Puerto Caldera · Cruise
Windstar Cruises in Costa Rica
Small ships along the Pacific coast
Windstar runs small-ship cruises that pair a Panama Canal transit with several days on Costa Rica's Pacific coast. The sailing ship Wind Star calls at Golfito, Quepos and Herradura and starts or ends at Puerto Caldera, and the line's all-suite motor yachts add stops such as Isla Tortuga and Playa Flamingo. It suits travelers who want a cruise with real time ashore and a ship small enough to use local anchorages.
What they offer
Windstar is a small-ship cruise line, and it's one of the few that still sends a real sailing ship to Costa Rica. Its winter Central America program links the Panama Canal with the Pacific coast of Costa Rica and Panama, with most days spent at small ports and anchorages rather than at sea.
Older readers may remember the Wind Song, the Windstar ship this site wrote about back in 2013. That ship is no longer in service, but the line's Costa Rica program carries on with its sister ship Wind Star and with the larger all-suite Star-class yachts.
The ships
Wind Star is the one sailors will care about. It's a 4-masted ship with computer-controlled sails, built for Windstar in the 1980s and carrying about 148 guests. It isn't a tall ship in the traditional sense, since the sails are handled from the bridge, but on a good breeze it really does sail, and the small size means you can anchor off places big cruise ships can't reach.
Star Legend and Star Pride are Windstar's all-suite motor yachts, each carrying around 300 guests. They don't sail, but they run Costa Rica itineraries too, and some of their routes reach spots the Wind Star skips, such as Isla Tortuga in the Gulf of Nicoya, Playa Flamingo in Guanacaste and Golfo Dulce near Puerto Jiménez.
Both types of ship have a water-sports platform at the stern, which on calm days opens up for swimming, kayaking and paddleboarding straight from the ship.
The trips
The core Costa Rica route is a 7-night or 8-night sailing between Colón in Panama and Puerto Caldera in Costa Rica, run in both directions. A typical Wind Star schedule for January 2027 looks like this: the Panama Canal transit, Panama City, the island of Isla Gamez in Panama, then Golfito, Quepos and, on some departures, Herradura, before arriving at Puerto Caldera. Longer voyages tack the Costa Rica coast onto a Pacific crossing to Tahiti.
Some sailings are also sold as cruise and land packages that add a few nights inland at places like Arenal or Monteverde.
Where you leave from
In Costa Rica, ships embark and disembark at Puerto Caldera, the Pacific cargo and cruise port just south of Puntarenas. It's roughly a 90-minute drive from the international airport near San José, depending on traffic. If you're sailing from the Panama end, you'll start in Colón on the Caribbean side of the canal.
Who it suits
- Travelers who want a cruise but dislike big crowds and huge ships.
- Couples and older travelers who like a relaxed pace with daily stops.
- Sailors who want to see the coast from the water before planning their own charter.
It's less suited to families wanting kids' clubs or people looking for nightlife onboard. If you want to handle the lines yourself, a private yacht charter is a better match.
Good to know before you book
- The Costa Rica season is short, running roughly December through February, and popular holiday dates fill early.
- Check which ship your sailing uses. If being under sail matters to you, make sure it's the Wind Star and not one of the motor yachts.
- Ports like Golfito and Quepos are small. Expect tenders or short walks rather than big terminals.
- December to April is the dry season on the Pacific coast, so you'll usually get sun. Humpback whales from the Northern Hemisphere pass through these waters from about December to March, so keep an eye out on deck.
Frequently asked questions
Does Windstar still sail in Costa Rica?
Yes. Published schedules show Wind Star sailing between Colón and Puerto Caldera in early 2027, with calls at Golfito, Quepos and Herradura.
Is the Wind Star a real sailing ship?
It has 4 masts and sails that are set and trimmed by computer, and it does sail when the wind allows. It also has engines, which it uses to keep to schedule.
Where does the cruise start in Costa Rica?
At Puerto Caldera, just south of Puntarenas on the Pacific coast.
Can I combine the cruise with time inland?
Yes. Windstar sells some sailings as cruise and land packages with extra nights in places such as Arenal or Monteverde.
