Unlimited travel planning when you book your trip with Andrew Harper
Join today for exclusive access
Open M-F 8:00 am – 6:00 pm CT
Maine is a place of vast beauty. When looking out over the rugged Atlantic coastline or taking in a flaming-red sky as the sun dips below the horizon, one can’t help but recall paintings by Frederic Church, Edward Hopper or N.C. Wyeth, all of whom were inspired by the landscapes and seascapes here. Today, visitors flock to Maine for the same reason Victorian “Rusticators” did in the late-1800s, to experience the natural wonders and clean, crisp air of the Pine Tree State. It may be known for its lighthouses and lobster, but Maine also has some surprises in store. Many people are unaware that it boasts 282 challenging miles of the Appalachian Trail and more than 170 craft breweries and distilleries.
On this nine-day itinerary, you’ll stay at three historic inns, go on a moose safari, visit some of Maine’s most iconic lighthouses, eat exceedingly well and enjoy the breathtaking scenery while on peaceful shoreline walks.
After landing in Portland, drive 25 minutes to Cape Elizabeth and check in at Inn by the Sea, a 60-room shingle-style, beach-chic resort. Relax in Adirondack chairs and enjoy drinks on the lawn while viewing the ocean in the distance. Have dinner at the hotel restaurant, Sea Glass.
Less than a 20-minute drive from Portland, the Inn by the Sea is a relaxing beachside retreat consisting of 61 accommodations.
View Hotel ListingAfter having a full breakfast in the Sea Glass dining room, set off this morning for Portland and tour Victoria Mansion (reservations required). This fine example of an Italianate villa was built between 1858 and 1860 as a summer home for New Orleans hotelier Ruggles Sylvester Morse. Ninety percent of the national historic landmark’s interior is original, with trompe l’oeil wall paintings, intricate plasterwork and lavish fabrics. Since 1941 it has been a museum, and restoration work continues to this day. We enjoyed a one-hour tour and browsing the unique gifts in the Carriage House Museum Shop.
After your tour, visit Batson River Brewing & Distilling, the newest location of this Maine favorite. Enjoy a cocktail made with Riparian Gin or one of the four other spirits (agave, vodka, bourbon and rum) distilled here. There is also a rotating selection of seasonal brews on tap. For a late lunch, act like a local and order a plate of the substantial — and delicious — poutine, fries topped with short ribs, jalapeños, fried onion, cheese curds and gravy. Beer lovers should visit East Bayside, which has many standout breweries within walking distance of one another.
Go back to Inn by the Sea and walk off lunch on Crescent Beach, a 1-mile expanse of sand that is part of a larger state park. Enjoy dinner at Sea Glass.
Less than a 20-minute drive from Portland, the Inn by the Sea is a relaxing beachside retreat consisting of 61 accommodations.
View Hotel ListingYesterday was a busy day, so enjoy the spa, pool or beach at the hotel, or take a leisurely tour of the area visiting nearby lighthouses. Portland Head Light, on the shores of Fort Williams Park, is the oldest lighthouse in Maine and was first lit in 1791. There is a museum on the property, walking trails and picnic areas to enjoy. Less than a half-mile away is the acclaimed Bite Into Maine food truck, where you can experience what some deem the best lobster roll in Maine. It comes with three choices of mayonnaise: regular, chipotle or wasabi.
If you want to see the cutest lighthouse in Maine, stop at Bug Light Park, and walk the path to the diminutive Portland Breakwater Light, which is only 26 feet tall. It has six Corinthian columns around it and was inspired by the Choragic Monument of Lysicrates, in Athens.
For dinner, drive into Portland and eat at Scales, an upscale seafood restaurant on the Maine Wharf, in the city’s historic waterfront district. We began with fresh Johns River Oysters and thoroughly enjoyed our sweet-potato-lobster bisque, baked haddock with chanterelles in a fumet-cream sauce and cod with trumpet mushrooms. If you want to eat nearby and are visiting during the summer, get reservations at the Well at Jordan’s Farm, a working farm of 122 acres where you can pick your own flowers before dinner.
Less than a 20-minute drive from Portland, the Inn by the Sea is a relaxing beachside retreat consisting of 61 accommodations.
View Hotel ListingCheck out of Inn by the Sea and drive three hours to Blair Hill Inn, a historic 10-room country house hotel overlooking Moosehead Lake in Greenville.
If you’ve arrived early enough, enjoy happy hour in the lounge (from 5 to 9 p.m.) or have dinner in the lovely dining room. (Note that dinner at Blair Hill Inn is not offered on Sunday or Monday.)
Blair Hill Inn is a charming country house hotel set on 80 acres overlooking Moosehead Lake, Maine’s largest glacial lake.
View Hotel ListingHave a leisurely homemade breakfast, and then start to explore the area.
Drive to downtown Greenville, and browse through its most interesting shop: Kamp Kamp Moosehead Lake Indian Store for old wool blankets, vintage framed photos, moose taxidermy and Maine décor.
Take Route 6 along the western edge of Moosehead Lake and head to Rockwood boat landing, where you can see the peninsular Mount Kineo, with its 700-foot rock face, presiding over the water. There are many popular hikes in the area, including the steep Indian Trail on Mount Kineo that leads to a climbable fire tower, providing 360-degree views of the lake.
If you are visiting between June and October, take a cruise aboard Katahdin, a 1914 steamboat, that was once one of many boats transporting passengers to surrounding resorts. To learn more about the history of the area, stop in to the Moosehead Marine Museum.
Alternatively, experienced hikers may want to drive 30 minutes east to Gulf Hagas, known as the “Grand Canyon of Maine," a popular if rugged region in the North Woods that is part of the Appalachian Trail. The Rim Trail, along a gorge, provides multiple lookout points to a series of waterfalls.
Return to your hotel and enjoy a treatment at the on-site spa or relax on the porch with a book. Have dinner at Blair Hill Inn.
Blair Hill Inn is a charming country house hotel set on 80 acres overlooking Moosehead Lake, Maine’s largest glacial lake.
View Hotel ListingWake up at dawn to go on a guided moose safari. (Ruth, a co-owner of Blair Hill Inn, can make all the arrangements for you.) Our registered guide, Ashley, from Lone Wolf Guiding Services, picked us up and provided hot coffee before we set off. During our four-hour tour, we learned much about moose (their gestation periods, eating habits and the differences between Maine moose and their Alaskan counterparts — the latter are more aggressive) and saw eight of these gentle giants, including a cow with twin calves.
Return to the hotel and enjoy happy hour in the lounge, mingling with other guests and watching the sunset. Have dinner at Blair Hill Inn or in Greenville.
Blair Hill Inn is a charming country house hotel set on 80 acres overlooking Moosehead Lake, Maine’s largest glacial lake.
View Hotel ListingCheck out of Blair Hill Inn and drive about 3.5 hours to Kennebunkport, where you will check in to White Barn Inn, a sophisticated Auberge property in town. Of the 27 stylish accommodations, we recommend booking one of the five spacious Cottages.
Begin your stay by relaxing next to the cozy fireplace or enjoying a therapeutic massage at the spa.
Have dinner in the rustically elegant White Barn Inn Restaurant.
The sophisticated White Barn Inn is situated by the colorful coastal town of Kennebunkport, about 30 minutes from Portland.
View Hotel ListingAfter breakfast, take a 10-minute walk to Dock Square, a robust shopping area. Some of our favorite stores were Abacus, for locally made art and gifts; Minka, which displays handmade fashion, art and home goods by color scheme; Sea Bags, for nautical-inspired totes; and the Good Earth, which has a showroom of handcrafted stoneware made by a husband-wife team.
Have lunch at the Boathouse Restaurant, a popular eatery on the dock, or, if there is a wait, drive to Port Lobster, a local favorite, and have a lobster roll outside for a more casual experience.
After lunch, drive down Ocean Avenue to St. Ann’s Episcopal Church and visit its historic Stone Chapel, which was consecrated in 1892. Along with a striking interior of sea-washed stone walls, it has 25 beautiful stained-glass windows dating to the late 1800s. Visitors are welcome and can even picnic on the grounds. From there, pass Walker’s Point, the Bush family compound jutting into the sea. There’s a convenient place to pull over and take photos.
Alternatively, drive south to York, home of the Nubble Lighthouse, the most photographed lighthouse in Maine. On your way, you’ll have the chance to patronize numerous antique stores along Route 1. You’ll also pass through the art community of Ogunquit, which is the Abenaki word for “beautiful place by the sea.” It is home to the Ogunquit Playhouse, opened in 1933 and one of the only remaining regional theaters to be part of the “Straw Hat Circuit” (summer stock). Musicals are produced there from mid-May to late October.
If you have time, enjoy the 1.25-mile Marginal Way, a paved cliffside walk along the shoreline. There are 39 benches that provide unobstructed views. You’ll find the entrance on Shore Road, near the Sparhawk Oceanfront Resort.
Back at your hotel, freshen up and have dinner by candlelight at Earth, the award-winning restaurant at Hidden Pond, a rustic resort 15 minutes from town. End the night with a digestif by the hotel’s fire pit.
The sophisticated White Barn Inn is situated by the colorful coastal town of Kennebunkport, about 30 minutes from Portland.
View Hotel ListingCheck out of White Barn Inn and head back toward Portland. If you have time before your flight, take a detour and visit Mackworth Island State Park for a memorable walk on Casco Bay outside Falmouth, a wonderful way to end your vacation.
Cross the causeway and park near the entrance (no cars are allowed beyond that point; note that parking is limited). Walk the gentle 1.25-mile trail around this delightful 100-acre island, passing through odiferous pine forests. There are benches and swings at lookout points along the way and a charming pet cemetery that is a loving tribute to the pets of former Maine governor Percival Baxter. He donated the island to the state to be used as a “sanctuary for wild beasts and birds.” Children — and those who are children at heart — will appreciate the fairy forest, where visitors can use natural materials like seashells, twigs, pine cones and branches to build houses for these magical beings.
Catch your flight and head home.
This is a sample itinerary designed to inspire your travels. Contact the Andrew Harper Travel Office to customize this journey to fit your needs.