⚓ 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

Virgin · Valiant Lady

6 ports
Round trip
Sails Nov 28, 2026
From $903 pp
Premium

St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island
Road Town Norman Island: The Indians & Sea Caves Sailing & Snorkel
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant

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14-night Caribbean from San Juan

Explora Journeys · EXPLORA III

9 ports
Round trip
Sails Nov 15, 2026
From $10,200 pp
Luxury

Road Bay Private Island Hopping: Prickly Pear & Sandy Island by Catamaran
St. John's Private Half-Day Island Adventure & Trunk Bay Beach
Ain Sokhna Private Pyramids of Giza, Sphinx & Grand Egyptian Museum

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16-night Caribbean from San Juan

Explora Journeys · EXPLORA III

11 ports
Round trip
Sails Jan 13, 2027
From $11,880 pp
Luxury

Philipsburg Random Wind 'Paradise Day Sail' — Schooner Sail, Snorkel & the Original Tarzan Swing
Terre-de-haut Private Catamaran Sail & Snorkel: Bay of Les Saintes
St. Georges Grenada Private Taxi Tour: Your Island, Your Way

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15-night Caribbean from San Juan

Explora Journeys · EXPLORA III

11 ports
Round trip
Sails Dec 13, 2026
From $12,600 pp
Luxury

Road Bay Private Island Hopping: Prickly Pear & Sandy Island by Catamaran
St. John's Private Half-Day Island Adventure & Trunk Bay Beach
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant

See the whole trip →

7-night Caribbean from San Juan

Virgin · Scarlet Lady

6 ports
Round trip
Sails Mar 11, 2028
From $903 pp
Premium

St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island
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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8-night Caribbean from San Juan

Virgin · Scarlet Lady

6 ports
Round trip
Sails Dec 18, 2027
From $1,112 pp
Premium

St. Maarten Maho Beach: Legendary Extreme Plane-Spotting Experience
St. John's Private Half-Day Island Adventure & Trunk Bay Beach
Roseau Boiling Lake Hike: Dominica's Ultimate Volcanic Pilgrimage

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7-night Caribbean from San Juan

Virgin · Valiant Lady

6 ports
Round trip
Sails Jan 2, 2027
From $1,113 pp
Premium

Road Town Norman Island: The Indians & Sea Caves Sailing & Snorkel
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

Virgin · Valiant Lady

6 ports
Round trip
Sails Mar 6, 2027
From $1,113 pp
Premium

St. Maarten Maho Beach: Legendary Extreme Plane-Spotting Experience
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

Virgin · Scarlet Lady

6 ports
Round trip
Sails Jan 15, 2028
From $763 pp
Premium

St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island
Bridgetown Swim with wild green sea turtles + two shipwrecks by luxury catamaran (El Tigre)
Port of Kingstown La Soufrière Volcano Summit Hike: St. Vincent's Crown

See the whole trip →

16-night San Juan to Miami

Explora Journeys · EXPLORA III

9 ports
One way
Sails Feb 12, 2027
From $10,085 pp
Luxury

Charlotte Amalie Private Full-Day Boat Charter: 35ft Scarab Triple 300s
St. John's Private Half-Day Island Adventure & Trunk Bay Beach
Terre-de-haut Private Catamaran Sail & Snorkel: Bay of Les Saintes

See the whole trip →

7-night Caribbean from San Juan

Silversea · Silver Dawn

6 ports
Round trip
Sails Dec 28, 2027
From $5,350 pp
Luxury

Cruz Bay Trunk Bay Underwater Snorkel Trail & VI National Park
Philipsburg Random Wind 'Paradise Day Sail' — Schooner Sail, Snorkel & the Original Tarzan Swing
Roseau Boiling Lake Hike: Dominica's Ultimate Volcanic Pilgrimage

See the whole trip →

8-night Caribbean from San Juan

Virgin · Valiant Lady

6 ports
Round trip
Sails Jan 29, 2027
From $1,592 pp
Premium

Port of Oranjestad Aruba: Snorkel with Turtles at WW2 Shipwreck & Sunset BBQ
Willemstad Private Full-Day Curaçao Island Tour with Local Expert
Kralendijk Klein Bonaire: Bioluminescence Snorkel at the Marine Park

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7-night Caribbean from San Juan

Explora Journeys · EXPLORA II

6 ports
Round trip
Sails Jan 16, 2028
From $4,020 pp
Luxury

Castries Cosol Tours: All-Island Private Safari with 7 Stops
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 →

15-night Caribbean from San Juan

Explora Journeys · EXPLORA I

10 ports
Round trip
Sails Dec 20, 2026
From $12,365 pp
Luxury

Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Road Town Norman Island: The Indians & Sea Caves Sailing & Snorkel
Gustavia Private Open-Top Mini Moke Island Tour of St. Barts

See the whole trip →

8-night Caribbean from San Juan

Virgin · Scarlet Lady

7 ports
Round trip
Sails Nov 12, 2027
From $1,112 pp
Premium

Road Town Norman Island: The Indians & Sea Caves Sailing & Snorkel
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

Windstar · Star Pride

6 ports
Round trip
Sails Nov 15, 2026
From $6,153 pp
Luxury

Cruz Bay Trunk Bay Underwater Snorkel Trail & VI National Park
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Gustavia Private Open-Top Mini Moke Island Tour of St. Barts

See the whole trip →

7-night Caribbean from San Juan

Windstar · Star Pride

6 ports
Round trip
Sails Nov 29, 2026
From $3,913 pp
Luxury

Cruz Bay Trunk Bay Underwater Snorkel Trail & VI National Park
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 →

7-night Caribbean from San Juan

Windstar · Star Pride

6 ports
Round trip
Sails Dec 13, 2026
From $3,983 pp
Luxury

Cruz Bay Trunk Bay Underwater Snorkel Trail & VI National Park
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 →

7-night Caribbean from San Juan

Windstar · Star Pride

6 ports
Round trip
Sails Dec 27, 2026
From $3,563 pp
Luxury

Cruz Bay Trunk Bay Underwater Snorkel Trail & VI National Park
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 →

7-night Caribbean from San Juan

Windstar · Star Pride

6 ports
Round trip
Sails Jan 10, 2027
From $4,928 pp
Luxury

Cruz Bay Trunk Bay Underwater Snorkel Trail & VI National Park
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Gustavia Private Open-Top Mini Moke Island Tour of St. Barts

See the whole trip →

7-night Caribbean from San Juan

Windstar · Star Pride

6 ports
Round trip
Sails Nov 15, 2027
From $2,443 pp
Luxury

Cruz Bay Trunk Bay Underwater Snorkel Trail & VI National Park
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Gustavia Private Open-Top Mini Moke Island Tour of St. Barts

See the whole trip →

7-night Caribbean from San Juan

Virgin · Valiant Lady

6 ports
Round trip
Sails Feb 20, 2027
From $1,043 pp
Premium

Road Town Norman Island: The Indians & Sea Caves Sailing & Snorkel
Castries Cosol Tours: All-Island Private Safari with 7 Stops
Bridgetown Swim with wild green sea turtles + two shipwrecks by luxury catamaran (El Tigre)

See the whole trip →

7-night Caribbean from San Juan

Virgin · Scarlet Lady

6 ports
Round trip
Sails Nov 27, 2027
From $903 pp
Premium

Road Town Norman Island: The Indians & Sea Caves Sailing & Snorkel
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

Virgin · Scarlet Lady

6 ports
Round trip
Sails Apr 8, 2028
From $903 pp
Premium

Road Town Norman Island: The Indians & Sea Caves Sailing & Snorkel
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 →

8-night Caribbean from San Juan

Virgin · Valiant Lady

6 ports
Round trip
Sails Mar 19, 2027
From $952 pp
Premium

St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island
Bridgetown Swim with wild green sea turtles + two shipwrecks by luxury catamaran (El Tigre)
Port of Kingstown La Soufrière Volcano Summit Hike: St. Vincent's Crown

See the whole trip →

6-night Caribbean from San Juan

Virgin · Scarlet Lady

5 ports
Round trip
Sails Jan 2, 2028
From $654 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)
Roseau Boiling Lake Hike: Dominica's Ultimate Volcanic Pilgrimage

See the whole trip →

11-night Caribbean from San Juan

Silversea · Silver Dawn

9 ports
Round trip
Sails Jan 4, 2028
From $5,950 pp
Luxury

Jost Van Dyke Private Catamaran Charter: White Bay & Sandy Spit by Sail
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 →

7-night Caribbean from San Juan

Virgin · Valiant Lady

4 ports
Round trip
Sails Feb 13, 2027
From $1,323 pp
Premium

Samana Humpback Whale Watching in Samaná Bay
Grand Turk Gibbs Cay Private Stingray Swim & Reef Snorkel
Cabo Rojo Bahía de las Águilas: Private All-Inclusive Beach Day

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21-night Caribbean from San Juan

Viking Ocean · Viking Sea

11 ports
Round trip
Sails Dec 15, 2026
From $11,999 pp
Luxury

Bridgetown Swim with wild green sea turtles + two shipwrecks by luxury catamaran (El Tigre)
Iles du Salut Île Royale Penal Colony Ruins: Guided Expert History Walk
Santarem Alter do Chão: Private Amazon Caribbean Beach & Village

See the whole trip →

21-night Caribbean from San Juan

Viking Ocean · Viking Sea

11 ports
Round trip
Sails Jan 6, 2028
From $23,599 pp
Luxury

Bridgetown Swim with wild green sea turtles + two shipwrecks by luxury catamaran (El Tigre)
Iles du Salut Île Royale Penal Colony Ruins: Guided Expert History Walk
Santarem Alter do Chão: Private Amazon Caribbean Beach & Village

See the whole trip →