A Weekend On Bailey Island

Around Maine

A Weekend On Bailey Island

September 27, 2019

Summer may be over but that doesn’t mean I’m not soaking up every last drop I can! If you didn’t know, one of the best perks of being a Portland Dine Around member is the Bailey Island getaway. 

All PDA members have access to this amazing deal. Seriously, it’s well worth it, and if you’re a PDA member who hasn’t enjoyed all that Bailey Island has to offer PDA members, you are missing out!

Seasonal prices are per person double occupancy:

$289.00 from May 10 to 24 & October 1 to 15

$315.00 from May 25 to June 21 & September 16 to 30

$335.00 from June 22 to September 16

The Food

For one thing, Bailey Island is home to some amazing seafood, including Morse’s Cribstone Grill and Cook’s Lobster & Ale House.

At Morse’s, you really can’t go wrong. The first night that we arrived, we went to Morse’s and we went all out. I got the Lobster Shore Dinner, which is steamed lobster, steamers, and an ear of corn, all at Market Price. 

Morse's Cribstone Grill on Bailey Island

Let me tell you, it’s a steal, considering the size of the platter that comes out and the fact that steamers alone are $14. You won’t leave hungry!

My boyfriend got the fried clams, which looked amazing as well. We also got drinks. I got the Blackberry Mint Cooler, which was strong but filled with plenty of blackberry flavor as well. 

The next day, we decided it was time to do a little bit of exploring. Bailey Island is an island on Harpswell. If you’re coming from somewhere like Westbrook (which is where we came from) it only takes about an hour and 15 minutes to get there. But it’s like a whole other world once you’re here!

For one thing, you’re surrounded by views, views, views, views! The ocean is pretty much everywhere as far as the eye can see on Bailey Island. It’s absolutely stunning! In total, there are about 6 restaurants on the island, and a few gift shops. 

We stopped by one called Seaside Creations on our way to find the Giant Stairs, another Bailey Island must see. Seaside Creations is filled with Maine-made creations and gifts by local artisans. If you’re looking for a one of a kind gift that is the essence of Maine and Bailey Island, you’ll find it here.

The Giant Stairs are a natural phenomenon built into the Bailey Island coastline. Don’t ask me how, but they really do look like giant stairs were carved into the cliffs somehow! They are gorgeous, and of course, a great spot for a selfie.

After all our walking and exploring, we made our way to the famous Cook’s Lobster & Ale House for lunch. I’ve certainly heard of Cook’s but I had never been before. It’s quite the large establishment, filled with plenty of kitschy Maine paintings and lobster accessories. 

All I cared about was the menu and finding myself some fried clams. I definitely experienced some FOMO watching my boyfriend eat his fried clams the night before. 

So you know that’s what I got at Cook’s. I started with the clam chowder, which was a little on the thin side, but it was filled with a generous amount of clams! 

Now, the fried clams. You have two options: you can get either the crumb batter or the Red Ale batter. 

I went with the crumb batter. Cook’s has been a Maine institution for a long time, and I can see why. The fried clams were out of this world good! 

The price was about what I expected, but it was an extremely generous portion, especially for lunch. I left stuffed but I assure you, I didn’t leave a single fried clam on my plate. 

They were on par with favorites I’ve had in Portland at Gilbert’s, Bob’s Clam Hut, and Luke’s

The Sailing

Considering the sheer amount of food we consumed for lunch on Saturday, we couldn’t eat dinner before our moonlit sail on the 70 foot Schooner ALERT. This is another part of what makes the Bailey Island Getaway such a treat for PDA members. 

You get a four hour cruise included in your Bailey Island Getaway package. Honestly, there’s no better way to experience an island than to sail around it! The ALERT is a beautiful boat, and the owners (or I guess captains), Bethany and Perry, are some of the nicest people. 

Not that that’s really a surprise, since most people in Maine are extremely nice to their core. It’s part of what I love about living here! But they are also incredibly knowledgeable and more importantly, flexible. 

Bethany watched the weather for a week before our sail. She called me on Friday afternoon to get an idea of how flexible we were with our plans. 

We ended up changing our original sail to a moonlit sail because the weather during the day looked dicey. I appreciate when people go above and beyond on things like that, especially if you’re going out on the water. 

The sail was so much fun, and there’s really nothing like a moonlight sail, even if it’s pitch black outside. What a cool experience!

The Bailey Island Motel

It’s important to note that you get to stay at the adorable Bailey Island Motel for your 3 day, 2 night stay as well. The motel was recently renovated by Paul and Rita Dube in 2016, so every room is in tip-top shape. 

I also learned that Rita’s own paintings are in the rooms as well, which adds another personal touch. There’s really nothing not to love about the Bailey Island Motel, especially since it’s walking distance to the two aforementioned restaurants. 

Why is Bailey Island so pretty?

Once you step out the doors, you have a perfect view of the water, shining and sparkling in front of you. If you’re looking for paradise, it might just be waiting for you here.