Caribbean cruises from San Juan

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

7-night Caribbean from San Juan

Royal Caribbean · Rhapsody of the Seas

6 ports
Round trip
2 departures Dec 2027 – Apr 2028
From $837 pp
Contemporary

Charlotte Amalie Private Full-Day Boat Charter: 35ft Scarab Triple 300s
St. John's Private Half-Day Island Adventure & Trunk Bay Beach
Philipsburg Random Wind 'Paradise Day Sail' — Schooner Sail, Snorkel & the Original Tarzan Swing

See the whole trip →

7-night Caribbean from San Juan

Royal Caribbean · Rhapsody of the Seas

6 ports
Round trip
2 departures Feb 2027
From $496 pp
Contemporary

Tortola Jost Van Dyke: Sandy Spit & Soggy Dollar Painkiller Sail
Philipsburg Random Wind 'Paradise Day Sail' — Schooner Sail, Snorkel & the Original Tarzan Swing
St. John's Private Half-Day Island Adventure & Trunk Bay Beach

See the whole trip →

13-night San Juan to Barcelona

Celebrity · Celebrity Constellation

5 ports
Repositioning
Sails Apr 3, 2027
From $892 pp
Premium

Philipsburg Random Wind 'Paradise Day Sail' — Schooner Sail, Snorkel & the Original Tarzan Swing
Tangier Tangier Kasbah, Medina & American Legation Private Tour
Malaga Granada & the Alhambra: Spain's Most Famous Monument

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10-night San Juan to Miami

Royal Caribbean · Vision of the Seas

9 ports
One way
Sails Apr 4, 2027
From $1,014 pp
Contemporary

Charlotte Amalie Private Full-Day Boat Charter: 35ft Scarab Triple 300s
St. Croix Buck Island Reef: Private Catamaran Sail & Snorkel
Philipsburg Random Wind 'Paradise Day Sail' — Schooner Sail, Snorkel & the Original Tarzan Swing

See the whole trip →

10-night San Juan to Miami

Royal Caribbean · Rhapsody of the Seas

9 ports
One way
Sails Mar 6, 2027
From $814 pp
Contemporary

Tortola Jost Van Dyke: Sandy Spit & Soggy Dollar Painkiller Sail
Philipsburg Random Wind 'Paradise Day Sail' — Schooner Sail, Snorkel & the Original Tarzan Swing
St. John's Private Half-Day Island Adventure & Trunk Bay Beach

See the whole trip →

7-night Caribbean from San Juan

Royal Caribbean · Rhapsody of the Seas

6 ports
Round trip
Sails Dec 26, 2026
From $1,169 pp
Contemporary

Tortola Jost Van Dyke: Sandy Spit & Soggy Dollar Painkiller Sail
Philipsburg Random Wind 'Paradise Day Sail' — Schooner Sail, Snorkel & the Original Tarzan Swing
St. John's Private Half-Day Island Adventure & Trunk Bay Beach

See the whole trip →

7-night Caribbean from San Juan

Royal Caribbean · Vision of the Seas

6 ports
Round trip
Sails Nov 28, 2027
From $612 pp
Contemporary

Charlotte Amalie Private Full-Day Boat Charter: 35ft Scarab Triple 300s
St. John's Private Half-Day Island Adventure & Trunk Bay Beach
Philipsburg Random Wind 'Paradise Day Sail' — Schooner Sail, Snorkel & the Original Tarzan Swing

See the whole trip →

7-night Caribbean from San Juan

Royal Caribbean · Vision of the Seas

6 ports
Round trip
Sails Jan 9, 2028
From $662 pp
Contemporary

Charlotte Amalie Private Full-Day Boat Charter: 35ft Scarab Triple 300s
St. John's Private Half-Day Island Adventure & Trunk Bay Beach
Philipsburg Random Wind 'Paradise Day Sail' — Schooner Sail, Snorkel & the Original Tarzan Swing

See the whole trip →

7-night Caribbean from San Juan

Royal Caribbean · Rhapsody of the Seas

6 ports
Round trip
Sails Jan 9, 2027
From $552 pp
Contemporary

St. Croix Buck Island Reef: Private Catamaran Sail & Snorkel
Philipsburg Random Wind 'Paradise Day Sail' — Schooner Sail, Snorkel & the Original Tarzan Swing
St. John's Private Half-Day Island Adventure & Trunk Bay Beach

See the whole trip →

7-night Caribbean from San Juan

Royal Caribbean · Vision of the Seas

6 ports
Round trip
Sails Nov 1, 2026
From $639 pp
Contemporary

Charlotte Amalie Private Full-Day Boat Charter: 35ft Scarab Triple 300s
St. John's Private Half-Day Island Adventure & Trunk Bay Beach
Philipsburg Random Wind 'Paradise Day Sail' — Schooner Sail, Snorkel & the Original Tarzan Swing

See the whole trip →

7-night Caribbean from San Juan

Royal Caribbean · Vision of the Seas

6 ports
Round trip
Sails Nov 15, 2026
From $541 pp
Contemporary

Charlotte Amalie Private Full-Day Boat Charter: 35ft Scarab Triple 300s
St. John's Private Half-Day Island Adventure & Trunk Bay Beach
Philipsburg Random Wind 'Paradise Day Sail' — Schooner Sail, Snorkel & the Original Tarzan Swing

See the whole trip →

7-night Caribbean from San Juan

Royal Caribbean · Vision of the Seas

6 ports
Round trip
Sails Mar 28, 2027
From $742 pp
Contemporary

Charlotte Amalie Private Full-Day Boat Charter: 35ft Scarab Triple 300s
St. John's Private Half-Day Island Adventure & Trunk Bay Beach
Philipsburg Random Wind 'Paradise Day Sail' — Schooner Sail, Snorkel & the Original Tarzan Swing

See the whole trip →

7-night Caribbean from San Juan

Royal Caribbean · Rhapsody of the Seas

6 ports
Round trip
Sails Dec 4, 2027
From $699 pp
Contemporary

Charlotte Amalie Private Full-Day Boat Charter: 35ft Scarab Triple 300s
Philipsburg Random Wind 'Paradise Day Sail' — Schooner Sail, Snorkel & the Original Tarzan Swing
St. John's Private Half-Day Island Adventure & Trunk Bay Beach

See the whole trip →

7-night Caribbean from San Juan

Royal Caribbean · Rhapsody of the Seas

6 ports
Round trip
Sails Jan 29, 2028
From $731 pp
Contemporary

Charlotte Amalie Private Full-Day Boat Charter: 35ft Scarab Triple 300s
Philipsburg Random Wind 'Paradise Day Sail' — Schooner Sail, Snorkel & the Original Tarzan Swing
St. John's Private Half-Day Island Adventure & Trunk Bay Beach

See the whole trip →

7-night Caribbean from San Juan

Royal Caribbean · Rhapsody of the Seas

6 ports
Round trip
Sails Feb 12, 2028
From $757 pp
Contemporary

Charlotte Amalie Private Full-Day Boat Charter: 35ft Scarab Triple 300s
Philipsburg Random Wind 'Paradise Day Sail' — Schooner Sail, Snorkel & the Original Tarzan Swing
St. John's Private Half-Day Island Adventure & Trunk Bay Beach

See the whole trip →

7-night Caribbean from San Juan

Royal Caribbean · Rhapsody of the Seas

6 ports
Round trip
Sails Feb 26, 2028
From $792 pp
Contemporary

Charlotte Amalie Private Full-Day Boat Charter: 35ft Scarab Triple 300s
Philipsburg Random Wind 'Paradise Day Sail' — Schooner Sail, Snorkel & the Original Tarzan Swing
St. John's Private Half-Day Island Adventure & Trunk Bay Beach

See the whole trip →

7-night Caribbean from San Juan

Royal Caribbean · Rhapsody of the Seas

6 ports
Round trip
Sails Mar 11, 2028
From $830 pp
Contemporary

Charlotte Amalie Private Full-Day Boat Charter: 35ft Scarab Triple 300s
Philipsburg Random Wind 'Paradise Day Sail' — Schooner Sail, Snorkel & the Original Tarzan Swing
St. John's Private Half-Day Island Adventure & Trunk Bay Beach

See the whole trip →

7-night Caribbean from San Juan

Royal Caribbean · Rhapsody of the Seas

6 ports
Round trip
Sails Mar 25, 2028
From $787 pp
Contemporary

Charlotte Amalie Private Full-Day Boat Charter: 35ft Scarab Triple 300s
Philipsburg Random Wind 'Paradise Day Sail' — Schooner Sail, Snorkel & the Original Tarzan Swing
St. John's Private Half-Day Island Adventure & Trunk Bay Beach

See the whole trip →

7-night Caribbean from San Juan

Royal Caribbean · Rhapsody of the Seas

6 ports
Round trip
Sails Jan 8, 2028
From $834 pp
Contemporary

Charlotte Amalie Private Full-Day Boat Charter: 35ft Scarab Triple 300s
St. Croix Buck Island Reef: Private Catamaran Sail & Snorkel
Philipsburg Random Wind 'Paradise Day Sail' — Schooner Sail, Snorkel & the Original Tarzan Swing

See the whole trip →

7-night Caribbean from San Juan

Royal Caribbean · Rhapsody of the Seas

6 ports
Round trip
Sails Sep 26, 2026
From $584 pp
Contemporary

Tortola Jost Van Dyke: Sandy Spit & Soggy Dollar Painkiller Sail
Philipsburg Random Wind 'Paradise Day Sail' — Schooner Sail, Snorkel & the Original Tarzan Swing
St. John's Private Half-Day Island Adventure & Trunk Bay Beach

See the whole trip →

7-night Caribbean from San Juan

Royal Caribbean · Rhapsody of the Seas

6 ports
Round trip
Sails Oct 10, 2026
From $591 pp
Contemporary

Tortola Jost Van Dyke: Sandy Spit & Soggy Dollar Painkiller Sail
Philipsburg Random Wind 'Paradise Day Sail' — Schooner Sail, Snorkel & the Original Tarzan Swing
St. John's Private Half-Day Island Adventure & Trunk Bay Beach

See the whole trip →

7-night Caribbean from San Juan

Royal Caribbean · Rhapsody of the Seas

6 ports
Round trip
Sails Oct 24, 2026
From $579 pp
Contemporary

Tortola Jost Van Dyke: Sandy Spit & Soggy Dollar Painkiller Sail
Philipsburg Random Wind 'Paradise Day Sail' — Schooner Sail, Snorkel & the Original Tarzan Swing
St. John's Private Half-Day Island Adventure & Trunk Bay Beach

See the whole trip →

7-night Caribbean from San Juan

Royal Caribbean · Vision of the Seas

6 ports
Round trip
Sails Nov 22, 2026
From $759 pp
Contemporary

Tortola Jost Van Dyke: Sandy Spit & Soggy Dollar Painkiller Sail
St. John's Private Half-Day Island Adventure & Trunk Bay Beach
Philipsburg Random Wind 'Paradise Day Sail' — Schooner Sail, Snorkel & the Original Tarzan Swing

See the whole trip →

7-night Caribbean from San Juan

Royal Caribbean · Rhapsody of the Seas

6 ports
Round trip
Sails Nov 28, 2026
From $531 pp
Contemporary

Tortola Jost Van Dyke: Sandy Spit & Soggy Dollar Painkiller Sail
Philipsburg Random Wind 'Paradise Day Sail' — Schooner Sail, Snorkel & the Original Tarzan Swing
St. John's Private Half-Day Island Adventure & Trunk Bay Beach

See the whole trip →

7-night Caribbean from San Juan

Royal Caribbean · Vision of the Seas

6 ports
Round trip
Sails Dec 6, 2026
From $611 pp
Contemporary

Tortola Jost Van Dyke: Sandy Spit & Soggy Dollar Painkiller Sail
St. John's Private Half-Day Island Adventure & Trunk Bay Beach
Philipsburg Random Wind 'Paradise Day Sail' — Schooner Sail, Snorkel & the Original Tarzan Swing

See the whole trip →

7-night Caribbean from San Juan

Royal Caribbean · Rhapsody of the Seas

6 ports
Round trip
Sails Dec 12, 2026
From $578 pp
Contemporary

Tortola Jost Van Dyke: Sandy Spit & Soggy Dollar Painkiller Sail
Philipsburg Random Wind 'Paradise Day Sail' — Schooner Sail, Snorkel & the Original Tarzan Swing
St. John's Private Half-Day Island Adventure & Trunk Bay Beach

See the whole trip →

7-night Caribbean from San Juan

Royal Caribbean · Rhapsody of the Seas

6 ports
Round trip
Sails Jan 23, 2027
From $502 pp
Contemporary

Tortola Jost Van Dyke: Sandy Spit & Soggy Dollar Painkiller Sail
Philipsburg Random Wind 'Paradise Day Sail' — Schooner Sail, Snorkel & the Original Tarzan Swing
St. John's Private Half-Day Island Adventure & Trunk Bay Beach

See the whole trip →

7-night Caribbean from San Juan

Royal Caribbean · Vision of the Seas

6 ports
Round trip
Sails Feb 14, 2027
From $602 pp
Contemporary

Tortola Jost Van Dyke: Sandy Spit & Soggy Dollar Painkiller Sail
St. John's Private Half-Day Island Adventure & Trunk Bay Beach
Philipsburg Random Wind 'Paradise Day Sail' — Schooner Sail, Snorkel & the Original Tarzan Swing

See the whole trip →

7-night Caribbean from San Juan

Royal Caribbean · Grandeur of the Seas

6 ports
Round trip
Sails May 8, 2027
From $595 pp
Contemporary

Tortola Jost Van Dyke: Sandy Spit & Soggy Dollar Painkiller Sail
Philipsburg Random Wind 'Paradise Day Sail' — Schooner Sail, Snorkel & the Original Tarzan Swing
St. John's Private Half-Day Island Adventure & Trunk Bay Beach

See the whole trip →

7-night Caribbean from San Juan

Royal Caribbean · Grandeur of the Seas

6 ports
Round trip
Sails May 22, 2027
From $689 pp
Contemporary

Tortola Jost Van Dyke: Sandy Spit & Soggy Dollar Painkiller Sail
Philipsburg Random Wind 'Paradise Day Sail' — Schooner Sail, Snorkel & the Original Tarzan Swing
St. John's Private Half-Day Island Adventure & Trunk Bay Beach

See the whole trip →

7-night Caribbean from San Juan

Royal Caribbean · Grandeur of the Seas

6 ports
Round trip
Sails Jun 5, 2027
From $756 pp
Contemporary

Tortola Jost Van Dyke: Sandy Spit & Soggy Dollar Painkiller Sail
Philipsburg Random Wind 'Paradise Day Sail' — Schooner Sail, Snorkel & the Original Tarzan Swing
St. John's Private Half-Day Island Adventure & Trunk Bay Beach

See the whole trip →

7-night Caribbean from San Juan

Royal Caribbean · Grandeur of the Seas

6 ports
Round trip
Sails Jun 19, 2027
From $886 pp
Contemporary

Tortola Jost Van Dyke: Sandy Spit & Soggy Dollar Painkiller Sail
Philipsburg Random Wind 'Paradise Day Sail' — Schooner Sail, Snorkel & the Original Tarzan Swing
St. John's Private Half-Day Island Adventure & Trunk Bay Beach

See the whole trip →

7-night Caribbean from San Juan

Royal Caribbean · Grandeur of the Seas

6 ports
Round trip
Sails Jul 3, 2027
From $1,099 pp
Contemporary

Tortola Jost Van Dyke: Sandy Spit & Soggy Dollar Painkiller Sail
Philipsburg Random Wind 'Paradise Day Sail' — Schooner Sail, Snorkel & the Original Tarzan Swing
St. John's Private Half-Day Island Adventure & Trunk Bay Beach

See the whole trip →

7-night Caribbean from San Juan

Royal Caribbean · Grandeur of the Seas

6 ports
Round trip
Sails Jul 17, 2027
From $1,029 pp
Contemporary

Tortola Jost Van Dyke: Sandy Spit & Soggy Dollar Painkiller Sail
Philipsburg Random Wind 'Paradise Day Sail' — Schooner Sail, Snorkel & the Original Tarzan Swing
St. John's Private Half-Day Island Adventure & Trunk Bay Beach

See the whole trip →

7-night Caribbean from San Juan

Royal Caribbean · Grandeur of the Seas

6 ports
Round trip
Sails Jul 31, 2027
From $949 pp
Contemporary

Tortola Jost Van Dyke: Sandy Spit & Soggy Dollar Painkiller Sail
Philipsburg Random Wind 'Paradise Day Sail' — Schooner Sail, Snorkel & the Original Tarzan Swing
St. John's Private Half-Day Island Adventure & Trunk Bay Beach

See the whole trip →

7-night Caribbean from San Juan

Royal Caribbean · Grandeur of the Seas

6 ports
Round trip
Sails Aug 14, 2027
From $777 pp
Contemporary

Tortola Jost Van Dyke: Sandy Spit & Soggy Dollar Painkiller Sail
Philipsburg Random Wind 'Paradise Day Sail' — Schooner Sail, Snorkel & the Original Tarzan Swing
St. John's Private Half-Day Island Adventure & Trunk Bay Beach

See the whole trip →

7-night Caribbean from San Juan

Royal Caribbean · Grandeur of the Seas

6 ports
Round trip
Sails Aug 28, 2027
From $648 pp
Contemporary

Tortola Jost Van Dyke: Sandy Spit & Soggy Dollar Painkiller Sail
Philipsburg Random Wind 'Paradise Day Sail' — Schooner Sail, Snorkel & the Original Tarzan Swing
St. John's Private Half-Day Island Adventure & Trunk Bay Beach

See the whole trip →

7-night Caribbean from San Juan

Royal Caribbean · Grandeur of the Seas

6 ports
Round trip
Sails Sep 11, 2027
From $609 pp
Contemporary

Tortola Jost Van Dyke: Sandy Spit & Soggy Dollar Painkiller Sail
Philipsburg Random Wind 'Paradise Day Sail' — Schooner Sail, Snorkel & the Original Tarzan Swing
St. John's Private Half-Day Island Adventure & Trunk Bay Beach

See the whole trip →

7-night Caribbean from San Juan

Royal Caribbean · Grandeur of the Seas

6 ports
Round trip
Sails Sep 25, 2027
From $606 pp
Contemporary

Tortola Jost Van Dyke: Sandy Spit & Soggy Dollar Painkiller Sail
Philipsburg Random Wind 'Paradise Day Sail' — Schooner Sail, Snorkel & the Original Tarzan Swing
St. John's Private Half-Day Island Adventure & Trunk Bay Beach

See the whole trip →

7-night Caribbean from San Juan

Royal Caribbean · Grandeur of the Seas

6 ports
Round trip
Sails Oct 9, 2027
From $671 pp
Contemporary

Tortola Jost Van Dyke: Sandy Spit & Soggy Dollar Painkiller Sail
Philipsburg Random Wind 'Paradise Day Sail' — Schooner Sail, Snorkel & the Original Tarzan Swing
St. John's Private Half-Day Island Adventure & Trunk Bay Beach

See the whole trip →

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