Star Pride • Windstar Cruises
11-night Eastern Caribbean Loop via Cruz Bay, Saint John, Saint-Barthélemy & Rodney Bay
Oct 28, 2026 → Nov 8, 2026 • San Juan ↔
Price unavailable
Price unavailable
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425 total
Explora II • Explora Journeys
7-night Eastern Caribbean Arc via Beef Island, Tortola & Road Bay
Nov 1, 2026 → Nov 8, 2026 • San Juan → Miami
Price unavailable
Price unavailable
Star Pride • Windstar Cruises
7-night Southern Caribbean Loop via Saint George's, Port Elizabeth, Bequia & Terre-de-Haut
Nov 8, 2026 → Nov 15, 2026 • San Juan ↔
Price unavailable
Price unavailable
Rhapsody of the Seas • Royal Caribbean International
7-night Eastern Caribbean Loop via Philipsburg, Saint John's & Roseau
Nov 14, 2026 → Nov 21, 2026 • San Juan ↔
From $639
$639
·
$91/night
$91/night
Explora II • Explora Journeys
7-night Eastern Caribbean Arc via Road Bay, Antigua & Christiansted, Saint Croix
Nov 15, 2026 → Nov 22, 2026 • San Juan → Miami
Price unavailable
Price unavailable
Star Pride • Windstar Cruises
7-night Eastern Caribbean Loop via Cruz Bay, Saint John, Basseterre, Saint Kitts & Saint-Barthélemy
Nov 15, 2026 → Nov 22, 2026 • San Juan ↔
Price unavailable
Price unavailable
Celebrity Constellation • Celebrity Cruises
11-night Southern Caribbean Loop via Tortola, Saint John's & Castries
Nov 17, 2026 → Nov 28, 2026 • San Juan ↔
From $944
$944
·
$86/night
$86/night
Star Pride • Windstar Cruises
7-night Southern Caribbean Loop via Saint George's, Port Elizabeth, Bequia & Terre-de-Haut
Nov 22, 2026 → Nov 29, 2026 • San Juan ↔
Price unavailable
Price unavailable
Celebrity Constellation • Celebrity Cruises
7-night Southern Caribbean Loop via Tortola, Basseterre, Saint Kitts & Roseau
Nov 28, 2026 → Dec 5, 2026 • San Juan ↔
From $733
$733
·
$105/night
$105/night
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
Price unavailable
Celebrity Constellation • Celebrity Cruises
7-night Eastern Caribbean Loop via Charlotte Amalie, Saint Thomas, Philipsburg & Saint John's
Dec 5, 2026 → Dec 12, 2026 • San Juan ↔
From $724
$724
·
$103/night
$103/night
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
Celebrity Constellation • Celebrity Cruises
7-night Southern Caribbean Loop via Tortola, Basseterre, Saint Kitts & Roseau
Dec 12, 2026 → Dec 19, 2026 • San Juan ↔
From $613
$613
·
$88/night
$88/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
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 $906
$906
·
$129/night
$129/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 $833
$833
·
$119/night
$119/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