A port a day, seven islands, and no passport to get there.
San Juan is the Southern Caribbean’s home port: start here and the islands are so close the ship visits a new one every morning, from St. Thomas and St. Maarten to St. Lucia, Barbados, Aruba and Curacao, with almost no sea days. Puerto Rico is US soil, so Americans fly in without a passport and start the trip in Old San Juan, two blocks from the pier. SmartCruiser shows every sailing leaving San Juan from every line, prices each one with taxes and fees included, and puts the sailings with SmartCruiser bonus onboard credit or instant savings at the top.
Three ways to sail from San Juan
San Juan is where you go for ports, not sea days. Pick the ship size and we find the week.
The 7 night Southern Caribbean
- Six islands in seven days: St. Thomas, St. Maarten or St. Kitts, Antigua, St. Lucia, Barbados and back
- Saturday and Sunday departures on Royal Caribbean, Celebrity, Princess and Norwegian, mostly November to April
- Deep-south islands like Aruba and Curacao on the ABC loops
Best for: first-time Southern Caribbean cruisers, beach collectors, anyone who hates sea days.
Virgin Voyages and the small ships
- Virgin’s adults-only Southern Caribbean loops from San Juan with late nights in port
- Windstar’s 310-guest sailing yachts and Seabourn’s 450-guest all-inclusives into the harbors big ships cannot reach: Bequia, Iles des Saintes, Jost Van Dyke
- Fewer guests on the pier than there are on one deck of a megaship
Best for: couples, honeymoons, repeat cruisers who want the quiet side of the islands.
Eastern Caribbean from San Juan
- St. Thomas, St. Croix, Tortola and St. Maarten are an overnight away, so the ship can linger until evening
- Some loops add a day in Puerto Rico’s own Ponce or in the Dominican Republic
- The best choice when you want beaches and shopping rather than volcanoes and rainforests
Best for: families, short winter escapes, anyone adding a few days in Old San Juan.
San Juan deals: SmartCruiser picks first
Every sailing leaving San Juan from every line, priced live with taxes, fees and port expenses included. The picks at the top are sailings where booking with SmartCruiser gets you something extra: instant savings, bonus onboard credit, a Special SmartCruiser rate, or a senior, resident or police & fire fare that beats the public price. Below them, every other sailing from San Juan with full sorting.
SmartCruiser picks
Sorted by what you save, biggest firstEvery sailing from San Juan
Stack any filters, then pick a sortPrices are per person, double occupancy, in US dollars, and include cruise fare, taxes, fees and port expenses as published by the cruise line at the moment you load this page. Fares are capacity controlled and change daily; the fare is confirmed when you book. Flights, hotels and transfers are extra unless the line’s offer says otherwise. SmartCruiser instant savings and bonus onboard credit are provided by SmartCruiser on top of the cruise line’s price and are not available when booking direct; amounts are per stateroom, vary by stateroom category and are shown for the lowest category offered. Special SmartCruiser rates are pricing SmartCruiser holds on that sailing for its clients, with extra onboard credit; you book your own stateroom and travel on your own. Senior fares apply to guests 55 and over; resident fares need proof of residency in a listed state or province at check-in; police and fire fares apply to active or retired police, fire and EMT personnel with ID. Qualifier-fare savings are measured against the best fare the cruise line offers the general public for the same stateroom category on the day the list was pulled, updated weekly.
Where ships from San Juan sail
Pick a destination and the list above filters to the San Juan sailings that go there.
Which line from San Juan?
Seven lines, from 5,000-guest Royal Caribbean ships to Windstar sailing yachts. Our one-line take on each.
When to go
San Juan’s big-ship season runs November to April. Summer is small-ship and bargain territory.
San Juan cruise questions we answer every day
Do I need a passport to cruise from San Juan?
US citizens do not need a passport to fly to Puerto Rico, and on a closed-loop cruise that starts and ends in San Juan you can sail with a government photo ID and an original or certified birth certificate, even though the ship visits foreign islands. We still recommend a passport: if you miss the ship in Barbados or need to fly home from St. Lucia, you cannot board that flight without one. Non-US citizens need a passport and any visas they would need for the islands.
Where do the ships dock in San Juan?
Two places. The Old San Juan piers sit on the waterfront with the old city at the top of the ramp, and the smaller ships and some big-ship turnarounds use them. Royal Caribbean, Celebrity and most of the other big homeported ships use the Pan American Pier across the bay on Isla Grande, a short fixed-fare taxi ride from Old San Juan. Your documents name the pier; the taxi drivers know both.
How far is the airport from the piers?
Luis Munoz Marin International is 8 miles east of Old San Juan, 20 to 30 minutes depending on traffic. Taxis from the airport charge fixed tourist-zone fares, about $21 to $25 to Old San Juan or any cruise pier plus a small per-bag charge; rideshares typically run a little less. The cruise lines sell transfers for about the same.
Should I arrive the night before?
Two nights before, if you can. Flights from the mainland can run late and a San Juan ship will not wait, but the real reason is Old San Juan itself: the blue cobblestones, the two forts, the rooftop bars and a proper mofongo dinner. Hotels inside the old city are a five-minute walk from the Old San Juan piers; Condado and Isla Verde are 10 to 15 minutes from either pier and on the beach. We add the nights to your booking.
Are taxes and fees included in the prices here?
Yes. Every price on this page includes cruise fare, taxes, fees and port expenses, per person, double occupancy. Gratuities, drinks packages and excursions are extra on the big ships; Seabourn fares include drinks and gratuities.
Why sail from San Juan instead of Florida?
Distance. From Miami the Southern Caribbean is two sea days away each direction, so a 7 night cruise sees three or four islands. From San Juan the same week sees six, and the islands are the deep-south ones: St. Lucia’s Pitons, Barbados, Antigua, Grenada, the ABCs. If you would rather be ashore than at the pool, this is the port.
Talk to a San Juan cruise specialist
Tell us your dates and who is coming, and we price every line sailing from San Juan side by side with the fares you qualify for, hotel nights included. Monday to Thursday 9 to 6, Friday 9 to 5, Saturday 10 to 6 ET.