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Departures Itineraries
Princess Cruises

Crown Princess • Princess Cruises

14-night Eastern Caribbean Loop via Saint Thomas, Philipsburg & Antigua

Jan 10, 2027 → Jan 24, 2027 • San Juan ↔

$1,639 · $117/night · typical price · ↑2% above typical
Royal Caribbean International

Vision of the Seas • Royal Caribbean International

7-night Eastern Caribbean Loop via Tortola, Cruz Bay, Saint John & Philipsburg

Nov 22, 2026 → Nov 29, 2026 • San Juan ↔

↗
$704 · $101/night · typical price · ↑1% above typical
Celebrity Cruises

Celebrity Constellation • Celebrity Cruises

7-night Eastern Caribbean Loop via Charlotte Amalie, Saint Thomas, Philipsburg & Saint John's

Mar 6, 2027 → Mar 13, 2027 • San Juan ↔

↗
$783 · $112/night · typical price · ↑1% above typical
SeaDream Yacht Club

SeaDream II • SeaDream Yacht Club

5-night Eastern Caribbean Loop via Cruz Bay, Saint John & Saint-Barthélemy

Jan 3, 2028 → Jan 8, 2028 • San Juan ↔

$3,211 · $642/night · typical price · ↑1% above typical
Regent Seven Seas Cruises

Seven Seas Prestige • Regent Seven Seas Cruises

10-night Eastern Caribbean Arc via Tortola, Basseterre, Saint Kitts & Saint John's

Mar 30, 2027 → Apr 9, 2027 • San Juan → Miami

$7,168 · $717/night · typical price · ↑1% above typical
Royal Caribbean International

Grandeur of the Seas • Royal Caribbean International

7-night Eastern Caribbean Loop via Charlotte Amalie, Saint Thomas, Frederiksted, Saint Croix & Philipsburg

May 15, 2027 → May 22, 2027 • San Juan ↔

↗
$819 · $117/night · typical price
Emerald Cruises

Emerald Kaia • Emerald Cruises

9-night Eastern Caribbean Arc: Saint-John, Ponce & Grand Turk Island

Jan 19, 2029 → Jan 28, 2029 • San Juan → Miami

$8,536 · $948/night · typical price
Royal Caribbean International

Rhapsody of the Seas • Royal Caribbean International

7-night Eastern Caribbean Loop via Charlotte Amalie, Saint Thomas, Frederiksted, Saint Croix & Philipsburg

Jul 25, 2026 → Aug 1, 2026 • San Juan ↔

Great balance
$3,304 · $472/night
Royal Caribbean International

Rhapsody of the Seas • Royal Caribbean International

7-night Eastern Caribbean Loop via Charlotte Amalie, Saint Thomas, Tortola & Cruz Bay, Saint John

Oct 17, 2026 → Oct 24, 2026 • San Juan ↔

Great balance
$624 · $89/night
Windstar Cruises

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
Explora Journeys

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
Royal Caribbean International

Vision of the Seas • Royal Caribbean International

7-night Eastern Caribbean Loop via Charlotte Amalie, Saint Thomas, Cruz Bay, Saint John & Philipsburg

Nov 1, 2026 → Nov 8, 2026 • San Juan ↔

Great balance
$516 · $74/night
Windstar Cruises

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 ↔

Great balance
Price unavailable
Royal Caribbean International

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 ↔

$614 · $88/night
Explora Journeys

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
Windstar Cruises

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 ↔

Great balance
Price unavailable
Celebrity Cruises

Celebrity Constellation • Celebrity Cruises

11-night Southern Caribbean Loop via Tortola, Saint John's & Castries

Nov 17, 2026 → Nov 28, 2026 • San Juan ↔

$993 · $90/night
Windstar Cruises

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 ↔

Great balance
Price unavailable
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
Celebrity Cruises

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 ↔

Great balance
$749 · $107/night