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
Price unavailable
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434 total
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 $479
$479
·
$68/night
$68/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 $669
$669
·
$96/night
$96/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
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
Price unavailable
Rhapsody of the Seas • Royal Caribbean International
7-night Eastern Caribbean Loop via Charlotte Amalie, Saint Thomas, Frederiksted, Saint Croix & Philipsburg
Dec 19, 2026 → Dec 26, 2026 • San Juan ↔
From $507
$507
·
$72/night
$72/night
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
Price unavailable
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 $934
$934
·
$133/night
$133/night
Celebrity Constellation • Celebrity Cruises
7-night Southern Caribbean Loop via Charlotte Amalie, Saint Thomas, Basseterre, Saint Kitts & Roseau
Jan 2, 2027 → Jan 9, 2027 • San Juan ↔
From $858
$858
·
$123/night
$123/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 $609
$609
·
$87/night
$87/night
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 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 $1,019
$1,019
·
$146/night
$146/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 $485
$485
·
$69/night
$69/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
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 $568
$568
·
$81/night
$81/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 $504
$504
·
$72/night
$72/night
Vision of the Seas • Royal Caribbean International
7-night Eastern Caribbean Loop via Tortola, Cruz Bay, Saint John & Roseau
Jan 31, 2027 → Feb 7, 2027 • San Juan ↔
From $494
$494
·
$71/night
$71/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 $911
$911
·
$130/night
$130/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 $539
$539
·
$77/night
$77/night
Celebrity Constellation • Celebrity Cruises
7-night Southern Caribbean Loop via Tortola, Basseterre, Saint Kitts & Roseau
Feb 27, 2027 → Mar 6, 2027 • San Juan ↔
From $786
$786
·
$112/night
$112/night