Departure months
Trip length
Search
MSC Cruises

MSC Opera • MSC Cruises

14-night Eastern Caribbean Loop via Fort-de-France, Antigua & Spanish Town

Jan 14, 2027 → Jan 28, 2027 • Bridgetown ↔

From $2,816

$201/night

Silversea Cruises

Silver Shadow • Silversea Cruises

10-night Eastern Caribbean Arc via Port Elizabeth, Bequia, Castries & Little Bay

Jan 20, 2027 → Jan 30, 2027 • Bridgetown → San Juan

From $7,200

$720/night

MSC Cruises

MSC Opera • MSC Cruises

14-night Eastern Caribbean Loop via Pointe-à-Pitre, Road Town, Tortola & La Romana

Feb 12, 2027 → Feb 26, 2027 • Fort-de-France ↔

From $1,748

$125/night

Silversea Cruises

Silver Nova • Silversea Cruises

11-night Eastern Caribbean Loop via San Juan & Saint-Barthélemy

Jan 9, 2028 → Jan 20, 2028 • Miami ↔

From $8,100

$736/night

Silversea Cruises

Silver Dawn • Silversea Cruises

10-night Eastern Caribbean Loop via Jost Van Dyke, Saint-Barthélemy & Basseterre, Saint Kitts

Jan 15, 2028 → Jan 25, 2028 • San Juan ↔

From $6,400

$640/night

Silversea Cruises

Silver Nova • Silversea Cruises

11-night Eastern Caribbean Loop via San Juan & Basseterre, Saint Kitts

Jan 20, 2028 → Jan 31, 2028 • Miami ↔

From $8,100

$736/night

Silversea Cruises

Silver Nova • Silversea Cruises

11-night Eastern Caribbean Loop via Saint-Barthélemy, Saint John's & Fort-de-France

Jan 31, 2028 → Feb 11, 2028 • Miami ↔

From $8,100

$736/night

P&O Cruises

Iona • P&O Cruises

14-night Southern Caribbean Loop via Tortola, Philipsburg & Fort-de-France

Feb 21, 2028 → Mar 6, 2028 • Basseterre, Saint Kitts ↔

1% below typical

From $2,607

$186/night

Typical price

↓1% below typical

Ponant Cruises

Le Bougainville • Ponant Cruises

7-night Eastern Caribbean Loop via Antigua, Spanish Town & Basseterre, Saint Kitts

Feb 10, 2027 → Feb 17, 2027 • Fort-de-France ↔

From $4,969

$710/night

Princess Cruises

Emerald Princess • Princess Cruises

14-night Eastern Caribbean Loop via Saint Thomas, Philipsburg & Antigua

Jan 2, 2028 → Jan 16, 2028 • San Juan ↔

1% below typical

From $1,836

$131/night

Typical price

↓1% below typical

Royal Caribbean International

Grandeur of the Seas • Royal Caribbean International

7-night Eastern Caribbean Loop via Tortola, Philipsburg & Saint John's

Jun 19, 2027 → Jun 26, 2027 • San Juan ↔

Great balance

From $975

$139/night

Typical price

↓1% below typical

Emerald Cruises

Emerald Sakara • Emerald Cruises

7-night Eastern Caribbean Arc via Basseterre, Saint Kitts, Road Bay & Spanish Town

Nov 27, 2027 → Dec 4, 2027 • Philipsburg ↔

Great balance

From $5,866

$838/night

Typical price

↓1% below typical

Regent Seven Seas Cruises

Seven Seas Grandeur • Regent Seven Seas Cruises

12-night Eastern Caribbean Loop via Puerto Plata, Cayo Levantado & San Juan

Mar 20, 2028 → Apr 1, 2028 • Miami ↔

From $7,669

$639/night

Holland America

Zuiderdam • Holland America

28-night Fort Lauderdale → Half Moon Cay → Fort-de-France → Scarborough + 8 more

Jan 6, 2028 → Feb 3, 2028 • Fort Lauderdale ↔

From $5,979

$214/night

MSC Cruises

MSC Seashore • MSC Cruises

14-night Eastern Caribbean Loop via Philipsburg, Basseterre, Saint Kitts & Ocean Cay

Jan 29, 2028 → Feb 12, 2028 • Miami ↔

↗ Trending up

From $1,248

$89/night

Typical price

↓1% below typical

Emerald Cruises

Emerald Sakara • Emerald Cruises

14-night Eastern Caribbean Arc via Soufriere, Antigua & Road Bay

Jan 29, 2028 → Feb 12, 2028 • Bridgetown → Philipsburg

1% below typical

From $11,957

$854/night

Typical price

↓1% below typical

Silversea Cruises

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

P&O Cruises

Iona • P&O Cruises

14-night Southern Caribbean Loop via Tortola, Philipsburg & Fort-de-France

Jan 10, 2028 → Jan 24, 2028 • Basseterre, Saint Kitts ↔

0% below typical

From $2,566

$183/night

Typical price
Explora Journeys

Explora II • Explora Journeys

7-night Eastern Caribbean Arc via Saint-Barthélemy & Ocean Cay

Feb 27, 2028 → Mar 5, 2028 • San Juan → Miami

From $4,020

$574/night

Typical price

↓1% below typical

Emerald Cruises

Emerald Sakara • Emerald Cruises

14-night Eastern Caribbean Arc via Basseterre, Saint Kitts, Road Bay & Spanish Town

Feb 5, 2028 → Feb 19, 2028 • Philipsburg → Bridgetown

0% below typical

From $11,957

$854/night

Typical price

Filters

Filters

Reset
Deal Signals
Trip Style
Cabin Type
Ports Visited
Cruise Line & Ship
Price

Per person