Families would be wise not to attempt the whole swath of the coast in a week of travel—that’s a too much time in the car. Instead, spend a few days wandering the cobblestones, shops, museums, and attractions of Portland, then focus on the surrounding towns, beaches, and attractions. This itinerary is designed so that you can have a home base anywhere within 30 miles of Portland. The beauty of it is that you could rearrange these days in any order.
Day 1: Portland
On Congress Square, begin exploring the city at two next-door museums: the Portland Museum of Art and the interactive Children’s Museum of Maine. Then, if your kids are good walkers, hoof it 7 blocks down to the cobblestoned streets of the Old Port, where you’ll find shops, boats, and plenty of lunch options. For the afternoon, let off steam at the Maine Narrow Gauge Railroad Co. & Museum with a (very slow) train ride tracing the foot of the cliffs framing Portland’s east end.
Day 2: Portland
One of the don’t-miss experiences of a Portland visit is a cruise around Casco Bay on a Casco Bay Lines ferry. You can take anywhere from a 20-minute run to a half-day mail-boat cruise. Two of my recommended destinations are Peaks Island—a favorite among stroller-pushing moms for its easy-to-cruise streets with Portland views—and Long Island, with an excellent beach.
Once back at the port, head up to the Eastern Promenade, a 68-acre hillside park with broad, grassy slopes and superb Casco Bay views. For more stupendous views, head up Congress Street to the distinctive shingled Portland Observatory, a National Historic Landmark built in 1807 to signal ship arrivals into the city’s port. From the observatory, it’s a 10-minute walk to the East End neighborhood, where Duckfat has Maine’s (New England’s? the world’s?) best milkshakes.
Day 3: Portland’s Beaches
Cross the Casco Bay Bridge into South Portland. On your way out to the Cape Elizabeth beaches, stop by Fort Williams Park to see the Portland Head Light, the state’s most photographed lighthouse. Then continue down the shore on Route 77 to either Two Lights State Park, with its long rocky beach and fun lobster shack, or Crescent Beach State Park, a mile-long sandy stretch with usually gentle surf.
In season, if the schedule’s right you can round off your Portland deep-dive with an afternoon or evening game at Hadlock Field, home of the Portland Sea Dogs, a minor-league club for the Boston Red Sox. Yankee fans, deal with it.
Day 4: Freeport
Dive into the busy shopping district in Freeport. Don’t miss the sprawling L.L.Bean complex, obviously. Not up for a full day of shopping? Sign up for a day clinic with the retailer’s Outdoor Discover Schools—maybe a 2 1/2-hour kayaking clinic at Bean’s Flying Point Paddling Center, just a 10-minute drive down the peninsula. Also in that direction, check out the seaside trails of Wolfe’s Neck Woods State Park and a demonstration barnyard full of cute animals at Wolfe’s Neck Farm.
Day 5: Inland
Head inland in the morning to visit the world’s last remaining Shakers at the Sabbathday Lake Shaker Community, with its museum, renowned crafts and furniture, and pastoral working farm. Get breakfast or lunch at the New Gloucester Village Store, the tiny hub of the tiny town, which has way better sandwiches and pizzas behind the counter than you’d expect. Then tour around glittery Sebago Lake before heading back to town, with maybe a stop for a dip at Sebago Lake State Park.
Day 6: Old Orchard Beach
Slot this, the theme-park-iest day of your trip, for a weekday to miss the crowds. Spend the bulk of your day on the sand and the old-school carnival rides at Palace Playland at Old Orchard Beach. Indulge all the tacky stuff on the boardwalk, because it’s worth it for the ambience; don’t leave without trying the famous crinkle-cut taters at Pier Fries. End the evening with a double feature at the Saco Drive-In in neighboring Saco.
Day 7: The Kennebunks
Start this day with one of two unmissable breakfasts: Either grab a stool at Palace Diner in Biddeford for tremendous updated diner chow or follow the coastal Route 9 from Biddeford to the Kennebunks to get farm/sea-to-table favorites at The Wayfarer in seaside Cape Porpoise. Then grab some blanket space at Kennebunk Beach or Gooch Rocks Beach —the latter’s my pick, longer and better for strolling.
In the afternoon, drop in on the Seashore Trolley Museum to catch a short ride on a handsomely restored streetcar, and then wander the shops at Dock Square and maybe tackle one last basket of fried seafood at the storied Clam Shack.
Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.