Playa Flamingo · Sailing tour
Serendipity Charters
Private sails on a 50-foot Beneteau from Flamingo
By Monirul Hoque on , updated on
Serendipity Charters is a family-run sailing company at Flamingo Marina in Guanacaste that takes guests out on Serendipity, a 50-foot Beneteau Oceanis monohull. It runs private morning, sunset, full-day and overnight charters plus a shared small-group sail called Lucky 13, and it suits people who want a real sailing yacht rather than a big party boat.
A proper sailing yacht out of Flamingo
Serendipity Charters is a family-owned sailing company that's been taking guests out of Playa Flamingo since 2012. Everything happens on one boat: Serendipity, a 50-foot Beneteau Oceanis. That's a single-hulled cruising yacht with a keel, a deep cockpit and cabins below, built to travel under sail. If your idea of a day on the water includes the engine going quiet and the boat leaning a little into the breeze, this is the kind of trip to look at.
Most outings are private: you book the yacht for your group and the crew plans the day around you. There's also a shared sail for people who don't want to charter the whole boat. You can read an older overview of the company on Costa Rica Journeys, and the current schedule lives on the official website.
Monohull or catamaran?
A monohull behaves differently from the broad, flat tourist catamarans that also sail from Flamingo. It heels when the wind fills the sails, the deck feels more intimate, and you're closer to the work of sailing. Some guests love that sense of movement. Others prefer the space and steadier ride of a big cat. Neither is better; it depends on the day you want.
The crew decides when wind and safety allow the sails to do the work, so some stretches may be under engine. That's normal seamanship. If sailing is the main point for you, talk about likely conditions when you book. Guanacaste's Papagayo winds can be perfect one day and too strong the next.
The trips
- Private morning charter: roughly 8:30 to 12:30, with a freshly made lunch on board. Mornings often bring calmer water, which helps if anyone in your group is new to boats, and you still get the afternoon for something else.
- Private sunset charter: leaves around 1:30 and comes back after the sun goes down, usually with a swim stop earlier in the outing.
- Private full-day charter: from about 11:00 until sunset, with time for more than one anchorage and a slower pace.
- Lucky 13 shared charter: an afternoon-to-sunset sail for a mixed group of up to 13 guests. It's seasonal and runs on set days, so check the calendar before you plan around it.
- Overnight trips: sails that stay out after the day boats have gone home, using the galley and cabins.
- Surf trips: the company also uses the boat to reach surf breaks along the coast.
Private charters include the crew and an open bar, and snorkeling stops are part of most outings. The captain picks anchorages on the day based on wind, swell and tide, so the beach or cove you visit may not be the one in the photos. That's a good sign: the route follows the real ocean.
Lucky 13: shared, but small
Not everyone needs a private yacht. Lucky 13 caps the group at 13, which makes it a good fit for couples or solo travelers who want a sailing atmosphere without booking the whole boat. It isn't a party cruise, and it doesn't run daily. Minimum numbers and any age rules are on the reservation page.
Overnight sails
Staying aboard after dark is a different trip altogether. Before you book one, ask about the itinerary, sleeping arrangements, bathrooms, meals, weather limits, what luggage to bring, shore access and cancellation terms. Don't assume a particular remote beach or surf spot is part of a given voyage; the crew decides what's possible on the day.
The crew
The company names Brad and Geneva as its owner-operators, with Bismark as head captain and a small team of captains and mates. Crew lists on any website are a snapshot, so if you need a particular language or have a special occasion planned, confirm who'll be aboard when you book.
Snorkeling, swimming and wildlife
In suitable conditions the crew anchors for a swim and provides snorkel gear. You might see reef fish, rays and rocky-bottom life, but visibility changes a lot with rain and swell, and some days it's simply murky. Swimming from a boat isn't the same as wading in from a beach, so ask about the ladder and follow the crew's directions about currents. Don't stand on coral or chase animals.
Dolphins, sea turtles and, in season, humpback whales do turn up in these waters, but no honest operator can promise them. A trip where you only see pelicans is still a lovely day on the coast.
Food and drinks
Private charters come with an open bar, and morning trips include a lunch made on board. If you've got allergies, need vegetarian or gluten-free food, want nonalcoholic drinks or are planning a celebration cake, tell the company in advance and get it confirmed. Don't count on last season's menu.
Where you leave from
Trips start at Flamingo Marina, on the north end of Playa Flamingo, with Potrero Bay and the Flamingo coastline as the home waters. The base suits anyone staying in Flamingo, Potrero, Brasilito or Playa Conchal. The company serves guests staying in Tamarindo too, but the yacht doesn't board on Tamarindo beach, so plan your own ride to the marina. Flamingo is about an hour by road from Liberia's international airport. Leave time to park, find the crew and get your boarding briefing.
Who it suits
This is a good fit if you want a quieter, more personal day than the big catamaran tours offer. Families, couples marking an occasion and groups of friends who want the boat to themselves are the core market, and experienced sailors will enjoy a monohull that actually sails. If your group is large, ask first: the private charter booking is set up for up to 10 guests, with extra guests possible on request.
If you'd rather have a private catamaran with lots of flat deck space, Manta Ray Sailing runs a small fleet from the same marina. For a shared catamaran, see Lazy Lizard Sailing. The Guanacaste section lists the other boats on this coast.
Good to know before you book
- Guanacaste's dry season runs roughly December to April. The company splits its calendar into a high season (mid-November to the end of April) and a green season for the rest of the year.
- Papagayo winds blow strongest from about December to March. That's good sailing but can mean a livelier ride and changed stops.
- Green-season rain doesn't ruin every day, but the captain may adjust the route or postpone. A crew that changes plans for the weather is doing its job.
- Bring reef-safe sunscreen, a hat, a towel, a dry pouch for your phone and soft-soled shoes. A light layer helps on the ride home after sunset.
- If you get seasick, talk to a pharmacist before the trip, not once you're on board, and ask the crew where the boat moves least.
- For current prices, inclusions and availability, check the official reservation page. Confirm taxes, passenger limits, cancellation terms and transport when you book.
Where to stay near the Guanacaste coast
Live prices from Booking.com, Expedia, Hotels.com and more.
Frequently asked questions
Is Serendipity a catamaran?
No. It's a 50-foot Beneteau Oceanis, a single-hull sailing yacht. It heels a bit under sail, which is part of the fun.
Can I join if I'm not booking the whole boat?
Yes, on the Lucky 13 shared sail for up to 13 guests, which runs on set days during high season.
Where do I meet the boat?
At Flamingo Marina in Playa Flamingo. It doesn't board in Tamarindo, and transport to the marina usually isn't included.
Do they do overnight trips?
Yes. The company offers overnight sails along the coast, as well as trips aimed at surfers.
Will we see dolphins or whales?
Possibly, but it's never certain. Dolphins and turtles are seen fairly often, and humpbacks pass through in season.
