Silver Spirit • Silversea Cruises
12-night Southern Caribbean Arc via San Juan, Oranjestad & Willemstad
Feb 6, 2027 → Feb 18, 2027 • Miami → Bridgetown
From $9,000
$750/night
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286 total
Silver Spirit • Silversea Cruises
10-night Southern Caribbean Loop via Port Elizabeth, Bequia, Saint George's & Kralendijk
Feb 18, 2027 → Feb 28, 2027 • Bridgetown ↔
From $7,500
$750/night
Iona • P&O Cruises
14-night Southern Caribbean Loop via Tortola, Philipsburg & Fort-de-France
Jan 10, 2028 → Jan 24, 2028 • Basseterre, Saint Kitts ↔
From $2,566
$183/night
Typical price
Arvia • P&O Cruises
14-night Southern Caribbean Loop via Tortola, Philipsburg & Roseau
Jan 3, 2028 → Jan 17, 2028 • Basseterre, Saint Kitts ↔
From $2,499
$179/night
Typical price
MSC Seaview • MSC Cruises
7-night Southern Caribbean Loop via Pointe-à-Pitre, Bridgetown & Kingstown
Dec 26, 2026 → Jan 2, 2027 • Fort-de-France ↔
From $1,803
$258/night
Iona • P&O Cruises
14-night Southern Caribbean Loop via Philipsburg, Fort-de-France & Antigua
Dec 13, 2027 → Dec 27, 2027 • Basseterre, Saint Kitts ↔
From $3,918
$280/night
Priced high
↑73% above typical
Valiant Lady • Virgin Voyages
7-night Southern Caribbean Loop via Philipsburg, Fort-de-France & Bridgetown
Dec 26, 2026 → Jan 2, 2027 • San Juan ↔
From $1,837
$262/night
Priced high
↑65% above typical
MSC World Europa • MSC Cruises
7-night Southern Caribbean Loop via Pointe-à-Pitre, Bridgetown & Kingstown
Dec 26, 2026 → Jan 2, 2027 • Fort-de-France ↔
From $1,916
$274/night
Priced high
↑61% above typical
Arvia • P&O Cruises
14-night Southern Caribbean Loop via Philipsburg, Roseau & Antigua
Dec 20, 2027 → Jan 3, 2028 • Basseterre, Saint Kitts ↔
From $4,093
$292/night
Priced high
↑60% above typical
Britannia • P&O Cruises
14-night Southern Caribbean Loop via Philipsburg, Antigua & Basseterre, Saint Kitts
Mar 6, 2027 → Mar 20, 2027 • Bridgetown ↔
From $2,904
$207/night
Priced high
↑59% above typical
Crown Princess • Princess Cruises
7-night Southern Caribbean Loop via San Juan, Philipsburg & Fort-de-France
Jan 15, 2027 → Jan 22, 2027 • Bridgetown ↔
From $1,270
$181/night
Priced high
↑56% above typical
Britannia • P&O Cruises
14-night Southern Caribbean Loop via Philipsburg, Antigua & Basseterre, Saint Kitts
Mar 5, 2027 → Mar 19, 2027 • Bridgetown ↔
From $2,836
$203/night
Priced high
↑56% above typical
Norwegian Viva • Norwegian Cruise Line
7-night Southern Caribbean Loop via Oranjestad & Bridgetown
Dec 19, 2027 → Dec 26, 2027 • San Juan ↔
From $1,769
$253/night
Priced high
↑55% above typical
MSC Seaview • MSC Cruises
7-night Southern Caribbean Loop via Pointe-à-Pitre, Castries & Bridgetown
Mar 20, 2027 → Mar 27, 2027 • Fort-de-France ↔
From $1,078
$154/night
Norwegian Viva • Norwegian Cruise Line
7-night Southern Caribbean Loop via Oranjestad & Bridgetown
Nov 21, 2027 → Nov 28, 2027 • San Juan ↔
From $1,369
$196/night
Priced high
↑52% above typical
Crown Princess • Princess Cruises
7-night Eastern Caribbean Loop via Saint Thomas, Basseterre, Saint Kitts & Roseau
Jan 3, 2027 → Jan 10, 2027 • San Juan ↔
From $1,189
$170/night
Priced high
↑46% above typical
MSC Seaview • MSC Cruises
7-night Transatlantic Crossing via Castries, Bridgetown & Saint George
Mar 21, 2027 → Mar 28, 2027 • Pointe-à-Pitre ↔
From $1,008
$144/night
Iona • P&O Cruises
14-night Southern Caribbean Loop via Tortola, Philipsburg & Fort-de-France
Nov 15, 2027 → Nov 29, 2027 • Basseterre, Saint Kitts ↔
From $2,566
$183/night
Priced high
↑43% above typical
Le Champlain • Ponant Cruises
7-night Southern Caribbean Loop via Portsmouth, Terre-de-Haut & Port Elizabeth
Feb 23, 2028 → Mar 1, 2028 • Vieux Fort ↔
From $5,630
$804/night
Carnival Firenze • Carnival Cruise Line
16-night Southern Caribbean Arc via Rio de Janeiro, Maceió & Saint George's
Feb 2, 2027 → Feb 18, 2027 • Buenos Aires → Miami
From $1,826
$114/night
Priced high
↑40% above typical