Celebrity Ascent • Celebrity Cruises
10-night Southern Caribbean Loop via Philipsburg, Castries & Saint George's
Dec 14, 2026 → Dec 24, 2026 • Fort Lauderdale ↔
From $1,068
$107/night
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286 total
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
Odyssey of the Seas • Royal Caribbean International
11-night Southern Caribbean Loop via Philipsburg & Castries
Jan 14, 2027 → Jan 25, 2027 • Cape Liberty, NJ (NYC) ↔
From $1,452
$132/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
Celebrity Ascent • Celebrity Cruises
10-night Southern Caribbean Loop via Philipsburg, Castries & Saint George's
Feb 5, 2027 → Feb 15, 2027 • Fort Lauderdale ↔
From $1,574
$157/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
Celebrity Eclipse • Celebrity Cruises
11-night Southern Caribbean Loop via Basseterre, Saint Kitts, Castries & Bridgetown
Feb 8, 2027 → Feb 19, 2027 • Fort Lauderdale ↔
From $1,672
$152/night
Grandeur of the Seas • Royal Caribbean International
7-night Southern Caribbean Loop via Cartagena & Oranjestad
Feb 13, 2027 → Feb 20, 2027 • Colón (Panama Canal) ↔
From $890
$127/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 $641
$92/night
Celebrity Eclipse • Celebrity Cruises
12-night Southern Caribbean Loop via Basseterre, Saint Kitts, Castries & Bridgetown
Feb 28, 2027 → Mar 12, 2027 • Fort Lauderdale ↔
From $1,578
$132/night
Vision of the Seas • Royal Caribbean International
7-night Southern Caribbean Loop via Charlotte Amalie, Saint Thomas, Cruz Bay, Saint John & Fort-de-France
Feb 28, 2027 → Mar 7, 2027 • San Juan ↔
From $699
$100/night
Celebrity Eclipse • Celebrity Cruises
10-night Southern Caribbean Loop via Saint John's, Castries & Bridgetown
Mar 12, 2027 → Mar 22, 2027 • Fort Lauderdale ↔
From $1,146
$115/night
Celebrity Constellation • Celebrity Cruises
7-night Southern Caribbean Loop via Charlotte Amalie, Saint Thomas, Saint John's & Roseau
Mar 20, 2027 → Mar 27, 2027 • San Juan ↔
From $763
$109/night
Celebrity Eclipse • Celebrity Cruises
11-night Southern Caribbean Loop via Basseterre, Saint Kitts, Castries & Bridgetown
Mar 22, 2027 → Apr 2, 2027 • Fort Lauderdale ↔
From $1,498
$136/night
Celebrity Summit • Celebrity Cruises
9-night Southern Caribbean Loop via Saint John's, Castries & Saint George's
Oct 29, 2027 → Nov 7, 2027 • San Juan ↔
From $786
$87/night
Celebrity Summit • Celebrity Cruises
7-night Southern Caribbean Loop via Roseau, Bridgetown & Castries
Nov 7, 2027 → Nov 14, 2027 • San Juan ↔
From $544
$78/night
Celebrity Summit • Celebrity Cruises
7-night Southern Caribbean Loop via Kingstown, Bridgetown & Castries
Nov 14, 2027 → Nov 21, 2027 • San Juan ↔
From $544
$78/night
Iona • P&O Cruises
14-night Southern Caribbean Loop via Saint George's, Castries & Bridgetown
Dec 4, 2027 → Dec 18, 2027 • Antigua ↔
From $2,269
$162/night
Typical price
Vision of the Seas • Royal Caribbean International
7-night Southern Caribbean Loop via Bridgetown, Saint George's & Roseau
Dec 5, 2027 → Dec 12, 2027 • San Juan ↔
From $679
$97/night
Celebrity Summit • Celebrity Cruises
7-night Southern Caribbean Loop via Kingstown, Bridgetown & Fort-de-France
Dec 12, 2027 → Dec 19, 2027 • San Juan ↔
From $568
$81/night