Mediterranean cruises from San Juan

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

17-night San Juan to Civitavecchia (Rome)

Norwegian · Norwegian Prima

11 ports
Repositioning
Sails Apr 4, 2027
From $2,769 pp
Contemporary

Ponta Delgada Sete Cidades Twin Lakes: Private Full-Island Jeep Safari
Funchal Pico do Arieiro to Pico Ruivo: Madeira's Rooftop Ridge Walk
Melilla Melilla la Vieja: Private Guided Fortress & Tunnel Secrets

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13-night San Juan to Barcelona

Viking Ocean · Viking Sea

6 ports
Repositioning
Sails Mar 6, 2027
From $3,599 pp
Luxury

Philipsburg Random Wind 'Paradise Day Sail' — Schooner Sail, Snorkel & the Original Tarzan Swing
Funchal Pico do Arieiro to Pico Ruivo: Madeira's Rooftop Ridge Walk
Cadiz (Seville) Real Alcázar de Sevilla: Private Expert-Led Palace Access

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13-night San Juan to Barcelona

Viking Ocean · Viking Sea

6 ports
One way
Sails Feb 26, 2028
From $3,299 pp
Luxury

Philipsburg Random Wind 'Paradise Day Sail' — Schooner Sail, Snorkel & the Original Tarzan Swing
Funchal Pico do Arieiro to Pico Ruivo: Madeira's Rooftop Ridge Walk
Cadiz (Seville) Real Alcázar de Sevilla: Private Expert-Led Palace Access

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11-night San Juan to Lisbon

Viking Ocean · Viking Sky

5 ports
Repositioning
Sails Feb 27, 2028
From $3,299 pp
Luxury

Las Palmas Roque Nublo & Tejeda: Gran Canaria's Sacred Heart by 4×4
Santa Cruz de Tenerife Teide National Park: Summit Cable Car & Volcanic Moonscape
Funchal Pico do Arieiro to Pico Ruivo: Madeira's Rooftop Ridge Walk

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12-night San Juan to Barcelona

Virgin · Scarlet Lady

5 ports
One way
Sails Apr 22, 2028
From $1,308 pp
Premium

St. Maarten Maho Beach: Legendary Extreme Plane-Spotting Experience
Funchal Pico do Arieiro to Pico Ruivo: Madeira's Rooftop Ridge Walk
Tangier Tangier Kasbah, Medina & American Legation Private Tour

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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 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

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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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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

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