from
$4,799.00
(USD)
Per Person
Jan 16, 2026
through Jan 28, 2026
through Jan 28, 2026
Nights:
12
Ship:
Allura
Price Per Night:$399.92 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Jan 16, 2026
through Jan 28, 2026
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$5,200.00
(USD)
Per Person
Jan 03, 2027
through Jan 10, 2027
through Jan 10, 2027
Nights:
7
Ship:
Silver Shadow
Price Per Night:$742.86 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Jan 03, 2027
through Jan 10, 2027
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$9,899.00
(USD)
Per Person
Nov 09, 2026
through Dec 19, 2026
through Dec 19, 2026
Nights:
40
Ship:
Insignia
Price Per Night:$247.48 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Nov 09, 2026
through Dec 19, 2026
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$2,499.00
(USD)
Per Person
+ $63.00 taxes/fees
Nov 15, 2026
through Nov 22, 2026
through Nov 22, 2026
Nights:
7
Ship:
Star Pride
Price Per Night:$357.00 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Nov 15, 2026
through Nov 22, 2026
Begin and end your journey where Old World meets New, in historic San Juan, littered with more than 400 restored Spanish colonial buildings. As you continue on this bewitching Caribbean cruise through the Virgin Islands, no two days are alike. One day, you’re shopping chic French boutiques for the latest fashions from Paris. On another, snorkeling a secluded cove known only to lucky yachtsmen – like you. Skip more common and commercial ports in favor of less-visited destinations like Montserrat.
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$4,120.00
(USD)
Per Person
Mar 07, 2026
through Mar 14, 2026
through Mar 14, 2026
Nights:
7
Ship:
Emerald Azzurra
Price Per Night:$588.57 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Mar 07, 2026
through Mar 14, 2026
Embark on an unforgettable Caribbean voyage exploring pristine beaches and coral reefs, island-hopping through diverse cultures, where the warmth of the locals will enhance your luxury yacht adventure.
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$3,999.00
(USD)
Per Person
+ $94.00 taxes/fees
Nov 08, 2026
through Nov 22, 2026
through Nov 22, 2026
Nights:
14
Ship:
Star Pride
Price Per Night:$285.64 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Nov 08, 2026
through Nov 22, 2026
Whether you’re passionate about swimming among rarely seen undersea wildlife or the intricate cultures and intertwined European histories of the Windward Islands, this 2-week cruise offers the best combinations of charm, island heritage and natural beauty. Shop unique designer apparel in St. Barts, where you’ll discover a fashionable confluence of high-end brands normally associated with places like Madison Avenue, but displayed in an ambiance that’s anything but intimidating.
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$2,599.00
(USD)
Per Person
+ $7,229.00 taxes/fees
Dec 22, 2025
through Jan 03, 2026
through Jan 03, 2026
Nights:
12
Ship:
Queen Mary 2
Price Per Night:$216.58 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Dec 22, 2025
through Jan 03, 2026
Make forever memories as you celebrate Christmas Day and New Year’s Eve on board Queen Mary 2. Arriving in the Caribbean, enjoy time ashore in Saint Kitts and Antigua, among other magical islands.
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$1,095.63
(USD)
Per Person
May 03, 2026
through May 10, 2026
through May 10, 2026
Nights:
7
Ship:
Norwegian Prima
Price Per Night:$156.52 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
May 03, 2026
through May 10, 2026
Your tropical paradise is on the horizon aboard this round-trip cruise from Port Canaveral. Fly high above the jungle floor on an exhilarating zipline then enjoy a refreshing dip in the pools below the breathtaking Damajagua waterfalls in Puerto Plata. In St Thomas, greet the green sea turtles and colorful fish as you snorkel the turquoise waters of Turtle Cove. Jump in a Jeep and head off-road to one of Tortola’s most secluded beaches, Smuggler’s Cove.
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$8,099.00
(USD)
Per Person
Feb 19, 2027
through Mar 11, 2027
through Mar 11, 2027
Nights:
20
Ship:
Allura
Price Per Night:$404.95 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Feb 19, 2027
through Mar 11, 2027
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$1,231.00
(USD)
Per Person
Mar 15, 2026
through Mar 29, 2026
through Mar 29, 2026
Nights:
14
Ship:
Grand Princess
Price Per Night:$87.93 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Mar 15, 2026
through Mar 29, 2026
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$2,789.00
(USD)
Per Person
+ $20,768.00 taxes/fees
Feb 16, 2027
through Mar 09, 2027
through Mar 09, 2027
Nights:
21
Ship:
Queen Elizabeth
Price Per Night:$132.81 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Feb 16, 2027
through Mar 09, 2027
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.
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$1,685.72
(USD)
Per Person
Jan 10, 2026
through Jan 24, 2026
through Jan 24, 2026
Nights:
14
Ship:
Norwegian Viva
Price Per Night:$120.41 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Jan 10, 2026
through Jan 24, 2026
Live it up in The Caribbean on a 14-day roundtrip cruise aboard one of our most innovative ships, Norwegian Viva. Sit back and relax in your private beachfront cabana in Great Stirrup Cay, our private island paradise that’s just for you. Enjoy a leisurely bike ride through Philipsburg’s historic sites and take in the spectacular views as you learn about St Maarten’s rich past. Soar above the jungle canopy on a series of ziplines in San Juan.
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$947.27
(USD)
Per Person
Jan 10, 2026
through Jan 17, 2026
through Jan 17, 2026
Nights:
7
Ship:
Norwegian Joy
Price Per Night:$135.32 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Jan 10, 2026
through Jan 17, 2026
Your tropical paradise is on the horizon aboard this round-trip cruise from Port Canaveral. Fly high above the jungle floor on an exhilarating zipline then enjoy a refreshing dip in the pools below the breathtaking Damajagua waterfalls in Puerto Plata. In St Thomas, greet the green sea turtles and colorful fish as you snorkel the turquoise waters of Turtle Cove. Jump in a Jeep and head off-road to one of Tortola’s most secluded beaches, Smuggler’s Cove.
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$950.37
(USD)
Per Person
Nov 02, 2025
through Nov 09, 2025
through Nov 09, 2025
Nights:
7
Ship:
Brilliance of the Seas
Price Per Night:$135.77 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Nov 02, 2025
through Nov 09, 2025
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$4,560.00
(USD)
Per Person
Jan 03, 2027
through Jan 09, 2027
through Jan 09, 2027
Nights:
6
Ship:
Emerald Sakara
Price Per Night:$760.00 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Jan 03, 2027
through Jan 09, 2027
Embark on an unforgettable Caribbean voyage exploring pristine beaches and coral reefs, island-hopping through diverse cultures, where the warmth of the locals will enhance your luxury yacht adventure.
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$2,599.00
(USD)
Per Person
+ $68.00 taxes/fees
Dec 14, 2025
through Dec 20, 2025
through Dec 20, 2025
Nights:
6
Ship:
Wind Surf
Price Per Night:$433.17 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Dec 14, 2025
through Dec 20, 2025
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
from
$965.48
(USD)
Per Person
Mar 22, 2026
through Mar 29, 2026
through Mar 29, 2026
Nights:
7
Ship:
Brilliance of the Seas
Price Per Night:$137.93 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Mar 22, 2026
through Mar 29, 2026
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$804.14
(USD)
Per Person
Sep 12, 2026
through Sep 19, 2026
through Sep 19, 2026
Nights:
7
Ship:
Radiance of the Seas
Price Per Night:$114.88 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Sep 12, 2026
through Sep 19, 2026
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$1,592.00
(USD)
Per Person
Oct 17, 2025
through Oct 25, 2025
through Oct 25, 2025
Nights:
8
Ship:
Brilliant Lady
Price Per Night:$199.00 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Oct 17, 2025
through Oct 25, 2025
This round-trip voyage from Miami stops at three beautiful islands including Tortola, Bimini (home to our exclusive beach club), and St. Maarten. In St. Maarten, you'll experience a Caribbean melting pot of cultures including Dutch and French (as both nations have their own "side" to the island), plus West African, British, Indian, and Spanish heritage influence the island as well.
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$1,102.84
(USD)
Per Person
Jan 05, 2026
through Jan 14, 2026
through Jan 14, 2026
Nights:
9
Ship:
Norwegian Sky
Price Per Night:$122.54 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Jan 05, 2026
through Jan 14, 2026
Explore breathtaking views on your 9-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
