Crown Princess • Princess Cruises
14-night Eastern Caribbean Loop via Saint Thomas, Basseterre, Saint Kitts & Roseau
Feb 14, 2027 → Feb 28, 2027 • San Juan ↔
From $1,559
$111/night
Good value
↓15% below typical
View by
1,390 total
Celebrity Apex • Celebrity Cruises
7-night Eastern Caribbean Loop via Puerto Plata & Charlotte Amalie, Saint Thomas
Feb 5, 2028 → Feb 12, 2028 • Port Canaveral ↔
From $897
$128/night
Good value
↓12% below typical
Icon of the Seas • Royal Caribbean International
7-night Eastern Caribbean Loop via Philipsburg & Coco Cay
Sep 19, 2026 → Sep 26, 2026 • Miami ↔
From $1,332
$190/night
Good value
↓19% below typical
Queen Elizabeth • Cunard Line
21-night Western Caribbean Loop via Georgetown, Grand Cayman, Montego Bay & Cozumel
Dec 8, 2026 → Dec 29, 2026 • Miami ↔
From $2,261
$108/night
Good value
↓15% below typical
Independence of the Seas • Royal Caribbean International
9-night Eastern Caribbean Loop via Kings Wharf & Labadee
Aug 5, 2027 → Aug 14, 2027 • Cape Liberty, NJ (NYC) ↔
From $1,415
$157/night
Good value
↓14% below typical
Vision of the Seas • Royal Caribbean International
7-night Eastern Caribbean Loop via Charlotte Amalie, Saint Thomas, Frederiksted, Saint Croix & Philipsburg
Mar 7, 2027 → Mar 14, 2027 • San Juan ↔
From $569
$81/night
Good value
↓20% below typical
Celebrity Ascent • Celebrity Cruises
10-night Southern Caribbean Loop via Philipsburg, Castries & Saint George's
Nov 13, 2026 → Nov 23, 2026 • Fort Lauderdale ↔
From $1,422
$142/night
Great deal
↓23% below typical
Iona • P&O Cruises
14-night Eastern Caribbean Loop via Basseterre, Saint Kitts, Tortola & Philipsburg
Jan 7, 2028 → Jan 21, 2028 • Bridgetown ↔
From $2,363
$169/night
Typical price
↓8% below typical
Iona • P&O Cruises
14-night Eastern Caribbean Loop via Basseterre, Saint Kitts, Tortola & Philipsburg
Jan 8, 2028 → Jan 22, 2028 • Bridgetown ↔
From $2,363
$169/night
Typical price
↓8% below typical
Carnival Venezia • Carnival Cruise Line
14-night Eastern Caribbean Loop via Saint Thomas, Antigua & Roseau
Nov 29, 2026 → Dec 13, 2026 • Port Canaveral ↔
From $995
$71/night
Good value
↓13% below typical
Arvia • P&O Cruises
14-night Eastern Caribbean Loop via Basseterre, Saint Kitts, Philipsburg & Tortola
Dec 3, 2027 → Dec 17, 2027 • Bridgetown ↔
From $2,161
$154/night
Good value
↓16% below typical
Emerald Sakara • Emerald Cruises
7-night Eastern Caribbean Loop: Basseterre, Saint Kitts & Road Bay
Dec 16, 2028 → Dec 23, 2028 • Philipsburg ↔
From $6,096
$871/night
Typical price
↓4% below typical
Emerald Sakara • Emerald Cruises
7-night Eastern Caribbean Loop: Basseterre, Saint Kitts & Road Bay
Dec 23, 2028 → Dec 30, 2028 • Philipsburg ↔
From $6,096
$871/night
Typical price
↓4% below typical
MSC Opera • MSC Cruises
7-night Eastern Caribbean Loop via Spanish Town, Philipsburg & Basseterre, Saint Kitts
Mar 1, 2027 → Mar 8, 2027 • La Romana ↔
From $579
$83/night
MSC Opera • MSC Cruises
7-night Eastern Caribbean Loop via Spanish Town, Philipsburg & Basseterre, Saint Kitts
Mar 15, 2027 → Mar 22, 2027 • La Romana ↔
From $579
$83/night
Crown Princess • Princess Cruises
7-night Eastern Caribbean Loop via Saint Thomas, Philipsburg & Antigua
Feb 7, 2027 → Feb 14, 2027 • San Juan ↔
From $785
$112/night
Good value
↓14% below typical
MSC World Europa • MSC Cruises
7-night Eastern Caribbean Loop via Pointe-à-Pitre, Antigua & Philipsburg
Dec 5, 2026 → Dec 12, 2026 • Fort-de-France ↔
From $1,001
$143/night
Good value
↓16% below typical
Brilliant Lady • Virgin Voyages
10-night Eastern Caribbean Loop via Philipsburg, Road Town, Tortola & Basseterre, Saint Kitts
Nov 15, 2026 → Nov 25, 2026 • Miami ↔
From $1,290
$129/night
Good value
↓13% below typical
Arvia • P&O Cruises
14-night Eastern Caribbean Loop via Fort-de-France, Basseterre, Saint Kitts & Tortola
Nov 21, 2026 → Dec 5, 2026 • Bridgetown ↔
From $1,863
$133/night
Good value
↓14% below typical
Arvia • P&O Cruises
27-night Transatlantic Crossing via Philipsburg, Fort-de-France & Roseau
Feb 28, 2028 → Mar 26, 2028 • Basseterre, Saint Kitts → Southampton
From $3,918
$145/night
Great deal
↓21% below typical