from
$1,015.98
(USD)
Per Person
Mar 22, 2026
through Mar 29, 2026
through Mar 29, 2026
Nights:
7
Ship:
Brilliance of the Seas
Price Per Night:$145.14 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Mar 22, 2026
through Mar 29, 2026
Itinerary:
San Juan, Puerto Rico, Charlotte Amalie, St. Thomas, Tortola, B.V.I., Basseterre, St Kitts & Nevis, St. Johns, Antigua, Bridgetown, Barbados, Cruising, San Juan, Puerto Rico
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$3,699.00
(USD)
Per Person
+ $120.00 taxes/fees
Mar 14, 2026
through Mar 28, 2026
through Mar 28, 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 14, 2026
through Mar 28, 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, 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.
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Inside
Outside
Balcony
Suite
from
$9,720.00
(USD)
Per Person
Dec 22, 2025
through Jan 05, 2026
through Jan 05, 2026
Nights:
14
Ship:
Explora II
Price Per Night:$694.29 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Dec 22, 2025
through Jan 05, 2026
Itinerary:
Miami, Ocean Cay, Charlotte Amalie (Saint Thomas), Spanish Town (Virgin Gorda), Marigot, San Juan, Road Bay, New Year Fireworks SJU, Saint John/Cruz Bay, New Year Fireworks SJU...
Season's greetings harmonise with warm island paradise and stress-free strolls on beaches of shimmering white sand. Relish sun-kissed relaxation aboard EXPLORA II as you gracefully traverse the turquoise waves. At Ocean Cay Marine Reserve, indulge in seaside massages and, in St Martin, sip delicious cocktails. Welcome the New Year with firework-bright Puerto Rico skies and weave through glorious island views to Florida's golden shores.
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Inside
Outside
Balcony
Suite
from
$973.00
(USD)
Per Person
+ N/A taxes/fees
Jan 24, 2026
through Jan 31, 2026
through Jan 31, 2026
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)
Jan 24, 2026
through Jan 31, 2026
Itinerary:
San Juan, Tortola, Sailing, Bridgetown, Fort-de-France, St. John's, Philipsburg, San Juan
This 7-night Caribbean journey starts in San Juan, stopping for a full day in Tortola on the British Virgin Islands. After, you'll island hop between Barbados and magnetic Martinique before arriving at the epitome of a Caribbean paradise - St. Johns on the island of Antigua. Next, you'll sail to St. Maarten, a tiny island bursting with beauty, before returning to San Juan.
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$3,090.00
(USD)
Per Person
+ N/A taxes/fees
Jan 17, 2026
through Jan 28, 2026
through Jan 28, 2026
Nights:
11
Ship:
Star Clipper
Price Per Night:$280.91 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Jan 17, 2026
through Jan 28, 2026
Itinerary:
Montego Bay, Jamaica, Port Antonio, Jamaica, Santo Domingo, Dominican Republic, 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)...
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$5,999.00
(USD)
Per Person
+ $457.00 taxes/fees
Nov 30, 2025
through Dec 20, 2025
through Dec 20, 2025
Nights:
20
Ship:
Star Pride
Price Per Night:$299.95 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Nov 30, 2025
through Dec 20, 2025
Itinerary:
San Juan, CRUZ BAY, ST. JOHN, Virgin Islands (U.S.), Gustavia, Basseterre, Philipsburg, St. Maarten, Jost Van Dyke, Great Harbour, Virgin Gorda / Prickly Pear, British Virgin Islands, San Juan, Santo Domingo, Cartagena...
Bird calls intermingle with primate chatter throughout the dense canopy of a Costa Rican cloudforest. Towering container ships glide past the Culbra Cut’s tiered rock slopes, formerly the most difficult stretch of the Panama Canal. Sweet rum cocktails provide cool respite on a hot white beach in Santo Domingo.
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$1,425.83
(USD)
Per Person
Dec 22, 2025
through Dec 29, 2025
through Dec 29, 2025
Nights:
7
Ship:
Norwegian Sky
Price Per Night:$203.69 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Dec 22, 2025
through Dec 29, 2025
Itinerary:
PUNTA CANA (LA ROMANA), DOMINICAN REPUBLIC, Oranjestad, Aruba, Willemstad, Netherland Antilles, Kralendijk, Netherland Antilles, ST LUCIA, SAINT LUCIA, Basseterre, Saint Kitts - Nevis, Tortola, British Virgin Islands, PUNTA CANA (LA ROMANA), DOMINICAN REPUBLIC
Explore breathtaking views on your 7-day cruise aboard the newly refurbished Norwegian Sky. In Curaçao, splash around the warm sea with some friendly dolphins or journey inland to discover the enchanting Hato Caves and then visit a unique Ostrich farm and hang with one of the biggest birds on earth. Uncover the best of Aruba as you soak in fantastic vistas from the California Lighthouse, explore the Aloe Museum and visit the island’s popular Natural Bridge ruins.
Other Categories Starting At:
Inside
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
$5,400.00
(USD)
Per Person
Jan 20, 2027
through Jan 30, 2027
through Jan 30, 2027
Nights:
10
Ship:
Silver Shadow
Price Per Night:$540.00 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Jan 20, 2027
through Jan 30, 2027
Itinerary:
Bridgetown, Bequia, Castries, Trois Ilets, Roseau, Les Saintes, Little Bay, Montserrat, Basseterre, St. Kitts, Gustavia, St Barthelemy, Jost Van Dyke (British Virgin Islands)...
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$1,899.00
(USD)
Per Person
+ $10,974.00 taxes/fees
Oct 28, 2025
through Nov 18, 2025
through Nov 18, 2025
Nights:
21
Ship:
Queen Elizabeth
Price Per Night:$90.43 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Oct 28, 2025
through Nov 18, 2025
Itinerary:
Miami, Florida, Amber Cove,Dominican Republic, Montego Bay, Jamaica, Belize City, Belize, Cozumel, Mexico, Miami, Florida, San Juan, Puerto Rico, Antigua, St Lucia, Saint Lucia, Barbados, Barbados...
Escape to a new tropical paradise almost every day on this 21-night voyage from Miami. You’ll have the chance to snorkel among coral reefs in Cozumel and Belize, before venturing to the Caribbean.
Other Categories Starting At:
Inside
Outside
Balcony
Suite
Feb 13, 2027
through Feb 20, 2027
through Feb 20, 2027
Nights:
7
Ship:
Celebrity Constellation
Price Per Night:$142.28 (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, Tortola, B.V.I., Basseterre, St Kitts & Nevis, Roseau, Dominica, Castries, St. Lucia, Bridgetown, Barbados, San Juan, Puerto Rico
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$1,609.00
(USD)
Per Person
+ $8,887.00 taxes/fees
Feb 04, 2027
through Feb 16, 2027
through Feb 16, 2027
Nights:
12
Ship:
Queen Elizabeth
Price Per Night:$134.08 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Feb 04, 2027
through Feb 16, 2027
Itinerary:
Miami, FL, USA, San Juan, Puerto Rico, Antigua, Martinique, Faroe Islands, Barbados, Barbados, St. Maarten, Netherlands Antilles, Tortola, B.V.I., Miami, FL, USA
A blend of sea days and time in port means you can have the best of both worlds. Treasure days on deck sunbathing when you’re not exploring the cultures, cuisines, and scenery across the Caribbean.
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$9,180.00
(USD)
Per Person
Feb 14, 2026
through Mar 03, 2026
through Mar 03, 2026
Nights:
17
Ship:
Explora II
Price Per Night:$540.00 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Feb 14, 2026
through Mar 03, 2026
Itinerary:
Miami, Key West, New Orleans, Merida (Progreso), Cozumel, Miami, Charlotte Amalie (Saint Thomas), Jost van Dyke, St. John's (Antigua), Gustavia...
We set out from the bright lights of Miami towards New Orleans, where the Mardi Gras good times flow. Step back in time to explore the haunting Mayan ruins of the Yucatán and plunge into amazing cenotes, then bask in exquisite tropical tranquillity and stunning scenery in Charlotte Amalie and Jost van Dyke. Indulge in the chic glamour of Gustavia and embrace the rich blend of architecture, history and Caribbean flair of Puerto Rico's vibrant capital.
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$1,899.00
(USD)
Per Person
+ $10,974.00 taxes/fees
Jan 08, 2026
through Jan 29, 2026
through Jan 29, 2026
Nights:
21
Ship:
Queen Elizabeth
Price Per Night:$90.43 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Jan 08, 2026
through Jan 29, 2026
Itinerary:
Miami, FL, USA, St. Thomas, Virgin Islands, U.S.A., Antigua, St Lucia, Saint Lucia, Barbados, Barbados, St. Maarten, Netherlands Antilles, Tortola, B.V.I., Miami, FL, USA, Amber Cove,Dominican Republic, Montego Bay, Jamaica...
Explore the varied landscapes and cultures of the Caribbean on this 21-night voyage. Wander vibrant ports by day and delight in all Queen Elizabeth has to offer between island stops.
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$6,299.00
(USD)
Per Person
+ $71.00 taxes/fees
Jan 04, 2026
through Jan 25, 2026
through Jan 25, 2026
Nights:
21
Ship:
Wind Surf
Price Per Night:$299.95 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Jan 04, 2026
through 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.
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$5,355.00
(USD)
Per Person
Dec 20, 2026
through Dec 28, 2026
through Dec 28, 2026
Nights:
8
Ship:
Explora III
Price Per Night:$669.38 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Dec 20, 2026
through Dec 28, 2026
Itinerary:
Miami, Porto Antonio, Isla Catalina, Jost van Dyke, St. Maarten/Philipsburg, Charlotte Amalie (Saint Thomas), San Juan
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, Basseterre, St. Kitts, Little Bay, Montserrat, Les Saintes, St. John's, Trois Ilets, Castries, St George's...
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$1,899.00
(USD)
Per Person
+ $10,974.00 taxes/fees
Oct 16, 2025
through Nov 06, 2025
through Nov 06, 2025
Nights:
21
Ship:
Queen Elizabeth
Price Per Night:$90.43 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Oct 16, 2025
through 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.
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$878.00
(USD)
Per Person
Apr 08, 2026
through Apr 18, 2026
through Apr 18, 2026
Nights:
10
Ship:
Caribbean Princess
Price Per Night:$87.80 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Apr 08, 2026
through Apr 18, 2026
Itinerary:
Fort Lauderdale, Princess Cays, St Thomas, St Maarten, Antigua, St Kitts, Tortola, Fort Lauderdale
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$1,490.00
(USD)
Per Person
+ $357.00 taxes/fees
Feb 08, 2027
through Feb 18, 2027
through Feb 18, 2027
Nights:
10
Ship:
Brilliant Lady
Price Per Night:$149.00 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Feb 08, 2027
through Feb 18, 2027
Itinerary:
Miami, Florida, Sailing, Philipsburg, St. Maarten, Tortola, St. Croix, San Juan, Puerto Plata, Sailing, Beach Club at Bimini, Miami, Florida
Spend 2 days sailing from Miami to the beautiful vistas and sprawling beaches of Philipsburg, St. Maarten, followed by the enticing vibes and sparkling waters of Tortola, British Virgin Islands then fanciful Fredrikstad, St. Croix. Then, celebrate Valentine's Day in sunny San Juan followed by the silver coasts of Puerto Plata. Finally, sail a day to the Beach Club at Bimini then return to Miami.
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Inside
Outside
Balcony
Suite
