Kennebunkport, Maine 3 Day Travel Itinerary

Kennebunkport is a Maine coast vacation destination with three neighborhoods to explore: Kennebunkport, Kennebunk, and Cape Porpoise. Our 3-day Kennebunkport, Maine travel itinerary will help you enjoy all the area’s attractions and things to do.

Legendary for its ship building history, Kennebunkport remains a working port for leisure yachts and lobster boats. Visitors will be charmed by the region’s quaint inns, art galleries, epicurean eateries, and the many outdoor activities the New England coast has to offer.

Marina Dinghies

Kennebunkport is a 4-season New England travel destination. Businesses change opening hours and days seasonally. Always check ahead to confirm your plans. Also, to best enjoy the region we recommend utilizing a personal vehicle as public transit is sparce.

Colony Hotel | Kennebunkport's Ocean Avenue | Maine Coast Travel Destination

Colony Hotel | Ocean Avenue

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Lobster Traps | Kennebunkport

Day 1: Explore Kennebunkport’s Dock Square. Take a Walking Tour of the Historic District or Harbor Cruise. Have Dinner by Kennebunkport Harbor.

The village of Kennebunkport is full of New England style capes and colonials perched upon the harbor and river. Take some time to wander the narrow streets of this lovely beach town.

Begin your exploration at the intersection of Summer Street and Western Ave. Walk across the Kennebunk River to Dock Square. Then, get to know town by wandering the restaurants and shops of the narrow streets between Maine Street, Ocean Avenue, and the Village Green.

Dock Square

Later in the day, learn about the region’s rich colonial and ship building past with a walking tour of Kennebunkport’s historic district. View colonial churches and the elegant homes of sea captains and wealthy merchants.

Or, if you would rather be out on the water, book a cruise along the Maine coast. From Dock Square you can book lobster boat tours, sailing excursions, whale watches, and fishing charters.

Boat Charters Kennebunkport

Spend the evening in Kennebunkport. A night at Federal Jacks is always fun. Do a Kennebunk Brewing Company brew tour on the first floor; then, head upstairs for dinner with great water views. Or, try the Pilot House, serving fresh seafood, and often live music.

Federal Jack's Restaurant | Kennebunkport Restaurants | Maine Coast

Federal Jack's and Shipyard Store

Day 2: Hike Parson’s Way Shore Walk. Take a Lunchtime Culinary Walking Tour. Enjoy a Scenic Drive along Ocean Avenue (St. Ann’s Church and Walker Point). Explore Cape Porpoise.

Begin the day with a brisk hike on the 2-mile Parson’s Way Shore Walk. The trail begins at Arundel (Colony) Beach and passes by Sprouting Rock and Blowing Cave, St. Ann’s Church, Walker Point, grand summer “cottages,” and the cliffs of the Ocean Avenue coast.

Outdoor Alter | Parson's Way Shore Walk

At lunchtime, take a culinary walking tour of Kennebunkport’s 5-star food scene. The reasonably priced tour gets you up close to some the town’s most celebrated chefs. You may sample chowders, desserts, lobster, and inventive spins on regional favorites as you trek through the village.

After lunch, take a scenic drive past some of Maine’s most stunning scenery. From Kennebunkport, take Ocean Avenue past the grand old resorts, like the Nonantum and Colony, to the palatial summer “cottages” on the outskirts of town.

St. Ann's Episcopal Church

Stop along the route at the magnificent St. Ann’s Episcopal Church. This rustic church has landscaped grounds and a commanding view of the southern Maine coast. The church and outside alter may be visited if open and not in use.

Further along Kennebunkport’s Ocean Avenue is the Walker Point Estate. The estate, or “Bush Compound,” is the summer home of the dynastic Bush family. There is a memorial to George “H” at one of the lookouts.

Walker Point Estate | Bush Compound

Continue your drive to the village of Cape Porpoise. Though only about 3-miles from Kennebunkport, the working lobstering and fishing community feels a world away. Walk the pier to view the Goat Island Lighthouse. There are several restaurants and lobster shacks in the area selling fresh seafood. Drive the surrounding country-side for scenes of down east coastal life.

Maine Coast

Day 3: Shop Kennebunk’s Downtown. Relax at Goose Rocks Beach.

Drive 5-miles to the town of Kennebunk. Like its neighbor, Kennebunk is full of fun shops, cafes, antique shops, and art studios. Park by the small park by Mousam River, and walk Main Street. Have lunch at the charming Kennebunk Inn Tavern.

The Kennebunk Inn

Next, head for Kennebunkport’s Goose Rocks Beach. A 15-minute ride from Kennebunk, the 3-mile beach is known for its white sand and gently rolling waves. In season, a sticker can be purchased at the Goose Rocks Beach General Store for parking. There are no refreshments or restrooms at the beach. However, across the street from the beach the Tides Restaurant can feed you, and provide facilities.