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Portland, Maine: Perfect 3-Day travel itinerary for a summer long weekend

If you're looking for an easy long weekend, 3-days in Portland, Maine is the perfect summer getaway. Did you know Portland has been named in the past as the best food destination in the USA? And is home to some of the best-voted lobster roll restaurants in the country too? In this guide, you can expect to find the best places to eat and explore all planned out in an easy-to-follow 3-day travel itinerary including lighthouse spotting, island hopping and plenty of good food.

Portland, Maine: A 3-Day travel guide of the top things to see, do, eat and drink
Portland, Maine: A 3-Day travel guide of the top things to see, do, eat and drink

We'd recommend 1 of two options for accommodation:

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If you don't have a car: Old Port

Old Port is full of the cutest cobblestone lanes, red brick buildings housing bars, restaurants, cafes and stores, plus is located right on the waterfront overlooking Casco Bay, with direct access to the piers where many of the ferries for island day trips and tours depart. Everywhere within Old Port is centrally located and within walking distance making it the perfect spot if you don't want to rent a car as part of your trip.

If you rent a car: South Portland by Willard Beach:

This is a great option for a more relaxed neighbourhood feel. The suburb is filled with beautiful beach houses and is within walking distance of the beach and cafes. There aren't many hotels located here, so the best option would be an Airbnb if you want to stay in this area.

Top things to see, do, eat and drink in Portland, Maine: A 4-Day itinerary

Day 1: South Portland, Willard Beach & Old Port

Morning Day 1:

Breakfast at Scratch Bakery, South Portland - Don't miss their bagels, arrive early as they sell out fast. They also do great coffee and pastries.

Visit Fort Prebble & Spring Point Lighthouse, walking distance from Scratch. Take the 20-minute coastal walk along Willard beach through to the lighthouse and back

Spring point lighthouse, south portland

End the morning with a swim at Willard Beach, also don't miss visiting Fishermans Point for the best views overlooking the beach

Views from Fishermans Point, at Willard Beach, South Portland, Maine
Views from Fishermans Point, at Willard Beach, South Portland, Maine

Afternoon Day 1:

Have lunch at Duck Fat Frites in Old Port and don't miss their Poulet, which is fries coasted in duck fat with gravy and shredded duck. Their original milkshakes are also great.

The Poulet from Duck Fat Frites, Old Port, Portland, Maine
The Poulet from Duck Fat Frites, Old Port, Portland, Maine

After wander around Old Port through the cobblestone streets. Be sure to stroll down Wharf Street and stop in the shops around Exchange and Market Streets. Commercial Street is great for restaurants and bars.

Evening Day 1:

Grab some takeaway food, we recommend the clam chowder from Gilberts and watch the sunset at Bug Light park and lighthouse in South Portland (10-minute drive from Old Port)

Bug Lightouse, South Portland
Bug Lighthouse, South Portland

Day 2: Visit Boothbay Harbour & Wiscasset

Morning Day 2:

Take a 1.5-hour scenic drive to Booth Bay Harbour. Have a quick breakfast along the waterfront at Red's Coffee House (We recommend the blueberry scrolls).

Red's Coffee House, Boothbay Harbor, Maine

Book a tour with Cap n' Fish cruises, they have 1-hour harbour sightseeing cruises, as well as longer 2-3 hour cruises including whale and puffin watching. We booked the Puffin watching, which we would recommend. If you do this one bring binoculars or a camera with a good zoom lens.

Afternoon Day 2:

Driving back in the direction of Portland, stop to try Red's Eats Lobster Rolls or Sprague Lobster in Wiscasset.

Red's Eats, Wiscasset, Maine
Red's Eats, Wiscasset, Maine

Red's Eats has been voted as the best Lobster rolls in Maine and has been featured on numerous travel shows like Somebody Feed Phil. You can expect to wait up to 2 hours to order here with long queues forming daily. If you don't want to wait, located right across the road is Sprague Lobster which we opted for and was the best lobster rolls we had of the trip. Be sure to order it with the melted butter.

After lunch take a de-tour drive through Bailey Island, stopping to enjoy the coastal walks and views.

Bailey Island, Maine
Bailey Island, Maine

Evening Day 2:

Have dinner at The Honey Paw (Asian Fusion) or Via Vecchia (Italian Food) in Old Port depending on what you are feeling like. If you can we recommend making a reservation in advance.

The Honey Paw:

Via Vecchia:

Day 3: Portland Head Lighthouse, Fort William Park, and Peaks Island

Morning Day 3:

Have breakfast in Old Port, picking up pastries from The Standard Baking Co (expect a queue if visiting over the weekend so arrive early) or the Holy Donut (Amazing potato-based donuts, their salted chocolate is their best seller).

The Holy Donut, Portland, Maine (Salted Chocolate & Vanilla)
The Holy Donut, Portland, Maine (Salted Chocolate & Vanilla)

Drive 20 minute south to explore Fort William Park and Port Headland Lighthouse. Be sure to take some of the coastal walking trails while there.

Portlandhead Lighthouse & Fort William Park
Portlandhead Lighthouse & Fort William Park

Have lobster rolls for lunch in Fort William Park from the Bite Into Maine food truck (Also featured as one of the best eats in Portland on Somebody Feed Phil).

Maine Lobster Roll (With Mayo & Chives) from Bite Into Maine food truck at Fort William Park
Maine Lobster Roll (With Mayo & Chives) from Bite Into Maine food truck at Fort William Park

Afternoon Day 3:

Take the ferry from Casco bay to Peaks Island, It's just a 15 minute ride across, with the ferry running around every hour

Getting around Peaks Island: The island is 4 miles around, and will take about 2 hours to explore. You can rent a bike from Brad's located just a 5 minute walk from the ferry terminal for $20 for 2hrs. Alternatively you can also rent golf buggies on arrival too for around $90 an hour, be sure to pre book these before your visit as they sell out (Try Peaks Island Rental).

Places to see: don't miss the Battery Steele and Civil War Museum.


Have dinner at the High Roller Lobster Co, for more amazing lobster rolls, the fresh oysters are great there too.

We hope you enjoyed our long weekend travel guide to Portland, Maine. To see more of our other USA destination guides click here.



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Little Sherpa Travels, Portland, Maine, USA travel guide



OUR AIM: is to help more people experience the world in just a weekend. We hope through sharing our easy-to-follow short break and weekend travel guides we can inspire others to make the most of their weekends and precious annual leave.


WE ARE: An Australian and British married couple living in Australia, which we recently moved back to after 7 years exploring Asia. By week we manage data forecasting and engineering projects. By the weekend we wander. This is the story of our weekend travels. We are passionate travellers who love taking photos, eating and going on adventures.  We hope you enjoy our travel blog.


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