Oct 18, 2025
through Oct 29, 2025
through Oct 29, 2025
Nights:
11
Ship:
Celebrity Reflection
Price Per Night:$123.90 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Oct 18, 2025
through Oct 29, 2025
Itinerary:
Fort Lauderdale, Florida, Philipsburg, St. Maarten, Fort- De- France, Martinique, Castries, St. Lucia, Bridgetown, Barbados, Roseau, Dominica, St. Johns, Antigua, Fort Lauderdale, Florida
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$6,899.00
(USD)
Per Person
Nov 24, 2026
through Dec 19, 2026
through Dec 19, 2026
Nights:
25
Ship:
Insignia
Price Per Night:$275.96 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Nov 24, 2026
through Dec 19, 2026
Itinerary:
Miami, Tortola, St. John's, Castries, Scarborough, Cruising The Amazon River, Santarem (Amazon River), Boca Da Valeria (Amazon River), Manaus (Amazon River), Parintins (Amazon River)...
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$2,020.00
(USD)
Per Person
+ N/A taxes/fees
Dec 13, 2025
through Dec 20, 2025
through Dec 20, 2025
Nights:
7
Ship:
Royal Clipper
Price Per Night:$288.57 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Dec 13, 2025
through Dec 20, 2025
Itinerary:
Bridgetown, Barbados, Rodney Bay, St. Lucia, Sail with Star Flyer to Cabrits, Cabrits, Dominica, Falmouth Harbour, Antigua, Basseterre, St. Kitts (morning), South Friars Bay - Beach, St. Kitts (afternoon), Terre de Haut, Iles des Saintes, Beach, Martinique, Bridgetown, Barbados
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$4,679.00
(USD)
Per Person
+ $214.00 taxes/fees
Jan 04, 2026
through Feb 08, 2026
through Feb 08, 2026
Nights:
35
Ship:
Queen Victoria
Price Per Night:$133.69 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Jan 04, 2026
through Feb 08, 2026
Itinerary:
London (Southampton), England, Madeira, Portugal, Barbados, Barbados, St Lucia, Saint Lucia, Grenada, Grenada, St. Vincent, St. Vincent/Grenadines, Curacao, Antilles, Aruba, Aruba, Dominica, Dominica, Antigua...
This roundtrip Caribbean voyage from Southampton is the perfect way to escape the January blues. Enjoy an enviable start to 2026, soaking up the sun on some of the world’s best white-sand beaches.
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$1,003.60
(USD)
Per Person
Dec 20, 2025
through Dec 27, 2025
through Dec 27, 2025
Nights:
7
Ship:
Jewel of the Seas
Price Per Night:$143.37 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Dec 20, 2025
through Dec 27, 2025
Itinerary:
San Juan, Puerto Rico, Charlotte Amalie, St. Thomas, Philipsburg, St. Maarten, St. Croix, U.S.V.I., Roseau, Dominica, Bridgetown, Barbados, Cruising, San Juan, Puerto Rico
Other Categories Starting At:
Inside
Outside
Balcony
Suite
Jan 23, 2026
through Feb 02, 2026
through Feb 02, 2026
Nights:
10
Ship:
Celebrity Ascent
Price Per Night:$160.34 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Jan 23, 2026
through Feb 02, 2026
Itinerary:
Fort Lauderdale, Florida, St. Johns, Antigua, Roseau, Dominica, Bridgetown, Barbados, Castries, St. Lucia, Basseterre, St Kitts & Nevis, Fort Lauderdale, Florida
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$3,529.00
(USD)
Per Person
+ $5,904.00 taxes/fees
Dec 20, 2026
through Jan 03, 2027
through Jan 03, 2027
Nights:
14
Ship:
Queen Mary 2
Price Per Night:$252.07 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Dec 20, 2026
through Jan 03, 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
Enjoy sunny days in Barbados, Dominica, and Saint Lucia, among other tropical islands, on this Christmas voyage to the Caribbean. You’ll also celebrate New Year’s on board – the perfect start to 2024.
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$1,121.33
(USD)
Per Person
Dec 27, 2026
through Jan 03, 2027
through Jan 03, 2027
Nights:
7
Ship:
Brilliance of the Seas
Price Per Night:$160.19 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Dec 27, 2026
through Jan 03, 2027
Itinerary:
San Juan, Puerto Rico, Charlotte Amalie, St. Thomas, St. Croix, U.S.V.I., St. Johns, Antigua, Roseau, Dominica, Cruising, Philipsburg, St. Maarten, San Juan, Puerto Rico
Other Categories Starting At:
Inside
Outside
Balcony
Suite
Mar 01, 2025
through Mar 22, 2025
through Mar 22, 2025
Nights:
21
Ship:
Eurodam
Price Per Night:$107.57 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Mar 01, 2025
through Mar 22, 2025
Itinerary:
Fort Lauderdale, Half Moon Cay, St Thomas, Antigua, Point-A-Pitre, Roseau, St Kitts, St Maarten, Fort Lauderdale, Half Moon Cay...
Other Categories Starting At:
Inside
Outside
Balcony
Suite
21-Day Southern & Eastern Caribbean: Abc & Leeward Islands
Roundtrip from Fort Lauderdale, Florida, US
Roundtrip from Fort Lauderdale, Florida, US
from
$3,071.00
(USD)
Per Person
+ $275.00 taxes/fees
Nov 29, 2025
through Dec 20, 2025
through Dec 20, 2025
Nights:
21
Ship:
Koningsdam
Price Per Night:$146.24 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Nov 29, 2025
through Dec 20, 2025
Itinerary:
Fort Lauderdale, Florida, US, Half Moon Cay, Bahamas, Grand Turk, Turks and Caicos, Amber Cove, Dominican Republic, Days At Sea, Willemstad, Curacao, Kralendijk, Bonaire, Oranjestad, Aruba, Days At Sea, Fort Lauderdale, Florida, US...
Other Categories Starting At:
Inside
Outside
Balcony
Suite
Mar 07, 2025
through Mar 17, 2025
through Mar 17, 2025
Nights:
10
Ship:
Celebrity Beyond
Price Per Night:$237.18 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Mar 07, 2025
through Mar 17, 2025
Itinerary:
Fort Lauderdale, Florida, Philipsburg, St. Maarten, Roseau, Dominica, St. George's, Grenada, Bridgetown, Barbados, St. Johns, Antigua, Fort Lauderdale, Florida
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$9,999.00
(USD)
Per Person
Mar 05, 2025
through Mar 19, 2025
through Mar 19, 2025
Nights:
14
Ship:
Seven Seas Grandeur
Price Per Night:$714.21 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Mar 05, 2025
through Mar 19, 2025
Itinerary:
Miami, Cruising The Florida Straits, Cruising The Caribbean Sea, Oranjestad, Willemstad, Bonaire (Kralendijk), St. George's, Kingstown, Bridgetown, Roseau...
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$3,709.00
(USD)
Per Person
+ $250.00 taxes/fees
Mar 22, 2025
through Apr 12, 2025
through Apr 12, 2025
Nights:
21
Ship:
Eurodam
Price Per Night:$176.62 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Mar 22, 2025
through Apr 12, 2025
Itinerary:
Fort Lauderdale, Florida, US, Days At Sea, Philipsburg, Sint Maarten, St. Johns, Antigua and Barbuda, Castries, Saint Lucia, Roseau, Dominica, Basseterre, St Kitts and Nevis, St. Thomas, U.S.V.I., Days At Sea, Half Moon Cay, Bahamas...
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$1,133.10
(USD)
Per Person
Dec 19, 2026
through Dec 26, 2026
through Dec 26, 2026
Nights:
7
Ship:
Radiance of the Seas
Price Per Night:$161.87 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Dec 19, 2026
through Dec 26, 2026
Itinerary:
San Juan, Puerto Rico, Charlotte Amalie, St. Thomas, St. Croix, U.S.V.I., Philipsburg, St. Maarten, St. Johns, Antigua, Roseau, Dominica, Cruising, San Juan, Puerto Rico
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$5,099.00
(USD)
Per Person
+ $95.00 taxes/fees
Jan 14, 2026
through Jan 31, 2026
through Jan 31, 2026
Nights:
17
Ship:
Wind Spirit
Price Per Night:$299.94 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Jan 14, 2026
through Jan 31, 2026
Itinerary:
Philipsburg, St. Maarten, Basseterre, Roseau, Castries, Anse Mitan, Les Saintes, Charlestown, Virgin Gorda / Prickly Pear, British Virgin Islands, Jost Van Dyke, Great Harbour, Gustavia...
Dive, dine, and delight in iconic Caribbean island destinations during a far-ranging Caribbean loop that conveniently begins and ends in Philipsburg on St. Maarten. Cruise a kayak through sapphire waters near Little Bay, Monserrat, and peer at shadowy fruit bats suspended throughout coastal caves. Drift and spin in a floating tube on a rainforest stream outside Roseau on Dominica prior to sipping rum cocktails mixed with tangy tropical juices.
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$4,376.00
(USD)
Per Person
+ $50.00 taxes/fees
Feb 07, 2026
through Feb 14, 2026
through Feb 14, 2026
Nights:
7
Ship:
Seabourn Ovation
Price Per Night:$625.14 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Feb 07, 2026
through Feb 14, 2026
Itinerary:
Barbados, Carambola Beach, Trois Ilets, Point-A-Pitre, Roseau, Rodney Bay, Barbados
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.
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$2,759.00
(USD)
Per Person
Dec 06, 2025
through Dec 19, 2025
through Dec 19, 2025
Nights:
13
Ship:
Azamara Quest
Price Per Night:$212.23 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Dec 06, 2025
through 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...
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$1,139.00
(USD)
Per Person
Dec 12, 2026
through Dec 18, 2026
through Dec 18, 2026
Nights:
6
Ship:
Azamara Journey
Price Per Night:$189.83 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Dec 12, 2026
through Dec 18, 2026
Itinerary:
Bridgetown, Castries, Roseau, Basseterre, Charlestown, Philipsburg, San Juan, Puerto Rico
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$3,499.00
(USD)
Per Person
+ $17.00 taxes/fees
Feb 08, 2025
through Feb 15, 2025
through Feb 15, 2025
Nights:
7
Ship:
Wind Spirit
Price Per Night:$499.86 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Feb 08, 2025
through Feb 15, 2025
Itinerary:
Bridgetown, Basseterre, Les Saintes, Roseau, Anse Mitan, Pigeon Island, Bridgetown
This is the Caribbean of days gone by – deep blue waters, quiet coves and tropical islands dotted with powdery beaches and lush green hillsides. Sail from the rugged natural beauty of St. Lucia to little-known isles that are off the tourist radar. From colorful Bequia and Mayreau in St. Vincent & the Grenadines to the open-air markets of exotic St. George’s, you’ll discover a part of the Caribbean that remains authentic and unspoiled.
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$2,020.00
(USD)
Per Person
+ N/A taxes/fees
Mar 21, 2026
through Mar 28, 2026
through Mar 28, 2026
Nights:
7
Ship:
Royal Clipper
Price Per Night:$288.57 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Mar 21, 2026
through Mar 28, 2026
Itinerary:
Bridgetown, Barbados, Rodney Bay, St. Lucia, Sail with Star Flyer to Cabrits, Cabrits, Dominica, Falmouth Harbour, Antigua, Basseterre, St. Kitts (morning), South Friars Bay - Beach, St. Kitts (afternoon), Terre de Haut, Iles des Saintes, Beach, Martinique, Bridgetown, Barbados
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$5,199.00
(USD)
Per Person
Jan 22, 2025
through Jan 29, 2025
through Jan 29, 2025
Nights:
7
Ship:
Sirena
Price Per Night:$742.71 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Jan 22, 2025
through Jan 29, 2025
Itinerary:
Bridgetown, Fort-De-France, Gustavia, Roseau, Castries, Kingstown, St. George's, Bridgetown
from
$7,200.00
(USD)
Per Person
Feb 16, 2027
through Feb 27, 2027
through Feb 27, 2027
Nights:
11
Ship:
Silver Shadow
Price Per Night:$654.55 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Feb 16, 2027
through Feb 27, 2027
Itinerary:
Bridgetown, Bequia, St George's, Castries, Trois Ilets, Roseau, Les Saintes, Little Bay, Montserrat, Basseterre, St. Kitts, Gustavia, St Barthelemy...
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$4,099.00
(USD)
Per Person
+ $79.00 taxes/fees
Jan 31, 2026
through Feb 14, 2026
through Feb 14, 2026
Nights:
14
Ship:
Wind Spirit
Price Per Night:$292.79 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Jan 31, 2026
through Feb 14, 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, Charlestown...
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.
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$6,034.00
(USD)
Per Person
+ $115.00 taxes/fees
Dec 02, 2025
through Dec 14, 2025
through Dec 14, 2025
Nights:
12
Ship:
Seabourn Ovation
Price Per Night:$502.83 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Dec 02, 2025
through Dec 14, 2025
Itinerary:
San Juan, Aruba, Curacao, Bonaire, Trois Ilets, Roseau, Montserrat, Carambola Beach, Antigua, Tortola...
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.
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$6,840.00
(USD)
Per Person
+ $450.00 taxes/fees
Dec 29, 2024
through Jan 06, 2025
through Jan 06, 2025
Nights:
8
Ship:
Le Champlain
Price Per Night:$855.00 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Dec 29, 2024
through Jan 06, 2025
Itinerary:
Fort-De-France, Port Elizabeth, Bequia Island, Mayreau Island, Tobago Cays, Union Island, Pigeon Island Beach, Soufrière, Les Saintes, Portsmouth, Fort-De-France
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$3,409.00
(USD)
Per Person
+ $260.00 taxes/fees
Dec 23, 2025
through Jan 10, 2026
through Jan 10, 2026
Nights:
18
Ship:
Zuiderdam
Price Per Night:$189.39 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Dec 23, 2025
through Jan 10, 2026
Itinerary:
Miami, Florida, US, Days At Sea, Philipsburg, Sint Maarten, St. Johns, Antigua and Barbuda, Castries, Saint Lucia, Roseau, Dominica, Basseterre, St Kitts and Nevis, St. Thomas, U.S.V.I., Days At Sea, Half Moon Cay, Bahamas...
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$2,099.00
(USD)
Per Person
+ $150.00 taxes/fees
Jan 03, 2026
through Jan 14, 2026
through Jan 14, 2026
Nights:
11
Ship:
Koningsdam
Price Per Night:$190.82 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Jan 03, 2026
through Jan 14, 2026
Itinerary:
Fort Lauderdale, Florida, US, Days At Sea, Philipsburg, Sint Maarten, St. Johns, Antigua and Barbuda, Fort-De-France, Martinique, Roseau, Dominica, Basseterre, St Kitts and Nevis, St. Thomas, U.S.V.I., Days At Sea, Half Moon Cay, Bahamas...
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$5,489.00
(USD)
Per Person
+ $120.00 taxes/fees
Feb 08, 2025
through Feb 22, 2025
through Feb 22, 2025
Nights:
14
Ship:
Wind Surf
Price Per Night:$392.07 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Feb 08, 2025
through Feb 22, 2025
Itinerary:
Philipsburg, St. Maarten, Charlestown, Roseau, Pigeon Island, Les Saintes, Basseterre, Gustavia, Philipsburg, St. Maarten, Falmouth Harbour, Jost Van Dyke, Great Harbour...
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.
Other Categories Starting At:
Inside
Outside
Balcony
Suite
21-Day Eastern & Southern Caribbean: Leeward & Abc Islands
Roundtrip from Fort Lauderdale, Florida, US
Roundtrip from Fort Lauderdale, Florida, US
from
$3,231.00
(USD)
Per Person
+ $275.00 taxes/fees
Nov 18, 2025
through Dec 09, 2025
through Dec 09, 2025
Nights:
21
Ship:
Koningsdam
Price Per Night:$153.86 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Nov 18, 2025
through Dec 09, 2025
Itinerary:
Fort Lauderdale, Florida, US, Days At Sea, Philipsburg, Sint Maarten, St. Johns, Antigua and Barbuda, Castries, Saint Lucia, Roseau, Dominica, Basseterre, St Kitts and Nevis, St. Thomas, U.S.V.I., Days At Sea, Half Moon Cay, Bahamas...
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$973.00
(USD)
Per Person
+ N/A taxes/fees
Dec 13, 2025
through Dec 20, 2025
through Dec 20, 2025
Nights:
7
Ship:
Valiant Lady
Price Per Night:$139.00 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Dec 13, 2025
through Dec 20, 2025
Itinerary:
San Juan, Basseterre, Castries, Roseau, Bridgetown, Sailing, Philipsburg, San Juan
This 7-night San Juan voyage sails the Caribbean Sea to the best islands of the Lesser Antilles including St. Kitts followed by St. Lucia's tropical city of Castries - home to splendid beaches, lush rainforests, and cascading waterfalls. Next up is Dominica (known for its natural springs), Barbados, and the tiny island of St. Maarten before returning to San Juan.
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$8,999.00
(USD)
Per Person
Jan 20, 2025
through Jan 30, 2025
through Jan 30, 2025
Nights:
10
Ship:
Seven Seas Navigator
Price Per Night:$899.90 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Jan 20, 2025
through Jan 30, 2025
Itinerary:
San Juan, St. George's, Kingstown, Roseau, Gustavia, St. John's, Pointe A Pitre, Fort De France, Basseterre, San Juan
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$944.82
(USD)
Per Person
Feb 13, 2027
through Feb 20, 2027
through Feb 20, 2027
Nights:
7
Ship:
Radiance of the Seas
Price Per Night:$134.97 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Feb 13, 2027
through Feb 20, 2027
Itinerary:
San Juan, Puerto Rico, Charlotte Amalie, St. Thomas, St. Croix, U.S.V.I., Basseterre, St Kitts & Nevis, St. Johns, Antigua, Roseau, Dominica, Cruising, San Juan, Puerto Rico
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$7,980.00
(USD)
Per Person
+ $390.00 taxes/fees
Feb 28, 2026
through Mar 07, 2026
through Mar 07, 2026
Nights:
7
Ship:
Le Ponant
Price Per Night:$1,140.00 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Feb 28, 2026
through Mar 07, 2026
Itinerary:
Pointe-À-Pitre, Portsmouth, Port Elizabeth, Bequia Island, Tobago Cays, Sandy Island, Carriacou, Sailing By Les Pitons, Soufrière, At Sea Aboard Le Ponant, Anses-D'arlet, Marie-Galante, Pointe-À-Pitre
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$5,399.00
(USD)
Per Person
+ $116.00 taxes/fees
Feb 17, 2026
through Mar 07, 2026
through Mar 07, 2026
Nights:
18
Ship:
Wind Surf
Price Per Night:$299.94 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Feb 17, 2026
through Mar 07, 2026
Itinerary:
Cozumel, Grand Cayman, Cayman Brac, Port Antonio, Santo Domingo, La Romana, Jost Van Dyke, Great Harbour, Virgin Gorda / Prickly Pear, British Virgin Islands, Philipsburg, St. Maarten, Charlestown...
Dive right into adventure in the underwater caverns of Cozumel’s Chankanaab eco-park - home to dolphins, manatees, and sea turtles. Then set sail for Isla Mujeres to wander the Mayan Temple of El Meco and Hacienda Mundaca ruins. On Grand Cayman, experience Stingray City, where you can feed and touch these mystical creatures. Explore Cayman Brac’s island-long bluff with caves, secluded beaches, and lush forests, and visit the marine life of Reach Falls from Port Antonio, Jamaica.
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$3,699.00
(USD)
Per Person
+ $120.00 taxes/fees
Mar 21, 2026
through Apr 04, 2026
through Apr 04, 2026
Nights:
14
Ship:
Wind Surf
Price Per Night:$264.21 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Mar 21, 2026
through Apr 04, 2026
Itinerary:
Philipsburg, St. Maarten, Charlestown, Roseau, Mayreau, Les Saintes, Basseterre, Gustavia, Philipsburg, St. Maarten, St. John's, Road Bay...
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.
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14-Day Eastern Caribbean: Antilles & Private Island Holiday
Roundtrip from Fort Lauderdale, Florida, US
Roundtrip from Fort Lauderdale, Florida, US
from
$2,999.00
(USD)
Per Person
+ $180.00 taxes/fees
Dec 21, 2025
through Jan 04, 2026
through Jan 04, 2026
Nights:
14
Ship:
Volendam
Price Per Night:$214.21 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Dec 21, 2025
through Jan 04, 2026
Itinerary:
Fort Lauderdale, Florida, US, Days At Sea, Cruz Bay, St. John, U.S. Virgin Islands, Days At Sea, Port-of-Spain, Trinidad and Tobago, Saint Georges, Grenada, Roseau, Dominica, Castries, Saint Lucia, Philipsburg, Sint Maarten, St. Johns, Antigua and Barbuda...
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Outside
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Suite
from
$2,999.00
(USD)
Per Person
Feb 16, 2026
through Feb 26, 2026
through Feb 26, 2026
Nights:
10
Ship:
Nautica
Price Per Night:$299.90 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Feb 16, 2026
through Feb 26, 2026
Itinerary:
Miami, Philipsburg, St. John's, Fort-De-France, Roseau, Frederiksted, Miami
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Outside
Balcony
Suite
from
$1,799.00
(USD)
Per Person
+ $11,868.00 taxes/fees
Mar 15, 2025
through Mar 29, 2025
through Mar 29, 2025
Nights:
14
Ship:
Queen Mary 2
Price Per Night:$128.50 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Mar 15, 2025
through Mar 29, 2025
Itinerary:
New York, New York, St. Maarten, Netherlands Antilles, St Lucia, Saint Lucia, Grenada, Grenada, 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.
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Outside
Balcony
Suite
from
$3,699.00
(USD)
Per Person
+ $120.00 taxes/fees
Dec 07, 2025
through Dec 21, 2025
through Dec 21, 2025
Nights:
14
Ship:
Wind Surf
Price Per Night:$264.21 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Dec 07, 2025
through Dec 21, 2025
Itinerary:
Philipsburg, St. Maarten, Charlestown, Roseau, Mayreau, Les Saintes, Basseterre, Gustavia, Philipsburg, St. Maarten, Falmouth Harbour, Road Bay...
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.
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$3,999.00
(USD)
Per Person
Oct 14, 2026
through Oct 21, 2026
through Oct 21, 2026
Nights:
7
Ship:
World Navigator
Price Per Night:$571.29 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Oct 14, 2026
through Oct 21, 2026
Itinerary:
Philipsburg, Gustavia, Carambola Beach, Pointe-á-Pitre, Cabrits (Portsmouth), Dominica, Fort-de-France, Port Elizabeth (Bequia), Bridgetown
Get swept away by the colorful scenes of the Caribbean. Departing late from Gustavia, take the time for a snorkeling adventure amid the island's underwater wonders. Carambola Beach begins your adventure to Canada Hill, where a natural guide can take you on an off-road hike through a former bustling sugar plantation. From Pointe-á-Pitre, an extended evening in port gives you time to venture out to Deshaies for a delectable encounter with French gastronomy enlivened by the unique zest of local flavors.
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Outside
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Suite
from
$2,539.00
(USD)
Per Person
Nov 28, 2026
through Dec 12, 2026
through Dec 12, 2026
Nights:
14
Ship:
Azamara Journey
Price Per Night:$181.36 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Nov 28, 2026
through Dec 12, 2026
Itinerary:
Bridgetown, Castries, Roseau, Basseterre, Charlestown, Philipsburg, Road Town, Tortola, San Juan, Puerto Rico, Virgin Gorda, St. John's, Antigua...
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Outside
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Mar 20, 2027
through Mar 27, 2027
through Mar 27, 2027
Nights:
7
Ship:
Celebrity Constellation
Price Per Night:$154.88 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Mar 20, 2027
through Mar 27, 2027
Itinerary:
San Juan, Puerto Rico, Charlotte Amalie, St. Thomas, St. Johns, Antigua, Roseau, Dominica, Castries, St. Lucia, Bridgetown, Barbados, San Juan, Puerto Rico
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$2,859.00
(USD)
Per Person
Dec 12, 2026
through Dec 28, 2026
through Dec 28, 2026
Nights:
16
Ship:
Azamara Journey
Price Per Night:$178.69 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Dec 12, 2026
through Dec 28, 2026
Itinerary:
Bridgetown, Castries, Roseau, Basseterre, Charlestown, Philipsburg, San Juan, Puerto Rico, Charlotte Amalie, St. Thomas, Virgin Gorda, St. John's, Antigua...
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Jan 24, 2025
through Feb 03, 2025
through Feb 03, 2025
Nights:
10
Ship:
Celebrity Beyond
Price Per Night:$916.71 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Jan 24, 2025
through Feb 03, 2025
Itinerary:
Fort Lauderdale, Florida, Tortola, B.V.I., Philipsburg, St. Maarten, Roseau, Dominica, Bridgetown, Barbados, St. Johns, Antigua, Fort Lauderdale, Florida
Other Categories Starting At:
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Outside
Balcony
Suite
from
$4,099.00
(USD)
Per Person
+ $34.00 taxes/fees
Mar 07, 2026
through Mar 21, 2026
through Mar 21, 2026
Nights:
14
Ship:
Wind Spirit
Price Per Night:$292.79 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Mar 07, 2026
through Mar 21, 2026
Itinerary:
Bridgetown, Basseterre, St. John's, Les Saintes, Roseau, Mayreau, Anse Mitan, Bridgetown, Tobago Cays, Pigeon Island...
The Windward Islands will enchant you with their natural beauty – dense rainforests, lush green peaks, cascading waterfalls, stunning black sand beaches. And on this two-week voyage you’ll visit the best of them, from islands so small they have only one village, to villages so small they have only one road. See nature’s artistry in the lush green volcanic pitons of St.
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