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Awesome sailboat rentals in Costa Rica.

4.8(Average of 42 reviews in this area)
View our Costa Rica sailing boating guide
1 - 24 of 26 listings
Private Sailing Tours onSailing in Playa Flamingo20 guests

Private Sailing Tours on

5.0
Superowner
$165person
Sailing Tours and Sightseeing in playa Potrero Guanacaste Province, Costa RicaSailing in Potrero12 guests

Sailing Tours and Sightseeing in playa Potrero Guanacaste Province, Costa Rica

5.0
$90person
PlayTide Charters Sailing Catamaran en Tamarindo, Costa RicaSailing in Tamarindo22 guests

PlayTide Charters Sailing Catamaran en Tamarindo, Costa Rica

5.0
$100person
46ft Bahia Cruising Catamaran Rental In Potrero, Costa RicaSailing in Playa Flamingo35 guests

46ft Bahia Cruising Catamaran Rental In Potrero, Costa Rica

5.0
$250hour
"Marlin del Rey" 66ft Catamaran Sailing in Playa TamarindoSailing in Tamarindo70 guests

"Marlin del Rey" 66ft Catamaran Sailing in Playa Tamarindo

5.0
$75person
65ft Sailing Catamaran in Playa del CocoSailing in Coco70 guests

65ft Sailing Catamaran in Playa del Coco

5.0
$75person
Pacific Soul Sailing Luxury Catamaran - Private CharterSailing in Potrero44 guests

Pacific Soul Sailing Luxury Catamaran - Private Charter

5.0
$120person
65ft Sailing Catamaran in Playa FlamingoSailing in Playa Flamingo70 guests

65ft Sailing Catamaran in Playa Flamingo

New
$75person
Charter 46ft Cruising Catamaran In Playa Flamingo, Costa RicaSailing in Playa Flamingo45 guests

Charter 46ft Cruising Catamaran In Playa Flamingo, Costa Rica

5.0
$425hour
Shared Catamaran Eco Adventure in Manuel Antonio, Costa RicaSailing in Quepos120 guests

Shared Catamaran Eco Adventure in Manuel Antonio, Costa Rica

5.0
$80person
Sailing Trimaran Yacht in Papagayo gulf!! Hammerhead 54Sailing in Culebra16 guests

Sailing Trimaran Yacht in Papagayo gulf!! Hammerhead 54

5.0
$120person
FOR SALE! Luxury ''Tom Cat II'' Cruising Catamaran in Costa RicaSailing in Quepos110 guests

FOR SALE! Luxury ''Tom Cat II'' Cruising Catamaran in Costa Rica

New
$80person
Manuel Antonio Catamaran Private ''Spanish Dancer''Sailing in Quepos12 guests

Manuel Antonio Catamaran Private ''Spanish Dancer''

New
$125person
Charter 37' Cruising Monohull in Bocas del Toro, PanamaSailing in El Empalme5 guests

Charter 37' Cruising Monohull in Bocas del Toro, Panama

5.0
$100person
Rent 9' Popeye Dinghy in El Empalme, PanamaPowerboats in El Empalme2 guests

Rent 9' Popeye Dinghy in El Empalme, Panama

New
$40day
Rent Naylamp Trimaran in El Empalme, PanamaSailing in El Empalme10 guests

Rent Naylamp Trimaran in El Empalme, Panama

New
$500day
Rent 24' Cruising Monohull in El Empalme, PanamaSailing in El Empalme4 guests

Rent 24' Cruising Monohull in El Empalme, Panama

3.0
$140day
Charter a Beach Catamaran in Herradura, Costa RicaSailing in Herradura12 guests

Charter a Beach Catamaran in Herradura, Costa Rica

New
$850day
Private Sunset Catamaran Cruise - Playa Flamingo, Costa Rica.Sailing in Playa Flamingo30 guests

Private Sunset Catamaran Cruise - Playa Flamingo, Costa Rica.

New
$3,000day
Morning Ocean Catamaran Experience in Playa Flamingo, Costa RicaSailing in Playa Flamingo30 guests

Morning Ocean Catamaran Experience in Playa Flamingo, Costa Rica

New
$2,700day
30' Mako Boat for Inshore/Offshore Fishing and Dolphin/Whale Watching ToursFishing in Agujitas de Drake5 guests

30' Mako Boat for Inshore/Offshore Fishing and Dolphin/Whale Watching Tours

New
$100hour
41' Gulf Star Monohull Sailing Adventures with Five Star Service and Dinning in GuanacasteSailing in Playa Hermosa12 guests

41' Gulf Star Monohull Sailing Adventures with Five Star Service and Dinning in Guanacaste

New
$100person
Custom Gulet 100' wooden sail ship in Quepos/Manuel AntonioSailing in Quepos46 guests

Custom Gulet 100' wooden sail ship in Quepos/Manuel Antonio

New
$125person
Enjoy Sailing On 80ft Schooner In Tamarindo, Costa RicaSailing in Tamarindo40 guests

Enjoy Sailing On 80ft Schooner In Tamarindo, Costa Rica

New
$85person

Sailing Reviews in Costa Rica

  1. Catina
    Catina
    46ft Bahia Cruising Catamaran Rental In Potrero, Costa Rica

    This is hands down the crew you want to book with. Great communication, amazing food, they took care of every need we could ever want, they kept drinks in our hands, and we simply put had such an amazing experience.

  2. LG
    Leandra
    PlayTide Charters Sailing Catamaran en Tamarindo, Costa Rica

    We had a great time celebrating my Birthday. The crew was very attentive, and had excellent customer service. They made sure we were taken care of. They provided drinks, snacks, and a nice lunch. Thank you. Just be aware that you do have to take a small boat from shore to get the yacht, which was a little challenging.

  3. NB
    Nikki
    Private Sailing Tours on

    The staff, the ship, the views, the food, the music…everything was awesome and was definitely the highlight of our trip to Costa Rica. Our kids even got to hold an octopus and a starfish while snorkeling! We did the full day private charter and I highly recommend it!

  4. MD
    Marina
    Sailing Tours and Sightseeing in playa Potrero Guanacaste Province, Costa Rica

    Our sailing trip was fantastic. We were a tough crew with five (cranky) kids, but Captain Jack and his crew were super patient, understanding and provided the best experience for us. We ate delicious food, swam in beautiful waters and sailed through the sunset. Thank you!

  5. jb
    jose
    46ft Bahia Cruising Catamaran Rental In Potrero, Costa Rica

    Absolutely the best day in Costa Rica, the crew was amazing, service spectacular and drinks totally available and limitless!!! 100% recommend this boat and crew!

  6. HW
    Holly
    Sailing Tours and Sightseeing in playa Potrero Guanacaste Province, Costa Rica

    When I asked my teenagers how they liked the trip, my oldest said "It was Magical, like something out of a movie"--I have to agree. The crew made it very special and everyone was so kind and friendly. The lunch they served was prepared by Jack's wife and it was so delicious-seriously one of our favorite meals in Costa Rica. Sailing back with music and the setting sun was absolutely fabulous. It's one of the highlights of our trip. My kids still talk about it. Highly recommend!

Boating Guide - Costa Rica Sailing

Set sail and experience Costa Rica from the deck of a sailboat rental.

Costa Rica is the best place to rent a sailboat. Book a sailboat with a captain if you've never sailed before. Get out on the water and experience the beautiful scenery while enjoying the company of friends and family. From celebrating a special occasion to family vacations, Costa Rica is the perfect sailboat rental destination.

Using GetMyBoat to rent your next sailboat.

Experiencing the water has never been easier thanks to GetMyBoat. GetMyBoat allows you to quickly search, compare prices, submit rental inquiries, and pay for your rental or charter from the convenience of your phone or computer. We offer a secure platform for renters to facilitate a seamless rental transaction. For boat owners, we connect millions of renters to their boat and provide the security and safe checks on each rental transaction.

Search for the perfect experience now and book your dream day out on the water.

GetMyBoat has 26 listings for Sailing experiences in Costa Rica with 42 reviews.

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