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Wind Surf

Philipsburg → San José → Funchal, Madeira → Lisbon

Mar 12, 2028 · 21 nights

$4,168 oceanview · $198/night

Star Pride

San Juan → Saint George's → Spanish Town (Virgin Gorda) → San Juan

Mar 13, 2028 · 14 nights

$4,014 oceanview · $287/night

MSC Opera

La Romana → Catalina Island → Saint George's → La Romana

Mar 20, 2028 · 14 nights

$1,492 interior · $107/night

4% below typical

Star Pride

San Juan → Basseterre, Saint Kitts → Saint-Barthélemy → San Juan

Mar 20, 2028 · 7 nights

$2,443 oceanview · $349/night

Star Pride

San Juan → Basseterre, Saint Kitts → Marmaris → San Juan

Mar 20, 2028 · 14 nights

$4,014 oceanview · $287/night

MSC Opera

La Romana → Catalina Island → Saint John's → La Romana

Apr 3, 2028 · 7 nights

$719 interior · $103/night

4% below typical

MSC Opera

Bridgetown → Fort-de-France → Antigua → Bridgetown

Sep 28, 2028 · 14 nights

$1,289 interior · $92/night

1% below typical

MSC Opera

La Romana → Catalina Island → Antigua → La Romana

Oct 2, 2028 · 7 nights

$709 interior · $101/night

4% below typical

MSC Opera

Fort-de-France → Pointe-à-Pitre → Philipsburg → Fort-de-France

Jun 25, 2027 · 7 nights

$1,050 interior · $150/night

SeaDream I

Philipsburg → Norman Island → Mayreau Island → Bridgetown

Nov 14, 2026 · 7 nights

$5,438 oceanview · $777/night

MSC Opera

Fort-de-France → Pointe-à-Pitre → Bridgetown → Fort-de-France

Nov 20, 2026 · 14 nights

$1,218 interior · $87/night

1% below typical

MSC Opera

Bridgetown → Fort-de-France → Catalina Island → Bridgetown

Dec 3, 2026 · 14 nights

$1,448 interior · $103/night

MSC Opera

Fort-de-France → Pointe-à-Pitre → Bridgetown → Fort-de-France

Dec 4, 2026 · 14 nights

$1,428 interior · $102/night

1% below typical

SeaDream I

Saint John's → Saint-Barthélemy → Norman Island → San Juan

Dec 5, 2026 · 7 nights

$5,342 oceanview · $763/night

Emerald Azzurra

Bridgetown → Soufriere → Saba → Marigot

Dec 6, 2026 · 14 nights

$15,833 balcony · $1,131/night

4% below typical

SeaDream I

San Juan → Culebra Island → Spanish Town (Virgin Gorda) → Charlotte Amalie, Saint Thomas

Dec 12, 2026 · 7 nights

$5,438 oceanview · $777/night

Emerald Azzurra

Marigot → Road Bay → Saba → Saint-Barthélemy

Dec 13, 2026 · 7 nights

$4,991 balcony · $713/night

3% below typical

Emerald Sakara

Saint Thomas → Saint-John → Saint-Barthélemy → Saint Thomas

Dec 13, 2026 · 7 nights

$4,763 oceanview · $680/night

Le Bougainville

Fort-de-France → Antigua → Grand-Bourg → Fort-de-France

Dec 16, 2026 · 7 nights

$5,668 balcony · $810/night

MSC Opera

Bridgetown → Fort-de-France → Catalina Island → Bridgetown

Dec 17, 2026 · 14 nights

$1,968 interior · $141/night

1% below typical

Philipsburg → San José → Funchal, Madeira → Lisbon

San Juan → Saint George's → Spanish Town (Virgin Gorda) → San Juan

La Romana → Catalina Island → Saint George's → La Romana

San Juan → Basseterre, Saint Kitts → Saint-Barthélemy → San Juan

San Juan → Basseterre, Saint Kitts → Marmaris → San Juan

La Romana → Catalina Island → Saint John's → La Romana

Bridgetown → Fort-de-France → Antigua → Bridgetown

La Romana → Catalina Island → Antigua → La Romana

Fort-de-France → Pointe-à-Pitre → Philipsburg → Fort-de-France

Philipsburg → Norman Island → Mayreau Island → Bridgetown

Fort-de-France → Pointe-à-Pitre → Bridgetown → Fort-de-France

Bridgetown → Fort-de-France → Catalina Island → Bridgetown

Fort-de-France → Pointe-à-Pitre → Bridgetown → Fort-de-France

Saint John's → Saint-Barthélemy → Norman Island → San Juan

Bridgetown → Soufriere → Saba → Marigot

San Juan → Culebra Island → Spanish Town (Virgin Gorda) → Charlotte Amalie, Saint Thomas

Marigot → Road Bay → Saba → Saint-Barthélemy

Saint Thomas → Saint-John → Saint-Barthélemy → Saint Thomas

Fort-de-France → Antigua → Grand-Bourg → Fort-de-France

Bridgetown → Fort-de-France → Catalina Island → Bridgetown

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