Serendipity Charters
Playa Flamingo · Sailing tour
Serendipity Charters runs private and small-group sails on a 50-foot Beneteau Oceanis out of Flamingo Marina in Guanacaste. It suits couples…
Since 2013 · Pacific and Caribbean
Sailing in Costa Rica, coast by coast
Two coasts, wild islands and sunset sails. Day trips and catamarans, crewed charters, fishing boats, marinas and the ships that call here, each with the place it really boards, checked against the operator's own website before it goes up.
Find a sailing tourRead the sailing guide
34 operators and marinas · last checked October 2026
A sailing catamaran at anchor off Playas del Coco, Guanacaste · Photo: A sailing catamaran at anchor off Playas del Coco, Guanacaste by Elcocobeach, CC BY-SA 3.0, via Wikimedia Commons
Step 1
What kind of day on the water?
- Sailing toursDay sails, sunset catamarans and snorkel trips along Costa Rica's coasts, with the real boarding point for…15 listings
- Yacht chartersPrivate crewed boats for a day or longer, from Guanacaste's bays to Quepos and Golfo Dulce, and what to ask…4 listings
- SportfishingFishing charters, marinas and lodges for billfish, tuna, dorado and roosterfish, from Papagayo and Los Sueños…11 listings
- MarinasCosta Rica's marinas, from Papagayo and Los Sueños to Quepos and Golfito: where to berth, refuel, clear in…9 listings
- Cruises and liveaboardsCruise lines, sailing ships and Cocos Island dive liveaboards that call at Costa Rica, and how to tell a port…7 listings
- Water sportsSnorkeling, scuba, surfing, kayaking and paddleboarding in Costa Rica: where to go, when, and how to stay…20 listings
Step 2
Choose your coast
Most sailing happens on the Pacific side, where the bays are sheltered and the marinas are. The Caribbean is a coast of reefs, rainforest canals and river launches instead. Wherever you go, check where the boat really boards: a "Tamarindo" cruise may leave from Flamingo, and a "Jacó" boat from Herradura.
- 01GuanacasteThe dry northwest: Flamingo, Potrero, Playas del Coco and the Gulf of Papagayo, Tamarindo and Sámara, with steady winds from…Blue Dolphin Sailing, Hotel Giada, Kuna Vela Sailing Tours and more
- 02Central PacificJacó, Herradura and Los Sueños, Puntarenas and the Gulf of Nicoya, Quepos and Manuel Antonio, where the rainforest runs down to…Adventure Tours Costa Rica, AdventureSmith Explorations, Iguana Tours and more
- 03Southern PacificUvita, Sierpe and Drake Bay, Puerto Jiménez and the calm, rainforest-ringed waters of Golfo Dulce around Golfito.AdventureSmith Explorations, Banana Bay Marina, Crocodile Bay Resort and Marina and more
- 04CaribbeanPuerto Limón's cruise port, Cahuita's reef, Tortuguero's canals and the boat and border route to Bocas del Toro.Caribe Shuttle, Princess Cruises
- 05Cocos IslandThe remote national park about 550 km offshore.Aggressor Adventures (Okeanos Aggressor II and Cocos Island Aggressor), Undersea Hunter
Step 3
Pick your boat
Adventure Tours Costa Rica
Jacó · Catamaran tour
Adventure Tours Costa Rica is a Jacó-based tour company whose water trips are a full-day catamaran run to Tortuga Island and private sportfishing…
Marina Bahía Golfito
Golfito · Marina
Marina Bahía Golfito is a full-service marina in Golfito on the Golfo Dulce, taking boats from 40 feet up to large superyachts, with high-speed fuel…
JacoVIP
Jacó · Yacht charter
JacoVIP is a concierge and vacation rental company in Jacó that arranges private party boat charters, fishing trips and Tortuga Island catamaran days…
Puerto Azul Hotel y Club Náutico
Puntarenas · Marina
Puerto Azul is a hotel with an attached marina in El Cocal, on the Puntarenas side of the Gulf of Nicoya. It suits cruisers with boats up to about 60…
Crocodile Bay Resort and Marina
Puerto Jiménez · Sportfishing
Crocodile Bay is a long-running sportfishing operation and marina at Puerto Jiménez on the Osa Peninsula, where Golfo Dulce meets the open Pacific.…
Before you book
4 things to check first
- 01Where the boat really boardsTours are sold in one town and board in another. Our pages name the actual dock, marina or beach, separately from where pickup is offered.
- 02Sail or motor?Some catamarans sail; others are motor cruise boats. If sailing matters to you, ask how much of the trip is usually under sail.
- 03When to goGuanacaste is driest from about December to April, with spells of strong Papagayo wind. Green season brings rain, a greener coast and often calm mornings.
- 04PricesFares change with the season, the boat and private versus shared trips, so we don't print them. Each listing links to the operator's own booking page.
Before you cast off
Guides
- 01Kayaking in Costa Rica: sea, mangrove and river trips for every levelCosta Rica has calm mangrove channels, sheltered gulfs, lakes and whitewater rivers, so there's kayaking for nearly every level.
- 02Sailboat types explained: a beginner's guide before you sail in Costa RicaMost sailboats you'll step aboard in Costa Rica are either catamarans (two hulls, stable and roomy) or monohull sloops (one hull, one mast, more of a…
- 03Scuba diving in Costa Rica: where to dive, when, and how to get certifiedCosta Rica is a big-animal dive destination rather than a calm coral one: think rays, sharks, turtles and schooling fish around Pacific islands and…
- 04Snorkeling in Costa Rica: where to go, when, and how to do it wellCosta Rica's best snorkeling is around offshore islands and protected reefs: Caño Island off the Osa Peninsula, Cahuita's coral reef on the…
- 05Sportfishing in Costa Rica: seasons, species, licenses and billfish rulesCosta Rica is best known for Pacific sailfish and marlin, with roosterfish, snapper, tuna and mahi-mahi closer in, and tarpon and snook on the…
- 06Surfing in Costa Rica: a beginner-friendly guide to breaks, seasons and safetyCosta Rica has surf all year: the Pacific gets its biggest, most consistent south swells from about May to November, and the Caribbean comes alive…
- 07Sailing in Costa Rica: where to go, when to sail and what to expectCosta Rica's sailing happens almost entirely on the Pacific coast, from the Gulf of Papagayo and Flamingo in Guanacaste down to the Gulf of Nicoya…
- 08Stand-up paddleboarding (SUP) in Costa Rica: calm bays, rivers and how to startStand-up paddleboarding is one of the easiest water sports to pick up in Costa Rica, as long as you choose sheltered water and go early before the…
Good to know
Frequently asked questions
Are Costa Rica catamarans really sailing boats?
Some are true sailing catamarans and some are motor cruise boats, and even a boat with sails may motor when the wind or the route calls for it. Read the boat description and ask the operator whether sailing is a normal part of the trip.
Where do most sailing trips leave from?
Playa Flamingo, Playa Potrero, Playas del Coco and Marina Pez Vela in Quepos are the main starting points. There are more departures around the Gulf of Nicoya and Golfo Dulce, but not every beach has its own dock.
Can I book a private boat instead of joining a group?
Yes. Private sailboats, catamarans, fishing boats and yachts run in several Pacific regions. Group minimums, passenger limits, what's included and boarding points vary, so see our yacht charters section.
Will I see dolphins or whales?
Nobody can promise that. Good operators look for wildlife without guaranteeing it, and sightings depend on the season, the place, the weather and luck.
Is the Caribbean coast good for sailing?
There's less tourist sailing than on the Pacific. On the Caribbean, reef snorkeling, Tortuguero's canals and river launches are the better fit.
Every operator, charter and marina here is checked against its own website and recent listings before we publish it. No paid rankings.