⚓ 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

Norwegian · Norwegian Prima

7 ports
Round trip
Sails Jan 8, 2028
From $1,219 pp
Contemporary

Tortola Jost Van Dyke: Sandy Spit & Soggy Dollar Painkiller Sail
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Bridgetown Swim with wild green sea turtles + two shipwrecks by luxury catamaran (El Tigre)

See the whole trip →

7-night Caribbean from San Juan

Norwegian · Norwegian Prima

7 ports
Round trip
Sails Feb 12, 2028
From $1,219 pp
Contemporary

Tortola Jost Van Dyke: Sandy Spit & Soggy Dollar Painkiller Sail
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Bridgetown Swim with wild green sea turtles + two shipwrecks by luxury catamaran (El Tigre)

See the whole trip →

7-night Caribbean from San Juan

Norwegian · Norwegian Prima

7 ports
Round trip
Sails Feb 26, 2028
From $1,229 pp
Contemporary

Tortola Jost Van Dyke: Sandy Spit & Soggy Dollar Painkiller Sail
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Bridgetown Swim with wild green sea turtles + two shipwrecks by luxury catamaran (El Tigre)

See the whole trip →

7-night Caribbean from San Juan

Norwegian · Norwegian Prima

7 ports
Round trip
Sails Mar 4, 2028
From $1,269 pp
Contemporary

Tortola Jost Van Dyke: Sandy Spit & Soggy Dollar Painkiller Sail
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Bridgetown Swim with wild green sea turtles + two shipwrecks by luxury catamaran (El Tigre)

See the whole trip →

7-night Caribbean from San Juan

Norwegian · Norwegian Prima

7 ports
Round trip
Sails Mar 11, 2028
From $1,269 pp
Contemporary

Tortola Jost Van Dyke: Sandy Spit & Soggy Dollar Painkiller Sail
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Bridgetown Swim with wild green sea turtles + two shipwrecks by luxury catamaran (El Tigre)

See the whole trip →

7-night Caribbean from San Juan

Norwegian · Norwegian Prima

7 ports
Round trip
Sails Mar 25, 2028
From $1,319 pp
Contemporary

Tortola Jost Van Dyke: Sandy Spit & Soggy Dollar Painkiller Sail
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Bridgetown Swim with wild green sea turtles + two shipwrecks by luxury catamaran (El Tigre)

See the whole trip →

7-night Caribbean from San Juan

Norwegian · Norwegian Prima

7 ports
Round trip
Sails Apr 1, 2028
From $1,269 pp
Contemporary

Tortola Jost Van Dyke: Sandy Spit & Soggy Dollar Painkiller Sail
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Bridgetown Swim with wild green sea turtles + two shipwrecks by luxury catamaran (El Tigre)

See the whole trip →

7-night Caribbean from San Juan

Norwegian · Norwegian Prima

7 ports
Round trip
Sails Apr 8, 2028
From $1,319 pp
Contemporary

Tortola Jost Van Dyke: Sandy Spit & Soggy Dollar Painkiller Sail
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Bridgetown Swim with wild green sea turtles + two shipwrecks by luxury catamaran (El Tigre)

See the whole trip →

7-night Caribbean from San Juan

Norwegian · Norwegian Prima

7 ports
Round trip
Sails Apr 15, 2028
From $1,259 pp
Contemporary

Tortola Jost Van Dyke: Sandy Spit & Soggy Dollar Painkiller Sail
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Bridgetown Swim with wild green sea turtles + two shipwrecks by luxury catamaran (El Tigre)

See the whole trip →

7-night Caribbean from San Juan

Norwegian · Norwegian Prima

5 ports
Round trip
Sails Dec 20, 2026
From $959 pp
Contemporary

Port of Oranjestad Aruba: Snorkel with Turtles at WW2 Shipwreck & Sunset BBQ
Willemstad Private Full-Day Curaçao Island Tour with Local Expert
St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island

See the whole trip →

7-night Caribbean from San Juan

Norwegian · Norwegian Prima

5 ports
Round trip
Sails Jan 3, 2027
From $1,159 pp
Contemporary

St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island
Tortola Jost Van Dyke: Sandy Spit & Soggy Dollar Painkiller Sail
Port of Oranjestad Aruba: Snorkel with Turtles at WW2 Shipwreck & Sunset BBQ

See the whole trip →

7-night Caribbean from San Juan

Norwegian · Norwegian Prima

5 ports
Round trip
Sails Jan 31, 2027
From $1,109 pp
Contemporary

Willemstad Private Full-Day Curaçao Island Tour with Local Expert
Port of Oranjestad Aruba: Snorkel with Turtles at WW2 Shipwreck & Sunset BBQ
St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island

See the whole trip →

7-night Caribbean from San Juan

Norwegian · Norwegian Prima

5 ports
Round trip
Sails Mar 7, 2027
From $1,409 pp
Contemporary

Tortola Jost Van Dyke: Sandy Spit & Soggy Dollar Painkiller Sail
St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island
Port of Oranjestad Aruba: Snorkel with Turtles at WW2 Shipwreck & Sunset BBQ

See the whole trip →

7-night Caribbean from San Juan

Norwegian · Norwegian Prima

5 ports
Round trip
Sails Mar 14, 2027
From $1,359 pp
Contemporary

Tortola Jost Van Dyke: Sandy Spit & Soggy Dollar Painkiller Sail
St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island
Willemstad Private Full-Day Curaçao Island Tour with Local Expert

See the whole trip →

7-night San Juan to New York

Norwegian · Norwegian Prima

5 ports
Repositioning
Sails Apr 22, 2028
From $899 pp
Contemporary

Tortola Jost Van Dyke: Sandy Spit & Soggy Dollar Painkiller Sail
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island

See the whole trip →

7-night Caribbean from San Juan

Norwegian · Norwegian Viva

5 ports
Round trip
Sails Nov 14, 2027
From $1,219 pp
Contemporary

Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
St. Lucia Gros Piton Summit Hike: Conquer St. Lucia's Iconic Peak
Willemstad Private Full-Day Curaçao Island Tour with Local Expert

See the whole trip →

7-night Caribbean from San Juan

Norwegian · Norwegian Viva

5 ports
Round trip
Sails Jan 2, 2028
From $933 pp
Contemporary

Port of Oranjestad Aruba: Snorkel with Turtles at WW2 Shipwreck & Sunset BBQ
Willemstad Private Full-Day Curaçao Island Tour with Local Expert
St. Lucia Gros Piton Summit Hike: Conquer St. Lucia's Iconic Peak

See the whole trip →

7-night San Juan to Fort Lauderdale (Port Everglades)

Princess · Emerald Princess

5 ports
One way
Sails Mar 26, 2028
From $914 pp
Premium

Curacao Klein Curaçao Private Day Trip: Deserted Island Escape
Port of Oranjestad Aruba: Snorkel with Turtles at WW2 Shipwreck & Sunset BBQ
Kralendijk Klein Bonaire: Bioluminescence Snorkel at the Marine Park

See the whole trip →

7-night Caribbean from San Juan

Norwegian · Norwegian Prima

5 ports
Round trip
Sails Mar 28, 2027
From $1,239 pp
Contemporary

Tortola Jost Van Dyke: Sandy Spit & Soggy Dollar Painkiller Sail
St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island
Kralendijk Klein Bonaire: Bioluminescence Snorkel at the Marine Park

See the whole trip →

7-night San Juan to Fort Lauderdale (Port Everglades)

Princess · Crown Princess

5 ports
One way
Sails Mar 28, 2027
From $619 pp
Premium

St. Maarten Maho Beach: Legendary Extreme Plane-Spotting Experience
Port of Oranjestad Aruba: Snorkel with Turtles at WW2 Shipwreck & Sunset BBQ
Curacao Klein Curaçao Private Day Trip: Deserted Island Escape

See the whole trip →

7-night Caribbean from San Juan

Norwegian · Norwegian Prima

5 ports
Round trip
Sails Jan 17, 2027
From $1,139 pp
Contemporary

Kralendijk Klein Bonaire: Bioluminescence Snorkel at the Marine Park
Willemstad Private Full-Day Curaçao Island Tour with Local Expert
St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island

See the whole trip →

7-night Caribbean from San Juan

Celebrity · Celebrity Constellation

6 ports
Round trip
Sails Dec 5, 2026
From $695 pp
Premium

Charlotte Amalie Private Full-Day Boat Charter: 35ft Scarab Triple 300s
Philipsburg Random Wind 'Paradise Day Sail' — Schooner Sail, Snorkel & the Original Tarzan Swing
St. John's Private Half-Day Island Adventure & Trunk Bay Beach

See the whole trip →

7-night Caribbean from San Juan

Celebrity · Celebrity Constellation

6 ports
Round trip
Sails Dec 26, 2026
From $1,092 pp
Premium

Charlotte Amalie Private Full-Day Boat Charter: 35ft Scarab Triple 300s
Philipsburg Random Wind 'Paradise Day Sail' — Schooner Sail, Snorkel & the Original Tarzan Swing
St. John's Private Half-Day Island Adventure & Trunk Bay Beach

See the whole trip →

7-night Caribbean from San Juan

Celebrity · Celebrity Constellation

6 ports
Round trip
Sails Jan 23, 2027
From $721 pp
Premium

Charlotte Amalie Private Full-Day Boat Charter: 35ft Scarab Triple 300s
Philipsburg Random Wind 'Paradise Day Sail' — Schooner Sail, Snorkel & the Original Tarzan Swing
St. John's Private Half-Day Island Adventure & Trunk Bay Beach

See the whole trip →

7-night Caribbean from San Juan

Celebrity · Celebrity Constellation

6 ports
Round trip
Sails Feb 20, 2027
From $707 pp
Premium

Charlotte Amalie Private Full-Day Boat Charter: 35ft Scarab Triple 300s
Philipsburg Random Wind 'Paradise Day Sail' — Schooner Sail, Snorkel & the Original Tarzan Swing
St. John's Private Half-Day Island Adventure & Trunk Bay Beach

See the whole trip →

7-night Caribbean from San Juan

Celebrity · Celebrity Constellation

6 ports
Round trip
Sails Mar 6, 2027
From $587 pp
Premium

Charlotte Amalie Private Full-Day Boat Charter: 35ft Scarab Triple 300s
Philipsburg Random Wind 'Paradise Day Sail' — Schooner Sail, Snorkel & the Original Tarzan Swing
St. John's Private Half-Day Island Adventure & Trunk Bay Beach

See the whole trip →

7-night Caribbean from San Juan

Celebrity · Celebrity Summit

6 ports
Round trip
Sails Dec 26, 2027
From $1,101 pp
Premium

Charlotte Amalie Private Full-Day Boat Charter: 35ft Scarab Triple 300s
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

Norwegian · Norwegian Viva

5 ports
Round trip
Sails Jan 23, 2028
From $896 pp
Contemporary

Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
St. Lucia Gros Piton Summit Hike: Conquer St. Lucia's Iconic Peak
Kralendijk Klein Bonaire: Bioluminescence Snorkel at the Marine Park

See the whole trip →

10-night Caribbean from San Juan

Viking Ocean · Viking Sea

9 ports
Round trip
2 departures Dec 2026 – Feb 2027
From $5,599 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 →

7-night Caribbean from San Juan

Celebrity · Celebrity Constellation

6 ports
Round trip
Sails Jan 9, 2027
From $839 pp
Premium

Charlotte Amalie Private Full-Day Boat Charter: 35ft Scarab Triple 300s
Philipsburg Random Wind 'Paradise Day Sail' — Schooner Sail, Snorkel & the Original Tarzan Swing
St. John's Private Half-Day Island Adventure & Trunk Bay Beach

See the whole trip →