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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364 total
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
Celebrity Constellation • Celebrity Cruises
11-night Southern Caribbean Loop via Tortola, Saint John's & Castries
Nov 17, 2026 → Nov 28, 2026 • San Juan ↔
From $993
$993
·
$90/night
$90/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
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 $669
$669
·
$96/night
$96/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
Spirit Of Adventure • Saga River Cruises (Saga Cruises)
73-night Transatlantic Crossing via Las Palmas de Gran Canaria, Praia & Panama Canal
Jan 7, 2027 → Mar 21, 2027 • Portsmouth ↔
Price unavailable
Price unavailable
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 $1,019
$1,019
·
$146/night
$146/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 $1,325
$1,325
·
$133/night
$133/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 $848
$848
·
$121/night
$121/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 $1,755
$1,755
·
$160/night
$160/night
Celebrity Ascent • Celebrity Cruises
10-night Southern Caribbean Loop via Philipsburg, Castries & Saint George's
Feb 26, 2027 → Mar 8, 2027 • Fort Lauderdale ↔
From $1,138
$1,138
·
$114/night
$114/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 $1,272
$1,272
·
$116/night
$116/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 $788
$788
·
$88/night
$88/night
Celebrity Summit • Celebrity Cruises
7-night Eastern Caribbean Loop via Charlotte Amalie, Saint Thomas, Basseterre, Saint Kitts & Saint John's
Nov 28, 2027 → Dec 5, 2027 • San Juan ↔
From $617
$617
·
$88/night
$88/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
8-night Eastern Caribbean Loop via Charlotte Amalie, Saint Thomas, Cruz Bay, Saint John & Roseau
Dec 19, 2027 → Dec 27, 2027 • San Juan ↔
From $1,129
$1,129
·
$141/night
$141/night
Celebrity Ascent • Celebrity Cruises
11-night Eastern Caribbean Loop via Philipsburg, Castries & Saint George's
Dec 23, 2027 → Jan 3, 2028 • Fort Lauderdale ↔
From $2,247
$2,247
·
$204/night
$204/night