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
Itinerary:
Miami, Charlotte Amalie, Gustavia, St. John's, Fort-De-France, Basseterre, Philipsburg, Tortola, Miami
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$1,128.06
(USD)
Per Person
Jan 18, 2026
through Jan 25, 2026
through Jan 25, 2026
Nights:
7
Ship:
Brilliance of the Seas
Price Per Night:$161.15 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Jan 18, 2026
through Jan 25, 2026
Itinerary:
San Juan, Puerto Rico, Tortola, B.V.I., St. Johns, Antigua, St. George's, Grenada, Kingstown, St. Vincent, Roseau, Dominica, Cruising, San Juan, Puerto Rico
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
Itinerary:
San Juan, St. George's, Bequia, Mayreau, Les Saintes, Marigot, St. Martin, San Juan, CRUZ BAY, ST. JOHN, Virgin Islands (U.S.), Gustavia, Basseterre...
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
$3,239.00
(USD)
Per Person
+ $14,025.00 taxes/fees
Mar 18, 2027
through Apr 13, 2027
through Apr 13, 2027
Nights:
26
Ship:
Queen Elizabeth
Price Per Night:$124.58 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Mar 18, 2027
through Apr 13, 2027
Itinerary:
Miami, FL, USA, San Juan, Puerto Rico, Antigua, St Lucia, Saint Lucia, Barbados, Barbados, St. Maarten, Netherlands Antilles, Tortola, B.V.I., Miami, FL, USA, St. Thomas, Virgin Islands, U.S.A., St. Maarten, Netherlands Antilles...
This 26-night sailing takes you to charming port towns across the Caribbean. See colorful murals in Castries, flit between beaches and boutiques in Bridgetown, and walk on cobblestones in San Juan.
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$991.17
(USD)
Per Person
Mar 01, 2026
through Mar 08, 2026
through Mar 08, 2026
Nights:
7
Ship:
Brilliance of the Seas
Price Per Night:$141.60 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Mar 01, 2026
through Mar 08, 2026
Itinerary:
San Juan, Puerto Rico, Cruising, Willemstad, Curacao, Oranjestad, Aruba, Cruising, Tortola, B.V.I., San Juan, Puerto Rico
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$5,849.00
(USD)
Per Person
Mar 09, 2026
through Mar 21, 2026
through Mar 21, 2026
Nights:
12
Ship:
Allura
Price Per Night:$487.42 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Mar 09, 2026
through Mar 21, 2026
Itinerary:
Miami, Oranjestad, Willemstad, St. George's, Kingstown, Fort-De-France, Tortola, Miami
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$1,299.00
(USD)
Per Person
Nov 07, 2026
through Nov 14, 2026
through Nov 14, 2026
Nights:
7
Ship:
Azamara Journey
Price Per Night:$185.57 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Nov 07, 2026
through Nov 14, 2026
Itinerary:
San Juan, Puerto Rico, Virgin Gorda, St. John's, Antigua, St. Pierre, Port Elizabeth, Bequia, Saint George's, Scarborough, Tobago, Bridgetown
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$10,199.00
(USD)
Per Person
Jan 04, 2026
through Jan 28, 2026
through Jan 28, 2026
Nights:
24
Ship:
Allura
Price Per Night:$424.96 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Jan 04, 2026
through Jan 28, 2026
Itinerary:
Miami, Costa Maya, Cozumel, Belize City, Santo Tomas, Roatan, Montego Bay, George Town, Key West, Miami...
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$2,368.00
(USD)
Per Person
+ $10,974.00 taxes/fees
Feb 19, 2026
through Mar 12, 2026
through Mar 12, 2026
Nights:
21
Ship:
Queen Elizabeth
Price Per Night:$112.76 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Feb 19, 2026
through Mar 12, 2026
Itinerary:
Miami, Florida, San Juan, Puerto Rico, Antigua, St Lucia, Saint Lucia, Barbados, Barbados, St. Maarten, Netherlands Antilles, Tortola, B.V.I., Miami, Florida, Grand Turk, Montego Bay, Jamaica...
From Bridgetown’s historic Garrison to the charms of Belize’s Barrier Reef and Jamaica’s bioluminescent bay. Diverse ecosystems, cultures, and adventures await on this Caribbean voyage.
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$4,299.00
(USD)
Per Person
Dec 28, 2026
through Jan 07, 2027
through Jan 07, 2027
Nights:
10
Ship:
Allura
Price Per Night:$429.90 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Dec 28, 2026
through Jan 07, 2027
Itinerary:
Miami, Charlotte Amalie, Philipsburg, Gustavia, Basseterre, Tortola, Miami
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$2,609.00
(USD)
Per Person
+ $15,549.00 taxes/fees
Oct 15, 2026
through Nov 05, 2026
through Nov 05, 2026
Nights:
21
Ship:
Queen Elizabeth
Price Per Night:$124.24 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Oct 15, 2026
through Nov 05, 2026
Itinerary:
Miami, FL, USA, San Juan, Puerto Rico, Antigua, St Lucia, Saint Lucia, Barbados, Barbados, St. Maarten, Netherlands Antilles, Tortola, B.V.I., Miami, FL, USA, Grand Turk, Curacao, Antilles...
This 21-night voyage brings plenty of time to relax on board and explore unique cultures ashore. Lush St. Lucia, vibrant Barbados, and idyllic Turks and Caicos are just a few islands that beckon.
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$1,079.15
(USD)
Per Person
Dec 20, 2026
through Dec 27, 2026
through Dec 27, 2026
Nights:
7
Ship:
Brilliance of the Seas
Price Per Night:$154.16 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Dec 20, 2026
through Dec 27, 2026
Itinerary:
San Juan, Puerto Rico, Tortola, B.V.I., St. Johns, Antigua, Roseau, Dominica, St. Croix, U.S.V.I., Cruising, Basseterre, St Kitts & Nevis, San Juan, Puerto Rico
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$2,010.00
(USD)
Per Person
Jan 09, 2027
through Jan 16, 2027
through Jan 16, 2027
Nights:
7
Ship:
Star Flyer
Price Per Night:$287.14 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Jan 09, 2027
through Jan 16, 2027
Itinerary:
Philipsburg, St. Maarten, Road Bay, Anguilla, White Bay, Jost van Dyke (B.V.I.), Sopers Hole - Tortola, British Virgin Islands (BVI, Sailing Sir Francis Drake Channel, The Bight - Norman Island, British Virgin Islands, Spanish Town - Virgin Gorda, British Virgin Island, Beach, Captain's Best, British Virgin Islands (B.V, Basseterre, St. Kitts (morning), South Friars Bay - Beach, St. Kitts (afternoon)...
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$1,184.00
(USD)
Per Person
Dec 20, 2025
through Dec 27, 2025
through Dec 27, 2025
Nights:
7
Ship:
Valiant Lady
Price Per Night:$169.14 (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, Philipsburg, Basseterre, St. John's, Castries, Sailing, Tortola, San Juan
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
