⚓ 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

Royal Caribbean · Vision of the Seas

6 ports
Round trip
Sails Mar 14, 2027
From $613 pp
Contemporary

Tortola Jost Van Dyke: Sandy Spit & Soggy Dollar Painkiller Sail
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

Norwegian · Norwegian Viva

5 ports
Round trip
Sails Jan 16, 2028
From $1,169 pp
Contemporary

Port of Oranjestad Aruba: Snorkel with Turtles at WW2 Shipwreck & Sunset BBQ
Bridgetown Swim with wild green sea turtles + two shipwrecks by luxury catamaran (El Tigre)
Philipsburg Random Wind 'Paradise Day Sail' — Schooner Sail, Snorkel & the Original Tarzan Swing

See the whole trip →

7-night Caribbean from San Juan

Royal Caribbean · Vision of the Seas

6 ports
Round trip
Sails Feb 28, 2027
From $616 pp
Contemporary

Charlotte Amalie Private Full-Day Boat Charter: 35ft Scarab Triple 300s
St. John's Private Half-Day Island Adventure & Trunk Bay Beach
Fort-de-France Mount Pelée & Saint-Pierre: Volcano, Ghost Town & Dark History

See the whole trip →

7-night Caribbean from San Juan

Royal Caribbean · Vision of the Seas

6 ports
Round trip
Sails Jan 23, 2028
From $681 pp
Contemporary

Port of Kingstown La Soufrière Volcano Summit Hike: St. Vincent's Crown
St. Georges Grenada Private Taxi Tour: Your Island, Your Way
Fort-de-France Mount Pelée & Saint-Pierre: Volcano, Ghost Town & Dark History

See the whole trip →

8-night Caribbean from San Juan

Royal Caribbean · Rhapsody of the Seas

7 ports
Round trip
Sails Dec 31, 2027
From $1,308 pp
Contemporary

Charlotte Amalie Private Full-Day Boat Charter: 35ft Scarab Triple 300s
St. Croix Buck Island Reef: Private Catamaran Sail & Snorkel
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant

See the whole trip →

7-night Caribbean from San Juan

Norwegian · Norwegian Viva

5 ports
Round trip
Sails Nov 28, 2027
From $867 pp
Contemporary

Port of Oranjestad Aruba: Snorkel with Turtles at WW2 Shipwreck & Sunset BBQ
Willemstad Private Full-Day Curaçao Island Tour with Local Expert
Philipsburg Random Wind 'Paradise Day Sail' — Schooner Sail, Snorkel & the Original Tarzan Swing

See the whole trip →

7-night Caribbean from San Juan

Norwegian · Norwegian Viva

5 ports
Round trip
Sails Dec 12, 2027
From $874 pp
Contemporary

Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Philipsburg Random Wind 'Paradise Day Sail' — Schooner Sail, Snorkel & the Original Tarzan Swing
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 Dec 26, 2027
From $1,414 pp
Contemporary

Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Philipsburg Random Wind 'Paradise Day Sail' — Schooner Sail, Snorkel & the Original Tarzan Swing
Willemstad Private Full-Day Curaçao Island Tour with Local Expert

See the whole trip →

7-night Caribbean from San Juan

Norwegian · Norwegian Prima

6 ports
Round trip
Sails Feb 14, 2027
From $1,259 pp
Contemporary

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

See the whole trip →

7-night Caribbean from San Juan

Norwegian · Norwegian Prima

6 ports
Round trip
Sails Mar 21, 2027
From $1,519 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

6 ports
Round trip
Sails Nov 20, 2027
From $1,439 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

6 ports
Round trip
Sails Dec 11, 2027
From $1,189 pp
Contemporary

St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Philipsburg Random Wind 'Paradise Day Sail' — Schooner Sail, Snorkel & the Original Tarzan Swing

See the whole trip →

7-night Caribbean from San Juan

Norwegian · Norwegian Prima

6 ports
Round trip
Sails Jan 29, 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

6 ports
Round trip
Sails Feb 5, 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
Philipsburg Random Wind 'Paradise Day Sail' — Schooner Sail, Snorkel & the Original Tarzan Swing

See the whole trip →

7-night Caribbean from San Juan

Norwegian · Norwegian Prima

6 ports
Round trip
Sails Feb 19, 2028
From $1,279 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

6 ports
Round trip
Sails Mar 18, 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

Princess · Emerald Princess

6 ports
Round trip
2 departures Jan – Mar 2028
From $1,154 pp
Premium

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

See the whole trip →

7-night Caribbean from San Juan

Norwegian · Norwegian Prima

7 ports
Round trip
Sails Nov 15, 2026
From $1,009 pp
Contemporary

Tortola Jost Van Dyke: Sandy Spit & Soggy Dollar Painkiller Sail
St. John's Private Half-Day Island Adventure & Trunk Bay Beach
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 Nov 27, 2027
From $1,309 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. John's Private Half-Day Island Adventure & Trunk Bay Beach

See the whole trip →

7-night Caribbean from San Juan

Norwegian · Norwegian Prima

7 ports
Round trip
Sails Dec 25, 2027
From $1,909 pp
Contemporary

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)
St. John's Private Half-Day Island Adventure & Trunk Bay Beach

See the whole trip →

7-night Caribbean from San Juan

Norwegian · Norwegian Prima

7 ports
Round trip
Sails Jan 15, 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 Jan 22, 2028
From $1,219 pp
Contemporary

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

5 ports
Round trip
Sails Jan 9, 2028
From $896 pp
Contemporary

Philipsburg Random Wind 'Paradise Day Sail' — Schooner Sail, Snorkel & the Original Tarzan Swing
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 Caribbean from San Juan

Norwegian · Norwegian Prima

6 ports
Round trip
Sails Feb 28, 2027
From $1,219 pp
Contemporary

Tortola Jost Van Dyke: Sandy Spit & Soggy Dollar Painkiller Sail
Roseau Boiling Lake Hike: Dominica's Ultimate Volcanic Pilgrimage
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 Viva

5 ports
Round trip
Sails Nov 21, 2027
From $1,369 pp
Contemporary

Port of Oranjestad Aruba: Snorkel with Turtles at WW2 Shipwreck & Sunset BBQ
Bridgetown Swim with wild green sea turtles + two shipwrecks by luxury catamaran (El Tigre)
St. Lucia Gros Piton Summit Hike: Conquer St. Lucia's Iconic Peak

See the whole trip →

7-night Caribbean from San Juan

Norwegian · Norwegian Viva

5 ports
Round trip
Sails Dec 5, 2027
From $844 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
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 Viva

5 ports
Round trip
Sails Dec 19, 2027
From $1,769 pp
Contemporary

Port of Oranjestad Aruba: Snorkel with Turtles at WW2 Shipwreck & Sunset BBQ
Bridgetown Swim with wild green sea turtles + two shipwrecks by luxury catamaran (El Tigre)
St. Lucia Gros Piton Summit Hike: Conquer St. Lucia's Iconic Peak

See the whole trip →

7-night Caribbean from San Juan

Norwegian · Norwegian Prima

7 ports
Round trip
Sails Nov 22, 2026
From $919 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 Nov 29, 2026
From $999 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 Dec 6, 2026
From $939 pp
Contemporary

Philipsburg Random Wind 'Paradise Day Sail' — Schooner Sail, Snorkel & the Original Tarzan Swing
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 →

7-night Caribbean from San Juan

Norwegian · Norwegian Prima

7 ports
Round trip
Sails Dec 13, 2026
From $899 pp
Contemporary

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
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 Dec 27, 2026
From $1,769 pp
Contemporary

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
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 Jan 10, 2027
From $1,219 pp
Contemporary

Tortola Jost Van Dyke: Sandy Spit & Soggy Dollar Painkiller Sail
Philipsburg Random Wind 'Paradise Day Sail' — Schooner Sail, Snorkel & the Original Tarzan Swing
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 Jan 24, 2027
From $1,169 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 7, 2027
From $1,269 pp
Contemporary

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
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 21, 2027
From $1,299 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 Nov 13, 2027
From $1,339 pp
Contemporary

Tortola Jost Van Dyke: Sandy Spit & Soggy Dollar Painkiller Sail
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 →

7-night Caribbean from San Juan

Norwegian · Norwegian Prima

7 ports
Round trip
Sails Dec 4, 2027
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 Dec 18, 2027
From $1,809 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 Jan 1, 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 →

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