⚓ 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 6 of 10

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

7-night Caribbean from San Juan

Celebrity · Celebrity Constellation

6 ports
Round trip
Sails Nov 28, 2026
From $723 pp
Premium

Tortola Jost Van Dyke: Sandy Spit & Soggy Dollar Painkiller Sail
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Roseau Boiling Lake Hike: Dominica's Ultimate Volcanic Pilgrimage

See the whole trip →

7-night Caribbean from San Juan

Celebrity · Celebrity Constellation

6 ports
Round trip
Sails Dec 19, 2026
From $681 pp
Premium

Tortola Jost Van Dyke: Sandy Spit & Soggy Dollar Painkiller Sail
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Roseau Boiling Lake Hike: Dominica's Ultimate Volcanic Pilgrimage

See the whole trip →

7-night Caribbean from San Juan

Celebrity · Celebrity Constellation

6 ports
Round trip
Sails Jan 30, 2027
From $642 pp
Premium

Tortola Jost Van Dyke: Sandy Spit & Soggy Dollar Painkiller Sail
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Roseau Boiling Lake Hike: Dominica's Ultimate Volcanic Pilgrimage

See the whole trip →

7-night Caribbean from San Juan

Celebrity · Celebrity Constellation

6 ports
Round trip
Sails Feb 13, 2027
From $670 pp
Premium

Tortola Jost Van Dyke: Sandy Spit & Soggy Dollar Painkiller Sail
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Roseau Boiling Lake Hike: Dominica's Ultimate Volcanic Pilgrimage

See the whole trip →

7-night Caribbean from San Juan

Celebrity · Celebrity Constellation

6 ports
Round trip
Sails Feb 27, 2027
From $547 pp
Premium

Tortola Jost Van Dyke: Sandy Spit & Soggy Dollar Painkiller Sail
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Roseau Boiling Lake Hike: Dominica's Ultimate Volcanic Pilgrimage

See the whole trip →

7-night Caribbean from San Juan

Celebrity · Celebrity Constellation

6 ports
Round trip
Sails Mar 27, 2027
From $806 pp
Premium

Tortola Jost Van Dyke: Sandy Spit & Soggy Dollar Painkiller Sail
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Roseau Boiling Lake Hike: Dominica's Ultimate Volcanic Pilgrimage

See the whole trip →

7-night Caribbean from San Juan

Celebrity · Celebrity Summit

6 ports
Round trip
Sails Nov 28, 2027
From $542 pp
Premium

Charlotte Amalie Private Full-Day Boat Charter: 35ft Scarab Triple 300s
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 Caribbean from San Juan

Celebrity · Celebrity Summit

6 ports
Round trip
Sails Dec 12, 2027
From $543 pp
Premium

Port of Kingstown La Soufrière Volcano Summit Hike: St. Vincent's Crown
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

Celebrity · Celebrity Constellation

6 ports
Round trip
Sails Mar 20, 2027
From $764 pp
Premium

Charlotte Amalie Private Full-Day Boat Charter: 35ft Scarab Triple 300s
St. John's Private Half-Day Island Adventure & Trunk Bay Beach
Roseau Boiling Lake Hike: Dominica's Ultimate Volcanic Pilgrimage

See the whole trip →

7-night Caribbean from San Juan

Celebrity · Celebrity Summit

6 ports
Round trip
Sails Nov 7, 2027
From $545 pp
Premium

Roseau Boiling Lake Hike: Dominica's Ultimate Volcanic Pilgrimage
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

Celebrity · Celebrity Summit

6 ports
Round trip
Sails Nov 21, 2027
From $570 pp
Premium

Roseau Boiling Lake Hike: Dominica's Ultimate Volcanic Pilgrimage
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

Celebrity · Celebrity Summit

6 ports
Round trip
Sails Dec 5, 2027
From $526 pp
Premium

Roseau Boiling Lake Hike: Dominica's Ultimate Volcanic Pilgrimage
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

Celebrity · Celebrity Summit

6 ports
Round trip
Sails Dec 19, 2027
From $789 pp
Premium

Roseau Boiling Lake Hike: Dominica's Ultimate Volcanic Pilgrimage
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

Disney · Disney Dream

5 ports
Round trip
Sails Apr 16, 2027
From $3,872 pp
Premium

Willemstad Private Full-Day Curaçao Island Tour with Local Expert
Port of Oranjestad Aruba: Snorkel with Turtles at WW2 Shipwreck & Sunset BBQ
Antigua Adventure Antigua: Xtreme Circumnavigation of the Entire Island

See the whole trip →

7-night Caribbean from San Juan

Celebrity · Celebrity Summit

6 ports
Round trip
Sails Nov 14, 2027
From $522 pp
Premium

Port of Kingstown La Soufrière Volcano Summit Hike: St. Vincent's Crown
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

Disney · Disney Fantasy

5 ports
Round trip
Sails Dec 3, 2027
From $2,094 pp
Premium

Port of Oranjestad Aruba: Snorkel with Turtles at WW2 Shipwreck & Sunset BBQ
Willemstad Private Full-Day Curaçao Island Tour with Local Expert
Dominica Boiling Lake & Valley of Desolation: Dominica's Epic Hike

See the whole trip →

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

See the whole trip →

7-night Caribbean from San Juan

Disney · Disney Fantasy

5 ports
Round trip
Sails May 6, 2028
From $2,085 pp
Premium

Bridgetown Swim with wild green sea turtles + two shipwrecks by luxury catamaran (El Tigre)
Castries Cosol Tours: All-Island Private Safari with 7 Stops
Dominica Boiling Lake & Valley of Desolation: Dominica's Epic Hike

See the whole trip →

6-night San Juan to Port Canaveral

Disney · Disney Fantasy

6 ports
One way
Sails May 13, 2028
From $1,613 pp
Premium

St. Maarten Maho Beach: Legendary Extreme Plane-Spotting Experience
St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island
Disney Lookout Cay Private Historical & Cultural SUV Tour of Eleuthera

See the whole trip →

7-night Caribbean from San Juan

Princess · Crown Princess

6 ports
Round trip
Sails Mar 21, 2027
From $789 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 →

5-night San Juan to Fort Lauderdale (Port Everglades)

Disney · Disney Fantasy

5 ports
One way
Sails Dec 10, 2027
From $1,358 pp
Premium

St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island
Disney Lookout Cay Private Historical & Cultural SUV Tour of Eleuthera
Castaway Cay Abaco Backcountry Fishing Adventure: Flats & Offshore

See the whole trip →

14-night Caribbean from San Juan

Princess · Crown Princess

8 ports
Round trip
Sails Feb 7, 2027
From $1,521 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 →

14-night Caribbean from San Juan

Princess · Emerald Princess

9 ports
Round trip
Sails Feb 13, 2028
From $1,723 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 →

14-night Caribbean from San Juan

Princess · Emerald Princess

9 ports
Round trip
Sails Feb 20, 2028
From $1,873 pp
Premium

Tortola Jost Van Dyke: Sandy Spit & Soggy Dollar Painkiller Sail
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
St. Georges Grenada Private Taxi Tour: Your Island, Your Way

See the whole trip →

9-night Caribbean from San Juan

Celebrity · Celebrity Summit

7 ports
Round trip
Sails Oct 29, 2027
From $687 pp
Premium

St. John's Private Half-Day Island Adventure & Trunk Bay Beach
Castries Cosol Tours: All-Island Private Safari with 7 Stops
St. Georges Grenada Private Taxi Tour: Your Island, Your Way

See the whole trip →

7-night Caribbean from San Juan

Celebrity · Celebrity Constellation

6 ports
Round trip
Sails Dec 12, 2026
From $728 pp
Premium

Tortola Jost Van Dyke: Sandy Spit & Soggy Dollar Painkiller Sail
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Roseau Boiling Lake Hike: Dominica's Ultimate Volcanic Pilgrimage

See the whole trip →

7-night Caribbean from San Juan

Celebrity · Celebrity Constellation

6 ports
Round trip
Sails Feb 6, 2027
From $579 pp
Premium

Charlotte Amalie Private Full-Day Boat Charter: 35ft Scarab Triple 300s
St. John's Private Half-Day Island Adventure & Trunk Bay Beach
Roseau Boiling Lake Hike: Dominica's Ultimate Volcanic Pilgrimage

See the whole trip →

7-night Caribbean from San Juan

Virgin · Valiant Lady

5 ports
Round trip
2 departures Dec 2026 – Feb 2027
From $973 pp
Premium

Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Fort-de-France Mount Pelée & Saint-Pierre: Volcano, Ghost Town & Dark History
Port of Oranjestad Aruba: Snorkel with Turtles at WW2 Shipwreck & Sunset BBQ

See the whole trip →

14-night Caribbean from San Juan

Princess · Emerald Princess

9 ports
Round trip
Sails Nov 21, 2027
From $1,683 pp
Premium

St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island
St. Maarten Maho Beach: Legendary Extreme Plane-Spotting Experience
Dominica Boiling Lake & Valley of Desolation: Dominica's Epic Hike

See the whole trip →

7-night Caribbean from San Juan

Disney · Disney Wish

5 ports
Round trip
Sails Nov 5, 2027
From $2,185 pp
Premium

Port of Oranjestad Aruba: Snorkel with Turtles at WW2 Shipwreck & Sunset BBQ
Kralendijk Klein Bonaire: Bioluminescence Snorkel at the Marine Park
Dominica Boiling Lake & Valley of Desolation: Dominica's Epic Hike

See the whole trip →

7-night Caribbean from San Juan

Princess · Crown Princess

6 ports
Round trip
Sails Jan 31, 2027
From $579 pp
Premium

St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island
Guadeloupe La Grande Soufrière: Private Guided Summit Hike
Dominica Boiling Lake & Valley of Desolation: Dominica's Epic Hike

See the whole trip →

14-night Caribbean from San Juan

Princess · Emerald Princess

9 ports
Round trip
Sails Dec 5, 2027
From $1,663 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 →

14-night Caribbean from San Juan

Princess · Emerald Princess

9 ports
Round trip
Sails Dec 12, 2027
From $1,603 pp
Premium

Tortola Jost Van Dyke: Sandy Spit & Soggy Dollar Painkiller Sail
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Dominica Boiling Lake & Valley of Desolation: Dominica's Epic Hike

See the whole trip →

14-night Caribbean from San Juan

Princess · Crown Princess

7 ports
Round trip
Sails Jan 10, 2027
From $1,716 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 →

14-night Caribbean from San Juan

Princess · Crown Princess

7 ports
Round trip
Sails Jan 17, 2027
From $1,726 pp
Premium

St. Maarten Maho Beach: Legendary Extreme Plane-Spotting Experience
St. Georges Grenada Private Taxi Tour: Your Island, Your Way
St. Lucia Gros Piton Summit Hike: Conquer St. Lucia's Iconic Peak

See the whole trip →

8-night San Juan to Miami

Oceania · Oceania Allura

7 ports
One way
Sails Feb 19, 2027
From $3,499 pp
Luxury

Gustavia Private Open-Top Mini Moke Island Tour of St. Barts
Philipsburg Random Wind 'Paradise Day Sail' — Schooner Sail, Snorkel & the Original Tarzan Swing
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant

See the whole trip →