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What to do in Boothbay Harbor – a 3 day hybrid itinerary for active travelers

Updated: Jan 24


I didn't realized how many small coastal towns even existed in Maine until my husband took me on a summer holiday with his cousins several years ago. These Boston based family members had been summer inhabitants of Bayville for decades. So he was fortunate enough to have spent many childhood summers learning how to sail and crack fresh-caught lobster. By happy coincidence, my brother who now lives in New Jersey, had also fallen in love with the Boothbay area. So now we have both sides of our family with investment in this seaside gem. I'm a lucky girl.

As of now, I've been to Boothbay three times and I have definitely acquired a list of experiences that I find myself adding to, or repeating, each visit. So that's what I want to share with you. And of course in typical Paradox hybrid travel fashion, I’m going to show you how to mix in luxury experiences with some cheaper thrills, and get in some outdoor physical activity as well. So let’s go to Boothbay Harbor, Maine!

Where to stay

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There are several agencies like Boothbay Summer Cottages that manage weekly rentals at several high-end homes around the area. But to me, a quintessential Boothbay experience includes a stay at a bed and breakfast inn. And there are plenty to choose from all over town. Whether harbor side or hilltop, many are walking distance to Boothbay's restaurants, galleries and shops. If you are looking for waterside elegance, try the Blue Heron Seaside Inn. Or on the same block, the rooms at Harbor Towne Inn have a more traditional Victorian feel. And Harborage Inn, a personal favorite, has one of the tastiest full breakfasts, including their infamous blueberry, creme brulee french toast. Yum. We loved room #8 at Harborage Inn - a lovely corner room with large windows facing the bay. However, If hilltop views and luxury linens are more your style, you can’t beat the Topside Inn. With sweeping views, a wraparound porch, fresh baked cookies and a rotating gourmet breakfast menu, the innkeepers have created a quiet, sophisticated haven above the bustling streets of Boothbay.

Click here for current prices and additional hotels in Boothbay Harbor


Day 1 – a lobster feast and an afternoon on the water

Life is relaxed in Boothbay. So sleep in, and start your day with a cup of coffee in an adirondack chair and then enjoy a leisurely breakfast. Take a stroll downtown or across the footbridge to get your bearings and appreciate the harbor in the morning light. But as you get closer to noon, head over to Boothbay Lobster Wharf, pick out your own fresh-caught lobster, have it steamed, and then sit on the deck with a beer and enjoy. This is classic Maine! After lunch, to get the full coastal experience, I'd recommend getting out on the water. Bay Harbor Oceanside Golf Resort offers luxury boat tours priced per person, as well as Cabbage Island Clam Bake excursions. If tall ships are more your style, Schooner Eastwind offers reasonably priced two hour sailing tours that pass by several local lighthouses and remote islands. Following your coastline exploration, have a cocktail to celebrate your adventure on the deck of Coastal Prime or on the outside rail bar of Harborside Tavern. Later that evening, top off your day with either a casual meal at the Blue Moon Café or on the outside deck of theThistle Inn.


Day 2 - a lighthouse picnic and beers on a pier

There are several lighthouses in the area, but Pemaquid Point is my favorite. Located about a 45-50 minute drive from downtown Boothbay, the beautiful rock formations that make up this seascape make it worth a half day of your time. On the way out of town, I’d recommend taking a short detour and grabbing a lobster roll to-go from Trevett County Store near Barters island. Not only are the village grocers where the locals hang out, but the lobster rolls are just as delicious as the infamous competition (Red’s), and you will avoid standing in long lines. At the end of the day, grab a beer on Robinson’s deck in Southport. This local favorite has live music on the weekends and some killer blackened haddock tacos. If you are still hungry later that night and need a break from seafood, Ports of Italy is the place to go for Italian fare.

TIP - Reservations are not required for the 'far bar' at Robinson's (walk through the restaurant, and outside to the bar area at the end of the pier.) You can order food here, relax, and enjoy a beer without being front row to the band.

TIP - If you are out on Southport early another day or heading to Hendricks Head Preserve, stop by the Southport General Store and try their breakfast pizza. Fantastic!


Day 3 – kayaking and downtown galleries

As your weekend draws to an end, one last on-water paddle experience will help you work off some of the previous nights pasta. Tidal Transit rents both kayaks and SUP’s by the hour and is conveniently located right next to the footbridge. When you are done, check out the many art galleries and quirky new age shops in town. Abacus gallery with its contemporary and diverse collection of décor and jewelry is my personal favorite, followed by the somewhat bizarre, eclectic collection of Enchantments metaphysical store. Complete your experience with rooftop cocktails and tapas at the Boat House Bistro followed by some Ice cream from Wannawaf (below Harborside Tavern, near the footbridge).


Have fun!


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