Frequently Asked Questions

Our frequently asked questions page will help to guide you through everything you need to know about our program offerings.

As always, feel free to call or email us with any questions you may have. We can be reached via email at or by calling (508) 255-7900.


General Questions

How can I book a lesson, charter, or rental?

You may book a lesson online, using our booking platform, or you may book over the phone at (508) 255-0994.

What happens if the weather doesn’t cooperate on the day of my booking?

Safety is our first priority. This is why we will reschedule lessons, charters and rentals due to weather. We’re always checking weather and will give you as much notice as possible if your booking needs to be rescheduled.

We will sail in light rain, as long as there is wind. We always reschedule lessons for heavy rain, thick fog, thunderstorms and gale watches/warnings. We will also reschedule sailing lessons and charters for lack of wind. Depending on the student’s skill level, we will sail in protected areas, with reefed sails, in small craft advisories.

We will make every effort to work with your schedule to reschedule lessons that have been canceled due to weather. Deposits are returned if lessons cannot be scheduled.

What if I have to cancel my booking?

Call or email us to cancel bookings. We’re happy to work with you to find a time to reschedule. Note, deposits for lessons that are canceled within 48 hours of the lesson cannot be refunded.

Sailing Lessons

I’ve never sailed before, can I jump into a lesson?

Absolutely! We offer lessons to students of all skill levels. Our private lessons are great for first time sailors because we provide the one-on-one, safety minded, instruction needed to make sure you’re comfortable and mastering the basics in no time.

What does a typical lesson look like?

On a typical lesson day, you’ll meet our instructor at our waterfront office 10-15 minutes before your lesson to check in and fill out your waiver. Next, you’ll be fitted for a life jacket and you and your instructor will motor down the Namequoit River to where we moor our boats. You and your instructor will discuss your goals and any previous sailing experience you have, then you’ll have a lesson based on your goals and your skill level.

What type of boats do you teach on?

The majority of our lessons are taught on 14’ Arey’s Pond catboats. They have one sail and are very stable, making them perfect for learning to sail.

We also offer lessons on our 16’ Arey’s Pond catboat for students looking to learn on a larger boat, and we have an 18’ Arey’s Pond Daysailer for students looking to learn to sail with a mainsail and jib sail.

Will Capsizing be part of my lesson?

Our boats are very wide, which makes them very stable and very hard to capsize. We do not capsize our boats as part of our lessons.

What do I need to bring to my lesson?

We have all of the safety equipment you need. We recommend bringing a water bottle, sunscreen, hat, sunglasses, and an extra layer. We also recommend wearing comfortable clothes that you don’t mind getting sea spray on, and closed toed shoes.

How much does a private lesson cost?

A two hour private lesson for one person is $144. Each additional person (up to 3 total) is $24. Each additional hour is $72 for the first person, and $12 for additional people.

Do you offer week-long programs for children?

We no longer offer week-long group programs for children but you may book multiple private lessons for up to 4 children. 

How many people can go on a private lesson?

Our 14’ catboats comfortably hold up for 4 adults. Three adults is the maximum for a private lesson, but this number can vary if children are included. Please call or email us if you have questions.

Are there any age restrictions for students?

Our lessons are for students of all ages. Students under the age of 8 must be accompanied by an adult.

What training do instructors receive?

All of our instructors are skilled sailors who have many hours on the water. They are all certified sailing instructors with training from the US Sailing Association and/or the American Sailing Association and all have first aid training. Additionally, they all have either their Launch License or Captain’s License from the US Coast Guard.


What type of boats can I rent?

Our rental offerings include 14’ Arey’s Pond Catboat, tandem kayak, single kayak and stand up paddle boards.

Do I have to take a lesson before I rent a sailboat?

We do not require customers to take a lesson before renting one of our sailboats, but previous sailing experience is required. We will have a conversation with you about your experience, and may ask you to take a short written assessment of basic sailing knowledge.

What are the costs for rental boats?

14' Catboat
  • $60 - 1 hour
  • $190 - 1/2 Day
Single Kayak
  • $25 - 1 hour
  • $55 - 1/2 Day
Paddle Board
  • $25 - 1 hour
  • $55 - 1/2 Day
Row Boat
  • $10 - 1 hour
  • $40 - 1/2 Day
Tandem Kayak
  • $35 - 1 hour
  • $75 - 1/2 Day

What do I need to bring on my rental?

We have all of the safety equipment you need (life jacket, chart and VHF radio).

We recommend bringing a water bottle, sunscreen, hat, sunglasses, and an extra layer. We recommend wearing comfortable clothes that you don’t mind getting sea spray on, and closed toed shoes. If you’re renting a kayak or paddleboard we recommend wearing water shoes or sandals that can get wet.

Where can I sail/paddle on my rental

Rental sailboats can be sailed all around Little Pleasant Bay. We will provide you with a chart and explain the sailing area.

Kayaks and paddleboards can be paddled in Arey’s Pond and the Namequoit River.