⚓ 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

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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

Silversea · Silver Shadow

5 ports
Round trip
Sails Dec 20, 2026
From $5,950 pp
Luxury

Jost Van Dyke Private Catamaran Charter: White Bay & Sandy Spit by Sail
Little Bay Soufrière Hills Volcano Exclusion Zone Helicopter Tour
Castries Cosol Tours: All-Island Private Safari with 7 Stops

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15-night Caribbean from San Juan

Azamara · Azamara Quest

14 ports
Round trip
Sails Nov 6, 2027
From $4,319 pp
Luxury

Charlotte Amalie Private Full-Day Boat Charter: 35ft Scarab Triple 300s
Virgin Gorda The Baths National Park: Private Guided Boulders & Devil's Bay
St. John's Private Half-Day Island Adventure & Trunk Bay Beach

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14-night Caribbean from San Juan

Azamara · Azamara Quest

13 ports
Round trip
Sails Dec 5, 2027
From $4,089 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

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7-night Caribbean from San Juan

Silversea · Silver Shadow

6 ports
Round trip
Sails Dec 27, 2026
From $7,050 pp
Luxury

Cruz Bay Trunk Bay Underwater Snorkel Trail & VI National Park
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Iles des Saintes Sunrise Hike to Le Chameau's Summit Fort

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7-night Caribbean from San Juan

Windstar · Star Pride

6 ports
Round trip
2 departures Dec 2026 – Jan 2027
From $3,636 pp
Luxury

St. Georges Grenada Private Taxi Tour: Your Island, Your Way
Bequia Tobago Cays & Mystique Full-Day Private Sail
Mayreau Salt Whistle Bay: Dawn Swim Before the Boats Arrive

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7-night San Juan to Bridgetown

Azamara · Azamara Journey

7 ports
One way
Sails Nov 21, 2026
From $1,909 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 →

7-night San Juan to Bridgetown

Azamara · Azamara Journey

7 ports
One way
Sails Dec 5, 2026
From $1,889 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 →

7-night Caribbean from San Juan

Silversea · Silver Dawn

6 ports
Round trip
Sails Dec 21, 2027
From $5,150 pp
Luxury

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

10-night San Juan to Bridgetown

Silversea · Silver Shadow

10 ports
One way
Sails Feb 6, 2027
From $4,250 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 →

10-night San Juan to Bridgetown

Silversea · Silver Shadow

10 ports
One way
Sails Jan 10, 2027
From $4,650 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
Codrington Barbuda's Pink Sand Beach at Dawn, Private & Empty

See the whole trip →

10-night Caribbean from San Juan

Silversea · Silver Dawn

10 ports
Round trip
Sails Dec 11, 2027
From $6,050 pp
Luxury

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

10-night Caribbean from San Juan

Silversea · Silver Dawn

10 ports
Round trip
Sails Jan 15, 2028
From $5,750 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 →

9-night Caribbean from San Juan

Silversea · Silver Dawn

8 ports
Round trip
Sails Feb 10, 2028
From $5,050 pp
Luxury

Anguilla Sandy Island by Private Boat: Barefoot Sandbar Escape
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 San Juan to Miami

Explora Journeys · EXPLORA IV

7 ports
One way
2 departures Mar – Apr 2028
From $4,020 pp
Luxury

Charlotte Amalie Private Full-Day Boat Charter: 35ft Scarab Triple 300s
Nydri Private Sailing Charter: Skorpios, Meganisi & Hidden Coves
Puerto Plata The full 27 jumps at the Damajagua Waterfalls (27 Charcos) with certified canyon guides

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7-night Caribbean from San Juan

Silversea · Silver Shadow

7 ports
Round trip
Sails Jan 3, 2027
From $6,650 pp
Luxury

Cruz Bay Trunk Bay Underwater Snorkel Trail & VI National Park
Gustavia Private Open-Top Mini Moke Island Tour of St. Barts
Codrington Barbuda's Pink Sand Beach at Dawn, Private & Empty

See the whole trip →

7-night Caribbean from San Juan

Silversea · Silver Shadow

7 ports
Round trip
Sails Jan 30, 2027
From $6,150 pp
Luxury

Cruz Bay Trunk Bay Underwater Snorkel Trail & VI National Park
Little Bay Soufrière Hills Volcano Exclusion Zone Helicopter Tour
Codrington Barbuda's Pink Sand Beach at Dawn, Private & Empty

See the whole trip →

7-night Caribbean from San Juan

Silversea · Silver Shadow

7 ports
Round trip
Sails Feb 26, 2027
From $5,450 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 →

11-night Caribbean from San Juan

Silversea · Silver Dawn

9 ports
Round trip
Sails Jan 25, 2028
From $6,050 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
Roseau Boiling Lake Hike: Dominica's Ultimate Volcanic Pilgrimage

See the whole trip →

11-night Caribbean from San Juan

Windstar · Star Pride

9 ports
Round trip
Sails Oct 28, 2026
From $3,930 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 Nov 8, 2026
From $2,411 pp
Luxury

St. Georges Grenada Private Taxi Tour: Your Island, Your Way
Bequia Tobago Cays & Mystique Full-Day Private Sail
Mayreau Salt Whistle Bay: Dawn Swim Before the Boats Arrive

See the whole trip →

7-night Caribbean from San Juan

Windstar · Star Pride

6 ports
Round trip
Sails Mar 13, 2028
From $2,656 pp
Luxury

St. Georges Grenada Private Taxi Tour: Your Island, Your Way
Bequia Tobago Cays & Mystique Full-Day Private Sail
Mayreau Salt Whistle Bay: Dawn Swim Before the Boats Arrive

See the whole trip →

7-night San Juan to Miami

Explora Journeys · EXPLORA IV

5 ports
One way
Sails Dec 30, 2027
From $5,160 pp
Luxury

Saint John Reversing Falls & Fundy Tidal Bore: Private Guided Experience
Nydri Private Sailing Charter: Skorpios, Meganisi & Hidden Coves
Puerto Plata The full 27 jumps at the Damajagua Waterfalls (27 Charcos) with certified canyon guides

See the whole trip →

4-night San Juan to Dover (London)

Windstar · Star Pride

3 ports
One way
Sails Mar 30, 2027
From $2,760 pp
Luxury

San Juan Walk El Morro & Old San Juan's City Walls
Lisbon Sintra: Pena Palace, Cabo da Roca & Cascais (small-group day trip)
Dover (London) White Cliffs of Dover: Private Guided Walk & Coastal Views

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6-night San Juan to Lisbon

Windstar · Star Legend

4 ports
One way
Sails Feb 28, 2028
From $2,839 pp
Luxury

Funchal Pico do Arieiro to Pico Ruivo: Madeira's Rooftop Ridge Walk
Casablanca Private Guided Tour of Casablanca with Hassan II Mosque Entry
Lisbon Sintra: Pena Palace, Cabo da Roca & Cascais (small-group day trip)

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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)

See the whole trip →

5-night San Juan to Miami

Virgin · Valiant Lady

4 ports
One way
Sails Apr 10, 2027
From $695 pp
Premium

Grand Turk Gibbs Cay Private Stingray Swim & Reef Snorkel
Bimini Swim with Wild Dolphins at Honeymoon Harbour
Miami Star Island & Millionaire's Row Skyline Cruise on Biscayne Bay

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14-night San Juan to Lisbon

Silversea · Silver Shadow

6 ports
One way
Sails Mar 9, 2027
From $7,000 pp
Luxury

Jost Van Dyke Private Catamaran Charter: White Bay & Sandy Spit by Sail
Codrington Barbuda's Pink Sand Beach at Dawn, Private & Empty
Santa Cruz de La Palma Tajogaite Volcano: Licensed Expert Trek into La Palma's Last Eruption

See the whole trip →