Silver Shadow • Silversea Cruises
7-night Eastern Caribbean Loop via Saint-Barthélemy, Saint John's & Little Bay
Jan 3, 2027 → Jan 10, 2027 • San Juan ↔
From $5,700
$5,700
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2,216 total
Sun Princess • Princess Cruises
7-night Eastern Caribbean Arc via Grand Turk Island & San Juan
Jan 3, 2027 → Jan 10, 2027 • Fort Lauderdale ↔
From $701
$701
Crown Princess • Princess Cruises
14-night Eastern Caribbean Loop via Saint Thomas & Basseterre, Saint Kitts
Jan 3, 2027 → Jan 17, 2027 • San Juan ↔
From $1,859
$1,859
MSC Opera • MSC Cruises
7-night Eastern Caribbean Loop via Samana, Spanish Town & Basseterre, Saint Kitts
Jan 4, 2027 → Jan 11, 2027 • La Romana ↔
From $1,171
$1,171
Sky Princess • Princess Cruises
6-night Eastern Caribbean Loop via Princess Cays & Puerto Plata
Jan 4, 2027 → Jan 10, 2027 • Port Canaveral ↔
From $684
$684
Explora I • Explora Journeys
7-night Eastern Caribbean Arc via Philipsburg & Little Bay
Jan 4, 2027 → Jan 11, 2027 • San Juan → Miami
From $4,200
$4,200
·
$600/night
·
typical price
$600/night
Typical price
Silver Ray • Silversea Cruises
11-night Eastern Caribbean Loop via San Juan, Basseterre, Saint Kitts & Deshaies
Jan 5, 2027 → Jan 16, 2027 • Miami ↔
From $9,700
$9,700
Enchanted Princess • Princess Cruises
10-night Eastern Caribbean Loop via Princess Cays, Puerto Plata & San Juan
Jan 6, 2027 → Jan 16, 2027 • Fort Lauderdale ↔
From $823
$823
Silver Nova • Silversea Cruises
12-night Eastern Caribbean Arc via San Juan, Saint-Barthélemy & Basseterre, Saint Kitts
Jan 6, 2027 → Jan 18, 2027 • Miami → Bridgetown
From $10,400
$10,400
Celebrity Eclipse • Celebrity Cruises
9-night Eastern Caribbean Loop via Saint John's & Roseau
Jan 8, 2027 → Jan 17, 2027 • Fort Lauderdale ↔
From $1,171
$1,171
·
$130/night
$130/night
Crown Princess • Princess Cruises
7-night Eastern Caribbean Loop via San Juan, Saint Thomas & Philipsburg
Jan 8, 2027 → Jan 15, 2027 • Bridgetown ↔
From $1,194
$1,194
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 $969
$969
·
$138/night
$138/night
Arvia • P&O Cruises
14-night Eastern Caribbean Loop via Castries, Saint George's & Bridgetown
Jan 9, 2027 → Jan 23, 2027 • Antigua ↔
From $2,404
$2,404
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 $552
$552
·
$79/night
$79/night
Carnival Pride • Carnival Cruise Line
14-night Eastern Caribbean Loop via Saint Thomas, Philipsburg & Roseau
Jan 10, 2027 → Jan 24, 2027 • Baltimore ↔
From $2,043
$2,043
Celebrity Xcel • Celebrity Cruises
7-night Eastern Caribbean Loop via Philipsburg & Charlotte Amalie, Saint Thomas
Jan 10, 2027 → Jan 17, 2027 • Miami ↔
From $964
$964
·
$138/night
$138/night
Carnival Venezia • Carnival Cruise Line
14-night Eastern Caribbean Loop via Grand Turk Island, Oranjestad & Curaçao
Jan 10, 2027 → Jan 24, 2027 • Port Canaveral ↔
From $1,016
$1,016
MSC Meraviglia • MSC Cruises
14-night Eastern Caribbean Loop via Grand Turk Island, Ocean Cay & Philipsburg
Jan 10, 2027 → Jan 24, 2027 • Miami ↔
From $1,096
$1,096
Crown Princess • Princess Cruises
14-night Eastern Caribbean Loop via Saint Thomas, Philipsburg & Antigua
Jan 10, 2027 → Jan 24, 2027 • San Juan ↔
From $1,639
$1,639
Sky Princess • Princess Cruises
8-night Eastern Caribbean Loop via Princess Cays & San Juan
Jan 10, 2027 → Jan 18, 2027 • Port Canaveral ↔
From $709
$709