from
$939.00
(USD)
Per Person
Dec 17, 2025
through Dec 27, 2025
through Dec 27, 2025
Nights:
10
Ship:
Enchanted Princess
Price Per Night:$93.90 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Dec 17, 2025
through Dec 27, 2025
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$2,039.00
(USD)
Per Person
+ $150.00 taxes/fees
Jan 29, 2027
through Feb 07, 2027
through Feb 07, 2027
Nights:
9
Ship:
Nieuw Amsterdam
Price Per Night:$226.56 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Jan 29, 2027
through Feb 07, 2027
Other Categories Starting At:
Inside
Outside
Balcony
Suite
Category N - Flash Special: Book by Sunday 07/06/2025
from
$5,199.00
(USD)
Per Person
Feb 26, 2026
through Mar 09, 2026
through Mar 09, 2026
Nights:
11
Ship:
Allura
Price Per Night:$472.64 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Feb 26, 2026
through Mar 09, 2026
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$4,199.00
(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:$221.00 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Nov 18, 2025
through Dec 07, 2025
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
$1,477.50
(USD)
Per Person
Feb 01, 2027
through Feb 13, 2027
through Feb 13, 2027
Nights:
12
Ship:
Norwegian Bliss
Price Per Night:$123.13 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Feb 01, 2027
through Feb 13, 2027
Set sail on a spectacular 12-day round-trip sailing from New York to the Caribbean with Norwegian. In Puerto Plata, visit Fortaleza San Felipe, which was built in the 16th century or head to the Amber Museum, which is filled with a unique collection of valuable Dominican amber. Wander San Juan's picturesque cobblestone streets, plazas and chapels, all reflecting its rich Spanish heritage. And on the island of St. Thomas, witness Charlotte Amalie's breathtaking harbor - once home to pirates but still full of many treasures today.
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
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$8,220.00
(USD)
Per Person
Dec 19, 2026
through Dec 26, 2026
through Dec 26, 2026
Nights:
7
Ship:
Le Ponant
Price Per Night:$1,174.29 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Dec 19, 2026
through Dec 26, 2026
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$4,099.00
(USD)
Per Person
Dec 10, 2026
through Dec 22, 2026
through Dec 22, 2026
Nights:
12
Ship:
Marina
Price Per Night:$341.58 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Dec 10, 2026
through Dec 22, 2026
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$3,090.00
(USD)
Per Person
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
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
Sep 29, 2025
through Oct 09, 2025
through Oct 09, 2025
Nights:
10
Ship:
Celebrity Reflection
Price Per Night:$406.75 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Sep 29, 2025
through Oct 09, 2025
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$1,660.00
(USD)
Per Person
Jan 10, 2027
through Jan 24, 2027
through Jan 24, 2027
Nights:
14
Ship:
Crown Princess
Price Per Night:$118.57 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Jan 10, 2027
through Jan 24, 2027
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$1,350.00
(USD)
Per Person
Mar 08, 2026
through Mar 22, 2026
through Mar 22, 2026
Nights:
14
Ship:
Grand Princess
Price Per Night:$96.43 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Mar 08, 2026
through Mar 22, 2026
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$5,399.00
(USD)
Per Person
Jan 07, 2027
through Jan 20, 2027
through Jan 20, 2027
Nights:
13
Ship:
Allura
Price Per Night:$415.31 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Jan 07, 2027
through Jan 20, 2027
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$1,782.00
(USD)
Per Person
Apr 08, 2026
through Apr 28, 2026
through Apr 28, 2026
Nights:
20
Ship:
Caribbean Princess
Price Per Night:$89.10 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Apr 08, 2026
through Apr 28, 2026
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$3,929.00
(USD)
Per Person
+ $225.00 taxes/fees
Nov 29, 2026
through Dec 20, 2026
through Dec 20, 2026
Nights:
21
Ship:
Nieuw Amsterdam
Price Per Night:$187.10 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Nov 29, 2026
through Dec 20, 2026
Other Categories Starting At:
Inside
Outside
Balcony
Suite
Category N - Flash Special: Book by Sunday 07/06/2025
from
$960.00
(USD)
Per Person
Jan 17, 2027
through Jan 24, 2027
through Jan 24, 2027
Nights:
7
Ship:
Norwegian Breakaway
Price Per Night:$137.14 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Jan 17, 2027
through Jan 24, 2027
Depart from San Juan, a city alive with vibrant hues and island rhythms, on a 7-day journey through the Caribbean. In La Romana, Dominican Republic, exotic landscapes and hidden caverns await -walk the mesmerizing Cueva de las Maravillas or savor authentic Dominican flavors as music fills the air. Sail onward to Oranjestad, Aruba, where pastel facades meet crystal-blue waters. Stroll lively streets or explore rugged coastlines dotted with wind-swept cacti under sunlit skies.
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$3,299.00
(USD)
Per Person
+ $20,768.00 taxes/fees
Feb 25, 2027
through Mar 18, 2027
through Mar 18, 2027
Nights:
21
Ship:
Queen Elizabeth
Price Per Night:$157.10 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Feb 25, 2027
through Mar 18, 2027
Soak up the atmosphere in bustling harbors in Antigua and Barbados, before exploring Miami’s fusion food scene and Maya ruins in Cozumel, on this 21-night Caribbean adventure on Queen Elizabeth.
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$846.33
(USD)
Per Person
Mar 02, 2026
through Mar 09, 2026
through Mar 09, 2026
Nights:
7
Ship:
Norwegian Sky
Price Per Night:$120.90 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Mar 02, 2026
through Mar 09, 2026
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
