⚓ 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 10 of 10

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

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

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10-night San Juan to Bridgetown

Azamara · Azamara Journey

9 ports
One way
Sails Dec 18, 2026
From $1,679 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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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 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

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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
Mayreau Salt Whistle Bay: Dawn Swim Before the Boats Arrive
Les Saintes Sail Into the Bay of Les Saintes at Dawn

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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
Mayreau Salt Whistle Bay: Dawn Swim Before the Boats Arrive
Les Saintes Sail Into the Bay of Les Saintes at Dawn

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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 →

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