Why Sail With Us

Our goal is for you to experience the best two-hour classic sailing trip in the world. We have been working on this experience in Boothbay Harbor for almost 50 years, have a strong local following, and have been featured in national, best-selling publications.

We have the best sailing vessel for exploring Boothbay Harbor. We use an onboard engine to get us to the sailing grounds quickly. The size of our vessel is perfect for exploring all the areas of our rocky harbor to see life along the Maine coast. There are no obstructions on our deck other than the masts, so you always have a full 360-degree view from every seating position.

Our docks are in the center of Boothbay Harbor's historic waterfront. You are literally steps away from great inns, shops, restaurants, and other activities on the water. We work with and support our waterfront community and will be happy to advise you on all the great experiences around us.

Our long history and focus of providing a great experience has made us the first page of Maine's official guidebook and the first page of the official region guide to the Boothbay area. We have many people who return year after year from abroad to go out with us multiple times a season.

Preparing For Your Trip

Please bring a couple layers and a windbreaker to stay warm, as well as a hat and sunscreen, according to the weather conditions. Even when it is hot onshore, please bring a layer or two as the ocean in Maine acts like a natural air conditioner.

You are free to bring your own food and beverages, including wine and cheese.

If you are driving, please plan to arrive in Boothbay Harbor 30 minutes before departure time so you can find parking before heading down to the boat. There are several paid parking lots a block or two away from the dock. Parking is not available at Fisherman's Wharf Inn. Our Directions Guide will get you to the boat from wherever you are.

Please use a bathroom onshore before boarding as the bathroom on the boat is downstairs and for emergency use. There are public bathrooms in the harbor-side Whale Park, which is directly adjacent to the parking lot of Fisherman's Wharf Inn, where our booth is located.


A crew member will open the gate for boarding ten minutes before departure and lead you to Eastwind. There is a prominent Schooner Eastwind Boarding sign in the Fisherman's Wharf Inn parking lot, to the right of and behind the Eastwind ticket booth. Eastwind is on the other side of the inn from the parking lot, so you will not see Eastwind at the dock until the crew brings you down. However, if you want to see Eastwind beforehand, you can go to the end of public dock connected to the Whale Park, or across the footbridge.

Please mute or turn off cell phones before we leave the dock. We understand that many people use their cell phones for taking pictures, which is encouraged. We want to create a peaceful and serene escape out on the water for you. The captain and crew are happy to answer questions both during the trip and when the trip is over.


Tips are not expected but are deeply appreciated by our captain and crew. If you would like to leave a tip, please leave it under your seat cushion once we have docked and the captain and crew will collect it when refreshing the cushions.


Reservations, boarding, and sailing are all done entirely outside in the open air. We try to arrange seating so you sit with people from your own group. If you are unhappy with the arrangement presented, you are welcome to decline to go out on that sail and receive a full refund. You are welcome to wear a mask aboard, but it is not required.


We listen and read every review. Please do not hesitate to reach out to us after your trip with any suggestions. We are always open to feedback on how to make your experience better.

Please see our online calendar for our schedule and to book online, or return to the home page.