Silver Spirit • Silversea Cruises
12-night Southern Caribbean Loop via Port Elizabeth, Bequia, Castries & Kralendijk
Jan 10, 2028 → Jan 22, 2028 • Bridgetown ↔
From $7,400
$617/night
View by
930 total
Seven Seas Mariner • Regent Seven Seas Cruises
14-night Eastern Caribbean Arc via Georgetown, Grand Cayman, Ocho Rios & Oranjestad
Dec 21, 2026 → Jan 4, 2027 • Tampa → Miami
From $9,561
$683/night
Emerald Princess • Princess Cruises
14-night Eastern Caribbean Loop via Tortola, Basseterre, Saint Kitts & Roseau
Nov 28, 2027 → Dec 12, 2027 • San Juan ↔
From $1,586
$113/night
Typical price
↓8% below typical
Arvia • P&O Cruises
14-night Eastern Caribbean Loop via Fort-de-France, Basseterre, Saint Kitts & Tortola
Jan 16, 2027 → Jan 30, 2027 • Bridgetown ↔
From $2,296
$164/night
Typical price
↓8% below typical
Iona • P&O Cruises
14-night Southern Caribbean Loop via Basseterre, Saint Kitts, Philipsburg & Fort-de-France
Dec 11, 2027 → Dec 25, 2027 • Bridgetown ↔
From $2,228
$159/night
Typical price
↓2% below typical
MSC Meraviglia • MSC Cruises
14-night Southern Caribbean Loop via Kingstown, Port-of-Spain & Saint George
Feb 22, 2028 → Mar 7, 2028 • Bridgetown ↔
From $2,262
$162/night
Typical price
↓2% below typical
Norwegian Prima • Norwegian Cruise Line
7-night Eastern Caribbean Loop via Philipsburg, Basseterre, Saint Kitts & Bridgetown
Dec 13, 2026 → Dec 20, 2026 • San Juan ↔
From $1,469
$210/night
Typical price
↓9% below typical
Emerald Sakara • Emerald Cruises
14-night Eastern Caribbean Arc via Basseterre, Saint Kitts, Road Bay & Spanish Town
Nov 27, 2027 → Dec 11, 2027 • Philipsburg → Bridgetown
From $11,054
$790/night
Typical price
↓7% below typical
Silver Shadow • Silversea Cruises
10-night Eastern Caribbean Arc via Philipsburg, Basseterre, Saint Kitts & Little Bay
Dec 10, 2026 → Dec 20, 2026 • Miami → San Juan
From $6,300
$630/night
Arvia • P&O Cruises
14-night Eastern Caribbean Loop via Fort-de-France, Basseterre, Saint Kitts & Tortola
Nov 6, 2026 → Nov 20, 2026 • Bridgetown ↔
From $2,134
$152/night
Typical price
↓1% below typical
Arvia • P&O Cruises
14-night Eastern Caribbean Loop via Castries, Saint George's & Bridgetown
Nov 14, 2026 → Nov 28, 2026 • Antigua ↔
From $2,134
$152/night
Typical price
↓1% below typical
Arvia • P&O Cruises
14-night Eastern Caribbean Loop via Basseterre, Saint Kitts, Tortola & Philipsburg
Nov 6, 2027 → Nov 20, 2027 • Bridgetown ↔
From $2,134
$152/night
Typical price
↓1% below typical
Arvia • P&O Cruises
14-night Eastern Caribbean Loop via Basseterre, Saint Kitts, Philipsburg & Tortola
Nov 20, 2027 → Dec 4, 2027 • Bridgetown ↔
From $2,134
$152/night
Typical price
↓1% below typical
Seven Seas Grandeur • Regent Seven Seas Cruises
10-night Southern Caribbean Loop via Saint George's, Oranjestad & Willemstad
Feb 4, 2028 → Feb 14, 2028 • Bridgetown ↔
From $5,960
$596/night
Coral Princess • Princess Cruises
11-night Eastern Caribbean Loop via Saint Thomas, Basseterre, Saint Kitts & Fort-de-France
Dec 26, 2026 → Jan 6, 2027 • Fort Lauderdale ↔
From $1,588
$144/night
Typical price
↓1% below typical
Carnival Pride • Carnival Cruise Line
14-night Eastern Caribbean Loop via Saint Thomas, Philipsburg & Basseterre, Saint Kitts
Oct 31, 2027 → Nov 14, 2027 • Baltimore ↔
From $1,572
$112/night
Typical price
↓7% below typical
MSC Seaview • MSC Cruises
7-night Eastern Caribbean Loop via Pointe-à-Pitre, Philipsburg & Saint John's
Jan 30, 2027 → Feb 6, 2027 • Fort-de-France ↔
From $770
$110/night
Vision of the Seas • Royal Caribbean International
7-night Eastern Caribbean Loop via Tortola, Cruz Bay, Saint John & Philipsburg
Nov 22, 2026 → Nov 29, 2026 • San Juan ↔
From $661
$94/night
Typical price
↓6% below typical
Norwegian Bliss • Norwegian Cruise Line
12-night Eastern Caribbean Loop via Puerto Plata, San Juan & Basseterre, Saint Kitts
Dec 11, 2026 → Dec 23, 2026 • New York ↔
From $1,219
$102/night
Typical price
↓8% below typical
Emerald Sakara • Emerald Cruises
14-night Eastern Caribbean Arc via Soufriere, Antigua & Road Bay
Nov 13, 2027 → Nov 27, 2027 • Bridgetown → Philipsburg
From $11,111
$794/night
Typical price
↓6% below typical