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 II

Departs
December 27th 2026
Duration
7 nights
From
$32,319
per person, double occupancy
Ports of call:
View Voyage & Fares Request a Quote
San Juan, Puerto Rico

9 Days One-Way from San Juan to Miami

MSC Explora 3

Departs
December 28th 2026
Duration
8 nights
From
$5,440
per person, double occupancy
Ports of call: +1 more port
View Voyage & Fares Request a Quote
San Juan, Puerto Rico

17 Days San Juan, Puerto Rico Round Trip

MSC Explora 3

Departs
December 28th 2026
Duration
16 nights
From
$12,620
per person, double occupancy
Ports of call: +4 more ports
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

9 Days One-Way from San Juan to Miami

Silver Nova

Departs
December 29th 2026
Duration
8 nights
From
$6,700
per person, double occupancy
Ports of call: +1 more port
View Voyage & Fares Request a Quote
San Juan, Puerto Rico

6 Days One-Way from San Juan to Bridgetown

Crown Princess

Departs
January 3rd 2027
Duration
5 nights
From
$847
per person, double occupancy
Ports of call:
View Voyage & Fares Request a Quote
San Juan, Puerto Rico

7 Days San Juan, Puerto Rico Round Trip

SeaDream I

Departs
January 3rd 2027
Duration
6 nights
From
$12,166
per person, double occupancy
Ports of call:
View Voyage & Fares Request a Quote
San Juan, Puerto Rico

17 Days One-Way from San Juan to Miami

MSC Explora 1

Departs
January 4th 2027
Duration
16 nights
From
$9,410
per person, double occupancy
Ports of call: +4 more ports
View Voyage & Fares Request a Quote
San Juan, Puerto Rico

10 Days One-Way from San Juan to Miami

Azamara Journey

Departs
January 5th 2027
Duration
9 nights
From
$1,959
per person, double occupancy
Ports of call: +2 more ports
View Voyage & Fares Request a Quote
San Juan, Puerto Rico

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

Emerald Sakara

Departs
January 9th 2027
Duration
7 nights
From
$3,595
per person, double occupancy
Ports of call: +1 more port
View Voyage & Fares Request a Quote
San Juan, Puerto Rico

8 Days San Juan, Puerto Rico Round Trip

SeaDream I

Departs
January 9th 2027
Duration
7 nights
From
$13,727
per person, double occupancy
Ports of call: +1 more port
View Voyage & Fares Request a Quote
San Juan, Puerto Rico

11 Days One-Way from San Juan to Bridgetown

Silver Shadow

Departs
January 10th 2027
Duration
10 nights
From
$7,700
per person, double occupancy
Ports of call: +5 more ports
View Voyage & Fares Request a Quote
San Juan, Puerto Rico

7 Days San Juan, Puerto Rico Round Trip

Ritz-Carlton Ilma

Departs
January 13th 2027
Duration
6 nights
From
$7,000
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