⚓ Cruises

Cruises from San Juan

397 itineraries with a bookable sailing ahead, 408 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 › Cruises from San Juan

Destination

Caribbean375 Mediterranean13 Bahamas7 Panama Canal1 Northern Europe1

Cruise line

Royal Caribbean122 Norwegian56 Princess33 Disney9 Celebrity30 Viking Ocean30 Oceania1 Silversea18 Virgin44 Windstar15 Regent1 Azamara9 Explora Journeys29

Page 9 of 10

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

7-night Caribbean from San Juan

Virgin · Scarlet Lady

6 ports
Round trip
Sails Apr 15, 2028
From $973 pp
Premium

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

Virgin · Scarlet Lady

5 ports
Round trip
Sails Dec 11, 2027
From $833 pp
Premium

St. Maarten Maho Beach: Legendary Extreme Plane-Spotting Experience
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
Sails Jan 22, 2028
From $763 pp
Premium

Port of Oranjestad Aruba: Snorkel with Turtles at WW2 Shipwreck & Sunset BBQ
Castries Cosol Tours: All-Island Private Safari with 7 Stops
St. John's Private Half-Day Island Adventure & Trunk Bay Beach

See the whole trip →

7-night Caribbean from San Juan

Virgin · Scarlet Lady

5 ports
Round trip
Sails Mar 18, 2028
From $903 pp
Premium

Port of Oranjestad Aruba: Snorkel with Turtles at WW2 Shipwreck & Sunset BBQ
Castries Cosol Tours: All-Island Private Safari with 7 Stops
St. John's Private Half-Day Island Adventure & Trunk Bay Beach

See the whole trip →

7-night Caribbean from San Juan

Virgin · Scarlet Lady

6 ports
Round trip
Sails Feb 12, 2028
From $833 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)
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 Dec 26, 2026
From $1,603 pp
Premium

St. Maarten Maho Beach: Legendary Extreme Plane-Spotting Experience
Fort-de-France Mount Pelée & Saint-Pierre: Volcano, Ghost Town & Dark History
Bridgetown Swim with wild green sea turtles + two shipwrecks by luxury catamaran (El Tigre)

See the whole trip →

8-night San Juan to Miami

Silversea · Silver Nova

7 ports
One way
Sails Dec 29, 2026
From $6,850 pp
Luxury

Cruz Bay Trunk Bay Underwater Snorkel Trail & VI National Park
Port of Charlestown Private Island Tour: Plantations, Rainforest & Rum Tasting
Roseau Boiling Lake Hike: Dominica's Ultimate Volcanic Pilgrimage

See the whole trip →

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

See the whole trip →

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

See the whole trip →

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

See the whole trip →

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

See the whole trip →

11-night San Juan to Lisbon

Viking Ocean · Viking Sky

5 ports
Repositioning
Sails Feb 27, 2028
From $3,299 pp
Luxury

Las Palmas Roque Nublo & Tejeda: Gran Canaria's Sacred Heart by 4×4
Santa Cruz de Tenerife Teide National Park: Summit Cable Car & Volcanic Moonscape
Funchal Pico do Arieiro to Pico Ruivo: Madeira's Rooftop Ridge Walk

See the whole trip →

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

See the whole trip →

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

See the whole trip →

7-night Caribbean from San Juan

Explora Journeys · EXPLORA II

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

Bequia Tobago Cays & Mystique Full-Day Private Sail
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 →

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 →

12-night San Juan to Barcelona

Virgin · Scarlet Lady

5 ports
One way
Sails Apr 22, 2028
From $1,308 pp
Premium

St. Maarten Maho Beach: Legendary Extreme Plane-Spotting Experience
Funchal Pico do Arieiro to Pico Ruivo: Madeira's Rooftop Ridge Walk
Tangier Tangier Kasbah, Medina & American Legation Private Tour

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

See the whole trip →

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 →

14-night Caribbean from San Juan

Azamara · Azamara Quest

13 ports
Round trip
Sails Nov 21, 2027
From $3,849 pp
Luxury

Virgin Gorda The Baths National Park: Private Guided Boulders & Devil's Bay
St. John's Private Half-Day Island Adventure & Trunk Bay Beach
Saint-Pierre Île aux Marins: Private Guided Walk on the Ghost Island

See the whole trip →

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