⚓ Cruises

Azamara Caribbean cruises from San Juan

8 itineraries with a bookable sailing ahead, 8 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 › Azamara Caribbean cruises from San Juan

Most popular first

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

Virgin Gorda

9-night San Juan to Miami

Azamara · Azamara Journey

8 ports
One way
Sails Jan 5, 2027
From $1,999 pp
Luxury

Virgin Gorda The Baths National Park: Private Guided Boulders & Devil's Bay
Gustavia Private Open-Top Mini Moke Island Tour of St. Barts
Philipsburg Random Wind 'Paradise Day Sail' — Schooner Sail, Snorkel & the Original Tarzan Swing

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Virgin Gorda

14-night Caribbean from San Juan

Azamara · Azamara Quest

13 ports
Round trip
Sails Nov 21, 2027
From $3,849 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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Charlotte Amalie

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

See the whole trip →

Virgin Gorda

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

See the whole trip →

Virgin Gorda

7-night San Juan to Bridgetown

Azamara · Azamara Journey

7 ports
One way
Sails Nov 7, 2026
From $2,341 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 →

Virgin Gorda

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 →

Virgin Gorda

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 →

Charlotte Amalie

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

See the whole trip →

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