Explora Journeys Caribbean cruises from San Juan

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

5 ports
One way
2 departures Mar – Apr 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
Marigot Pinel Island Private Catamaran Day: Snorkel, Swim & Rosé

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7-night San Juan to Miami

Explora Journeys · EXPLORA II

6 ports
One way
2 departures Jan 2028
From $4,020 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

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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 →

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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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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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

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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 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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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 →

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

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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

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

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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 →

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

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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

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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 →

11-night San Juan to Manaus

Explora Journeys · EXPLORA II

8 ports
One way
Sails Feb 6, 2028
From $7,580 pp
Luxury

Little Bay Soufrière Hills Volcano Exclusion Zone Helicopter Tour
Bridgetown Swim with wild green sea turtles + two shipwrecks by luxury catamaran (El Tigre)
Devils Island Îles du Salut: Private Guided History & Wildlife Immersion

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12-night San Juan to Manaus

Explora Journeys · EXPLORA I

9 ports
One way
Sails Feb 5, 2027
From $8,190 pp
Luxury

Gustavia Private Open-Top Mini Moke Island Tour of St. Barts
Saint-Pierre Île aux Marins: Private Guided Walk on the Ghost Island
Bridgetown Swim with wild green sea turtles + two shipwrecks by luxury catamaran (El Tigre)

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