Iona • P&O Cruises
14-night Eastern Caribbean Loop via Castries, Saint George's & Bridgetown
Dec 18, 2027 → Jan 1, 2028 • Antigua ↔
From $3,377
$241/night
Priced high
↑49% above typical
View by
930 total
Oceania Allura • Oceania Cruises
10-night Eastern Caribbean Loop via Charlotte Amalie, Saint Thomas, Philipsburg & Saint-Barthélemy
Dec 28, 2026 → Jan 7, 2027 • Miami ↔
From $6,649
$665/night
Priced high
↑48% above typical
Crown Princess • Princess Cruises
5-night Eastern Caribbean Loop via Saint Thomas, Basseterre, Saint Kitts & Roseau
Jan 3, 2027 → Jan 8, 2027 • San Juan → Bridgetown
From $857
$171/night
Priced high
↑48% above typical
Celebrity Ascent • Celebrity Cruises
11-night Eastern Caribbean Loop via Philipsburg, Saint John's & Castries
Dec 24, 2026 → Jan 4, 2027 • Fort Lauderdale ↔
From $2,398
$218/night
Priced high
↑47% above typical
Crown Princess • Princess Cruises
7-night Eastern Caribbean Loop via Saint Thomas, Basseterre, Saint Kitts & Roseau
Jan 3, 2027 → Jan 10, 2027 • San Juan ↔
From $1,189
$170/night
Priced high
↑46% above typical
Norwegian Prima • Norwegian Cruise Line
7-night Eastern Caribbean Loop via Tortola, Basseterre, Saint Kitts & Bridgetown
Nov 22, 2026 → Nov 29, 2026 • San Juan ↔
From $1,729
$247/night
Priced high
↑44% above typical
Norwegian Prima • Norwegian Cruise Line
7-night Eastern Caribbean Loop via Tortola, Basseterre, Saint Kitts & Bridgetown
Dec 18, 2027 → Dec 25, 2027 • San Juan ↔
From $1,809
$258/night
Priced high
↑44% above typical
Iona • P&O Cruises
14-night Eastern Caribbean Loop via Tortola, Philipsburg & Antigua
Dec 27, 2027 → Jan 10, 2028 • Basseterre, Saint Kitts ↔
From $3,242
$232/night
Priced high
↑43% above typical
Iona • P&O Cruises
14-night Southern Caribbean Loop via Tortola, Philipsburg & Fort-de-France
Nov 15, 2027 → Nov 29, 2027 • Basseterre, Saint Kitts ↔
From $2,566
$183/night
Priced high
↑43% above typical
Star of the Seas • Royal Caribbean International
7-night Eastern Caribbean Loop via Coco Cay & Charlotte Amalie, Saint Thomas
Jun 14, 2026 → Jun 21, 2026 • Port Canaveral ↔
From $3,287
$470/night
Priced high
↑42% above typical
Silver Shadow • Silversea Cruises
7-night Eastern Caribbean Loop via Basseterre, Saint Kitts & Terre-de-Haut
Dec 27, 2026 → Jan 3, 2027 • San Juan ↔
From $7,100
$1,014/night
MSC Seaview • MSC Cruises
14-night Eastern Caribbean Loop via Kingstown, Saint George & Fort-de-France
Mar 9, 2027 → Mar 23, 2027 • Bridgetown ↔
From $1,981
$142/night
Celebrity Beyond • Celebrity Cruises
7-night Eastern Caribbean Loop via Puerto Plata & Tortola
Oct 11, 2026 → Oct 18, 2026 • Miami ↔
From $1,056
$151/night
Priced high
↑39% above typical
Celebrity Apex • Celebrity Cruises
7-night Eastern Caribbean Loop via Puerto Plata & Charlotte Amalie, Saint Thomas
Feb 13, 2027 → Feb 20, 2027 • Port Canaveral ↔
From $1,390
$199/night
Priced high
↑39% above typical
Arvia • P&O Cruises
14-night Southern Caribbean Loop via Roseau, Castries & Saint George's
Dec 26, 2026 → Jan 9, 2027 • Antigua ↔
From $3,512
$251/night
Priced high
↑39% above typical
Norwegian Viva • Norwegian Cruise Line
7-night ABC Islands Loop via Oranjestad & Willemstad
Jan 2, 2028 → Jan 9, 2028 • San Juan ↔
From $1,219
$174/night
Priced high
↑39% above typical
Celebrity Eclipse • Celebrity Cruises
12-night Southern Caribbean Loop via Basseterre, Saint Kitts, Castries & Bridgetown
Dec 22, 2026 → Jan 3, 2027 • Fort Lauderdale ↔
From $2,084
$174/night
Priced high
↑39% above typical
Iona • P&O Cruises
14-night Southern Caribbean Loop via Basseterre, Saint Kitts, Philipsburg & Fort-de-France
Mar 3, 2028 → Mar 17, 2028 • Bridgetown ↔
From $2,836
$203/night
Priced high
↑38% above typical
Britannia • P&O Cruises
14-night Southern Caribbean Loop via Saint George's, Curaçao & Oranjestad
Jan 23, 2027 → Feb 6, 2027 • Bridgetown ↔
From $3,174
$227/night
Priced high
↑38% above typical
Explora I • Explora Journeys
12-night Southern Caribbean Arc via Parintins, Port Elizabeth, Bequia & Bridgetown
Feb 17, 2027 → Mar 1, 2027 • Manaus → San Juan
From $10,100
$842/night
Priced high
↑37% above typical