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
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155 total
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 Ascent • Celebrity Cruises
10-night Southern Caribbean Loop via Philipsburg, Castries & Saint George's
Dec 4, 2026 → Dec 14, 2026 • Fort Lauderdale ↔
From $1,159
$1,159
·
$116/night
$116/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
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
Celebrity Ascent • Celebrity Cruises
10-night Southern Caribbean Loop via Philipsburg, Castries & Saint George's
Feb 5, 2027 → Feb 15, 2027 • Fort Lauderdale ↔
From $1,380
$1,380
·
$138/night
$138/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 $842
$842
·
$120/night
$120/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 $1,743
$1,743
·
$158/night
$158/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 $629
$629
·
$90/night
$90/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 $1,199
$1,199
·
$109/night
$109/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 $813
$813
·
$90/night
$90/night
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 $636
$636
·
$91/night
$91/night
Vision of the Seas • Royal Caribbean International
7-night Southern Caribbean Loop via Bridgetown, Saint George's & Castries
Jan 16, 2028 → Jan 23, 2028 • San Juan ↔
From $761
$761
·
$109/night
$109/night
Vision of the Seas • Royal Caribbean International
7-night Southern Caribbean Loop via Bridgetown, Saint George's & Kingstown
Jan 30, 2028 → Feb 6, 2028 • San Juan ↔
From $729
$729
·
$104/night
$104/night