinerary:
San Juan, Road Bay, St. John's (Antigua), St. Maarten/Philipsburg, Spanish Town (Virgin Gorda), Miami, Charlotte Amalie (Saint Thomas), Terre-de-Haut, Bridgetown, Martinique/Fort de France...
Sapphire shorelines and emerald hilltops dazzle under the Caribbean sun on our exploration from the paradise of Road Bay through St John's striking shoreline to the patchwork peaks of Phillipsburg. Gentle winds escort us onwards to the heritage of Spanish Town, the rhythms of Miami and heart-shaped, heart-stopping Magen's Bay in St Thomas. Pause to browse through pretty French-influenced markets in Terre-de-Haut and Fort-de-France, then watch the sunrise sparkle over lively St Kitts.
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$1,272.00
(USD)
Per Person
+ $238.00 taxes/fees
Nov 08, 2026
through Nov 16, 2026
through Nov 16, 2026
Nights:
8
Ship:
Resilient Lady
Price Per Night:$159.00 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Nov 08, 2026
through Nov 16, 2026
Itinerary:
Miami, Florida, Sailing, Puerto Plata, San Juan, Tortola, Sailing, Beach Club at Bimini, Miami, Florida
This stunning sojourn leaves Miami and sails a day to the picturesque silvers coasts, crystalline cenotes and lush jungles of Puerto Plata, Dominican Republic. Next, awake to the blissful sound of crashing waves in San Juan before arriving the next day in magical Tortola, nestled into the British Virgin Islands. Then sail two days to our private Beach Club at Bimini before returning to Miami.
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$1,385.14
(USD)
Per Person
Dec 31, 2026
through Jan 07, 2027
through Jan 07, 2027
Nights:
7
Ship:
Norwegian Getaway
Price Per Night:$197.88 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Dec 31, 2026
through Jan 07, 2027
Itinerary:
Orlando-Beaches-Port Canaveral, Fl, PUERTO PLATA, DOMINICAN REPUBLIC, ST THOMAS, VI, Tortola, British Virgin Islands, Great Stirrup Cay, Bahamas, Orlando-Beaches-Port Canaveral, Fl
Feel Free to turn up the chill in The Caribbean with Norwegian. In Puerto Plata, learn about the local history at the 16th century Fortaleza San Felipe or embark on a jungle adventure with a zip line, ATV and hiking to reach the cascading Damajagua waterfalls. Then snorkel among colorful tropical fish and green sea turtles in St. Thomas at Turtle Cove. Unwind on our private island, Great Stirrup Cay, with a dip in our new exclusive lagoon and a massage at Mandara Spa.
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$2,575.00
(USD)
Per Person
Feb 15, 2026
through Mar 07, 2026
through Mar 07, 2026
Nights:
20
Ship:
Enchanted Princess
Price Per Night:$128.75 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Feb 15, 2026
through Mar 07, 2026
Itinerary:
Fort Lauderdale, Princess Cays, St Thomas, St Maarten, Antigua, St Kitts, Tortola, Fort Lauderdale, Princess Cays, St Thomas...
Other Categories Starting At:
Inside
Outside
Balcony
Suite
Oct 29, 2025
through Nov 08, 2025
through Nov 08, 2025
Nights:
10
Ship:
Celebrity Reflection
Price Per Night:$154.04 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Oct 29, 2025
through Nov 08, 2025
Itinerary:
Fort Lauderdale, Florida, Tortola, B.V.I., St. Johns, Antigua, Bridgetown, Barbados, Castries, St. Lucia, Basseterre, St Kitts & Nevis, Fort Lauderdale, Florida
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$2,399.00
(USD)
Per Person
+ $68.00 taxes/fees
Mar 28, 2026
through Apr 03, 2026
through Apr 03, 2026
Nights:
6
Ship:
Wind Surf
Price Per Night:$399.83 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Mar 28, 2026
through Apr 03, 2026
Itinerary:
Philipsburg, St. Maarten, St. John's, 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.
Other Categories Starting At:
Inside
Outside
Balcony
Suite
