A road trip along Maine’s coast allows you to experience it as it’s meant to be: one small town at a time, punctuated by memorable meals and luxurious stays that reflect each destination.
The Pine Tree State’s magic reveals itself in its breathtaking views, picturesque harbors and in the journey itself. The following itinerary blends iconic landscapes, beloved local institutions and lots of lobster rolls — Maine’s most famous dish — along the way.
Savoring All that Portland Has to Offer
Portland earned its reputation as Maine’s culinary capital through its focus on fresh, high-quality seafood. Many of the city’s restaurants rely heavily on the state’s fisheries, farms and producers. Fore Street remains a cornerstone with a wood-grilled menu that celebrates Maine’s seasons without pretense. Nearby sister restaurant Scales overlooks the harbor and takes a more refined approach to classic coastal fare. Reservations fill up early, so plan ahead.
If you are looking for something more casual, head to The Highroller Lobster Co., a retro-diner-like throwback renowned for its high-quality lobster rolls. Follow them up with dessert from Standard Baking Company. The line here often winds through the parking lot, a testament to pastries and breads so consistently excellent that locals and visitors alike are willing to wait.
Portland also has seemingly endless activities to enjoy. Admire the epic coastline from the water on a sightseeing cruise. Portland Schooner Co. sails past lighthouses and islands via a historic schooner, providing a quiet, romantic perspective of Casco Bay.
For families, the Children’s Museum & Theatre of Maine is widely regarded one of the finest institutions of its kind in the nation. The interactive 30,000-square-foot museum features exhibits that are accessible to all ages and abilities and the country’s longest-running children’s theater.
Taking in Acadia National Park and Bar Harbor
Wake up early to venture North and meander along the coast. Stops in Freeport, Georgetown, Waldoboro, Rockland and Lincolnville reveal working harbors, galleries and stretches of coastline that feel largely untouched. These pauses are unhurried and quaint — and that’s precisely the appeal.
Don’t miss a stop in Wiscasset for one of our favorite lobster rolls in the state at Red’s Eats. The cash-only spot also serves outstanding whoopie pies — another Maine specialty — and unique lobster kabobs. Go early to avoid long lines.
When you finally arrive in Bar Harbor, check into Harborside Hotel, Spa & Marina, which offers front-row views of the harbor and easy access to both town and park entrances. The vistas are stunning, especially at sunrise and dusk, when the water reflects Mount Desert Island’s changing light. Sit down for a meal at the hotel’s Italian restaurant, La Bella Vita, before settling in for an early night ahead of an exciting day of outdoor splendor in Acadia National Park.
The park shows off some of the most striking scenery in the Northeast, from rocky headlands to quiet coves. Popular stops include Bass Harbor Head Lighthouse, best visited around golden hour; Sand Beach, a quick but memorable photo op; Thunder Hole, go about an hour before high tide for maximum impact; and Otter Cliffs, where an easy coastal walk delivers expansive Atlantic panoramas.
If you come in the warmer months, Jordan Pond House is a classic for lunch. Skip the formal dining room and just grab the famous popovers outdoors instead, where you can avoid long waits and keep soaking in the scenery. Be forewarned, parking here can be a struggle, so consider taking a taxi or the Island Explorer shuttle from town.
Basking in Kennebunkport Tradition
The next stop on your journey is Kennebunkport, which combines classic New England charm with a sense of occasion.
There’s no better place to experience this than Forbes Travel Guide Four-Star White Barn Inn, one of Maine’s most celebrated properties. It is the kind of place that justifies a detour all its own. The inn’s atmosphere is quietly elegant, steeped in history yet impeccably current.
Dinner at the inn’s Five-Star restaurant is exceptional. Every dish showcases Maine ingredients in memorable ways — for example, the mini lobster roll comes with caviar here and a citrus hollandaise accompanies the butter-poached Kennebunkport lobster entrée. It’s not just a meal, but an experience that lingers long after the final course.
Browsing local shops is a favorite Kennebunkport pastime. When you get hungry, The Clam Shack serves some of the area’s best lobster rolls in a casual, no-frills setting. Nearby, Big Daddy’s Ice Cream is hard to beat — order a scoop à la mode alongside what may be the best blueberry pie in town (when available), a fitting tribute to Maine’s most beloved fruit.
Admiring the Coast from Cliff House
Save the best views for the final stop on your tour. The Four-Star Cliff House is perched dramatically above the Atlantic near Ogunquit. The resort manages to feel both expansive and intimate, thanks to the sweeping ocean views that command attention the moment you arrive.
The setting is the star here. Floor-to-ceiling windows frame the coastline, while cliffside walking paths and lookout points invite quiet reflection. Inside, the design is modern and coastal without leaning into cliché — clean lines, natural textures and a sense of calm that mirrors the landscape outside.
Whether you’re enjoying the nine-treatment-room spa, lingering over a fresh seafood meal or simply watching the waves crash below from a fire pit (possibly while roasting marshmallows), Cliff House creates a feeling of coziness and serenity that’s unmistakably Maine.
