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Day One · May 29
Depart Boston at 2:00 PM via I-95 North (roughly 2 hours). Arrive Kennebunkport by 4:15 PM and check into your Airbnb. Settle in, change into comfortable clothes, and grab an early dinner at Alisson's Restaurant (Ocean Avenue)—a casual, wood-lined spot known for impeccably fresh local fish and vegetable-forward sides. Skip the tourist trap near the dock; Alisson's attracts locals and families alike. Afterward, walk the Kennebunkport Village Green as the sun sets around 8:30 PM—the clear skies mean golden light will linger, and children can burn off travel energy while you spot sailboats in the harbor.
Day Two · May 30
Book a guided fishing charter with Persistent (or comparable local outfitter) departing 6:30 AM from Cape Porpoise Harbor (10 minutes from most accommodations). The May waters are prime for striped bass and mackerel; crews are accustomed to families and children. Even reluctant anglers find magic in dawn on open water. You'll return by 11:30 AM.
Head directly to The Clam Shack (Restaurant Row) for a post-fishing late breakfast—lobster rolls, fried clams, and fresh lemonade in a no-frills, standing-room setup beloved by locals. Refuel and dry off. At 1:30 PM, drive 12 minutes to Cape Arundel State Park (Kennebunkport side). Hike the Cliff Walk Trail (1.5 miles, mostly flat, spectacular Atlantic views). At 20°C with clear skies, conditions are ideal—not too hot, excellent visibility. The trail winds past dramatic rocky outcrops and offers multiple photo stops. Children under 10 should be supervised on cliff sections. Return to town by 4:00 PM. Grab espresso and pastries at Brew in Kennebunkport (a local favorite coffee bar on Maine Street with excellent pastry sourcing). Spend an hour at Kennebunkport Public Library or exploring the small galleries on Dock Square while kids decompress.
Dinner at Pier 77 Restaurant (Ocean Avenue)—upscale-casual, absolutely fresh seafood (ask the staff what the boat brought in that morning), and accommodating to families. If your group prefers lighter fare, Tangled Oats (a breakfast/brunch spot that opens for early dinner Friday–Saturday) offers grain bowls, smoked salmon plates, and house-made granola in a bright, child-friendly space. Post-dinner, stroll the Town Pier (free, public, magical at dusk) and hunt for starfish in tide pools if the light holds.
Day Three · May 31
Brunch at AC Restaurant (Ocean Avenue)—New England ingredients prepared simply, outstanding coffee, and genuinely welcoming to young families. Order the lobster Benedict or a vegetable-loaded scramble; the açai bowls are locally sourced and Instagram-worthy. Arrive by 9:00 AM to avoid crowds. After brunch (around 10:30 AM), take a 15-minute drive to Ogunquit Beach (technically just south, in neighboring Ogunquit). The sand is pristine, and May mornings are wonderfully uncrowded. Rent beach chairs/umbrellas or simply explore. At 20°C, water is cold but the shoreline and sand dunes are perfect for families. Spend until 12:30 PM.
Leave Ogunquit by 1:00 PM, heading back to Boston via I-95 South. Stop at Stonewall Kitchen (York, 10 minutes south of Kennebunkport on the way) for late lunch snacks—artisanal sandwiches, preserves, and prepared foods. This delays your drive by 30 minutes but gives everyone a proper send-off and time to stretch. Arrive Boston by 4:00 PM.
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