Sailboat and Kayak Reservations

Rental Season and Hours

Our sailing season starts in mid-June and goes through Labor Day.  Weather permitting, we hope to extend the sailing season through September, with a limited fleet.

Monday – Friday: 1 PM – 3:30 PM and 4:30 PM – 7 PM

Saturday: 9:30 AM – 12:00 PM and 1 PM – 3:30 PM

Sunday: 1 PM – 3:30 PM

All renters must be able to rig and handle their vessel independently. Our friendly staff are available to direct you towards equipment, transport you to a moored boat, help lift kayaks and small sailboats, and answer questions. We ask that you de-rig your boat and return your equipment by the end of the your rental period, so please plan your excursion accordingly!

Please contact our rental office at or 508-367-7099 if you have any questions.

Beach Fleet: Sunfish & Kayaks

Available for visitors and all Pleasant Bay Pass holders. Sunfish and kayaks can be rented during one of the time slots above on a per-use basis, or by using a Pleasant Bay Pass.

All rentals will be cancelled if sustained winds exceed 15 MPH.

Core Fleet: Flying Scots, Catboats, 420’s & Lasers

Only Pleasant Bay Pass holders that have passed a skills check are able to rent boats from our core fleet. We have a variety of Pass “sizes”, so we encourage you to purchase one online and contact one of our staff to request a skills check:

Flying Scots, 420’s, Lasers: Tom Leach – Waterfront Director –

Catboats: Suzanne Leahy – Catboat Coordinator –

All rentals will be cancelled if sustained winds exceed 15 MPH. To sail a catboat in winds of 10-15 MPH, you must know how to reef!

Check the following weather sources before you come: Willy Weather, Windy, NOAA, PBCB website.

Required Paperwork

Please read our Rules and sign a waiver before your visit! We must collect a new waiver each year. 

For those bringing guests: please have them bring a signed Guest Medical Waiver