Star Pride • Windstar Cruises
7-night Eastern Caribbean Loop via Cruz Bay, Saint John, Saint-Barthélemy & Basseterre, Saint Kitts
Dec 13, 2026 → Dec 20, 2026 • San Juan ↔
Price unavailable
Price unavailable
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1,257 total
Utopia of the Seas • Royal Caribbean International
7-night Eastern Caribbean Loop via Coco Cay & Charlotte Amalie, Saint Thomas
Dec 24, 2026 → Dec 31, 2026 • Port Canaveral ↔
From $1,309
$1,309
·
$187/night
$187/night
Rhapsody of the Seas • Royal Caribbean International
7-night Eastern Caribbean Loop via Tortola, Philipsburg & Saint John's
Dec 26, 2026 → Jan 2, 2027 • San Juan ↔
From $906
$906
·
$129/night
$129/night
Oasis of the Seas • Royal Caribbean International
7-night Eastern Caribbean Loop via Coco Cay & Charlotte Amalie, Saint Thomas
Dec 28, 2026 → Jan 4, 2027 • Fort Lauderdale ↔
From $1,421
$1,421
·
$203/night
$203/night
Rotterdam • Holland America
21-night Western Caribbean Loop via Half Moon Cay, Falmouth & Cozumel
Jan 2, 2027 → Jan 23, 2027 • Fort Lauderdale ↔
From $2,424
$2,424
·
$115/night
·
typical price
$115/night
Typical price
Explora I • Explora Journeys
7-night Eastern Caribbean Arc via Philipsburg & Little Bay
Jan 4, 2027 → Jan 11, 2027 • San Juan → Miami
From $4,200
$4,200
·
$600/night
·
typical price
$600/night
Typical price
Celebrity Eclipse • Celebrity Cruises
9-night Eastern Caribbean Loop via Saint John's & Roseau
Jan 8, 2027 → Jan 17, 2027 • Fort Lauderdale ↔
From $1,208
$1,208
·
$134/night
$134/night
Celebrity Constellation • Celebrity Cruises
7-night Eastern Caribbean Loop via Charlotte Amalie, Saint Thomas, Philipsburg & Saint John's
Jan 9, 2027 → Jan 16, 2027 • San Juan ↔
From $994
$994
·
$142/night
$142/night
Rhapsody of the Seas • Royal Caribbean International
7-night Eastern Caribbean Loop via Frederiksted, Saint Croix, Philipsburg & Saint John's
Jan 9, 2027 → Jan 16, 2027 • San Juan ↔
From $497
$497
·
$71/night
$71/night
Celebrity Xcel • Celebrity Cruises
7-night Eastern Caribbean Loop via Philipsburg & Charlotte Amalie, Saint Thomas
Jan 10, 2027 → Jan 17, 2027 • Miami ↔
From $989
$989
·
$141/night
$141/night
Vision of the Seas • Royal Caribbean International
7-night Eastern Caribbean Loop via Charlotte Amalie, Saint Thomas, Frederiksted, Saint Croix & Philipsburg
Jan 10, 2027 → Jan 17, 2027 • San Juan ↔
From $496
$496
·
$71/night
$71/night
Rhapsody of the Seas • Royal Caribbean International
7-night Eastern Caribbean Loop via Tortola, Philipsburg & Saint John's
Jan 23, 2027 → Jan 30, 2027 • San Juan ↔
From $502
$502
·
$72/night
$72/night
Star of the Seas • Royal Caribbean International
7-night Eastern Caribbean Loop via Coco Cay & Charlotte Amalie, Saint Thomas
Jan 24, 2027 → Jan 31, 2027 • Port Canaveral ↔
From $1,251
$1,251
·
$179/night
$179/night
Celebrity Ascent • Celebrity Cruises
11-night Eastern Caribbean Loop via Philipsburg, Saint John's & Castries
Jan 25, 2027 → Feb 5, 2027 • Fort Lauderdale ↔
From $1,417
$1,417
·
$129/night
$129/night
Odyssey of the Seas • Royal Caribbean International
12-night Eastern Caribbean Loop via Labadee, Puerto Plata & Cruz Bay, Saint John
Jan 25, 2027 → Feb 6, 2027 • Cape Liberty, NJ (NYC) ↔
From $1,669
$1,669
·
$139/night
$139/night
Rhapsody of the Seas • Royal Caribbean International
7-night Eastern Caribbean Loop via Charlotte Amalie, Saint Thomas, Frederiksted, Saint Croix & Philipsburg
Jan 30, 2027 → Feb 6, 2027 • San Juan ↔
From $511
$511
·
$73/night
$73/night
Celebrity Ascent • Celebrity Cruises
10-night Southern Caribbean Loop via Philipsburg, Castries & Saint George's
Feb 5, 2027 → Feb 15, 2027 • Fort Lauderdale ↔
From $1,380
$1,380
·
$138/night
$138/night
Celebrity Eclipse • Celebrity Cruises
11-night Southern Caribbean Loop via Basseterre, Saint Kitts, Castries & Bridgetown
Feb 8, 2027 → Feb 19, 2027 • Fort Lauderdale ↔
From $1,743
$1,743
·
$158/night
$158/night
MSC Opera • MSC Cruises
14-night Eastern Caribbean Loop via Pointe-à-Pitre, Road Town, Tortola & La Romana
Feb 12, 2027 → Feb 26, 2027 • Fort-de-France ↔
From $1,748
$1,748
·
$125/night
·
typical price
$125/night
Typical price
Vision of the Seas • Royal Caribbean International
7-night Eastern Caribbean Loop via Tortola, Cruz Bay, Saint John & Philipsburg
Feb 14, 2027 → Feb 21, 2027 • San Juan ↔
From $522
$522
·
$75/night
$75/night