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Friday night Social Sails with SailMaine in Casco Bay (no sailing experience necessary)!

Friday night Social Sails with SailMaine in Casco Bay (no sailing experience necessary)!

The wind in the sails. The bow nodding in the waves. The silhouettes of passing schooners.

Sailing in Casco Bay rules.

And by “sailing” I mean sitting aboard a small-but-comfy J22, alternately taking in the scenery and waving hello to every passing boat while someone who actually knows how to sail does the sailing.

(For my part, I only slightly understand the difference between “jib” and “jibe,” and that’s because I just googled both terms. I definitely have no business being anywhere near the tiller (a.k.a., the steering lever thing).

But lucky for us locals, SailMaine’s weekly Social Sails allow us novices to get out on Casco Bay, even if we don’t know a darn thing about sailing.

Social Sail aboard a J22 on a recent Friday night. Shannon Bryan photo
J/22 sailboat on Casco Bay with fort in background
SailMaine Social Sail in Casco Bay. Shannon Bryan photo

SailMaine leads learn-to-sail programs for kids and adults on Casco Bay, so if you’re interested in learning to sail or refreshing those sailing skills you picked up on a local lake when you were a kid, SailMaine has you covered. You can also rent their boats.

But if you’d like to get a taste of sailing in Casco Bay and you’re not presently close friends with any sailors willing to steer you around in their own boats, then there’s the weekly Social Sail.

Check out this Social Sail video by Juliette Films

Social Sails take place on Friday nights from 5-8 p.m. all summer. (This year, sails continue until the end of August. If there’s continued interest, that schedule could be extended.) Cost is $25, which includes everything you need for a superb evening sail: a J22 sailboat and a skipper to sail aforementioned sailboat.

Those J22s are sweet rides, too. They generally accommodate five people (four people plus the skipper), which means they’re decidedly smaller than those windjammers you’ve seen/cruised on in Casco Bay. And that translates into a much more intimate experience on the water.

SailMaine’s office at the water’s edge in Portland. Shannon Bryan photo
SailMaine boats (those are the J22s farther out) in Casco Bay. Shanno Brya photo

The whole evening begins at SailMaine, located off Fore Street in Portland. (More specifically, you’ll find them off the Eastern Prom bike path, not far from Ocean Gateway.)

Social Sailors gather under the big tent, where the group is divided among boats and skippers. (Note: the skippers are all volunteers, which is really awesome and the reason the Social Sails are possible, so be sure to thank them/tell them they’re amazing. And SailMaine is always looking for experienced sailors to volunteer, so if you know someone, send ’em over.)

Jordan Parks, SailMaine operations manager, welcomes everyone to a recent Social Sail. Shannon Bryan photo

After signing the waiver and putting on a life jacket (bring your own or there are plenty there to borrow), everyone makes their way to the dock where the SailMaine dingy awaits, which will ferry folks to their boats for the evening. And so begins the fun of ungracefully climbing into, out of, and over things, which will continue for much of the evening.

Ready to go! Social Sailors make their way down to the dingy. Shannon Bryan photo
Dingy ride! This photo is from a Social Sail a couple of years ago. Shannon Bryan photo

Once on our boat, our skipper Andy led the charge in getting ready to sail (he did most of the things, but gave us direction on what to untie, roll up, and put below deck). That’s what’s so neat about these Social Sails. While there’s no pressure to know or do anything, you CAN learn things, help out, ask questions to your heart’s content. You can steer the boat if you’d like. Or you can just sit back and enjoy the ride. It’s totally up to you.

All aboard! Time to ready the boat for sail. They look ready and rightfully excited! Shannon Bryan
Our skipper for the evening, Andy, unties the mainsail. Shannon Bryan photo

Before long, we were under way. It just so happened to be a gorgeous Friday evening – good wind, warm temperatures, bright blue sky – and Casco Bay was busy with activity. One woman in my boat, Heidi, took over the tiller and sailed us for much of the evening (she’s an experienced sailor and knew what she was doing, but Andy offered all of us the opportunity to steer, under his guidance, of course).

Most of us chose to just hang out and gaze out on the water, waving at passing boats and remarking on how fun it is to see Spring Point Ledge Light from the other side. Of course, it’s not all idling. We all got to participate one way or another, even if that participation mostly involved scrambling to the other side of the boat when it was heeling (the boat will tip, but it won’t tip over, our skipper Andy said) or taking the slack up in a line when Andy said to.

Heidi steers the boat during a Social Sail with SailMaine. Shannon Bryan photo
Another boat in the Social Sail fleet for the evening. Shannon Bryan photo
The view from the bow. Shannon Bryan photo
Phoebe tightens a line on our boat during a recent Social Sail. Shannon Bryan photo

We all did right to just listen to Andy and do whatever he told us to do. And he was a supremely friendly and welcoming skipper who didn’t abuse his power but did talk to us about wind and sailing terms and he answered questions as we asked them. But we also spent plenty of time chatting about entirely not-sailing-related things. Like kids and traveling and favorite Maine places and local trivia and the deliciousness of pub cheese.

Guess that’s the “social” part of the Social Sail.

Getting social during the Social Sail. From left: Heidi, our skipper Andy, Wendy, and Phoebe. Shannon Bryan photo
Another throwback photo from a Social Sail a couple of years ago. But same great weather and fun, friendly sailing atmosphere. Shannon Bryan photo
Easy going sail – this photo is from 2016. Shannon Bryan photo

I don’t remember how much time we really spent on the water – an hour and a half, I think? – but here’s what I do recall: the feeling of contented calm I had as we puttered around on those waves. The not-caring-about-anything but watching ducks and cormorants and passing pleasure boats. The splash of cold water on my feet when I let my legs dangle over the sides of the boat. The sunset behind a sail. The salt-sticky sensation on my skin.

The most surprising thing about the Social Sails is that so many locals didn’t know they happened. EVERYONE SHOULD KNOW. They’re an excellent way to get on Casco Bay and learn a bit more about what SailMaine has going on. Maybe you’ll fall for sailing and choose to sign up for lessons. Maybe you’ll Social Sail every Friday night all summer long. Or maybe you’ll enjoy it for one perfect evening – adding it to your List of Things I Did in Maine that Rocked.

Whatever your sailing future looks like – it could start with a Social Sail. (If you’re lucky, you’ll get a cool skipper like Andy and you’ll be on a boat with Phoebe and she’ll have pub cheese and crackers.)

Social Sails with SailMaine

5-8 p.m. Friday nights during the summer
SailMaine, 58 Fore Street, Portland
$25. Advanced registration recommended
Boats generally hold five people (four people plus the volunteer skipper).
FMI: www.sailmaine.org/friday-night-socials

Shannon Bryan

Shannon Bryan

I don't like "exercise" any more than you do. But you know what I do like? Paddleboarding with a friend all afternoon (and then sitting in the grass to drink chardonnay). Bike rides and nachos, hikes, yoga classes held in breweries, group paddles to Fort Gorges, you get the idea. Because Maine is my gym.