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Awesome sailboat rentals in Costa Rica.

4.9(Average of 2,796 reviews in this area)
View our Costa Rica sailing boating guide
25 - 48 of 240 listings
"Marlin del Rey" 66ft Catamaran Sailing in Playa Tamarindo
Sailing in Tamarindo · 70 guests

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

5.0
$75person
Enjoy Sailing On 80ft Schooner In Tamarindo, Costa Rica
Sailing in Tamarindo · 40 guests

Enjoy Sailing On 80ft Schooner In Tamarindo, Costa Rica

New
$85person
Luxury Fountaine Pajot 61 feet in Tamarindo
Adventures in Tamarindo · 20 guests

Luxury Fountaine Pajot 61 feet in Tamarindo

New
$1,400day
PlayTide Charters Sailing Catamaran en Tamarindo, Costa Rica
Sailing in Tamarindo · 22 guests

PlayTide Charters Sailing Catamaran en Tamarindo, Costa Rica

5.0
$100person
Monohull Charter in San Juan del Sur, Nicaragua
Sailing in Lake Nicaragua · 8 guests

Monohull Charter in San Juan del Sur, Nicaragua

New
$40person
34' Gemini Catamaran Cruising Catamaran Charter in El Gigante, Nicaragua
Sailing in El Gigante · 15 guests

34' Gemini Catamaran Cruising Catamaran Charter in El Gigante, Nicaragua

New
$950person
Captained Charter on 47ft
Sailing in Coclé Province · 8 guests

Captained Charter on 47ft

5.0
$2,000person
Crewed Sailing Charter on 50' Eole Sailboat in San Blas Islands, Panama
Sailing in Coclé Province · 6 guests

Crewed Sailing Charter on 50' Eole Sailboat in San Blas Islands, Panama

New
$180person
Catamaran Sailing Tours, Sunset Cruises & Yacht Charters in Buenaventura / Rio Hato / Panama
Sailing in Rio Hato · 10 guests

Catamaran Sailing Tours, Sunset Cruises & Yacht Charters in Buenaventura / Rio Hato / Panama

New
$95person
Beneteau 50 Sailing Yacht Charter in San Blas Islands
Colón · 10 guests

Beneteau 50 Sailing Yacht Charter in San Blas Islands

New
$1,400day
Beach Catamaran and Windsurf Rental in Playa Blanca Beach
Sailing in Rio Hato · 1 guest

Beach Catamaran and Windsurf Rental in Playa Blanca Beach

New
$45hour
Custom Sailboat for Charter in San Carlos Panama
Panamá Oeste · 10 guests

Custom Sailboat for Charter in San Carlos Panama

New
$950day
Sun Odyssey 52' Sailboat for Charter in Provincia de Colón
Sailing in Puerto Lindo · 8 guests

Sun Odyssey 52' Sailboat for Charter in Provincia de Colón

New
$220day
Charter on 44ft Feeling 446 Sailing Yacht In Panama, Panama
Sailing in Panamá Oeste · 6 guests

Charter on 44ft Feeling 446 Sailing Yacht In Panama, Panama

New
$900day
Charter on 46ft "Nikita" Bahia 46 Catamaran Boat In Panama, Panama
Sailing in Panamá Oeste · 8 guests

Charter on 46ft "Nikita" Bahia 46 Catamaran Boat In Panama, Panama

New
$1,720day
Charter on 40ft Cruising Catamaran Boat In Panama, Panama
Sailing in Panamá Oeste · 7 guests

Charter on 40ft Cruising Catamaran Boat In Panama, Panama

New
$1,725day
Charter on 50ft "Lagoon 500" Sailing Catamaran Boat In Panama, Panama
Sailing in Panamá Oeste · 8 guests

Charter on 50ft "Lagoon 500" Sailing Catamaran Boat In Panama, Panama

New
$2,500day
Charter 78' Cruising Catamaran In Panama, Panama
Sailing in Panama City · 4 guests

Charter 78' Cruising Catamaran In Panama, Panama

New
$1,300day
56' Beach Catamaran Charter in Panama, Panama
Sailing in Panama City · 15 guests

56' Beach Catamaran Charter in Panama, Panama

New
$2,500day
Cruising Catamaran 56' SANBLASCAT,  Panama City, Republik of PanamaLAS PERLAS, TABOGA DAY TRIPS
Fishing in Panama City · 14 guests

Cruising Catamaran 56' SANBLASCAT, Panama City, Republik of PanamaLAS PERLAS, TABOGA DAY TRIPS

5.0
$140day
Large 80' Catamaran Boat at the Panama Bay, Panama
Sailing in Panama City · 36 guests

Large 80' Catamaran Boat at the Panama Bay, Panama

New
$2,900day
44' Lagoon Catamaran with 3 cabins for rent in Panama
Sailing in Panama City · 20 guests

44' Lagoon Catamaran with 3 cabins for rent in Panama

New
$1,950day
Boat Tours in Panamá
Sailing in Panama City · 70 guests

Boat Tours in Panamá

1.0
$125day
Book the Lycka Classic Sailing Yacht in San Blas, Panamá
Sailing in Tocumen · 3 guests

Book the Lycka Classic Sailing Yacht in San Blas, Panamá

New
$190night

Sailing Reviews in Costa Rica

  1. CI
    Che
    PlayTide Charters Sailing Catamaran en Tamarindo, Costa Rica

    This was an amazing experience. Though the boat is not a luxury boat, it’s still fit me, and seven of my friends very comfortably. The drinks were flowing, the snacks we’re good, and the views were unmatched. I would definitely recommend it!

  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. CS
    Clifford
    PlayTide Charters Sailing Catamaran en Tamarindo, Costa Rica

    Massillon was great to help us book our awesome day. And Captain Jonathan and Toncho were amazing for our trip. They took us on a beautiful ride, had drinks and food the whole time and were so nice to me, my wife and my children. We will cherish those memories for a very long time. I highly recommend this for anyone who wants a private charter for the day for their family. Thank you Massimo, Jonathan, and Toncho!

  4. KA
    Kelli
    PlayTide Charters Sailing Catamaran en Tamarindo, Costa Rica

    BOOK THIS BOAT AND TEAM! By far the best excursion we have done in CR. We come every summer. The food was amazing, the drinks were cold and the crew was the absolute BEST! We had a BLAST and plan to book this every summer.

  5. Kelsey
    Kelsey
    PlayTide Charters Sailing Catamaran en Tamarindo, Costa Rica

    We had such an amazing time! Best hospitality we could have asked for. The boat was clean and well kept. The food was delicious. My friends and I had the best time. Would surely book again in the future!!

  6. AM
    Alexa
    PlayTide Charters Sailing Catamaran en Tamarindo, Costa Rica

    it was amazing, the experience, the crew, the food, the service--all amazing!

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 240 listings for Sailing experiences in Costa Rica with 2,796 reviews.

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