Cruises from San Juan

16 cruise lines and 34 ships sailing from San Juan, Puerto Rico

Cruises visiting San Juan

San Juan puts a remarkable piece of Caribbean history within easy reach of your ship. Founded in 1521, Old San Juan is a compact district of blue cobbles, pastel façades and Spanish colonial landmarks. Walk its steep lanes to El Morro, the 16th-century fortress that guards the harbor. From its ramparts, the Atlantic comes into view. Beyond the old walls, cafés, galleries and contemporary restaurants show a city still shaped by its maritime past.

Cruises from San Juan, Puerto Rico

Sailings departing from San Juan, earliest departure first.

140 Sailings Found
San Juan, Puerto Rico

8 Days One-Way from San Juan to St Thomas Island USVI

SeaDream I

Departs
December 12th 2026
Duration
7 nights
From
$10,019
per person, double occupancy
Ports of call: +3 more ports
View Voyage & Fares Request a Quote
San Juan, Puerto Rico

16 Days San Juan, Puerto Rico Round Trip

MSC Explora 3

Departs
December 13th 2026
Duration
15 nights
From
$10,460
per person, double occupancy
Ports of call: +5 more ports
View Voyage & Fares Request a Quote
San Juan, Puerto Rico

8 Days San Juan, Puerto Rico Round Trip

Ritz-Carlton Ilma

Departs
December 14th 2026
Duration
7 nights
From
$7,400
per person, double occupancy
Ports of call:
View Voyage & Fares Request a Quote

Why Book With Waterways Cruise?

Four decades of expertise, one dedicated advisor, and every detail handled, from your front door to the gangway and back.

Personal Service

Cruise Concierge

A dedicated advisor who learns your name, your travel style and your preferences, then stays with you from the first conversation to the day you return home. Not a call center. Never a stranger.

Tailor-Made

100% Custom‑Built

No cookie-cutter packages. Flights, hotels, transfers and shore days are designed from scratch around how you actually like to travel, then refined until the trip feels like yours.

Expertise

40+ Years in Travel

Founded by J. Richard, a four-decade veteran of the travel industry, and focused solely on premium river and ocean cruising. Decades of ship and itinerary knowledge go into every recommendation.

Security

Book With Total Confidence

A travel agency that is a proud member of Signature Travel Network, CLIA, ASTA and IATA.

San Juan, Puerto Rico

21 Days San Juan, Puerto Rico Round Trip

Viking Sea

Departs
December 16th 2026
Duration
20 nights
From
$11,499
per person, double occupancy
Ports of call: +5 more ports
View Voyage & Fares Request a Quote
San Juan, Puerto Rico

19 Days San Juan, Puerto Rico Round Trip

Azamara Journey

Departs
December 18th 2026
Duration
18 nights
From
$4,719
per person, double occupancy
Ports of call: +8 more ports
View Voyage & Fares Request a Quote
San Juan, Puerto Rico

11 Days One-Way from San Juan to Bridgetown

Azamara Journey

Departs
December 18th 2026
Duration
10 nights
From
$1,979
per person, double occupancy
Ports of call: +3 more ports
View Voyage & Fares Request a Quote
San Juan, Puerto Rico

9 Days San Juan, Puerto Rico Round Trip

SeaDream II

Departs
December 19th 2026
Duration
8 nights
From
$11,979
per person, double occupancy
Ports of call: +1 more port
View Voyage & Fares Request a Quote
San Juan, Puerto Rico

8 Days One-Way from San Juan to Miami

MSC Explora 1

Departs
December 20th 2026
Duration
7 nights
From
$4,200
per person, double occupancy
Ports of call:
View Voyage & Fares Request a Quote
San Juan, Puerto Rico

16 Days San Juan, Puerto Rico Round Trip

MSC Explora 1

Departs
December 20th 2026
Duration
15 nights
From
$12,365
per person, double occupancy
Ports of call: +5 more ports
View Voyage & Fares Request a Quote
San Juan, Puerto Rico

8 Days San Juan, Puerto Rico Round Trip

Silver Shadow

Departs
December 20th 2026
Duration
7 nights
From
$4,400
per person, double occupancy
Ports of call:
View Voyage & Fares Request a Quote
San Juan, Puerto Rico

15 Days San Juan, Puerto Rico Round Trip

Crown Princess

Departs
December 27th 2026
Duration
14 nights
From
$1,322
per person, double occupancy
Ports of call: +3 more ports
View Voyage & Fares Request a Quote
San Juan, Puerto Rico

8 Days San Juan, Puerto Rico Round Trip

Crown Princess

Departs
December 27th 2026
Duration
7 nights
From
$649
per person, double occupancy
Ports of call:
View Voyage & Fares Request a Quote

Cruise lines embarking (starting) at San Juan (16)

Cruise lineCategoryTypeShips departing from San Juan
Regent Seven Seas Cruises Ultra Luxury Ocean Seven Seas Prestige
Ritz-Carlton Yacht Collection Ultra Luxury Ocean Ritz-Carlton Evrima, Ritz-Carlton Ilma
SeaDream Yacht Club Ultra Luxury Ocean SeaDream I, SeaDream II
Silversea Cruises Ultra Luxury Ocean Silver Dawn, Silver Nova, Silver Ray, Silver Shadow
MSC Explora Journeys Luxury Ocean MSC Explora 1, MSC Explora 2, MSC Explora 3, MSC Explora 4
Oceania Cruises Luxury Ocean Oceania Allura
Azamara Cruises Premium Ocean Azamara Journey, Azamara Quest
Crystal Cruises Premium Ocean Crystal Serenity, Crystal Symphony
Emerald Cruises Premium Ocean Emerald Kaia, Emerald Sakara
Viking Cruises Premium Ocean Viking Sea, Viking Sky
Windstar Cruises Premium Ocean Star Legend, Star Pride
Celebrity Cruises Contemporary Ocean Celebrity Constellation, Celebrity Summit
Norwegian Cruise Line Contemporary Ocean Norwegian Prima
Princess Cruises Contemporary Ocean Crown Princess, Emerald Princess
Royal Caribbean Contemporary Ocean Grandeur Of The Seas, Rhapsody Of The Seas, Vision Of The Seas
Virgin Voyages Contemporary Ocean Scarlet Lady, Valiant Lady

The complete Waterways Cruise destination guide to San Juan, Puerto Rico →

16
Cruise lines
34
Ships departing

Published September 22, 2026