Escape to Vacationland: A Summer Road Trip in Maine

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Maine has long been a preferred destination for adventurers seeking a rural escape outside the city. Summertime is the perfect season to explore the wonders of the state known as Vacationland.  In pursuit of “the way life should be,” many travelers head further north up the coast towards the Acadian mountains in Mount Desert Island or the Moose River Region of Jackman, overlooking the rugged cliffs and sandy beaches of Southeastern Maine. Luckily, we’ve highlighted three of our favorite cities in southern Maine, less than a 30-minute drive apart. A road trip up the New England coast is never more beautiful than in the summer months when the blue of the sky is reflected in the cerulean waves of the ocean. 

Read on for the top spots to visit in Portland, Prouts Neck, and Kennebunkport, and prepare to book your ultimate Maine escape for later this summer.  


Port in Portland

(Image of Portland provided by Cru of Two PR)

Portland is always a favorite destination in Maine for travelers looking for some small-town charm on their New England escapes. And it’s not hard to see why it has become an increasingly popular hot-spot for New Yorkers and other city-folk looking to escape the urban lifestyle — whether for a weekend or eternity. Book a stay at the Canopy, located right in the center of town, and grab cocktails and lobster rolls at Luke’s Lobster, the flagship restaurant on Portland Pier. Other places to grab a sundowner include Batson River Brewing & Distilling, which offers an extensive and refined selection of local spirits. Follow up your aperitifs with dinner at Via Vecchia, an atmospheric (and delicious) institution downtown offering small plate Italian cuisine. 

As for shopping, check out Sea Bags to purchase totes made of recycled sails, or peruse the curated collection at Ember, a locally-owned boutique perfect for chic additions to your wardrobe. Finally, when in Maine, it’s a sin not to get out on the water. Seafaring is not only a summertime pastime in Maine; it’s a way of life. Luckily, you don’t need to dedicate your life to the high seas to experience a taste of what it must feel like to be a lobsterman. Rocky Bottom Fisheries offers harbor tours and sunset cruises, where you can try your hand at crabbing and retrieving lobster traps. (Not as easy as it looks, but the apparel makes up for the discomfort of liberating crustaceans from the briny cages). 

Prouts Neck

Boat sailing on the water

(Image of sailing boat provided by Cru of Two PR)

Despite its location only twenty minutes south of Portland, Prouts has remained a hidden gem, with miles of unspoiled shoreline and dramatic bluffs overlooking the Atlantic. And, with only one hotel in town, it’s unlikely ever to become too much of a tourist trap. But the privacy and seclusion are what sets this coastal oasis apart. A peninsula on the southern tip of Scarborough, Prouts is something of a local secret—residents deliberately discourage development that would turn their haven into a tourist trap. As a result, the landscape that famously inspired the American painter Winslow Homer has remained just as wild and unspoiled as it was at the turn of the century. The Portland Museum of Art offers guided tours of the Winslow Homer Studio, the artist’s old residence, where he spent the last 25 years of his life. 

The roughly four-mile loop of the Cliff Walk weaves alongside the jagged cliffs and sandy beaches that inspired Homer’s paintings. The trail winds through a bird sanctuary and offers stunning views of the rocky Atlantic coast. Be sure to check out the shingled cottages dotting the coast — many of which have been in the same family for over a century. Afterward, opt for post-trail drinks at the Black Point Inn, the only hotel in Prouts. Order a spiked cider and relax on the Adirondack chairs on the front lawn after completing the loop. A stop at the Lobster Shack on Cape Elizabeth on your way out of town is the perfect send-off for your day. Sit outside at a picnic table below the lighthouses to enjoy one last view of the Cliff Walk and the rugged coast. You’ll leave wanting to plan your next trip soon—though try not to tell your friends.



(Image of Kennebunkport provided by Adobe Stock)

Kennebunkport is as bustling as Prouts Neck is serene and quiet, so combining the two is the perfect juxtaposition for your trip up north. The coastal resort town is famous for its fishing and shipbuilding and is well-known as a preferred retreat of America’s First Families (it’s the preferred getaway for former President Bush). But don’t be overwhelmed by its illustrious history: It’s easily conquerable and enjoyed on a long weekend stay. Book a stay at Cape Arundell Inn or the Colony Hotel and start your day with coffee from Mornings in Paris. Head to the beach at Goose Rocks, and enjoy a cocktail at the Tides Beach Club upon arrival. Book a sailing cruise with The Pineapple Ketch — if you reserve a sail with enough people, you have the option to make it private. 

As for where to eat, Allison’s Restaurant and the Ramp Bar & Grill are favorite local spots — just be prepared to wait in line for the latter. If you’re in the mood for something a little fancier, check out Earth at Hidden Pond or Windows on the Water. As for cocktails, Federal Jack’s is a favorite bar for rowdy college kids and old salts alike, while Pilot House is a local’s favorite, and Old Vines is a tasty wine bar in town. One entirely mandatory activity? Poolside sundowners at the Colony Hotel offer the perfect opportunity to enjoy the sunset over the Atlantic. You’re in Vacationland, after all. 

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