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All listings in Costa Rica

Awesome sailboat rentals in Costa Rica.

5.0
(80 Reviews)

Page 1 of 124 listings

Why Not Oceanic Experience- Luxury Fountaine Pajot 61 feet in Flamingo
Sailing in Tamarindo · 20 guests

Why Not Oceanic Experience- Luxury Fountaine Pajot 61 feet in Flamingo

5.0
$2,000/day
Full Day Sailing Potrero Guanacaste Province, Costa Rica
Sailing in Potrero · 12 guests

Full Day Sailing Potrero Guanacaste Province, Costa Rica

5.0
Best of 2025
$950/day
Foilborne Power Catamaran 40´Party Boat For Your Next Adventure!
Sailing in Herradura · 35 guests

Foilborne Power Catamaran 40´Party Boat For Your Next Adventure!

5.0
$500/hour
Charter 40ft Catamaran In Playa Flamingo, Costa Rica
Sailing in Playa Flamingo · 30 guests

Charter 40ft Catamaran In Playa Flamingo, Costa Rica

New
$475/hour
46ft Bahia Cruising Catamaran Rental In Potrero, Costa Rica
Sailing in Playa Flamingo · 40 guests

46ft Bahia Cruising Catamaran Rental In Potrero, Costa Rica

5.0
$275+/hour
Instant Book
Private Catamaran Tour and Snorkeling all-Inclusive, Tamarindo, Costa Rica
Sailing in Tamarindo · 22 guests

Private Catamaran Tour and Snorkeling all-Inclusive, Tamarindo, Costa Rica

5.0
$300/hour
Pacific Soul Sailing - Luxury Lagoon Private Catamaran
Sailing in Culebra · 50 guests

Pacific Soul Sailing - Luxury Lagoon Private Catamaran

5.0
$525/hour
Instant Book
Private Sailing Tours in Playa Flamingo, Guanacaste
Sailing in Playa Flamingo · 17 guests

Private Sailing Tours in Playa Flamingo, Guanacaste

5.0
Superowner
$186+/hour
Private Sailing Tour Flamingo, Guanacaste - Unforgettable Ocean Adventure
Sailing in Potrero · 12 guests

Private Sailing Tour Flamingo, Guanacaste - Unforgettable Ocean Adventure

New
Best of 2025
$650/day
65ft Sailing Catamaran in Playa del Coco
Sailing in Coco · 70 guests

65ft Sailing Catamaran in Playa del Coco

5.0
$532/hour
Manuel Antonio Catamaran Private ''Spanish Dancer''
Sailing in Quepos · 12 guests

Manuel Antonio Catamaran Private ''Spanish Dancer''

5.0
$1,500/hour
"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
$532/hour
Experience the Gulf Star 41' Sailing and Dining in Guanacaste
Sailing in Guanacaste Province · 12 guests

Experience the Gulf Star 41' Sailing and Dining in Guanacaste

5.0
$200/hour
Instant Book
Charter 45ft Cruising Catamaran In Playa Flamingo, Costa Rica
Sailing in Playa Flamingo · 45 guests

Charter 45ft Cruising Catamaran In Playa Flamingo, Costa Rica

5.0
$712/hour
Sail into adventure in Costa Rica, playa Flamingo
Sailing in Playa Flamingo · 12 guests

Sail into adventure in Costa Rica, playa Flamingo

New
$2,640/hour
50' Beneteau Sailboat All-Inclusive Charter
Sailing in Playa Flamingo · 20 guests

50' Beneteau Sailboat All-Inclusive Charter

New
$315/hour
Catamaran lagoon 42ft Luxury In Costa Rica
Sailing in Guanacaste Province · 25 guests

Catamaran lagoon 42ft Luxury In Costa Rica

New
$700/hour
Luxury ''Tom Cat II'' Cruising Catamaran in Flamingo, Costa Rica
Sailing in Quepos · 90 guests

Luxury ''Tom Cat II'' Cruising Catamaran in Flamingo, Costa Rica

New
$99/day
65ft Sailing Catamaran in Playa Flamingo
Sailing in Playa Flamingo · 70 guests

65ft Sailing Catamaran in Playa Flamingo

New
$532/hour
Catamaran Located in Jaco/Herradura
Sailing in Herradura · 12 guests

Catamaran Located in Jaco/Herradura

New
$425/hour
Captained Helia 44ft Sailing Catamaran in Culebra
Sailing in Culebra · 8 guests

Captained Helia 44ft Sailing Catamaran in Culebra

New
$720+/hour
Trimaran Charter in Herradura
Sailing in Herradura · 6 guests

Trimaran Charter in Herradura

New
$109+/hour
SAILING THE GULF OF NICOYA ON A LUXURY 37" YACHT
Sailing in Punta Arenas · 4 guests

SAILING THE GULF OF NICOYA ON A LUXURY 37" YACHT

New
$150/hour
30' Mako Boat for Inshore/Offshore Fishing and Dolphin/Whale Watching Tours
Fishing in Agujitas de Drake · 5 guests

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

New
$90+/hour

Sailing Reviews in Costa Rica

  1. Lauren

    Lauren

    Private Catamaran Tour and Snorkeling all-Inclusive, Tamarindo, Costa Rica

    Incredible trip! The weather was a bit windy and choppy on the way out but improved as time went on. Food was delicious and the crew were so helpful and friendly. I was sad I wasn’t able to snorkel but the weather did not permit. Overall incredible trip and would book again!

  2. Michael

    Michael

    Why Not Oceanic Experience- Luxury Fountaine Pajot 61 feet in Flamingo

    The tour was great. The crew members were hospitable and personable, and the Chef was excellent. She was able to create delicious dishes catering to everyones dietary needs and preferences. We were provided with good informstion about the area as we cruised. We were given plenty of time for water activites, relaxing, and whatever else the party felt like doing. The condition of the yacht was excellent, indicating the crew takes great care of the vessel. It was very clean and comfortable.

  3. DL

    Daniella

    Why Not Oceanic Experience- Luxury Fountaine Pajot 61 feet in Flamingo

    A wonderful boat! Unfortunately, the day we did our sunset cruise, we were caught in rain for the first half of the time. However, the team did all the could to help make it a wonderful experience. The second half of our time on the boat was met with some clear skies and so many dolphins! Our dolphin sighting really made the trip, it was so peaceful watching them pass by our boat. Thereafter, we were lucky enough to still catch a sunset! Would definitely like to ride with this team again when we're back in costa rica!

  4. SM

    Starr

    Why Not Oceanic Experience- Luxury Fountaine Pajot 61 feet in Flamingo

    This catamaran and team was absolutely AMAZING! 10/10 recommend. There were 9 of us girls on this catamaran for my birthday. The food was amazing and they kept the drinks coming. I am recommending to all of my friends and on TikTok! Worth every dollar!!!

  5. Harrison

    Harrison

    Why Not Oceanic Experience- Luxury Fountaine Pajot 61 feet in Flamingo

    What an incredible day! From start to finish, this was everything we were hoping for. The crew was fun and professional. The boat was clean and spacious. The gods and drinks were delicious and abundant! This was a day for the books and highly recommend booing this boat if you are a fan of good times 🤙

  6. MD

    Micah

    Why Not Oceanic Experience- Luxury Fountaine Pajot 61 feet in Flamingo

    The crew is amazing! Very attentive and welcoming. The boat had ample room for the 20 of us. The kids enjoyed the netting you could lay on at the front of the boat. The crew went above and beyond to help with the elderly members of our party. The food is so delicious! Overall, a very relaxing and beautiful experience! 10/10