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

24 Days One-Way from San Juan to Amsterdam

Star Pride

Departs
March 27th 2028
Duration
23 nights
From
$4,151
per person, double occupancy
Ports of call: +3 more ports
San Juan, Puerto Rico

17 Days One-Way from San Juan to Amsterdam

Star Pride

Departs
April 3rd 2028
Duration
16 nights
From
$2,760
per person, double occupancy
Ports of call:
San Juan, Puerto Rico

13 Days One-Way from San Juan to Barcelona

Scarlet Lady

Departs
April 22nd 2028
Duration
12 nights
From
$1,896
per person, double occupancy
Ports of call:

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

15 Days One-Way from San Juan to Malaga

SeaDream I

Departs
April 22nd 2028
Duration
14 nights
Ports of call:
San Juan, Puerto Rico

10 Days San Juan, Puerto Rico Round Trip

SeaDream I

Departs
December 29th 2028
Duration
9 nights
From
$31,149
per person, double occupancy
Ports of call:
San Juan, Puerto Rico

12 Days One-Way from San Juan to Bridgetown

SeaDream I

Departs
February 3rd 2029
Duration
11 nights
From
$22,471
per person, double occupancy
Ports of call: +4 more ports
San Juan, Puerto Rico

8 Days One-Way from San Juan to West Palm Beach

SeaDream I

Departs
March 24th 2029
Duration
7 nights
From
$14,327
per person, double occupancy
Ports of call: +1 more port
San Juan, Puerto Rico

15 Days One-Way from San Juan to Malaga

SeaDream II

Departs
April 28th 2029
Duration
14 nights
From
$16,260
per person, double occupancy
Ports of call: