⚓ Cruises

Princess Caribbean cruises

236 itineraries with a bookable sailing ahead, 246 sailings, most popular first. Each card: how long, how many ports, when, from what price — and the bucket-list thing to do at every stop.

All cruises › Princess Caribbean cruises

Sailing from

New York3 Port Canaveral34 Miami12 Los Angeles3 Fort Lauderdale (Port Everglades)122San Juan33 Bridgetown29

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Ranked by what people search for and where the cruise lines send the most ships.

16-night Caribbean from Fort Lauderdale (Port Everglades)

Princess · Island Princess

11 ports
Round trip
Sails Apr 3, 2028
From $1,649 pp
Premium

St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island
St. Maarten Maho Beach: Legendary Extreme Plane-Spotting Experience
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant

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14-night Caribbean from San Juan

Princess · Emerald Princess

9 ports
Round trip
Sails Nov 21, 2027
From $1,683 pp
Premium

St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island
St. Maarten Maho Beach: Legendary Extreme Plane-Spotting Experience
Dominica Boiling Lake & Valley of Desolation: Dominica's Epic Hike

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12-night Caribbean from Fort Lauderdale (Port Everglades)

Princess · Island Princess

7 ports
Round trip
Sails Nov 30, 2026
From $1,454 pp
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Port of Oranjestad Aruba: Snorkel with Turtles at WW2 Shipwreck & Sunset BBQ
Curacao Klein Curaçao Private Day Trip: Deserted Island Escape
St. Lucia Gros Piton Summit Hike: Conquer St. Lucia's Iconic Peak

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7-night Caribbean from San Juan

Princess · Crown Princess

6 ports
Round trip
Sails Jan 31, 2027
From $579 pp
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St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island
Guadeloupe La Grande Soufrière: Private Guided Summit Hike
Dominica Boiling Lake & Valley of Desolation: Dominica's Epic Hike

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7-night Caribbean from Bridgetown

Princess · Crown Princess

6 ports
Round trip
Sails Jan 29, 2027
From $1,439 pp
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San Juan Walk El Morro & Old San Juan's City Walls
St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island
Guadeloupe La Grande Soufrière: Private Guided Summit Hike

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14-night Caribbean from San Juan

Princess · Emerald Princess

9 ports
Round trip
Sails Dec 5, 2027
From $1,663 pp
Premium

St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island
St. Maarten Maho Beach: Legendary Extreme Plane-Spotting Experience
Antigua Adventure Antigua: Xtreme Circumnavigation of the Entire Island

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14-night Caribbean from San Juan

Princess · Emerald Princess

9 ports
Round trip
Sails Dec 12, 2027
From $1,603 pp
Premium

Tortola Jost Van Dyke: Sandy Spit & Soggy Dollar Painkiller Sail
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Dominica Boiling Lake & Valley of Desolation: Dominica's Epic Hike

See the whole trip →

14-night Caribbean from San Juan

Princess · Crown Princess

7 ports
Round trip
Sails Jan 10, 2027
From $1,716 pp
Premium

St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island
St. Maarten Maho Beach: Legendary Extreme Plane-Spotting Experience
Antigua Adventure Antigua: Xtreme Circumnavigation of the Entire Island

See the whole trip →

14-night Caribbean from San Juan

Princess · Crown Princess

7 ports
Round trip
Sails Jan 17, 2027
From $1,726 pp
Premium

St. Maarten Maho Beach: Legendary Extreme Plane-Spotting Experience
St. Georges Grenada Private Taxi Tour: Your Island, Your Way
St. Lucia Gros Piton Summit Hike: Conquer St. Lucia's Iconic Peak

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14-night Caribbean from San Juan

Princess · Crown Princess

9 ports
Round trip
Sails Dec 27, 2026
From $3,046 pp
Premium

St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island
St. Maarten Maho Beach: Legendary Extreme Plane-Spotting Experience
Antigua Adventure Antigua: Xtreme Circumnavigation of the Entire Island

See the whole trip →

14-night Caribbean from San Juan

Princess · Crown Princess

9 ports
Round trip
Sails Jan 3, 2027
From $1,876 pp
Premium

St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Dominica Boiling Lake & Valley of Desolation: Dominica's Epic Hike

See the whole trip →

14-night Caribbean from San Juan

Princess · Crown Princess

9 ports
Round trip
Sails Feb 14, 2027
From $1,561 pp
Premium

St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Dominica Boiling Lake & Valley of Desolation: Dominica's Epic Hike

See the whole trip →

14-night Caribbean from San Juan

Princess · Crown Princess

9 ports
Round trip
Sails Mar 7, 2027
From $1,711 pp
Premium

St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island
St. Maarten Maho Beach: Legendary Extreme Plane-Spotting Experience
Antigua Adventure Antigua: Xtreme Circumnavigation of the Entire Island

See the whole trip →

14-night Caribbean from San Juan

Princess · Crown Princess

9 ports
Round trip
Sails Mar 14, 2027
From $1,731 pp
Premium

St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Dominica Boiling Lake & Valley of Desolation: Dominica's Epic Hike

See the whole trip →

14-night Caribbean from San Juan

Princess · Emerald Princess

9 ports
Round trip
Sails Jan 16, 2028
From $1,493 pp
Premium

St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island
St. Maarten Maho Beach: Legendary Extreme Plane-Spotting Experience
Antigua Adventure Antigua: Xtreme Circumnavigation of the Entire Island

See the whole trip →

14-night Caribbean from San Juan

Princess · Emerald Princess

9 ports
Round trip
Sails Jan 23, 2028
From $1,493 pp
Premium

St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Dominica Boiling Lake & Valley of Desolation: Dominica's Epic Hike

See the whole trip →

14-night Caribbean from San Juan

Princess · Emerald Princess

10 ports
Round trip
Sails Nov 28, 2027
From $1,683 pp
Premium

Tortola Jost Van Dyke: Sandy Spit & Soggy Dollar Painkiller Sail
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Dominica Boiling Lake & Valley of Desolation: Dominica's Epic Hike

See the whole trip →

14-night Caribbean from San Juan

Princess · Emerald Princess

10 ports
Round trip
Sails Dec 19, 2027
From $1,798 pp
Premium

St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island
St. Maarten Maho Beach: Legendary Extreme Plane-Spotting Experience
Antigua Adventure Antigua: Xtreme Circumnavigation of the Entire Island

See the whole trip →

14-night Caribbean from San Juan

Princess · Emerald Princess

10 ports
Round trip
Sails Dec 26, 2027
From $1,798 pp
Premium

Tortola Jost Van Dyke: Sandy Spit & Soggy Dollar Painkiller Sail
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Dominica Boiling Lake & Valley of Desolation: Dominica's Epic Hike

See the whole trip →

14-night Caribbean from San Juan

Princess · Emerald Princess

10 ports
Round trip
Sails Jan 2, 2028
From $1,553 pp
Premium

St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island
St. Maarten Maho Beach: Legendary Extreme Plane-Spotting Experience
Antigua Adventure Antigua: Xtreme Circumnavigation of the Entire Island

See the whole trip →

14-night Caribbean from San Juan

Princess · Emerald Princess

10 ports
Round trip
Sails Jan 9, 2028
From $1,553 pp
Premium

Tortola Jost Van Dyke: Sandy Spit & Soggy Dollar Painkiller Sail
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Dominica Boiling Lake & Valley of Desolation: Dominica's Epic Hike

See the whole trip →

14-night Caribbean from San Juan

Princess · Emerald Princess

10 ports
Round trip
Sails Jan 30, 2028
From $1,553 pp
Premium

St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island
St. Maarten Maho Beach: Legendary Extreme Plane-Spotting Experience
Antigua Adventure Antigua: Xtreme Circumnavigation of the Entire Island

See the whole trip →

14-night Caribbean from San Juan

Princess · Emerald Princess

10 ports
Round trip
Sails Feb 6, 2028
From $1,553 pp
Premium

Tortola Jost Van Dyke: Sandy Spit & Soggy Dollar Painkiller Sail
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Dominica Boiling Lake & Valley of Desolation: Dominica's Epic Hike

See the whole trip →

14-night Caribbean from San Juan

Princess · Emerald Princess

10 ports
Round trip
Sails Feb 27, 2028
From $2,013 pp
Premium

St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island
St. Maarten Maho Beach: Legendary Extreme Plane-Spotting Experience
Antigua Adventure Antigua: Xtreme Circumnavigation of the Entire Island

See the whole trip →

14-night Caribbean from San Juan

Princess · Emerald Princess

10 ports
Round trip
Sails Mar 5, 2028
From $2,113 pp
Premium

Tortola Jost Van Dyke: Sandy Spit & Soggy Dollar Painkiller Sail
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Dominica Boiling Lake & Valley of Desolation: Dominica's Epic Hike

See the whole trip →

14-night Caribbean from San Juan

Princess · Emerald Princess

10 ports
Round trip
Sails Mar 12, 2028
From $2,153 pp
Premium

St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island
St. Maarten Maho Beach: Legendary Extreme Plane-Spotting Experience
Antigua Adventure Antigua: Xtreme Circumnavigation of the Entire Island

See the whole trip →

14-night Caribbean from Fort Lauderdale (Port Everglades)

Princess · Coral Princess

8 ports
Round trip
Sails Oct 15, 2026
From $1,489 pp
Premium

St. Maarten Maho Beach: Legendary Extreme Plane-Spotting Experience
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Dominica Boiling Lake & Valley of Desolation: Dominica's Epic Hike

See the whole trip →

14-night Caribbean from Fort Lauderdale (Port Everglades)

Princess · Enchanted Princess

8 ports
Round trip
Sails Dec 3, 2026
From $1,599 pp
Premium

St. Maarten Maho Beach: Legendary Extreme Plane-Spotting Experience
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Dominica Boiling Lake & Valley of Desolation: Dominica's Epic Hike

See the whole trip →

14-night Caribbean from San Juan

Princess · Crown Princess

8 ports
Round trip
Sails Feb 21, 2027
From $1,327 pp
Premium

St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island
St. Maarten Maho Beach: Legendary Extreme Plane-Spotting Experience
Antigua Adventure Antigua: Xtreme Circumnavigation of the Entire Island

See the whole trip →

14-night Caribbean from San Juan

Princess · Crown Princess

8 ports
Round trip
Sails Feb 28, 2027
From $1,297 pp
Premium

St. Maarten Maho Beach: Legendary Extreme Plane-Spotting Experience
Dominica Boiling Lake & Valley of Desolation: Dominica's Epic Hike
St. Georges Grenada Private Taxi Tour: Your Island, Your Way

See the whole trip →

18-night Fort Lauderdale (Port Everglades) to Buenos Aires

Princess · Majestic Princess

8 ports
One way
Sails Nov 19, 2026
From $1,791 pp
Premium

St. Maarten Maho Beach: Legendary Extreme Plane-Spotting Experience
St. Lucia Gros Piton Summit Hike: Conquer St. Lucia's Iconic Peak
Bridgetown Swim with wild green sea turtles + two shipwrecks by luxury catamaran (El Tigre)

See the whole trip →