Ready to discover the magic of this charming coastal gem? Here is your ultimate Portland, Maine itinerary!
The temperatures here on the East Coast are getting warmer, the snow is melting away, and the flowers are starting to bloom … spring time is here and all of this means it’s time to start planning your trip up the New England Coast with your destination being the picturesque seaside city of Portland, Maine!
Hands down one of my favorite places to visit here in the US, the Maine Coast is in a category of beauty all of its own. There are lighthouses standing tall against the rugged coastline, lobster boats bobbing in the harbor, and a salty sea breeze that fills the air as you walk down the cobblestone streets of the Old Port.
If I have a choice, I usually prefer to explore new destinations each time I travel. However, I look forward to going back to Portland over and over again. Each time I do, I discover something new and exciting and am reminded why I fell in love with this city.
Everything from lobster to craft beer, Portland is an exciting city that just may have you wanting to pack your bags and move here. At least, that’s what it did for me!
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Short on Time?? Here are our Portland Maine Travel Highlights
Portland is a city with stunning ocean views, rich maritime history and the freshest seafood you will find. When you’re visiting Portland for the first time it may be difficult to pack all there is to do into a few short days.
This blog post is going to break down the best things to do so you can get the most out of your trip. Consider this your ultimate travel guide to Portland.
We will go over everything from the best places to get fresh seafood, which lighthouses to visit, the Maine Brewers Guild beer trail, where you should stay, and everything you need to know about Portland, Maine to make planning your trip a breeze!
Portland Maine Travel Itinerary
Whether you just have one day in Portland, Maine or are looking to enjoy a full weekend (or longer) in this coastal city, our Portland travel guide has you covered.
In my opinion, you should spend at least 2 or 3 days in Portland, Maine to give yourself time to explore the Old Port, soak in all of the scenic beauty and rich history, indulge in the fresh seafood, and fill up your itinerary with a bunch of fun activities.
My hope is that you will use this itinerary more as a list of suggestions that you can add to and/or eliminate so you can craft your own perfect getaway. I’m going to give you a 3 day itinerary in this blog post.
Day 1: Exploring Portland’s Charm
When I take a road trip, I like to arrive the night before, have a nice meal and get settled into my hotel. This way the next morning I can hit the ground running. But if you are arriving the morning of Day 1 that’s okay, just customize this day as you see fit.
Day 1 is going to be all about exploring Portland’s charm.
Breakfast
Becky’s Diner: For your first day, we are going to start at this iconic diner with views of the waterfront. Be prepared to wait for a seat, but it’s worth it.
AM Activity: Lighthouses
When you think of Maine, the first thing that probably comes to mind are lighthouses, more specifically Portland Headlight. I guarantee you have seen a picture of it sometime in your life, even if you don’t know that’s what you’re looking at. This is one of the most photographed lighthouses in the world and the oldest lighthouse in the state of Maine.
It sits on Maine’s rugged coastline in Cape Elizabeth, located about 15 minutes from downtown Portland. It is the epitome of New England charm with gorgeous ocean views, an old military fort, and Fort Williams Park where you can picnic, fly a kite, and let the kids run around.
All of Portland’s lighthouses offer a sense of historical charm and are perfect for a quick visit while exploring Portland.
If you don’t have time to visit all of these and want to pick just one, my top pick is Portland Head Light.
There are 5 other lighthouses, all within 15 minutes of downtown Portland, that you should also be sure to check out during your travels.
- Bug Light – properly known as Portland Breakwater Light, it gets its nickname from its small size and offers views of downtown Portland. This lighthouse guides ships from Casco Bay into the Portland Harbor.
- Spring Point Ledge Light – the claim to fame here is that you can walk the breakwater rocks to the tower and be greeted with sweeping views of Casco Bay.
- Two Lights State Park – although these lighthouses are not open to the public, they are still worth it to check out while in Cape Elizabeth. They were the first twin lighthouses built on the Maine coast and the eastern light is still active (the western one is now a private home).
- Ram Island Ledge Light – you cannot directly access this lighthouse, but it can be seen from Portland Head Light and on a boat tour. This is the oldest looking lighthouse on this list and it adds a bit of mystery as the waves crash against it on all sides.
- Halfway Rock Lighthouse – This lighthouse sits on an island and not accessible, so your best bet to see it is on a boat tour like the one I have linked below.
Want to see all of these lighthouses?
Consider taking THIS TOUR HERE where you can see all of the lighthouses on this list by boat!!
Lunch
Since you’ll be out and about exploring, grab a fresh lobster roll from Bite Into Maine in Fort Williams State Park when you are visiting Portland Headlight. It’s said they have the best lobster rolls in town. You can choose between Maine Style which is cold and tossed in mayo or the Connecticut style which is served hot with melted butter.
If you don’t get a chance to have these lobster rolls today, or maybe you just want to have them a second time during your visit to Portland, you will have another opportunity to stop by their food truck at Allagash Brewery (which we will talk about on Day 2).
PM Activity: Boat Tour
There may not be a better way to see Portland than from the water. This afternoon, let’s set out on a coastal exploration and cruise around the bay on a boat tour.
There are so many boat tours that you can choose to take here in Portland depending on your area of interest. Let’s briefly go over a few of them.
Casco Bay Lines – They offer all different options from ferry rides to the islands, sunset cruises around the harbor, to the popular mailboat run which stops at all of the islands during its actual mail route. Many of their options are operated year round and allow you to pack your own refreshments for a picnic. You can just cruise around or make this into a day trip.
Pro Tip: if you take the ferry to Peaks Island, be sure to do some sea glass hunting, because it’s just super cool when you find it.
Lucky Catch Cruises – my personal favorite. You will embark on an authentic lobster fishing experience where you can participate in hauling traps, handling the lobsters, and learning about the local lobster industry. You may also get to see some seals! This adventure will take you past all of Portland’s famous lighthouses and you may even get to see some seals! This hands-on adventure is perfect for families.
Pro Tip: You can purchase the lobsters and take them to the restaurant next door for cooking! You won’t get much fresher than that.
Rocky Bottom Fisheries – Another fun lobster excursion. They also offer sunset cruises that are BYOB with music and fresh lobster rolls.
Maine Duck Tours – This is a great way to explore Portland by sea AND land. This unique narrated 60 minute tour will take you around the major highlights of the city and into the water of the Casco Bay.
Portland Schoonover Co – Sail on an iconic windjammer with a glass of your favorite wine (because they are byob!)
Dinner
We are going to wrap up Day 1 with a meal at D’Millo’s On the Water. This floating restaurant offers fresh catch seafood and beautiful harbor views. You’ll want to make a reservation in advance.
Alternative Option: If you chose to take the ferry to Peaks Island, consider having dinner at the Inn on Peaks Island.
Day 2: Portland's Craft Beer Scene
Portland has one of the best craft beer scenes in the country. With 165 different breweries in the state, it will be hard to pick your favorite.
Breakfast
Today we are going to opt for a lighter breakfast because we are going to have an early lunch! I suggest going to Holy Donut to try their famous potato donuts – a Maine staple. There are 4 locations around the city, but if you go to the one on Commercial St you will be on the waterfront.
If potato donuts don’t sound like your cup of tea, you can always try Coffee by Design or Tandem Coffee Roasters for a quick bite and a caffeine boost
AM Activity: Shop and Explore the Old Port
Even though you’re going to spend a majority of the day immersing yourself in Portland’s craft beer scene, I don’t want you to start out too early so we are going to add in a casual morning activity – exploring the Old Port.
Unless you want to start out early – it’s 5 o’clock somewhere right?
Spend your morning wandering through Portland’s historic Old Port district located right on the waterfront. You can walk along the cobblestone streets that are lined with red-brick buildings, boutiques, cafes, art galleries, restaurants, and bars.
Commercial St (the waterfront) and the Old Port is the best area to go shopping in Portland Maine. You’ll find places such as Shipwreck & Cargo or The Blue Lobster for gifts and souveniers, Portland Dry Goods and other clothing boutiques, and of course, Sea Bags where you will find recycled sails turned into tote bags.
Insider Tip: the souvenir shops on Commercial St are going to be the most expensive. If you walk up even one block the prices get significantly cheaper the further up you go. Think $20 for a t-shirt vs 3 for $18.
If you’re up for a short drive, you can visit the LL Bean flagship store in Freeport, ME – about 25 minutes north of Portland.
Lunch
I am so excited for this part of your trip because this is my favorite place to eat in Portland!! If you know me, you won’t be surprised to know that it’s a pizza place.
I’m talking about Flatbread Company located on the waterfront on the far end of Commercial St right before the parking garage for the ferries. So if you are standing on Commercial St and looking at the waterfront, it will be all the way at the end on the left.
This restaurant is super family-friendly and they serve organic wood-fired pizzas with locally sourced, organic ingredients.
PM Activity: Maine Brewers Guild Beer Trail
Portland is a dream for craft beer lovers and has over 30 breweries in the greater Portland area alone each one with its unique flavors and styles.
This doesn’t include the rest of the 130 or so scattered throughout the state, so if you are visiting any other parts of Maine be sure to make some stops along your way.
The Maine Brewers Guild has put together an awesome beer trail. Their website is a great resource for you to pick the breweries you want, map out your own personalized trail, and filter out breweries by the area you are visiting.
They also have a Beer Trail Passport where you get a passport stamp for each brewery you visit. When you’re all done, you turn it in for prizes! I’ve done this twice and it’s such a fun time!
Several breweries offer tours (like this one we did here in STL) so you can see behind the scenes just how your favorite brews are made as well as some exlusive tastings.
A few of the most popular breweries in Portland Maine are:
Allagash Brewing Company
Rising Tide Brewing Company
Sea Dog Brewing Company
Shipyard Brewing Company
Want to visit several of Portland’s breweries but don’t want to drive? I’ve got you covered!
Take the Maine Brew Cruise tour so you can drink in the scene and the local brews.
Dinner
If you’re having too much fun on the beer trail and aren’t quite ready to quit, there are several breweries that double as pubs serving food such as Sea Dog Brewing Company and Gritty McDuff’s.
But if you’re in the mood for a more relaxing atmosphere for dinner, consider dining at Eventide for some fresh seafood and oysters.
Day 3: Outdoor Activities, Relaxation, and Local Exploration
Breakfast
You can’t miss grabbing a bagel from Scratch Bakery while in Portland. Get there early though, because their bagels will sell out super fast.
However, if you are in the mood for more of a sit down breakfast/brunch, I suggest you try Sinful Kitchen for one of their waffle pizzas or a “friends with benedict”.
AM Activity
On your last day in Portland, I want to give you options for local exploration and relaxation.
Walking Trails
If you are looking to relax and take in the views, I suggest you take the time to walk around one of Portland’s best parks: Eastern Promenade Waterfront Park. There are wooded and paved walking trails, over the 68 acre park with Casco Bay and the harbor as your backdrop.
If you are staying on the East End of Portland, don’t skip a morning walk on the Back Cove Trail. We stayed over in this area in an Airbnb on a past trip. The locals love it here and you will often see them running, walking, and biking. The trail is about a 3.5 mile loop with lovely views of the city skyline.
Portland's Beaches
Although the water is cold all year round (not usually getting above 64 degrees at its peak of summer) Portland still has several beaches, even though swimming isn’t necessarily the most popular thing to do here.
People mostly enjoy sunbathing, exploring, and searching for crabs, sand dollars, and more.
The most popular beaches in, and near, Portland Maine are:
East End Beach: This beach is located on Portland’s Eastern Promenade. The beach is small and sandy and is a popular spot for kayaking and paddleboarding.
Willard Beach: If you go across the bridge into South Portland, you will find the local favorite: Willard Beach. It offers a beautiful view of Casco Bay and is a small, charming, sandy beach perfect for picnicking. It is a great spot for families and they often have a lifeguard during the summer months. They do have a free parking lot
Scarborough Beach: If you want to brave the cool waters and go for a swim, this is your best place to do so. This beach has a long, sandy shoreline and gentle waves. You will often find people here surfing, bodyboarding, and fishing. You will have to drive to get here.
Crescent Beach: You will find this beach in Cape Elizabeth (the same town where Portland Headlight is located). There are grassy areas with picnic tables and walking trails that wind through the grass dunes making this a peaceful and scenic spot for a walk.
Higgins Beach: Located in the town of Scarborough, about a 20 minute drive from Portland, this hidden gem is an excellent beach to explore. At low tide, you can see the remains of a shipwreck.
Old Orchard Beach: Although this is about a 25 minute drive outside of Portland, it is home to Palace Playland which is an awesome place for families traveling with children. It is a seaside amusement park with the largest arcade in the state of Maine, over 25 rides, and lots of events during the summer (think a fireworks show over the ocean).
Lunch
Today, let’s have lunch at a local favorite: Duckfat. You can’t miss the famous fries that are fried in, yep you guessed it, duck fat.
They have a Frites Shack that is a walk-up counter, or you can dine in at their brick-and-mortar location. The fries are hand cut and made from locally sourced ingredients and they have a really great sandwich menu as well.
PM Activity
Portland Observatory – Climb to the top for panoramic views of the city, the harbor, Casco Bay, Halfway Rock Lighthouse, and even catch a glimpse of the White Mountains of New Hampshire and Mt. Washington.
Here you can learn about Portland’s maritime history and why its unique design has helped it withstand over 200 years of weather and use being that this is the last wooden signal tower on the entire continent!
Cryptozoology Museum – For one of the most unique things to do in Portland, Maine, you will want to stop by the International Cryptozoology Museum. Cryptozoology means “the study of hidden animals” so you will be immersed into a world of the unknown. Think Big Foot and Nessie.
You’ll see exhibits of artifacts, eyewitness accounts, footprint casts and so much more. This is the world’s only cryptozoology museum so it is a one-of-a-kind destination, and a hidden gem to Portland, for anyone interested in cryptids.
This is a great activity for those traveling to Portland with kids because they provide educational and informative displays from a scientific perspective, folklore, and historical context.
Dinner
I can never get enough lobster when I am in Portland and one of my favorite places to go is Portland Lobster Company.
Much like the rest of Portland, this spot has a casual, laid-back dining atmosphere right on the waterfront. They have live music, local beer on tap, and it is a counter-service restaurant.
Of course, the lobster roll is what they are known for, but don’t skip over the rest of the menu (like the clam chowder or the fried shrimp!).
Insider Tip: We have visited Portland in all different seasons, and as the weather starts to get cold, they offer outdoor, heated seating.
After Dinner Activity
For a fun activity for the whole family, be sure to check out a Portland Sea Dogs baseball game. They are the minor league affiliate to the Boston Red Sox and they play from late April through the beginning of September. They have all sorts of contests, games, events, and entertainment throughout their season.
But if you’re not a sports enthusiast, or maybe you’re visiting Portland in the fall or winter, consider a visit to the Portland Museum of Art. There is an impressive collection of over 18,000 pieces including works from famous artists such as Claude Monet, Pablo Picasso, and Andy Warhol.
Exploring the smaller art galleries in the Arts District can be a romantic thing to do in Portland Maine if you are traveling with your partner, and certainly one of the best free things to do in Portland.
There are several performing arts venues, galleries and independent studios, historical homes, such as that of poet Henry Wadsworth Longfellow, and festivals and events throughout art district bringing this area of Portland to life. You can expect to find a dynamic mix of all art forms here.
Other Fun Portland Activities
I wanted to give you a 3 day itinerary for Portland with all of the can’t miss attractions and things to do. However, there are a few more things to do that I wanted to add in and to give you options in case any of the ones listed above did not resonate with you or peak your interest.
Cap ‘n Fish Cruises – Although this activity is located about 1.5 hours away from Portland at Boothbay Harbor, this is a great day trip destination where you can head out on the water and see puffins and whales.
Looking for a whale watching tour that leaves right from Portland?
Rippin Lips Charters – their “Fish Lips Deep Sea Fish” charter is geared towards kids giving them an enjoyable and memorable first deep sea fishing experience.
Go for a scenic drive up Highway 1 – If you are looking to experience the rugged beauty and charming small towns that line Maine’s coast, consider taking a drive up Highway 1. You can just drive and soak in the panoramic views of the Atlantic, or stop and explore whenever you feel called to along the way.
Unlike the breathtaking PCH in California, this route is NOT going to give you ocean views the entire time.
Portland Freedom Trail – Besides visiting Portland’s beaches, one of the best free things to do in Portland is the Portland Freedom Trail. This is a self-guided walking tour that highlights significant sites around the city related to the Underground Railroad. You will find markers along your journey that tell the stories of notable figures and events that took place on this fight for freedom.
Note: Remember to do the Freedom Trail when in Boston too!!
Portland Maine Tours
Portland has some awesome adventures where you can just kick back and relax. These range from whale watching, sunset sails, foodie tours, and a super cool fort only accessible by kayak.
Want to read more about what tours are available in Portland? CLICK HERE.
Best Restaurants in Portland Maine
I know we have gone over some of these already in the previous sections, but just in case you skipped through to this part, let’s quickly go over where to find the best food in Portland Maine.
For reference, Commercial St is where you will find lots of restaurants and bars. The locals frequent here just as much as tourists do.
Best Breakfast and Brunch in Portland
- Holy Donut: a Maine staple made with potatoes with 4 locations across the city.
- Becky’s Diner: a local favorite right on the waterfront
- Sinful Kitchen: a great brunch spot with fun things on the menu like waffle pizzas
- Hot Suppa: a cozy restaurant serving hearty, southern-inspired dishes
- Little Taphouse: a cozy, rustic space with a small menu, local beer on tap, and daily happy hour specials.
Best Cafes in Portland Maine
- Scratch Bakery
- Tandem Coffee Roasters
- Coffee by Design
Best Lunch and Dinner Spots in Portland
- Flatbread Company: the best spot in town for wood-fired pizza with locally sourced organic ingredients
- East Ender: known as a local favorite, the vibe here is very laid-back and they have a geat drink menu.
- Izakaya Minato: high-end Japanese cuisine with local Maine ingredients
- Local 188: a very hip and romantic Spanish restaurant. They also serve brunch on the weekends.
Portland Maine’s Waterfront Restaurants
During your trip to Portland, you will want to be sure to have dinner on the wharf at least once during your trip.
- Portland Lobster Company: a very popular spot with limited indoor seating and an outdoor tent. This is a counter-service restaurant and they will bring food to your table. The lobster rolls don’t get much fresher than this.
- D’Millo’s On the Water: a floating restaurant is on everyone’s bucket list when in Portland. Be sure to make reservations.
- Gilbert’s Chowder House: serving up the best clam chowder in town.
- Scales: fresh seafood on the waterfront with oysters on the half shell all locally caught. Menu rotates seasonally.
Best Snacks and Desserts
- Coastal Creamery: they serve up some awesome ice cream sandwiches
- East End Cupcakes
Places to Stay in Portland
If you see any of these hotels you like, just click the links to book!
Step out the front door of this hotel onto the cobblestone streets of the Old Port. offers a prime location within walking distance to bars, restaurants, downtown shopping, and the waterfront.
A newly renovated luxury hotel located in the Old Port downtown with rooms overlooking the harbor. You can’t beat the location of this hotel if you want to be in the heart of downtown.
This boutique hotel is filled with historical charm yet modern amenities. There are 15 rooms available in this renovated historic mansion.
Courtyard Portland Downtown/Waterfront
Provides easy access to the waterfront with restaurants and shopping in walking distance.
FAQ
When to Visit Portland
Spring is when everything starts to come back to life in Portland. If you have other places in New England, such as Newport, Rhode Island for the daffodil days, on your radar I think it’s definitely worth taking a day trip to Portland.
Portland Maine in June, July and August is going to be the time of year tourist flock to the Maine Coast. Hotel prices increase and so do restaurant wait times. Your chances of taking a photo without someone else in the background at some of the major tourist spots is slim to none. But, this time of year offers the best temperatures to do all there is to do outdoors.
A visit to Portland Maine in fall is definitely worth it if you are planning a road trip up the New England coast to see the foliage. The weather in September will average in the upper 60’s to low 70’s, but October brings much cooler temps.
If you are contemplating heading up to Portland Maine in the winter, I think it can offer a beautifully different perspective of this city that comes alive in the warmer months. You’ll find the waterfront much less crowded and the town a lot more quiet. Breweries are still open in the winter with places like Allagash offering campfires and outdoor heated areas.
How to Get to Portland Maine
The closest airport is Portland International Jetport (PDX). However, many people choose to fly into Boston Logan International Airpot (BOS), rent a car, and enjoy the drive to Maine.
If you are driving, here are some of the distances from some of the major tourist destinations in New England.
Boston, MA to Portland Maine – 1 hour 45 min
Portland Maine to Bar Harbor Maine and Acadia National Park – 3 hours
Portland Maine to Newport, Rhode Island – 3 hours
Portland Maine to North Conway, NH – 1 hour 25 min
Portland Maine to Stowe, VT – 3 hours 50 minutes
Portland Maine to Burlington VT – 3 hours 45 min
Portland Maine to NYC – 5 hours 35 min
As you can see, Portland makes a great day trip from many of New England’s popular destinations.
Related Posts:
Lake Winnipesaukee and Mill Falls at the Lake
A Perfect Weekend in Mystic, CT
A Weekend in Newport, Rhode Island
Is Portland a Walkable Town?
Yes! Portland is a very walkable town. There are plenty of restaurants, shopping, and historical sites that are all within walking distance from the Old Port and the waterfront.
I find that even though you are downtown in a city, traffic always yields to pedestrians crossing the street and I felt very safe with my children when walking around.
Can you do a day trip to Acadia National Park from Portland?
You can do whatever you want, friend!! The drive from Portland to Acadia is going to be about 3 hours, so it will make for a long day (6 hours total driving on the road) especially if you are traveling with small children.
However, if you want to go for a day trip, have a nice meal and see a few of the most popular sites in Acadia I say it’s definitely doable.
Conclusion: Is Portland Worth Visiting?
Portland is a city that will keep you coming back time and time again. Whether here for a quick visit to just see the highlights or a long weekend trip, this itinerary offers you a balance of cultural experiences, outdoor activities, and the best seafood around.
I hope this Portland Maine itinerary was helpful in planning your trip to this Southern Maine city on the Casco Bay.
