⚓ 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 8 of 10

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

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

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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

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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

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7-night San Juan to Miami

Explora Journeys · EXPLORA IV

5 ports
One way
Sails Apr 29, 2028
From $3,755 pp
Luxury

Saint John Reversing Falls & Fundy Tidal Bore: Private Guided Experience
Pointe-a-Pitre Death in Paradise Filming Locations & Botanical Garden
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant

See the whole trip →

14-night Caribbean from San Juan

Princess · Crown Princess

9 ports
Round trip
Sails Jan 24, 2027
From $1,217 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 →

7-night San Juan to Miami

Explora Journeys · EXPLORA II

5 ports
One way
Sails Dec 19, 2027
From $4,815 pp
Luxury

Road Town Norman Island: The Indians & Sea Caves Sailing & Snorkel
Pointe-a-Pitre Death in Paradise Filming Locations & Botanical Garden
Gustavia Private Open-Top Mini Moke Island Tour of St. Barts

See the whole trip →

7-night San Juan to Miami

Explora Journeys · EXPLORA III

6 ports
One way
Sails Nov 29, 2026
From $5,585 pp
Luxury

Road Town Norman Island: The Indians & Sea Caves Sailing & Snorkel
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 San Juan to Miami

Explora Journeys · EXPLORA IV

6 ports
One way
Sails Feb 19, 2028
From $4,200 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
Road Bay Private Island Hopping: Prickly Pear & Sandy Island by Catamaran

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9-night San Juan to Miami

Azamara · Azamara Journey

8 ports
One way
Sails Jan 5, 2027
From $1,999 pp
Luxury

Virgin Gorda The Baths National Park: Private Guided Boulders & Devil's Bay
Gustavia Private Open-Top Mini Moke Island Tour of St. Barts
Philipsburg Random Wind 'Paradise Day Sail' — Schooner Sail, Snorkel & the Original Tarzan Swing

See the whole trip →

7-night San Juan to Miami

Explora Journeys · EXPLORA IV

7 ports
One way
Sails Nov 13, 2027
From $4,200 pp
Luxury

Charlotte Amalie Private Full-Day Boat Charter: 35ft Scarab Triple 300s
Ain Sokhna Private Pyramids of Giza, Sphinx & Grand Egyptian Museum
Puerto Plata The full 27 jumps at the Damajagua Waterfalls (27 Charcos) with certified canyon guides

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7-night San Juan to Miami

Explora Journeys · EXPLORA I

6 ports
One way
Sails Mar 1, 2027
From $4,340 pp
Luxury

St. John's Private Half-Day Island Adventure & Trunk Bay Beach
Road Bay Private Island Hopping: Prickly Pear & Sandy Island by Catamaran
Virgin Gorda The Baths National Park: Private Guided Boulders & Devil's Bay

See the whole trip →

7-night San Juan to Miami

Explora Journeys · EXPLORA III

6 ports
One way
Sails Jan 29, 2027
From $5,240 pp
Luxury

Road Town Norman Island: The Indians & Sea Caves Sailing & Snorkel
St. John's Private Half-Day Island Adventure & Trunk Bay Beach
Providenciales Iguana Island & Reef: Small-Group Sail to Little Water Cay

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8-night San Juan to Miami

Silversea · Silver Ray

7 ports
One way
Sails Dec 26, 2027
From $7,050 pp
Luxury

Cruz Bay Trunk Bay Underwater Snorkel Trail & VI National Park
Codrington Barbuda's Pink Sand Beach at Dawn, Private & Empty
Fort-de-France Mount Pelée & Saint-Pierre: Volcano, Ghost Town & Dark History

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7-night San Juan to Miami

Explora Journeys · EXPLORA III

6 ports
One way
Sails Apr 5, 2027
From $4,760 pp
Luxury

Gustavia Private Open-Top Mini Moke Island Tour of St. Barts
Little Bay Soufrière Hills Volcano Exclusion Zone Helicopter Tour
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant

See the whole trip →

7-night San Juan to Miami

Explora Journeys · EXPLORA III

6 ports
One way
Sails Nov 1, 2026
From $5,680 pp
Luxury

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

5 ports
Round trip
Sails Oct 31, 2026
From $1,113 pp
Premium

Willemstad Private Full-Day Curaçao Island Tour with Local Expert
Port of Oranjestad Aruba: Snorkel with Turtles at WW2 Shipwreck & Sunset BBQ
Fort-de-France Mount Pelée & Saint-Pierre: Volcano, Ghost Town & Dark History

See the whole trip →

7-night Caribbean from San Juan

Virgin · Valiant Lady

5 ports
Round trip
Sails Dec 5, 2026
From $903 pp
Premium

Port of Oranjestad Aruba: Snorkel with Turtles at WW2 Shipwreck & Sunset BBQ
Willemstad Private Full-Day Curaçao Island Tour with Local Expert
Fort-de-France Mount Pelée & Saint-Pierre: Volcano, Ghost Town & Dark History

See the whole trip →

7-night Caribbean from San Juan

Virgin · Valiant Lady

5 ports
Round trip
Sails Jan 9, 2027
From $1,043 pp
Premium

Port of Oranjestad Aruba: Snorkel with Turtles at WW2 Shipwreck & Sunset BBQ
Willemstad Private Full-Day Curaçao Island Tour with Local Expert
Fort-de-France Mount Pelée & Saint-Pierre: Volcano, Ghost Town & Dark History

See the whole trip →

7-night Caribbean from San Juan

Virgin · Valiant Lady

5 ports
Round trip
Sails Apr 3, 2027
From $1,253 pp
Premium

Port of Oranjestad Aruba: Snorkel with Turtles at WW2 Shipwreck & Sunset BBQ
Willemstad Private Full-Day Curaçao Island Tour with Local Expert
Fort-de-France Mount Pelée & Saint-Pierre: Volcano, Ghost Town & Dark History

See the whole trip →

7-night San Juan to Miami

Explora Journeys · EXPLORA IV

7 ports
One way
Sails Jan 22, 2028
From $4,020 pp
Luxury

Gustavia Private Open-Top Mini Moke Island Tour of St. Barts
Charlotte Amalie Private Full-Day Boat Charter: 35ft Scarab Triple 300s
Nydri Private Sailing Charter: Skorpios, Meganisi & Hidden Coves

See the whole trip →

7-night San Juan to Miami

Explora Journeys · EXPLORA II

6 ports
One way
Sails Mar 12, 2028
From $4,020 pp
Luxury

Road Town Norman Island: The Indians & Sea Caves Sailing & Snorkel
Gustavia Private Open-Top Mini Moke Island Tour of St. Barts
Ocean Cay Shipwreck Snorkel Safari: Explore Ocean Cay's Sunken Fleet

See the whole trip →

16-night Caribbean from San Juan

Explora Journeys · EXPLORA III

9 ports
Round trip
Sails Dec 28, 2026
From $14,585 pp
Luxury

St. John's Private Half-Day Island Adventure & Trunk Bay Beach
Pointe-a-Pitre Death in Paradise Filming Locations & Botanical Garden
Saint John Reversing Falls & Fundy Tidal Bore: Private Guided Experience

See the whole trip →

8-night San Juan to Miami

Silversea · Silver Dawn

7 ports
One way
Sails Feb 24, 2028
From $5,250 pp
Luxury

Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Gustavia Private Open-Top Mini Moke Island Tour of St. Barts
Deshaies Jardin Botanique de Deshaies at Opening Hour

See the whole trip →

7-night Caribbean from San Juan

Virgin · Scarlet Lady

6 ports
Round trip
Sails Jan 29, 2028
From $763 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)
Fort-de-France Mount Pelée & Saint-Pierre: Volcano, Ghost Town & Dark History

See the whole trip →

7-night Caribbean from San Juan

Virgin · Scarlet Lady

6 ports
Round trip
Sails Feb 26, 2028
From $833 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)
Fort-de-France Mount Pelée & Saint-Pierre: Volcano, Ghost Town & Dark History

See the whole trip →

7-night Caribbean from San Juan

Virgin · Scarlet Lady

6 ports
Round trip
Sails Mar 25, 2028
From $903 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)
Fort-de-France Mount Pelée & Saint-Pierre: Volcano, Ghost Town & Dark History

See the whole trip →

6-night Caribbean from San Juan

Virgin · Valiant Lady

5 ports
Round trip
Sails Mar 13, 2027
From $894 pp
Premium

Road Town Norman Island: The Indians & Sea Caves Sailing & Snorkel
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 San Juan to Miami

Explora Journeys · EXPLORA IV

7 ports
One way
Sails Nov 27, 2027
From $4,200 pp
Luxury

Gustavia Private Open-Top Mini Moke Island Tour of St. Barts
Virgin Gorda The Baths National Park: Private Guided Boulders & Devil's Bay
Charlotte Amalie Private Full-Day Boat Charter: 35ft Scarab Triple 300s

See the whole trip →

8-night Caribbean from San Juan

Virgin · Valiant Lady

6 ports
Round trip
Sails Nov 20, 2026
From $1,112 pp
Premium

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

See the whole trip →

7-night Caribbean from San Juan

Virgin · Scarlet Lady

6 ports
Round trip
Sails Dec 26, 2027
From $1,673 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)
Fort-de-France Mount Pelée & Saint-Pierre: Volcano, Ghost Town & Dark History

See the whole trip →

7-night Caribbean from San Juan

Virgin · Valiant Lady

5 ports
Round trip
Sails Feb 6, 2027
From $1,043 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 →

7-night Caribbean from San Juan

Virgin · Scarlet Lady

5 ports
Round trip
Sails Nov 20, 2027
From $903 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 →

7-night Caribbean from San Juan

Virgin · Scarlet Lady

5 ports
Round trip
Sails Dec 4, 2027
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 →

7-night Caribbean from San Juan

Virgin · Scarlet Lady

5 ports
Round trip
Sails Jan 8, 2028
From $763 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 →

7-night Caribbean from San Juan

Virgin · Scarlet Lady

5 ports
Round trip
Sails Feb 19, 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 →

7-night Caribbean from San Juan

Virgin · Scarlet Lady

5 ports
Round trip
Sails Apr 1, 2028
From $903 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 →

16-night San Juan to Miami

Explora Journeys · EXPLORA I

10 ports
One way
Sails Jan 4, 2027
From $8,995 pp
Luxury

Philipsburg Random Wind 'Paradise Day Sail' — Schooner Sail, Snorkel & the Original Tarzan Swing
St. John's Private Half-Day Island Adventure & Trunk Bay Beach
Little Bay Soufrière Hills Volcano Exclusion Zone Helicopter Tour

See the whole trip →

7-night Caribbean from San Juan

Virgin · Valiant Lady

6 ports
Round trip
Sails Nov 7, 2026
From $1,603 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 · Valiant Lady

6 ports
Round trip
Sails Dec 12, 2026
From $973 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 · Valiant Lady

6 ports
Round trip
Sails Jan 16, 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 →

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