Emerald Princess • Princess Cruises
7-night Eastern Caribbean Loop via San Juan, Tortola & Basseterre, Saint Kitts
Dec 24, 2027 → Dec 31, 2027 • Bridgetown ↔
From $1,709
$1,709
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2,215 total
Silver Shadow • Silversea Cruises
12-night Eastern Caribbean Loop via George Town, Great Exuma Island, Samana & San Juan
Dec 24, 2027 → Jan 5, 2028 • Miami ↔
From $7,000
$7,000
Iona • P&O Cruises
14-night Eastern Caribbean Loop via Basseterre, Saint Kitts, Tortola & Philipsburg
Dec 25, 2027 → Jan 8, 2028 • Bridgetown ↔
From $2,539
$2,539
Arvia • P&O Cruises
14-night Eastern Caribbean Loop via Castries, Curaçao & Bridgetown
Dec 25, 2027 → Jan 8, 2028 • Antigua ↔
From $2,769
$2,769
Celebrity Summit • Celebrity Cruises
7-night Eastern Caribbean Loop via Charlotte Amalie, Saint Thomas, Bridgetown & Castries
Dec 26, 2027 → Jan 2, 2028 • San Juan ↔
From $1,076
$1,076
·
$154/night
$154/night
MSC Seashore • MSC Cruises
14-night Eastern Caribbean Loop via Grand Turk Island, Puerto Plata & Ocean Cay
Dec 26, 2027 → Jan 9, 2028 • Miami ↔
From $1,825
$1,825
Emerald Princess • Princess Cruises
14-night Eastern Caribbean Loop via Tortola, Basseterre, Saint Kitts & Roseau
Dec 26, 2027 → Jan 9, 2028 • San Juan ↔
From $1,961
$1,961
Sky Princess • Princess Cruises
7-night Eastern Caribbean Loop via Puerto Plata & San Juan
Dec 26, 2027 → Jan 2, 2028 • Fort Lauderdale ↔
From $1,136
$1,136
Symphony of the Seas • Royal Caribbean International
9-night Eastern Caribbean Loop via Puerto Plata, Charlotte Amalie, Saint Thomas & Coco Cay
Dec 26, 2027 → Jan 4, 2028 • Fort Lauderdale ↔
From $2,156
$2,156
·
$240/night
$240/night
Silver Ray • Silversea Cruises
8-night Eastern Caribbean Arc via Cruz Bay, Saint John & Fort-de-France
Dec 26, 2027 → Jan 3, 2028 • San Juan → Miami
From $7,400
$7,400
Celebrity Beyond • Celebrity Cruises
7-night Eastern Caribbean Arc: Bimini & Grand Turk Island
Dec 26, 2027 → Jan 2, 2028 • Fort Lauderdale ↔
From $1,391
$1,391
·
$199/night
$199/night
Celebrity Xcel • Celebrity Cruises
7-night Eastern Caribbean Loop: Philipsburg & San Juan
Dec 26, 2027 → Jan 2, 2028 • Fort Lauderdale ↔
From $1,687
$1,687
·
$241/night
$241/night
MSC Opera • MSC Cruises
7-night Eastern Caribbean Loop via Catalina Island, Spanish Town & Philipsburg
Dec 27, 2027 → Jan 3, 2028 • La Romana ↔
From $3,269
$3,269
Iona • P&O Cruises
14-night Eastern Caribbean Loop via Tortola, Philipsburg & Antigua
Dec 27, 2027 → Jan 10, 2028 • Basseterre, Saint Kitts ↔
From $3,174
$3,174
Regal Princess • Princess Cruises
6-night Eastern Caribbean Loop via Princess Cays & Puerto Plata
Dec 27, 2027 → Jan 2, 2028 • Miami ↔
From $1,621
$1,621
Sun Princess • Princess Cruises
11-night Eastern Caribbean Loop via Puerto Plata, San Juan & Basseterre, Saint Kitts
Dec 28, 2027 → Jan 8, 2028 • Fort Lauderdale ↔
From $1,493
$1,493
MSC Meraviglia • MSC Cruises
14-night Eastern Caribbean Loop via Port-of-Spain, Saint George & Fort-de-France
Dec 28, 2027 → Jan 11, 2028 • Bridgetown ↔
From $1,912
$1,912
Silver Dawn • Silversea Cruises
7-night Eastern Caribbean Loop via Philipsburg & Roseau
Dec 28, 2027 → Jan 4, 2028 • San Juan ↔
From $5,900
$5,900
Silver Nova • Silversea Cruises
11-night Eastern Caribbean Loop via Key West & Saint Thomas
Dec 29, 2027 → Jan 9, 2028 • Miami ↔
From $9,400
$9,400
Harmony of the Seas • Royal Caribbean International
9-night Eastern Caribbean Loop via Coco Cay, San Juan & Philipsburg
Dec 30, 2027 → Jan 8, 2028 • Port Canaveral ↔
From $1,994
$1,994
·
$222/night
$222/night