Portland Maine Itinerary: Top Things To See and Do

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Maine is one of my favorite states in the US. I love the coast, the seafood, and the historic lighthouses. There are a lot of seaside towns to visit along the coast of Maine but one of the best cities in Maine for a true city vibe is Portland. Although still pretty small, it’s Maine’s largest city, situated along a peninsula extending into Casco Bay. Portland is known for its working waterfront, historic Old Port, lively arts community, and buzzing culinary scene.  

Between all the galleries, museums, bars, restaurants, lighthouses, boat tours, and day trips possible from the Portland area, you could spend a couple of weeks in the city and not get bored. If you at least have a long weekend, you can enjoy a lot of what this vibrant city has to offer.

I’ve been to Portland a few times, staying for two or more days at a time, and have also used it as an overnight stop while on some longer New England road trips. There are a few good spots to car camp in Portland and a Planet Fitness right in town-car campers will know how valuable that one is!

In this post, I’m sharing some of my favorite things to do in the city that will help you plan a two-day (or more) itinerary for visiting Portland.

The Best Things To Do During a Portland, Maine Itinerary

One thing to note: South Portland is located immediately southwest of the city of Portland, across the Fore River. Although it is not a part of the city of Portland, South Portland is another excellent area to explore. It sits along Portland Harbor and offers access to Casco Bay, beaches, and the surrounding islands, as well as many green spaces, and is home to the iconic Portland Head Lighthouse. I tend to talk about South Portland like it is a part of Portland, so I just wanted to clarify. I spend a lot of time in this area when I travel solo to Portland because of the views, quaint neighborhoods, and neighborhood feel.

Enjoy Portland’s Neighborhoods

I can easily fill a day just walking around the city’s neighborhoods. They are filled with scenic views and old-time charm with shops, restaurants, and bars. There are a lot of fun areas to explore in Portland, with some of my favorites including Munjoy Hill, East End, West End and the Old Port.

The East End/Munjoy Hill

Located on the eastern side of Portland, these two areas but up to one another and feel the same to me. The highlight of this area is the Eastern Promenade Park, which wraps along the waterfront and offers walking and biking trails, picnic areas, playgrounds, and green spaces for recreation and relaxation. Enjoy beautiful views of Casco Bay while ship-watching along the harbor. I love going for early morning or evening strolls in this area. While you have to be aware, I’ve always felt safe here walking alone at dusk.

The Old Port District

Your Portland, Maine, itinerary would not be complete without exploring the Old Port District, one of the last active-working waterfronts in America. This is also one of the largest fishing ports in the US, which is why Portland is abundant with wonderful fresh seafood.

This district is full of unique charm where you will be able to see historical buildings and walk along cobblestone streets. This setting is beautiful at any time of the year, but the summer period is known for its lively atmosphere (which translates into larger crowds). 

Walking around Portland’s Old Port district is the best way to get to know the city. Walk down the different streets, each offering a unique atmosphere enriched with an array of shops, eateries, and so much more! Commercial Street is the most popular street in the Old Port Downtown area, where the largest number of bars and activities are located. For fashion boutiques and gift shops, head to Exchange Street, immerse yourself in Portland’s history on Wharf Street, and stop by Fore Street for ice cream at Gorgeous Gelato.

The West End

Welcome to the quiet side of Portland with tree-lined streets and lovely architecure. This neighborhood shines with Victorian mansions and has a more residential feel. A highlight of the West End is the Victoria Mansion, an Italianate brownstone mansion renowned for its lavish interiors and architectural beauty built between 1858 and 1860.

Enjoy Art Galleries and Museums

If you feel like slowing down and enjoying a day inside, check out some of Portland’s most notable museums. Portland offers a variety of cultural and historical institutions that cater to different interests, ranging from art and history to maritime heritage and science.

Maine Historical Society Museum

This museum offers a comprehensive look at Maine’s history through exhibits, artifacts, and interactive displays, providing insight into the state’s past and cultural heritage.

Victoria Mansion

Also known as the Morse-Libby House, this historic mansion is a stunning example of pre-Civil War architecture and offers guided tours showcasing its opulent interiors and decorative arts. It is a National Historic Landmark.

Wadsworth-Longfellow House

This historic house museum was once the childhood home of poet Henry Wadsworth Longfellow and provides a glimpse into life in 19th-century New England

Portland Museum of Art

Located in the art district, The Portland Art Museum is the oldest and largest public art institution in all of Maine. This museum displays more than 20 thousand works by various authors, including Andy Warhol, Winslow Homer, and Claude Monet.

Portland Observatory

Nestled proudly on Congress Street, the Portland Observatory stands as a towering symbol of the city’s rich maritime history. At over 200 years old, the 86-foot octagonal-shaped maritime signal tower is the sole surviving structure of its kind. It was once a vital communication hub, its telescope and fluttering flags helped identify ships up to thirty miles away, ensuring timely arrivals and departures. Guided tours are offered from May to October, where you can access the tower and see as far as Mount Washington in New Hampshire on a clear day.

Try Local Flavors

Visiting a new city also means diving deeper into local cuisine. If you love sea food, Portland has you covered. From fresh lobster dinners at The Porthole to steamed clams and chowder and Gilbert’s Chowder House, Portland is a seafood lover’s dream. Expect menus with fresh lobster rolls (try Portland’s famous brown butter lobster roll from Eventide Oyster Co. for a unique take on a New England classic), lobster bisque, lobster mac and cheese, and other creative lobster dishes throughout the city, along with seafood chowders, clams, and oysters. 

Beyond seafood, Portland has gained recognition for its farm-to-table dining establishments, where chefs prioritize locally sourced ingredients to create innovative and flavorful dishes. The city’s culinary scene also encompasses a variety of international cuisines, including Italian, Thai, Mexican, and more. Food festivals and events, such as Harvest on the Harbor and the Maine Lobster Festival, showcase Portland’s culinary talents while drawing food enthusiasts from near and far. 

Another speciality unique to Maine is Holy Donut. It’s a Portland staple with the best potato donuts in the state. These donuts come in multiple flavors and varieties, so one is never enough! There are two locations around the city, one on Commercial Street and one on Park Ave. Both locations close once they sell out, so getting there before noon is recommended.

Relax at a Brewery or Beer Café

While Portland, Maine, has become a culinary destination, it also made a name for itself in the craft brew scene. The city is home to numerous breweries, brewpubs, and taprooms scattered throughout its neighborhoods. Portland’s craft beer culture is characterized by its creativity, quality, and diversity of offerings. Many local breweries pride themselves on using high-quality ingredients and experimenting with various brewing techniques to produce unique and flavorful beers.

Some of the best breweries in Portland include Oxbow Blending, whose specialties include barrel-aged and blended beers; Allagash Brewing Company, known for its Belgian-style ales; Bissell Brothers Brewing Company, recognized for its hop-forward IPAs; and Rising Tide Brewing Company, which offers a diverse range of handcrafted beers. The Novare Res Beer Café welcomes you with a family friendly atmosphere and serves up an ambiance reminiscent of international beer gardens to go along with their healthy selection of brews. 

Take a Boat Ride in Casco Bay 

For a different perspective of the city, head out on a boat ride along Casco Bay. It’s the perfect afternoon activity to add to your Portland, Maine, itinerary. You will have the opportunity to see some of the islands around Portland, such as Little Diamond, Great Diamond, Cliff, Chebeague, and Long Island.

Casco Bay Lines offers a variety of boat tours, including sunrise and sunset rides, concert cruises, and more. You even have the opportunity to ride an active mail boat carrying freight and mail to the surrounding islands. Casco Bay is an excellent area for a whale-watching adventure if you are visiting in summer to early fall. Between May and October, you’ll have a chance to see humpback, Minke and fin whales, along with other exciting wildlife. 

Visit Peaks Island 

Peaks Island is one of the many islands located in Casco Bay, just off the coast of Portland, Maine. It’s the most populous island in Casco Bay, with a vibrant community known for its creative atmosphere. It offers residents and visitors a charming retreat from the hustle and bustle of mainland life. 

A scenic ferry ride will get you there in 20 minutes. Enjoy recreational activities, including biking, hiking, kayaking, and swimming at one of the several beaches around the island. Caso Bay also offers parks and trails for outdoor enthusiasts to explore and is a great day trip for history lovers. Its rich history dates back to the colonial era. During World War II, the island served as a strategic military outpost, with forts and gun batteries still visible today. Visitors can explore these historic sites and learn about the island’s role in defending the coast.

See Some of Maine’s Best Lighthouses

Maine is known for its picturesque coastline and historic lighthouses. There are at least 65 lighthouses along the coast of Maine with some of the most iconic ones right along Portland’s coast. Although they are just outside of Portland City, all of these lighthouses are great options to add to your Portland, Maine itinerary. 


Spring Point Ledge Lighthouse

This lighthouse was first lit in 1897 and continues to operate today as an active aid to navigation. Its light, visible for up to 8 nautical miles, helps guide ships safely through the main shipping channel of Portland Harbor. It’s a beloved landmark in south Portland and offers tours to the public during certain times of the year. Walking along its breakwater is the perfect way to enjoy a sunset over Casco Bay!


Bug Light Park

Bug Light Park, adjacent to Spring Point Ledge, is a lovely green space for enjoying views of the busy Portland Harbor. Bug Light, also known as Portland Breakwater Lighthouse, was built in 1875 and sits on the edge of the park. Its unique design and position at the mouth of the harbor attract tourists who love watching the ships come in. It’s a great spot to relax and unwind after a busy day of seeing Portland. 


Portland Head Lighthouse

Portland Head Lighthouse is arguably the most iconic lighthouse in the US. It’s the oldest lighthouse in Maine, with a history dating back to 1791. Located in Cape Elizabeth, in Fort Williams Park, this lighthouse has gated access and is open year-round from sunrise to sunset. Enjoy the Portland Head Light Museum in the former keeper’s house, walk along the grounds, and snap a photo of this beauty from the scenic coastal trails nearby. 

Enjoy a Day Trip

If you feel like getting away from the city, you are in good hands as Portland, Maine, is in a great location to enjoy more of what the Pine Tree state has to offer. There is something for everyone, from excellent beach towns and Acadia National Park to cozy fishing towns and lighthouse tours.

Acadia National Park in Bar Harbor

If you’re a nature enthusiast, Acadia National Park in Bar Harbor is the perfect day trip from Portland. Since it is 3 hours away, it would make a better overnight trip so you can have more time to hike, enjoy the scenic Park Loop Road, and also be the first in the US to watch the sun come up over Cadillac Mountain, but if a day is all you have, you can make the most of your day by getting an early start to avoid the crowds.

Visit in the shoulder season, April, May, October, or November, to have an easier time parking while enjoying your day in Acadia. While multiple days are best for Acadia, with only one day, you can still enjoy a walk through downtown Bar Harbor, drive Park Loop Road, face your fear of heights along Precipice Trail, and soak up the views along the coast. 


Located about a forty-minute drive from Downtown Portland, is one of my favorite seaside towns in Maine, Kennebunkport. Its got historic charm, picturesque scenery, and a vibrant seaside atmosphere. You can spend a day strolling down its quaint streets lined with shops, galleries, and seafood restaurants, head to its beaches, or enjoy outdoor activities like hiking and kayaking. Kennebunkport is the perfect blend of relaxation and adventure!


Just a litter further than Kennebunkport is Ogunquit, another charming seaside town in Maine and a great option for a day trip from Portland. Known for its rich artistic heritage and scenic coastal views, you can spend the day along its sandy peninsula, where locals and visitors love to enjoy the sun and surf, head to Perkins Cove, a charming fishing village known for its scenic harbor, boutique shops, and art galleries. Don’t skip a walk along the stunning cliff walk, Marginal Way. At just over a mile, it stretches along the coast to Perkins Cove and makes for a spectacular scenic walk. 



Under an hour from Portland is one of Maine’s most Iconic landmarks, The Nubble Lighthouse, located on Cape Neddick. This light has been used to navigate ships since 1879 and is still in use today. Nubble Light is the main reason why visitors come to York, but this charming coastal Maine town has so much more to offer.

York boasts several beautiful beaches, including Long Sands Beach and Short Sands Beach, which offer opportunities for swimming and sunbathing during the summer months. You’ll have opportunities for outdoor recreation, including hiking, biking, kayaking, SUP, and fishing. Nature lovers will enjoy the panoramic views and trails in the nearby Mount Agamenticus Conservation Region. If you time you visit right, you’ll be able to enjoy the artistic side of town with an art festival or cultural event, including art shows, music concerts, and historical reenactments. 


I hope you enjoy your time in Portland and found this post helpful in planning your Portland, Maine itinerary!

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