Puerto Rico Cruises: Sailings, Embarkations & Ports of Call
89 ships from 21 cruise lines
Puerto Rico cruises at a glance
Waterways Cruise lists 430 upcoming sailings on 89 ships from 21 cruise lines visiting Puerto Rico, calling at 3 places. Cruises can start in San Juan and end in San Juan. Of 430 upcoming sailings, 140 start in Puerto Rico and 142 end there. More Caribbean cruises.
Reviewed and fact-checked by J. Richard · About this page · About us
Compare Puerto Rico cruise lines
See every Puerto Rico cruise line by ocean and river and by ultra-luxury, luxury, premium and contemporary style, with fares, cruise lengths, ships and ports.
About Puerto Rico
Puerto Rico offers the familiar ease of a U.S. territory—dollars, no passport, U.S. air traffic control—with a Caribbean pulse that feels genuinely foreign. For the traveler who wants milestone scenery without being herded, the sweet spot is a small ship that uses San Juan as a true homeport and spends time on the island's less crowded coasts and offshore cays.
Typical routes
- Eastern Caribbean & Spanish Main: San Juan to the U.S. and British Virgin Islands, sometimes as far south as Aruba, Curaçao, and the Spanish Main coast.
- Greater Antilles & Western Caribbean: San Juan to the Dominican Republic, Haiti, Jamaica, Grand Cayman, and sometimes Cuba, often with one or two Puerto Rico calls.
Ports overview
San Juan is the island's cruise anchor—one of the largest homeports in the Caribbean—while Ponce and Fajardo offer small-ship alternatives. The result is a destination that works both for big-ship passengers who want a convenient embarkation point and for travelers who want to skip the herd.
Cruise season
High season December through April; hurricane season June through November, with September historically quietest for cruising. Small-ship operators often run winter departures from San Juan.
Find your Puerto Rico sailing
Upcoming sailings calling at Puerto Rico, earliest departure first.
10 Days Port Canaveral, USA Round Trip
Visits Puerto Rico. Also visits United States, Turks And Caicos Islands, Dominican Republic
Star Princess
27 Days One-Way from Monte Carlo to San Juan
Ends in Puerto Rico. Also visits Monaco, France, Spain
Silver Dawn
12 Days One-Way from Lisbon to San Juan
Ends in Puerto Rico. Also visits Portugal, Spain
Viking Sea
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.
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.
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.
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.
Book With Total Confidence
A travel agency that is a proud member of Signature Travel Network, CLIA, ASTA and IATA.
10 Days Miami, USA Round Trip
Visits Puerto Rico. Also visits United States, Bahamas, Dominican Republic
Norwegian Joy
12 Days One-Way from Lisbon to San Juan
Ends in Puerto Rico. Also visits Portugal, Spain
Viking Sky
8 Days One-Way from San Juan to St Johns Antigua
Starts in Puerto Rico. Also visits U.S. Virgin Islands, Sint Maarten, Saint Barthélemy
Emerald Kaia
15 Days San Juan, Puerto Rico Round Trip
Starts and ends in Puerto Rico. Also visits U.S. Virgin Islands, Sint Maarten, Saint Barthélemy
Emerald Kaia
8 Days One-Way from Miami to San Juan
Ends in Puerto Rico. Also visits United States, U.S. Virgin Islands, Antigua and Barbuda
MSC Explora 4
16 Days Miami, USA Round Trip
Visits Puerto Rico. Also visits United States, Belize, Honduras
Regal Princess
8 Days San Juan, Puerto Rico Round Trip
Starts and ends in Puerto Rico. Also visits Aruba, Curaçao, Antigua and Barbuda
Scarlet Lady
8 Days One-Way from San Juan to Philipsburg St Maarten
Starts in Puerto Rico. Also visits BVI, Anguilla, Saint Barthélemy
SeaDream II
15 Days San Juan, Puerto Rico Round Trip
Starts and ends in Puerto Rico. Also visits BVI, Antigua and Barbuda, St Vincent and Grenadines
Azamara Quest
Where Puerto Rico cruises start and end
Embarkation ports (1)
San Juan (430) (cruises from)
Disembarkation ports (1)
San Juan (430)
Ships by type: 89 ocean · a ship that visits several places here is counted once; an expedition ship that also sails as an ocean ship appears under both types.
Plan your Puerto Rico cruise
Puerto Rico cruise port guide
Cruise ports, what to see, history and practical advice.
Puerto Rico cruise port guide →More Caribbean cruises
Sint Maarten · Bahamas · Dominican Republic · Bermuda · Curacao · St Kitts and Nevis · Aruba · Antigua and Barbuda
Frequently asked questions about Puerto Rico cruises
How many places do cruises visit in Puerto Rico?
3 Puerto Rico places are visited by 89 ships from 21 cruise lines.
When is the best time to take a Puerto Rico cruise?
High season December through April; hurricane season June through November, with September historically quietest for cruising. Small-ship operators often run winter departures from San Juan.
Sources and further reading
Background on Puerto Rico draws on these references. Sailing, fare and port data come from cruise line itineraries and are refreshed regularly.
- Discover Puerto Rico: Official Tourism Website
- Encyclopaedia Britannica: Puerto Rico
- CIA: Puerto Rico - The World Factbook
- National Park Service: San Juan National Historic Site
- USDA Forest Service: El Yunque National Forest
Created by the Waterways Cruise content team and reviewed and fact-checked by J. Richard, Sr. Cruise Travel Agent and Founder of Waterways Cruise.
Published September 9, 2026 · Last updated October 31, 2026
Fares, availability and itineraries change often. Confirm current details with your cruise line or a Waterways Cruise agent before you book.
Cruise Disclosure
Good to know: Prices are quoted per person based on double occupancy and include all applicable taxes and fees. Availability and prices can change quickly, so please continue through the booking process to confirm the latest availability and pricing before you pay.
We work hard to make sure everything on this website is accurate and up to date. However, some information may be incomplete or inaccurate, including details supplied by third parties or otherwise outside our control, and we cannot be held responsible for such errors. We work with 0 cruise line operators, that are providing cruises on 0 ships visiting 0 ports across 0 unique cruises, creating 0 itineraries. This is a great deal of data to continually update daily from our suppliers. If a pricing error, misrepresentation, or omission occurs, we reserve the right to adjust the pricing, correct the information, or cancel or decline any booking made in error, with notice to you. Thank you for your understanding!