⚓ Cruises

Caribbean cruises from San Juan

375 itineraries with a bookable sailing ahead, 385 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 › Caribbean cruises from San Juan

Cruise line

Royal Caribbean121 Norwegian55 Princess33 Disney6 Celebrity30 Viking Ocean27 Oceania1 Silversea17 Virgin42 Windstar10 Azamara8 Explora Journeys25

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

7-night Caribbean from San Juan

Celebrity · Celebrity Constellation

6 ports
Round trip
Sails Mar 27, 2027
From $806 pp
Premium

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

See the whole trip →

7-night Caribbean from San Juan

Celebrity · Celebrity Summit

6 ports
Round trip
Sails Nov 28, 2027
From $542 pp
Premium

Charlotte Amalie Private Full-Day Boat Charter: 35ft Scarab Triple 300s
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
St. John's Private Half-Day Island Adventure & Trunk Bay Beach

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7-night Caribbean from San Juan

Celebrity · Celebrity Summit

6 ports
Round trip
Sails Dec 12, 2027
From $543 pp
Premium

Port of Kingstown La Soufrière Volcano Summit Hike: St. Vincent's Crown
Bridgetown Swim with wild green sea turtles + two shipwrecks by luxury catamaran (El Tigre)
Fort-de-France Mount Pelée & Saint-Pierre: Volcano, Ghost Town & Dark History

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7-night Caribbean from San Juan

Celebrity · Celebrity Constellation

6 ports
Round trip
Sails Mar 20, 2027
From $764 pp
Premium

Charlotte Amalie Private Full-Day Boat Charter: 35ft Scarab Triple 300s
St. John's Private Half-Day Island Adventure & Trunk Bay Beach
Roseau Boiling Lake Hike: Dominica's Ultimate Volcanic Pilgrimage

See the whole trip →

7-night Caribbean from San Juan

Celebrity · Celebrity Summit

6 ports
Round trip
Sails Nov 7, 2027
From $545 pp
Premium

Roseau Boiling Lake Hike: Dominica's Ultimate Volcanic Pilgrimage
Bridgetown Swim with wild green sea turtles + two shipwrecks by luxury catamaran (El Tigre)
Castries Cosol Tours: All-Island Private Safari with 7 Stops

See the whole trip →

7-night Caribbean from San Juan

Celebrity · Celebrity Summit

6 ports
Round trip
Sails Nov 21, 2027
From $570 pp
Premium

Roseau Boiling Lake Hike: Dominica's Ultimate Volcanic Pilgrimage
Bridgetown Swim with wild green sea turtles + two shipwrecks by luxury catamaran (El Tigre)
Castries Cosol Tours: All-Island Private Safari with 7 Stops

See the whole trip →

7-night Caribbean from San Juan

Celebrity · Celebrity Summit

6 ports
Round trip
Sails Dec 5, 2027
From $526 pp
Premium

Roseau Boiling Lake Hike: Dominica's Ultimate Volcanic Pilgrimage
Bridgetown Swim with wild green sea turtles + two shipwrecks by luxury catamaran (El Tigre)
Castries Cosol Tours: All-Island Private Safari with 7 Stops

See the whole trip →

7-night Caribbean from San Juan

Celebrity · Celebrity Summit

6 ports
Round trip
Sails Dec 19, 2027
From $789 pp
Premium

Roseau Boiling Lake Hike: Dominica's Ultimate Volcanic Pilgrimage
Bridgetown Swim with wild green sea turtles + two shipwrecks by luxury catamaran (El Tigre)
Castries Cosol Tours: All-Island Private Safari with 7 Stops

See the whole trip →

7-night Caribbean from San Juan

Disney · Disney Dream

5 ports
Round trip
Sails Apr 16, 2027
From $3,872 pp
Premium

Willemstad Private Full-Day Curaçao Island Tour with Local Expert
Port of Oranjestad Aruba: Snorkel with Turtles at WW2 Shipwreck & Sunset BBQ
Antigua Adventure Antigua: Xtreme Circumnavigation of the Entire Island

See the whole trip →

7-night Caribbean from San Juan

Celebrity · Celebrity Summit

6 ports
Round trip
Sails Nov 14, 2027
From $522 pp
Premium

Port of Kingstown La Soufrière Volcano Summit Hike: St. Vincent's Crown
Bridgetown Swim with wild green sea turtles + two shipwrecks by luxury catamaran (El Tigre)
Castries Cosol Tours: All-Island Private Safari with 7 Stops

See the whole trip →

7-night Caribbean from San Juan

Disney · Disney Fantasy

5 ports
Round trip
Sails Dec 3, 2027
From $2,094 pp
Premium

Port of Oranjestad Aruba: Snorkel with Turtles at WW2 Shipwreck & Sunset BBQ
Willemstad Private Full-Day Curaçao Island Tour with Local Expert
Dominica Boiling Lake & Valley of Desolation: Dominica's Epic Hike

See the whole trip →

7-night San Juan to Miami

Explora Journeys · EXPLORA II

6 ports
One way
2 departures Jan 2028
From $4,020 pp
Luxury

Road Town Norman Island: The Indians & Sea Caves Sailing & Snorkel
Pointe-a-Pitre Death in Paradise Filming Locations & Botanical Garden
Gustavia Private Open-Top Mini Moke Island Tour of St. Barts

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7-night Caribbean from San Juan

Disney · Disney Fantasy

5 ports
Round trip
Sails May 6, 2028
From $2,085 pp
Premium

Bridgetown Swim with wild green sea turtles + two shipwrecks by luxury catamaran (El Tigre)
Castries Cosol Tours: All-Island Private Safari with 7 Stops
Dominica Boiling Lake & Valley of Desolation: Dominica's Epic Hike

See the whole trip →

7-night Caribbean from San Juan

Princess · Crown Princess

6 ports
Round trip
Sails Mar 21, 2027
From $789 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 7, 2027
From $1,521 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 Feb 13, 2028
From $1,723 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 Feb 20, 2028
From $1,873 pp
Premium

Tortola Jost Van Dyke: Sandy Spit & Soggy Dollar Painkiller Sail
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
St. Georges Grenada Private Taxi Tour: Your Island, Your Way

See the whole trip →

9-night Caribbean from San Juan

Celebrity · Celebrity Summit

7 ports
Round trip
Sails Oct 29, 2027
From $687 pp
Premium

St. John's Private Half-Day Island Adventure & Trunk Bay Beach
Castries Cosol Tours: All-Island Private Safari with 7 Stops
St. Georges Grenada Private Taxi Tour: Your Island, Your Way

See the whole trip →

7-night Caribbean from San Juan

Celebrity · Celebrity Constellation

6 ports
Round trip
Sails Dec 12, 2026
From $728 pp
Premium

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

See the whole trip →

7-night Caribbean from San Juan

Celebrity · Celebrity Constellation

6 ports
Round trip
Sails Feb 6, 2027
From $579 pp
Premium

Charlotte Amalie Private Full-Day Boat Charter: 35ft Scarab Triple 300s
St. John's Private Half-Day Island Adventure & Trunk Bay Beach
Roseau Boiling Lake Hike: Dominica's Ultimate Volcanic Pilgrimage

See the whole trip →

7-night Caribbean from San Juan

Virgin · Valiant Lady

5 ports
Round trip
2 departures Dec 2026 – Feb 2027
From $973 pp
Premium

Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Fort-de-France Mount Pelée & Saint-Pierre: Volcano, Ghost Town & Dark History
Port of Oranjestad Aruba: Snorkel with Turtles at WW2 Shipwreck & Sunset BBQ

See the whole trip →

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

See the whole trip →

7-night Caribbean from San Juan

Disney · Disney Wish

5 ports
Round trip
Sails Nov 5, 2027
From $2,185 pp
Premium

Port of Oranjestad Aruba: Snorkel with Turtles at WW2 Shipwreck & Sunset BBQ
Kralendijk Klein Bonaire: Bioluminescence Snorkel at the Marine Park
Dominica Boiling Lake & Valley of Desolation: Dominica's Epic Hike

See the whole trip →

7-night Caribbean from San Juan

Princess · Crown Princess

6 ports
Round trip
Sails Jan 31, 2027
From $579 pp
Premium

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

See the whole trip →

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

See the whole trip →

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

See the whole trip →

8-night San Juan to Miami

Oceania · Oceania Allura

7 ports
One way
Sails Feb 19, 2027
From $3,499 pp
Luxury

Gustavia Private Open-Top Mini Moke Island Tour of St. Barts
Philipsburg Random Wind 'Paradise Day Sail' — Schooner Sail, Snorkel & the Original Tarzan Swing
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant

See the whole trip →