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Sailing in Costa Rica!

March 23rd - 30th, 2024

Sailing across the crystal-clear waters of the Pacific Ocean, the warm Costa Rican sun, and a gentle breeze carrying you to new horizons. Our expedition offers the chance to learn the art of sailing, gain leadership skills, immerse yourself in Costa Rican culture, unplug and have fun. Whether you're a complete novice or have some experience, all are welcome. 

Trip Overview

For the sailing portion of the trip (less than 1/3), we will be partnering with "Costa Rica Sailing Center who will provide the instruction, safety equipment and the boats. Participants will be given expert training on how to sail on a variety of different boats.


For the remaining portion of the trip (afternoon and evenings), we will then take expeditions throughout the week which could include; fishing, snorkeling, hiking, paddle-boarding & other beach activities. On these expeditions, participants can expect to; witness the ever beautiful Pacific Ocean, unplug from their hectic schedules, immerse themselves in a different culture and enjoy all that Costa Rica has to offer. 

After a long day on the water, participants will settle into a shared Airbnb and have time and space to reflect on the challenges and successes of their day with their fellow sailors while taking in the sights and sounds of the beach & forest. 


March 23rd - 30th

Group Size

6-8 Campers

2+ Guides


13 - 18

No experience necessary 


Do you have questions about this trip or want more information? Let us know!

Adirondacks Itineray

Expedition Itinerary

Day 1

Participants will meet their guides at a pre-determined US airport or Juan Santamaria Airport (SJO) in Costa Rica. The group will then travel by van for ~4 hours to our Apartment in Potrero. We'll set up and celebrate the start of our trip with a welcome ceremony. 

Days 2-5

We will attend sail school each morning from 9:00am to 1:00pm where participants will learn the art of sailing on the Pacific Ocean. In keeping with our choice-based learning and leadership philosophy, participants will then collectively plan the rest of the day-to-day itinerary. Together as a group, we'll choose which activities we try, creating a one-of-a-kind experience that reflects the unique interests and personalities of our group. Such as; fishing, paddle-boarding, snorkeling, hiking or just taking a needed break on the beach.

Day 6

This day will be saved for a possible culminating sailing experience.

Day 7

On the final day of our trip, we'll pack up our gear, say our goodbyes, and head back to the airport.

Trip Highlights

Here's what you can look forward to on your Costa Rican expedition:

  • Sailing Instruction

  • Leadership development

  • Learning another culture and trying a different language

  • Warm temperatures (High: 80, Low: 70)

  • Gusty conditions (Excellent)

  • Other exciting local expeditions, snorkeling, hiking, etc.


This is Gerald, Camp Lookout's sailing instructor in 2023. He works at the sailing center and is excited to have a few former campers down to see his hometown.

Registration is OPEN

Enrollment for our 2024 Costa Rica Sailing expedition is open!

Click the "ENROLL" button below to complete your registration form.


Flights and getting there

There are several options for traveling to Costa Rica for this trip, please reach out to chat about what's best for your participant. We envision a mixture of meeting campers at DTW, or at a stop-over airport so we can all travel the final leg into Costa Rica together. As of early October, expect flights to cost around $800.

Upon arrival, we plan on renting a van as the small beach community we'll be staying in is about 4 hours from the airport.

We  plan on arriving back home on Saturday evening, allowing a day to get ready for school on Monday.

Questions about this trip?

Fill out the form below and we'll be in touch ASAP to answer your questions.

Thank you!

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About Costa Rica Sailing Center

We hired a legendary sailing instructor from Costa Rica who recommended his sailing center to us.

Each class consists of specialized instruction with a maximum of 7 kids per instructor. Classes are taught mostly in English, but Spanish is also spoken.

Sailing will be taught by instructors who have proven their ability and expertise in the specialized area. The entire staff is trained in First Aid, CPR, Water Rescue, making sure that learning is safe and fun. Sailing is taught to CANSail International Standards.

Water Safety is stressed in all classes. Basic Swimming skills as well as feeling comfortable in the water are a must. All participants will be given a swimming assessment the first day of camp. This will involve swimming 50 yards, treading water for 1+ min as well as fully submerging underwater.

Learn more here

More Trips to Consider

Check out our lineup of upcoming trips and expeditions to find the one that's right for you!  

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