Kennebunkport, Maine 3 Day Travel Itinerary
- May 14, 2025
- 5 min read
Updated: Jul 24
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Kennebunkport is a Maine coast vacation destination with three neighborhoods to explore: Kennebunkport, Kennebunk, and Cape Porpoise. Our 3-day travel itinerary will help you enjoy all the best things to do in Kennebunkport Maine.
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, and New England coast eateries. Let us introduce you to the best things to do in Kennebunkport Maine.
Kennebunkport is a 4-season New England travel destination. Businesses change opening hours and days seasonally, with some business closing or shortening hours in the winter. Always check ahead to confirm your plans. Also, the region has sparse public transportation. We recommend utilizing a personal vehicle or car rentals for your trip.
Kennebunkport Maine Hotels
In Kennebunkport you will find a range of lodgings from B&B's in old captain's houses to luxury resorts to affordable chain options. Check out Kennebunkport hotels here. Here are a few long-time favorites:
Kennebunkport Inn - Casually elegant guest rooms in the heart of Kennebunkport
Nonantum Resort - tradtional Maine waterfront resort
Kennebunkport Captains Collection - historic hotel in prime location
Colony Hotel - overlooks Kennebunk River & Atlantic Ocean
Click for information of car rentals in the region.
MAINE TOURS & EXCURSIONS
Things to Do in Kennebunkport Maine in 3 Days
Day 1: Explore the Dock Square, Historic District, and Harbor of Kennebunkport Maine
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.
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.
TRIP ESSENTIALS
On the Maine coast, and almost every travel destination, I find myself reaching for my Eddie Bauer Rainfoil Jacket, Frogg Toggs Hat, and Crocs Strappy Sandals (wear to dinner or the pool).
Other items I rely on include my Huk Sunglasses and Contigo Autoseal Water Bottle (no spills in the backpack).
But by far, my number one can’t-do-without essential is my Sony RX100 Compact Camera. It fits perfectly into a pocket. Or, mounted on a Mini-Tripod it slips into my Travelon Sling Bag.
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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. For a fun twist, tray a local ghost walking tour.
Day 2: Explore Shore Walk, Walking Tour, Ocean Avenue, and 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.
At lunchtime, walk downtown to sample some of Kennebunkport’s 5-star food scene. The town is home to some of the regions most celebrated chefs. 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.
NEW ENGLAND TOURS & EXCURSIONS
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 Walkers Point. The estate, or “Bush Compound Kennebunkport,” is the summer home of the dynastic Bush family. There is a memorial to George “H” at one of the lookouts.
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 or take a kayak paddle around the harbor.
This evening, drive a half-hour north to the city of Portland. Walk the Portland Old Port and check out its famed brewery scene with a bus tour of local breweries.
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.
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.
PACKING ESSENTIALS
We rely on a combination of bags: Our Level-8 28” and Level-8 20” spinners are fun and stylish. Our Delsey Helium 28” hardshell is a workhorse. Our Tomtoc Backpack is great for short trips.
Randy doesn’t use them, but I swear by segregating items into Compression Packing Cubes and Wet Bags.
For security, we place an Apple Air Tag in each bag, and keep a supply of RFID Blocking Sleeves on hand.
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Hope you enjoyed the sun, surf, and “summer cottages,” Laura and Randy
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