⚓ 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

Page 8 of 10

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

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

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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

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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

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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

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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

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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

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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 →

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 →

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