7 Activities
Fascinating Day Trip to Portland
Starts from
Boston
Transportation
By Car
Guidance
Self-Guided
Activities
7
Duration
9 hours
Length
66 mi
Guide details
Starts from
Boston
Transportation
By Car
Guidance
Self-Guided
Duration
9 hours
Length
66 mi
Kelsey Perrett
Travel Expert
- Sample sweets in Perkins Cove and Old Orchard Beach.
- Lunch on the waterfront of adorable Kennebunkport, ME.
- Stroll Congress Street through the heart of downtown Portland, ME.
Portland, ME, a hip and artistic city on the Casco Bay, may be the perfect day trip destination. A scenic coastal drive, great shopping, and great food are the highlights of this journey.
This road trip visits the traditional lands of the Wabanaki, Aucocisco, Abenaki, Pequawket, Pennacook, and Pentucket peoples. Travel in the warmer months, when shops are open and outdoor activities are at their most pleasant.
This road trip visits the traditional lands of the Wabanaki, Aucocisco, Abenaki, Pequawket, Pennacook, and Pentucket peoples. Travel in the warmer months, when shops are open and outdoor activities are at their most pleasant.
Categories
Portland, ME, a hip and artistic city on the Casco Bay, may be the perfect day trip destination. A scenic coastal drive, great shopping, and great food are the highlights of this journey.
This road trip visits the traditional lands of the Wabanaki, Aucocisco, Abenaki, Pequawket, Pennacook, and Pentucket peoples. Travel in the warmer months, when shops are open and outdoor activities are at their most pleasant.
This road trip visits the traditional lands of the Wabanaki, Aucocisco, Abenaki, Pequawket, Pennacook, and Pentucket peoples. Travel in the warmer months, when shops are open and outdoor activities are at their most pleasant.
Kelsey Perrett
Travel Expert
- Sample sweets in Perkins Cove and Old Orchard Beach.
- Lunch on the waterfront of adorable Kennebunkport, ME.
- Stroll Congress Street through the heart of downtown Portland, ME.
Day Itinerary
7 Activities
Day 1
66 mi0.7 mi
Taking Coastal Cruise to Portland, ME
Head up the coast to Portland, one of the best day trip options. On the way, you'll stop through the stunning beach towns of southern Maine, including Ogunquit, Kennebunkport, and Old Orchard Beach.
10:1545 min
Portsmouth Love Wall
Other Great Outdoors
Open Details
There’s a lot to love about Portsmouth, NH. So if you find yourself strolling through the city struck by Cupid’s arrow, pay a visit to the “Love Wall” in Prescott Park. This chain-link fence above the parking area is adorned with padlocks symbolizing eternal love — an homage to the Pont des Arts “Love Lock” bridge in Paris. The tradition is to write your name on the lock and toss the key into the Piscataqua River, but be cool and don’t litter.
16.9 mi
25 min
11:301 hr 30 min
Marginal Way
Promenade
Open Details
Perkins Cove, or simply “The Cove” is a historic fishing and arts community that has embraced the summer tourist scene with a collection of walkable shops and restaurants.
Leave your car at the start of the Marginal Way, an about one-mile paved oceanside path from Ogunquit, ME. The drawbridge and the basin dock make great photo opportunities, but there’s also a great candy store for the sweet tooth in your car.
Leave your car at the start of the Marginal Way, an about one-mile paved oceanside path from Ogunquit, ME. The drawbridge and the basin dock make great photo opportunities, but there’s also a great candy store for the sweet tooth in your car.
11.9 mi
25 min
13:301 hr 30 min
Alisson's Restaurant
Restaurant
Open Details
Stop for lunch in the adorable riverfront town of Kennebunkport, ME. This quaint harbor is a tourist darling, with some quality restaurants to boot. Alisson’s Restaurant on Dock Square is a star among stars with an easygoing vibe. Expect traditional seafood and pub fare with a few wacky twists. You haven’t really experienced Kennebunkport until you try the lobster pizza.
18.3 mi
30 min
15:305 min
Parking Lot
Parking
Open Details
Leave your car in this parking lot, and head to the beach for some fun in the sun.
0.2 mi
5 min
15:4530 min
Old Orchard Beach Pier
Pier
Open Details
Stretch your legs with a stroll around the boardwalk of Old Orchard Beach. There is a lively lineup of beachfront bars and restaurants where you can snack or drink with your toes in the sand, while the Palace Playland amusement park bustles with carnival vibes in the summertime. Wander out the Old Orchard Beach fishing pier to drink in the full experience.
18.8 mi
30 min
16:451 hr
Portland Museum of Art
Museum
Open Details
The Portland Museum of Art in Congress Square is the heart and soul behind Portland’s funky, artsy atmosphere. Here, at the largest and oldest public art institution in the state of Maine, you’ll find the works of acclaimed painters like Winslow Homer, Andy Warhol, and Claude Monet. Visitors can also indulge in more contemporary exhibitions in the free outdoor sculpture park and surrounding Portland Arts District.
0.6 mi
10 min
18:001 hr 30 min
Central Provisions
Restaurant
Open Details
Portland, ME, has such a wealth of great dining establishments that it's tough to label them with superlatives like "best" or "most popular." But if one had to narrow it down, Central Provisions would certainly be high on that list. This intimate brick space (formerly a storehouse for The East India Trading Company) serves small plates and snacks on a rotating menu. They also have an extensive wine list, so be sure to ask for a pairing! Reservations are recommended and can be made on the official website.