Sadler House

Sadler House

Rockland, Maine

Sailing in Midcoast Maine: How to Arrange a Day Sail

August 21, 2018 | Comments Off on Sailing in Midcoast Maine: How to Arrange a Day Sail


I can finally write a post about how to go sailing in midcoast Maine. Why didn’t I do this sooner? It’s because I’d never done it and I couldn’t get over my nervousness about figuring out how to make it happen. What I’m going to share here is not as much for people who are experienced in sailing and who have boats and connections. It’s for those of you who, like me, didn’t grow up near the water and want to experience sailing in midcoast Maine – possibly for the first time.

Sailing in Midcoast Maine Just for the Day

As a newbie, of course you are not going to want to get on a boat by yourself and throw caution (literally) to the wind. There are numerous gorgeous schooners in the midcoast that will take people out for overnight or multiple day sails. These are a thing of beauty, but it’s a commitment some of us (especially with kids) may not be ready to make. What I needed was to get my kids on a boat for a few hours and see how it went.

Bufflehead Sailing Charters

Sailing in Maine on The BuffleheadPoking around town, I finally heard about a wonderful ship called The Bufflehead. This 32′ wooden gaff sloop is owned by Daniel and Amanda Bennett, who have a great website with a calendar and lots of information about all the different types of sails they can provide for up to six people at a time.  Because I didn’t even know how my kids would react to sailing, I jumped at the chance to take just a two hour trip. I emailed Daniel and Amanda and easily arranged for an August morning when we would have our first sail as a family!

How it Works

On the day of the sail, we simply walked down to the Windjammer Wharf, which is right near the ferry terminal in Rockland. We needed to bring very little – just a few bottles of water, some extra sunscreen, and some baseball caps to keep the sun off. I also brought my checkbook, as the Bufflehead folks only require payment on the day of the sail. The fee was $55 for each of us adults and the kids were their age times the number of hours (quite a deal!). So it was 2x their ages for each of them for a 2 hour sail.

Spotting the Bufflehead was super easy, and we were quickly settled on board. We were able to put our waters in the little refrigerator inside the cabin and life jackets were provided (mandatory for the kids). Besides the four of us, there was a couple visiting from Kansas on the sail, too. It didn’t take long for us to get underway. A motto on the Bufflehead is “Do What You Want” and, in keeping with that, you are allowed to bring snacks or drinks (including wine, for example). If you don’t have the time to manage your own snacks and drinks, they also offer catering. We kept it simple, but you can plan your day to suit your needs.

Daniel did all the work during the sail, but he was also happy to explain how the sails functioned and would simply ask us to move around the boat a bit if we were in the way at any point. Since our sail (on an absolutely beautiful day!) was just two hours, he took us on a really fun and informative tour of the Rockland Harbor. You will not only enjoy the scenery, but you’ll learn a lot of history, too.

Family-Friendly Sailing in Midcoast Maine

Sailing in Maine on The Bufflehead with KidsOur boys are 9 and 11, and Daniel was fantastic at chatting with them and answering their questions. It turns out, nobody in our family is prone to seasickness, and Daniel didn’t mind if they went below into the cabin or asked lots of questions. You can definitely feel comfortable that your kids won’t be a bother when sailing on The Bufflehead.

Sightseeing from the Water

One thing we didn’t expect from our sail was how many beautiful sights we’d see from our new vantage point. Not only did we spy many other boats (which Daniel knew all about) but we got to sail right by the Breakwater and wave to people at the lighthouse. We also saw a bit of wildlife, including a seal!

Sailing in Maine - Rockland BreakwaterAll in all, our two hour sail was everything we had hoped and more. From a parental standpoint, it was also easy to set up and fun for everyone in the family. What more can you ask for when undertaking a new adventure on a family vacation?

Sailing in Maine View of Schooner Heritage and Rockland BreakwaterI can tell you that we are already pondering longer sails in the future and thinking about all the other fun options offered by the folks at The Bufflehead.

Additional Resources for Sailing in Midcoast Maine

As you can see, we really enjoyed our small group on the Bufflehead, but there are other boats offering shorter sails that you can look into, to find the right fit for you and your family or friends. The end of hte sailing seasons is dependent on the weather (think October) so check with each captain to find out when he or she will stop offering sails in the fall. Check out these links for more information:


A Morning in Maine 


Schooner Surprise

Sloop Anjaaca

Schooner Lazy Jack II

Sloop Liberation

Schooners Olad and Owl

Whatever option you choose, you’re sure to have a quintessential coastal Maine experience on your day sail. Don’t be intimidated! Now that we’ve got this great list of resources, we’ll be back out on the water in no time. We hope you get out there, too.

For other day trip ideas during your stay, check out our tips on the best midcoast beaches or browse our list of articles on things to do in midcoast Maine.