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Portland Old Port 3 Day Travel Itinerary

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J's Oyster | Portland Old Port 3 Day Travel Itinerary
J's Oyster

The perfect base for a trip to Portland, Maine is the historic Old Port. The district’s cobblestone streets and working waterfront are packed with things to do. Our Portland Old Port 3-day travel itinerary will help you get to know Maine’s largest city.

Portland is not a city that puts on airs. It proudly embraces its working-class artisan and nautical roots. The city has a vibrant arts community, a healthy bar scene, and an eclectic landscape of fine-dining, casual restaurants, and cafes featuring many types of cuisine.

Boothby Square | Portland Old Port | Maine Coast
Boothby Square | Old Port

Whether wandering the boutiques and bars of Old Port’s restored warehouses or rubbing shoulders with fishermen on the Commercial Street wharves, a large part of Portland’s charm is how easy it is to immerse in the city. The accessibility of the waterfront as well as the walkability of Old Port make it simple for visitors to soak in the sea, sky, docks, and 18th century architecture.

Commercial Street Wharf | Portland Old Port Itinerary
Commercial Street Wharf
Simon Pearce | Shopping | Portland Old Port 3 Day Travel Itinerary
Simon Pearce | Shopping Old Port

For more information on Maine Coast travel destinations read our articles on:

18th Century Brick Buildings of Portland Old Port | Maine coast vacation destination
18th Century Brick Buildings of Portland Old Port

Day 1. City Walk: Old Port and Commercial Street. Visit Fort Williams and Port Head Lighthouse. Dinner & Evening in Old Port

On our morning city walk, we will take in the restaurants, breweries, shops, cemeteries, fish markets, and scenic views of Old Port and Commercial Street. The walk as Google mapped is about 1.5-miles, but you are encouraged to veer from the path to explore.

Google Map Old Port and Commercial Street City Walk
Google Map Old Port and Commercial St. Walk
 Commercial Street Wharves | Portland Waterfront Historic District
Commercial Street Wharves

Make your way to the Ocean Gateway Pier. Stop at the Portland Maine Information Center for pamphlets on excursions (sailing, schooner, kayak, lobstering, trolley, and others). Begin the walk by taking Hancock Street to the Eastern Cemetery. Established in 1668, the cemetery holds over 4.000 marked graves, and is the city’s oldest historical site.

Marina | Historic Old Port | Maine Coast Travel
Marina | Historic Old Port

Retrace your steps until reaching the Shipyard Brewing Company (tasting room and brewery shop opens daily at 11). Turn onto Middle Street. On this next stretch, note some of Portland’s best loved eateries as you pass Duckfat (European sandwich shop and café), Evantide Oyster Company (American Oyster Bar), and Honey Paw (Korean).

At Franklin Street turn toward the water until you hit Fore Street. Walk past Standard Baking Company (Breads and Pastries) toward Boothby Square and the heart of Old Port. Spend the next hour exploring the blocks between Silver, Milk, and Exchange Streets. The district’s cobblestone streets, unique shops, and restored brick buildings will charm you.

Bakery | Portland Old Port things to do

From Fore Street veer down Union to Commercial Street. Spend the remainder of your trek exploring Union Wharf (home to the Portland Waterfront Historic District), Widgery, Fisherman’s, DiMillo’s, and the Custom House Wharves as well as the Portland and Maine State Piers. Walking these 7-wharves you will see lobstermen, fish markets, bait shops, a bottling company, marinas, yacht clubs, eateries and bars.

Water Trough | Historic Old Port | Portland Old Port Itinerary
Water Trough | Historic Old Port

This afternoon, take a trip to Fort Williams Park and the Port Head Light in nearby Cape Elizabeth. The lighthouse is the oldest lighthouse in Maine, and the most photographed in America. The 90-acre Fort Williams Park has a cliff-side loop that veers past the lighthouse, a rocky beach, and playground.

This evening, have dinner in Old Port. We suggest the Evantide Oyster Company or DiMillos Floating Restaurant. Later, wander the taverns of Old Port in search of live music and libations.

Old Port and Commercial Street | Maine Coast Travel
Old Port and Commercial Street

Day 2. Morning tour or sea excursion. Afternoon trek on the Eastern Promenade. Dinner at Sea Glass in Cape Elizabeth. Sunset walk on Crescent Beach.

Begin the day with a tour. There are many to choose from including culinary, seafood, history, and brewery tours as well as lobster, tall ship, and whale watch excursions.

Shopping Historic Old Port | Portland Old Port things to do
Shopping Historic Old Port

In the afternoon, hike along Portland’s Eastern Promenade shore trail. Begin (again) at the Portland Information Center at the Ocean Gateway Pier. The Eastern Promenade trail follows the shore past the Maine Narrow Gauge Railroad (historical train with ocean views) and several marinas to the tiny East End Beach. Turn around here. Retrace your steps, or head back on the Eastern Promenade Mid-slope trail through Fort Allen Park and Fore Street. The route is about 2.5-miles with priceless views.

Google Map Eastern Promenade Trail Walk
Google Map Eastern Promenade Trail Walk
Harbor Fish Market | Old Port and Commercial Street | Maine coast travel
Harbor Fish Market

Tonight, travel 8-miles south to Cape Elizabeth. Drive to the Inn by the Sea resort and have dinner (inside or out) at the Sea Glass restaurant. The views and ambience are spectacular. If there is still light after dinner, drive to the mile-long Crescent Beach. Walk the white sand beach as the sun sets.

Bell Buoy Park | Waterfront | Portland Old Port Itinerary
Bell Buoy Park | Waterfront

Day 3. Trip to Freeport Maine. Scenic drive through Falmouth. Sunset Sail. Dinner in Old Port.

In the morning, take I-295 north 20-miles to Freeport, Maine. Freeport is home to the LL Bean Flagship Store and an impressive town-wide assemblage of upscale outlet stores and eateries. Park the car and experience retail heaven. On the way back to Portland, take Route 88 and 1 through Falmouth and Yarmouth. The route is consistently ranked as one of the most beautiful drives in America. Be aware, the speed limit drops to 35 mph for much of the drive.

Bull Feeney Building | Portland Old Port | Maine coast vacation
Bull Feeney Building

Tonight, enjoy dinner and a sunset sail along the magnificent Maine coast.

You’ll be sad to leave. You can never get too much of the southern Maine coast, Laura and Randy

For more information on Maine Coast vacation destinations read our articles on:

Boone's Fish House and Oyster Bar | Restaurants Portland Old Port
Boone's Fish House and Oyster Bar


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