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Windstar Cruises

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 ↔

Great balance

Price unavailable

Windstar Cruises

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 ↔

Great balance

Price unavailable

Royal Caribbean International

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 ↔

Great balance

From $550

$79/night

Celebrity Cruises

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 Journeys

Explora II • Explora Journeys

7-night Eastern Caribbean Arc via Road Bay & Antigua

Dec 13, 2026 → Dec 20, 2026 • San Juan → Miami

Price unavailable

Windstar Cruises

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 ↔

Great balance

Price unavailable

Windstar Cruises

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 ↔

Great balance

Price unavailable

Royal Caribbean International

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 ↔

Great balance

From $673

$96/night

Royal Caribbean International

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

Royal Caribbean International

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 Cruises

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

Royal Caribbean International

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 Cruises

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 ↔

Great balance

From $699

$100/night

Royal Caribbean International

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 Cruises

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 ↔

Great balance

From $548

$78/night

Royal Caribbean International

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 ↔

Great balance

From $532

$76/night

Celebrity Cruises

Celebrity Constellation • Celebrity Cruises

7-night Southern Caribbean Loop via Tortola, Basseterre, Saint Kitts & Roseau

Jan 30, 2027 → Feb 6, 2027 • San Juan ↔

Great balance

From $597

$85/night

Celebrity Cruises

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

Royal Caribbean International

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

Royal Caribbean International

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 ↔

Great balance

From $548

$78/night

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