from
$4,699.00
(USD)
Per Person
+ $255.00 taxes/fees
Jan 17, 2027
through Feb 07, 2027
through Feb 07, 2027
Nights:
21
Ship:
Nieuw Amsterdam
Price Per Night:$223.76 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Jan 17, 2027
through Feb 07, 2027
Other Categories Starting At:
Inside
Outside
Balcony
Suite
Category N - Flash Special: Book by Sunday 07/06/2025
Jan 02, 2026
through Jan 12, 2026
through Jan 12, 2026
Nights:
10
Ship:
Celebrity Ascent
Price Per Night:$116.86 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Jan 02, 2026
through Jan 12, 2026
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$915.87
(USD)
Per Person
Nov 29, 2026
through Dec 06, 2026
through Dec 06, 2026
Nights:
7
Ship:
Norwegian Breakaway
Price Per Night:$130.84 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Nov 29, 2026
through Dec 06, 2026
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.
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$14,799.00
(USD)
Per Person
Oct 23, 2026
through Dec 19, 2026
through Dec 19, 2026
Nights:
57
Ship:
Insignia
Price Per Night:$259.63 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Oct 23, 2026
through Dec 19, 2026
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$4,199.00
(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:$299.93 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Dec 07, 2025
through Dec 21, 2025
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
$861.83
(USD)
Per Person
Dec 06, 2026
through Dec 13, 2026
through Dec 13, 2026
Nights:
7
Ship:
Brilliance of the Seas
Price Per Night:$123.12 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Dec 06, 2026
through Dec 13, 2026
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$645.00
(USD)
Per Person
Oct 26, 2025
through Nov 02, 2025
through Nov 02, 2025
Nights:
7
Ship:
Grand Princess
Price Per Night:$92.14 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Oct 26, 2025
through Nov 02, 2025
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$2,153.00
(USD)
Per Person
+ $15,856.00 taxes/fees
Dec 09, 2025
through Dec 30, 2025
through Dec 30, 2025
Nights:
21
Ship:
Queen Elizabeth
Price Per Night:$102.52 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Dec 09, 2025
through Dec 30, 2025
This 21-night voyage on Queen Elizabeth gives you the chance to revel in life on board, as well as soak up plenty of Caribbean sunshine with port calls in Barbados, Jamaica, and Saint Lucia.
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$1,762.00
(USD)
Per Person
Mar 29, 2026
through Apr 18, 2026
through Apr 18, 2026
Nights:
20
Ship:
Caribbean Princess
Price Per Night:$88.10 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Mar 29, 2026
through Apr 18, 2026
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$3,545.00
(USD)
Per Person
+ $13,163.00 taxes/fees
Sep 24, 2026
through Oct 27, 2026
through Oct 27, 2026
Nights:
33
Ship:
Queen Elizabeth
Price Per Night:$107.42 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Sep 24, 2026
through Oct 27, 2026
Dusty hilltops. Verdant jungles. Sugar white sands. This 33-night sailing allows you to explore natural beauty across the Americas, plus the manmade wonder that is the Panama Canal on the way.
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$8,099.00
(USD)
Per Person
Dec 21, 2026
through Jan 04, 2027
through Jan 04, 2027
Nights:
14
Ship:
Seven Seas Mariner
Price Per Night:$578.50 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Dec 21, 2026
through Jan 04, 2027
Other Categories Starting At:
Outside
Balcony
Suite
from
$6,549.00
(USD)
Per Person
Dec 19, 2026
through Dec 29, 2026
through Dec 29, 2026
Nights:
10
Ship:
Seven Seas Grandeur
Price Per Night:$654.90 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Dec 19, 2026
through Dec 29, 2026
Other Categories Starting At:
Outside
Balcony
Suite
from
$11,899.00
(USD)
Per Person
Nov 02, 2026
through Dec 19, 2026
through Dec 19, 2026
Nights:
47
Ship:
Insignia
Price Per Night:$253.17 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Nov 02, 2026
through Dec 19, 2026
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$2,222.67
(USD)
Per Person
Dec 03, 2025
through Dec 22, 2025
through Dec 22, 2025
Nights:
19
Ship:
Norwegian Sky
Price Per Night:$116.98 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Dec 03, 2025
through Dec 22, 2025
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$2,799.00
(USD)
Per Person
+ $61.00 taxes/fees
Feb 21, 2026
through Feb 28, 2026
through Feb 28, 2026
Nights:
7
Ship:
Wind Spirit
Price Per Night:$399.86 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Feb 21, 2026
through Feb 28, 2026
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
$1,464.00
(USD)
Per Person
Dec 20, 2025
through Dec 27, 2025
through Dec 27, 2025
Nights:
7
Ship:
Valiant Lady
Price Per Night:$209.14 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Dec 20, 2025
through Dec 27, 2025
This 7-night idyllic journey departs from San Juan and docks the next day in St. Maarten. From there you'll head to St. Kitts followed by St. Johns in Antigua - the quintessential paradise lover's paradise - where you'll discover the epitome of a tropical haven. From there you'll dock in St. Lucia, then spend a day sailing to the British Virgin Islands before finally returning to San Juan.
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
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
$3,999.00
(USD)
Per Person
+ $94.00 taxes/fees
Nov 22, 2026
through Dec 06, 2026
through Dec 06, 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 22, 2026
through Dec 06, 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
$973.00
(USD)
Per Person
Nov 22, 2025
through Nov 29, 2025
through Nov 29, 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)
Nov 22, 2025
through Nov 29, 2025
This 7-night Thanksgiving voyage departs from San Juan, arriving the next day on the shores of Tortola, BVI. The journey continues with a stop in St. Kitts & Nevis, followed by Antigua, a true paradise for any traveler. From there explore the waterfalls and lagoons of Castries, St. Lucia before spending Thanksgiving at sea. Finally, wake up to the beauty of St. Thomas before returning to San Juan.
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$4,760.00
(USD)
Per Person
Jan 27, 2027
through Feb 03, 2027
through Feb 03, 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)
Jan 27, 2027
through Feb 03, 2027
Other Categories Starting At:
Inside
Outside
Balcony
Suite
