⚓ 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.

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 →

6-night Caribbean from San Juan

Virgin · Valiant Lady

5 ports
Round trip
2 departures Nov 2026 – Jan 2027
From $894 pp
Premium

Road Town Norman Island: The Indians & Sea Caves Sailing & Snorkel
St. John's Private Half-Day Island Adventure & Trunk Bay Beach
Castries Cosol Tours: All-Island Private Safari with 7 Stops

See the whole trip →

7-night Caribbean from San Juan

Virgin · Scarlet Lady

5 ports
Round trip
2 departures Feb – Mar 2028
From $833 pp
Premium

Port of Oranjestad Aruba: Snorkel with Turtles at WW2 Shipwreck & Sunset BBQ
Willemstad Private Full-Day Curaçao Island Tour with Local Expert
St. John's Private Half-Day Island Adventure & Trunk Bay Beach

See the whole trip →

10-night Caribbean from San Juan

Viking Ocean · Viking Sea

9 ports
Round trip
Sails Nov 5, 2026
From $5,399 pp
Luxury

St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Castries Cosol Tours: All-Island Private Safari with 7 Stops

See the whole trip →

10-night Caribbean from San Juan

Viking Ocean · Viking Sea

9 ports
Round trip
Sails Nov 15, 2026
From $4,999 pp
Luxury

St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Castries Cosol Tours: All-Island Private Safari with 7 Stops

See the whole trip →

10-night Caribbean from San Juan

Viking Ocean · Viking Sea

9 ports
Round trip
Sails Nov 25, 2026
From $4,999 pp
Luxury

St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Castries Cosol Tours: All-Island Private Safari with 7 Stops

See the whole trip →

10-night Caribbean from San Juan

Viking Ocean · Viking Sea

9 ports
Round trip
Sails Jan 5, 2027
From $6,399 pp
Luxury

St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island
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 →

10-night Caribbean from San Juan

Viking Ocean · Viking Sea

9 ports
Round trip
Sails Jan 15, 2027
From $6,099 pp
Luxury

St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Castries Cosol Tours: All-Island Private Safari with 7 Stops

See the whole trip →

10-night Caribbean from San Juan

Viking Ocean · Viking Sea

9 ports
Round trip
Sails Jan 25, 2027
From $6,899 pp
Luxury

St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Castries Cosol Tours: All-Island Private Safari with 7 Stops

See the whole trip →

10-night Caribbean from San Juan

Viking Ocean · Viking Sea

9 ports
Round trip
Sails Feb 14, 2027
From $6,299 pp
Luxury

St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Castries Cosol Tours: All-Island Private Safari with 7 Stops

See the whole trip →

10-night Caribbean from San Juan

Viking Ocean · Viking Sea

9 ports
Round trip
Sails Feb 24, 2027
From $6,299 pp
Luxury

St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Castries Cosol Tours: All-Island Private Safari with 7 Stops

See the whole trip →

10-night Caribbean from San Juan

Viking Ocean · Viking Sea

9 ports
Round trip
Sails Nov 27, 2027
From $4,399 pp
Luxury

St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Castries Cosol Tours: All-Island Private Safari with 7 Stops

See the whole trip →

10-night Caribbean from San Juan

Viking Ocean · Viking Sky

9 ports
Round trip
Sails Nov 29, 2027
From $4,399 pp
Luxury

St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Castries Cosol Tours: All-Island Private Safari with 7 Stops

See the whole trip →

10-night Caribbean from San Juan

Viking Ocean · Viking Sea

9 ports
Round trip
Sails Dec 7, 2027
From $3,999 pp
Luxury

St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Castries Cosol Tours: All-Island Private Safari with 7 Stops

See the whole trip →

10-night Caribbean from San Juan

Viking Ocean · Viking Sky

9 ports
Round trip
Sails Dec 9, 2027
From $3,899 pp
Luxury

St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Castries Cosol Tours: All-Island Private Safari with 7 Stops

See the whole trip →

10-night Caribbean from San Juan

Viking Ocean · Viking Sea

9 ports
Round trip
Sails Dec 17, 2027
From $3,599 pp
Luxury

St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Castries Cosol Tours: All-Island Private Safari with 7 Stops

See the whole trip →

10-night Caribbean from San Juan

Viking Ocean · Viking Sky

9 ports
Round trip
Sails Dec 19, 2027
From $3,599 pp
Luxury

St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Castries Cosol Tours: All-Island Private Safari with 7 Stops

See the whole trip →

10-night Caribbean from San Juan

Viking Ocean · Viking Sea

9 ports
Round trip
Sails Dec 27, 2027
From $3,799 pp
Luxury

St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Castries Cosol Tours: All-Island Private Safari with 7 Stops

See the whole trip →

10-night Caribbean from San Juan

Viking Ocean · Viking Sky

9 ports
Round trip
Sails Dec 29, 2027
From $3,799 pp
Luxury

St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Castries Cosol Tours: All-Island Private Safari with 7 Stops

See the whole trip →

10-night Caribbean from San Juan

Viking Ocean · Viking Sky

9 ports
Round trip
Sails Jan 8, 2028
From $4,299 pp
Luxury

St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Castries Cosol Tours: All-Island Private Safari with 7 Stops

See the whole trip →

10-night Caribbean from San Juan

Viking Ocean · Viking Sky

9 ports
Round trip
Sails Jan 18, 2028
From $4,299 pp
Luxury

St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Castries Cosol Tours: All-Island Private Safari with 7 Stops

See the whole trip →

10-night Caribbean from San Juan

Viking Ocean · Viking Sea

9 ports
Round trip
Sails Jan 27, 2028
From $4,299 pp
Luxury

St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Castries Cosol Tours: All-Island Private Safari with 7 Stops

See the whole trip →

10-night Caribbean from San Juan

Viking Ocean · Viking Sky

9 ports
Round trip
Sails Jan 28, 2028
From $4,299 pp
Luxury

St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Castries Cosol Tours: All-Island Private Safari with 7 Stops

See the whole trip →

10-night Caribbean from San Juan

Viking Ocean · Viking Sea

9 ports
Round trip
Sails Feb 6, 2028
From $4,299 pp
Luxury

St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Castries Cosol Tours: All-Island Private Safari with 7 Stops

See the whole trip →

10-night Caribbean from San Juan

Viking Ocean · Viking Sky

9 ports
Round trip
Sails Feb 7, 2028
From $4,299 pp
Luxury

St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Castries Cosol Tours: All-Island Private Safari with 7 Stops

See the whole trip →

10-night Caribbean from San Juan

Viking Ocean · Viking Sea

9 ports
Round trip
Sails Feb 16, 2028
From $4,299 pp
Luxury

St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Castries Cosol Tours: All-Island Private Safari with 7 Stops

See the whole trip →

10-night Caribbean from San Juan

Viking Ocean · Viking Sky

9 ports
Round trip
Sails Feb 17, 2028
From $4,499 pp
Luxury

St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Castries Cosol Tours: All-Island Private Safari with 7 Stops

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 →

7-night San Juan to Miami

Explora Journeys · EXPLORA III

6 ports
One way
Sails Mar 7, 2027
From $5,100 pp
Luxury

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

See the whole trip →