Star Pride • Windstar Cruises
7-night Eastern Caribbean Loop via Cruz Bay, Saint John, Saint-Barthélemy & Basseterre, Saint Kitts
Nov 29, 2026 → Dec 6, 2026 • San Juan ↔
Price unavailable
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436 total
Star Pride • Windstar Cruises
7-night Southern Caribbean Loop via Saint George's, Port Elizabeth, Bequia & Terre-de-Haut
Dec 6, 2026 → Dec 13, 2026 • San Juan ↔
Price unavailable
Vision of the Seas • Royal Caribbean International
7-night Eastern Caribbean Loop via Tortola, Cruz Bay, Saint John & Philipsburg
Dec 6, 2026 → Dec 13, 2026 • San Juan ↔
From $550
$79/night
Celebrity Constellation • Celebrity Cruises
7-night Southern Caribbean Loop via Tortola, Basseterre, Saint Kitts & Roseau
Dec 12, 2026 → Dec 19, 2026 • San Juan ↔
From $678
$97/night
Explora II • Explora Journeys
7-night Eastern Caribbean Arc via Road Bay & Antigua
Dec 13, 2026 → Dec 20, 2026 • San Juan → Miami
Price unavailable
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
Star Pride • Windstar Cruises
7-night Southern Caribbean Loop via Saint George's, Port Elizabeth, Bequia & Terre-de-Haut
Dec 20, 2026 → Dec 27, 2026 • San Juan ↔
Price unavailable
Vision of the Seas • Royal Caribbean International
7-night Eastern Caribbean Loop via Tortola, Cruz Bay, Saint John & Roseau
Dec 20, 2026 → Dec 27, 2026 • San Juan ↔
From $673
$96/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 $908
$130/night
Vision of the Seas • Royal Caribbean International
7-night Eastern Caribbean Loop via Charlotte Amalie, Saint Thomas, Cruz Bay, Saint John & Roseau
Jan 3, 2027 → Jan 10, 2027 • San Juan ↔
From $659
$94/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 $614
$88/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 $580
$83/night
Celebrity Constellation • Celebrity Cruises
7-night Southern Caribbean Loop via Charlotte Amalie, Saint Thomas, Basseterre, Saint Kitts & Roseau
Jan 16, 2027 → Jan 23, 2027 • San Juan ↔
From $699
$100/night
Vision of the Seas • Royal Caribbean International
7-night Eastern Caribbean Loop via Tortola, Cruz Bay, Saint John & Fort-de-France
Jan 17, 2027 → Jan 24, 2027 • San Juan ↔
From $629
$90/night
Celebrity Constellation • Celebrity Cruises
7-night Eastern Caribbean Loop via Charlotte Amalie, Saint Thomas, Philipsburg & Saint John's
Jan 23, 2027 → Jan 30, 2027 • San Juan ↔
From $548
$78/night
Vision of the Seas • Royal Caribbean International
7-night Eastern Caribbean Loop via Charlotte Amalie, Saint Thomas, Frederiksted, Saint Croix & Philipsburg
Jan 24, 2027 → Jan 31, 2027 • San Juan ↔
From $532
$76/night
Celebrity Constellation • Celebrity Cruises
7-night Southern Caribbean Loop via Tortola, Basseterre, Saint Kitts & Roseau
Jan 30, 2027 → Feb 6, 2027 • San Juan ↔
From $597
$85/night
Celebrity Constellation • Celebrity Cruises
7-night Southern Caribbean Loop via Charlotte Amalie, Saint Thomas, Saint John's & Roseau
Feb 6, 2027 → Feb 13, 2027 • San Juan ↔
From $617
$88/night
Rhapsody of the Seas • Royal Caribbean International
7-night Eastern Caribbean Loop via Charlotte Amalie, Saint Thomas, Frederiksted, Saint Croix & Basseterre, Saint Kitts
Feb 13, 2027 → Feb 20, 2027 • San Juan ↔
From $584
$83/night
Rhapsody of the Seas • Royal Caribbean International
7-night Eastern Caribbean Loop via Tortola, Philipsburg & Saint John's
Feb 20, 2027 → Feb 27, 2027 • San Juan ↔
From $548
$78/night