Your Guide To A Perfect Portland Maine Itinerary: Experience Coastal Charm

Headed to Portland Maine? Don’t forget to add these stops to your itinerary!

On the rocky shores of the East Coast of the United States is Portland, Maine.

This vibrant city, nestled on the stunning shores of Casco Bay, offers a perfect blend of natural beauty, rich history, and a thriving culinary scene.

From picturesque lighthouses and scenic coastal trails to a bustling and historic downtown, Portland has something for everyone.

If you are looking for your next great East Coast trip, Portland Maine might be just the spot!

About Portland Maine

Founded in 1632, Portland boasts a captivating past that includes Native American settlements, European explorers, and a bustling maritime trade. As one of the oldest cities in the United States, it has witnessed significant historical events, including the American Revolution and the War of 1812. The city’s maritime heritage is evident in its well-preserved 19th-century architecture, charming cobblestone streets, and vibrant working port and waterfront.

Portland is also home to the Portland Head Light, one of the most iconic lighthouses in the country. It has stood proudly on Cape Elizabeth since 1791, guiding ships into the harbor for centuries. Today, Portland blends its rich history with a thriving arts and culture scene, evident in its numerous art galleries, museums, and music venues.

How Many Days Do You Need To Visit?

While it’s possible to experience some of the city’s highlights in a day or two, spending three to four days will allow you to take your time and truly immerse yourself in Portland’s charm and discover its diverse offerings. With this timeframe, you can explore the city’s historic Old Port district, visit museums and art galleries, indulge in the local culinary scene, take scenic walks along the waterfront, and venture out to nearby attractions such as lighthouses, islands, and coastal towns.

Additionally, having a few extra days will provide you with the opportunity to engage in outdoor activities, such as hiking, kayaking, or exploring nearby nature parks. Whether you have a long weekend or a week to spare, you can tailor your visit to make the most of your time and create an unforgettable experience in Portland, Maine.

When Is The Best Time To Visit?

Our visit fell in the first week of June, as spring was slowly turning to summer, but just before the peak tourism season started. We were treated to mild temperatures, bright green scenery, and vivid flowers, but also a fairly consistent pattern of morning clouds and light rain. It is understandable to see why tourism peaks in the later summer where the weather is more predictable and sunny, but we felt the spring trade-off was perfect due to the smaller crowds.

As native New Englanders, we are well aware of how unpredictable weather can be in this part of the country, but here is a bit of what you can (possibly) expect in each season in Portland, Maine:

• Summer (June to August): Summer is the peak tourist season in Portland. The weather is pleasant, with average temperatures ranging from the 70s to 80s. This is the ideal time for exploring the city’s waterfront, enjoying outdoor dining, and taking part in festivals and events. However, it can be crowded, and accommodations may be more expensive. Advanced bookings are recommended.

• Fall (September to November): Fall in Portland brings beautiful foliage as the leaves change color, creating a picturesque setting. The weather remains mild, with temperatures gradually dropping. September and early October are particularly lovely, with fewer crowds. Fall is an excellent time for scenic drives, hiking trails, and enjoying seasonal harvest events.

• Winter (December to February): Winter in Portland is cold, with temperatures ranging from the 20s to 30s. While the city experiences a charming winter ambiance, it is quieter and less crowded. If you enjoy winter sports like skiing or ice skating, this is a great time to visit Maine and the Northeast. The city also celebrates the holiday season with festive decorations and events.

• Spring (March to May): Spring in Portland brings a gradual transition from winter to warmer weather. Temperatures start to rise, ranging from the 40s to 60s. Spring is a great time for exploring parks, gardens, and hiking trails as nature begins to awaken. It is also a quieter time to visit before the peak tourist season.

The Perfect Stops For Your Portland Maine Itinerary

As full-time RVers, we have been fortunate enough to explore many places in North America with our home on wheels. As avid hikers and nature lovers, we are drawn to destinations with great natural spaces to explore, rich history to learn about, and room to roam free.

With this, we rarely find ourselves in cities…and when we do, can admittedly be a bit out of our element. Not to mention, our dually truck sticks out like a sore thumb in the narrow downtown cobblestone streets of an old city like Portland, Maine.

While making our way up the coast of Maine toward Canada, we were pleasantly surprised at what we discovered during our week-long stay at this working port turned foodie heaven. We crafted our itinerary in a way that allowed us to explore the beautiful coastline that frames Portland against the Atlantic, while also enjoying some of the local delights.

Next we will break down some of our favorite stops during our visit, as well as provide a few examples of Portland Maine itineraries, depending on the time you have available!

Check Out The Local Lighthouses

While RVing up the East Coast, we admittedly found ourselves on a bit of a lighthouse tour. Portland Maine is no exception and matches the 6 major lighthouses of the Outer Banks of North Carolina, with 6 interesting lighthouses of its own!

Bug Light (Portland Breakwater Light)

Situated in South Portland’s Bug Light Park, the Portland Breakwater Lighthouse, also known as Bug Light, is a small yet charming lighthouse. Built in 1875, it stands at the end of a breakwater and offers a peaceful and picturesque setting. The park surrounding the lighthouse provides picnic areas, walking paths, and scenic views of Portland Harbor.

Cost: FREE! Park in the Bug Light Park parking area

Spring Point Ledge Lighthouse

Spring Point Ledge Light is known for its unique location at the end of a granite breakwater. This cast-iron lighthouse was built in 1897 and is connected to the shore by a walkable breakwater. Visitors can stroll along the breakwater to reach the lighthouse, providing an up-close view of this impressive structure and panoramic views of Portland Harbor.

Cost: FREE! Park in the Bug Light Park parking area or further down by the parking lots by the Port Harbor Marine and Fort Preble

Ram Island Ledge Lighthouse

Located offshore from Cape Elizabeth, Ram Island Ledge Light is a striking lighthouse that marks a treacherous reef near the entrance to Portland Harbor. It was first lit in 1905 and is visible from Fort Williams Park. While visitors cannot access the lighthouse directly, they can appreciate its beauty and significance from the park’s vantage points, including the viewing area of Portland Head Lighthouse.

Portland Head Lighthouse, Fort Williams Park

Also located in Cape Elizabeth, Portland Head Light is one of the most iconic and historic lighthouses in the United States. It was first lit in 1791 and stands at the entrance of Portland Harbor. The lighthouse is situated in Fort Williams Park, which offers stunning views of the rugged coastline and the picturesque Casco Bay.

This is the oldest lighthouse in Portland Maine and one of the most photographed lighthouses in the world! As such, you can expect this to be a busy spot. We visited on a weekday for sunrise before work and it was beautiful and not busy at all!

Cost: Parking is $2/hour with a minimum of 2 hours or you can purchase a full-day pass for $10.

Cape Elizabeth Twin Lights

The Cape Elizabeth Lighthouses (East and West) are historic lighthouses that once guided ships into Portland Harbor. These two lighthouses, known as the “Twin Lights,” were first lit in 1828 and are located on a headland in Cape Elizabeth. While they are no longer active, they serve as a fascinating reminder of the area’s maritime heritage.

You can choose to visit nearby Two Lights State Park (which charges an entrance fee) or you can find FREE parking at the end of Two Lights Road, where you can explore the surrounding area of rocks and a small stretch of beach on a rocky point on the gulf of Maine. This area, known as “On the Rocks at Two Lights”, offers beautiful coastal views over Dyer Cove and is a great spot for photography or a picnic.

There is a very popular seafood spot, The Lobster Shack at Two Lights, which has amazing ocean views, which can create a big uptick in cars around its lunchtime opening. The line was long only minutes after the 12pm openining! We recommend arriving earlier in the morning to avoid the rush and secure parking...and if you want to grab a bite to eat you can then also be ready to be one of the first in line!

Explore Off-Shore

Fort Gorges on Hog Island and Peaks Island are dominant features when looking out over the Casco Bay from the shoreline of Portland Maine. If you don’t have time, you can enjoy the sights most closely from Bug Light Park, or from a different vantage point in Old Port and downtown Portland.

If your schedule allows, you might even consider hopping on the Portland-Peaks Island Ferry and taking a day trip over to Peaks Island where you can explore the small island town with local gems including restaurants, art galleries, a museum, and the historic Battery Steele. We loved our experiences exploring little island towns like Bald Head Island and Ocracoke Island in North Carolina and have heard great things about Peak Island as well! We didn’t take the trip over on this trip, but here is a Peak Island itinerary you can check out!

Cost of the Ferry to Peaks Island: Passenger Ferry ($7.70/ Adult) and Vehicle Ferry Rates (starting at $62 during the peak season); 17-minute ride each way

Discover Old Port

The Old Port of Portland is a charming and picturesque neighborhood known for its cobblestone streets, 19th-century brick buildings, and bustling working waterfront and port area, that doubles as a picturesque spot for a high-quality meal at a local restaurant.

You can easily walk around Old Port after strolling along the oceanfront Eastern Promenade, and find some of the city’s great food spots, like Holy Donut, Scales, and Dimillio’s On The Water.

The main downtown area of Portland is located just behind Old Port and has a more traditional feel, with more great restaurants, galleries and museums, hotels, and the local arena.

Eastern Promenade Trail

If you only choose one outdoor activity while you are in Portland, the Eastern Promenade trail is one of the best things you could choose! This path has some of the best views around and is a beautiful place to get some fresh air and exercise…before or after indulging in some delicious food or sweet treats!

This 4.2 mile (each way) trail, takes you right along Portland’s waterfront, offering breathtaking ocean views and large green spaces on one end and with just a short walk takes you into the heart of Old Port at the other. Portland makes great use of its location, reserving plenty of space for outdoor activities and walking paths, trails, and parks.

Bring your four-legged friend for an adventure, check out the food truck park, keep an eye out for the narrow gauge train, and perhaps take a seat on the art installment that doubles as unique chairs while enjoying some sunshine and a salty breeze!

Portland Observatory

A historic maritime signal tower, that is the only known surviving tower of its type in the United States. Now a National Historic Landmark, it is open to the public as a museum.

• Portland Observatory: Admission ($10/ Adult)

This is also a perfect sightseeing stop as part of a nature and food mini-tour of Portland! We passed this on a loop which included a stroll along the Eastern Promenade waterfront trail, delicious fries from Duckfat, an amazing gluten-free and dairy-free indulgence from Sticky Sweet, and enjoying the view from the grassy hill overlooking Back Cove.

Other Outdoor Activities, State Parks & Sandy Beaches

In addition to the likes of Fort Williams Park or Bug Light Park, these other state parks and natural areas are perfect for enjoying the great outdoors, while also still only being a short drive to the city center of Portland!

• Crescent Beach State Park (17 minutes from Portland)
• Scarborough Beach State Park (20 minutes from Portland)
• Sebago Lake (1 hour 15 from Portland): Perfect for a day trip to a great Maine lake!
• Old Orchard Beach (25 minutes from Portland)
• Ferry Beach State Park in Saco Maine (29 minutes from Portland)

Great Local Bites & Craft Beer

Portland is well-known for its food scene, and it is also a great spot for beer lovers! With several great local breweries to choose from, a variety of dining options, and amazing gluten-free selections, you are bound to find something you will love. Eating and drinking are some of the best things to do in Portland Maine!

Below are some of our favorite stops, as well as highly recommended ones from our foodie friends and family, to add to your Portland Maine itinerary (menus are linked):

• Holy Donut: Mouth-watering Maine potato donuts, including gluten-free and vegan options. The gluten-free fresh lemon and dark chocolate sea salt were my first donuts in 10 years since going gluten-free and were amazing! Zach thoroughly enjoyed his blueberry glazed and honey lavender as well! Order ahead online to save time if you can and go early to ensure the best chance at the flavors you want. There are multiple locations in Portland and Scarborough to choose from.

• Flatbread Company: Right on a dock in Old Port, serving up delicious pizza and gluten-free pizza with fresh local ingredients. You can expect a wait time even on a weekday night, but it is well worth it!

• Sticky Sweet: A great option for gluten-free folk and vegans alike! 100% gluten-free and dairy-free ice cream in amazing flavors with gluten-free waffle cones to boot! The peanut butter fudge and minty dark chocolate flavors were *chef’s kiss*!

• Duckfat: Consistently ranked one of the best places for fries. Crispy, fresh, and not overly greasy, with fun dipping sauces to choose from! (We highly recommend the truffle ketchup). It is a small space but does have indoor and outdoor seating available. You can expect some wait time during peak hours. (They have also opened a second location that is a walk-up window)

• Salvage BBQ: Smokehouse serving BBQ in a rustic environment with rave reviews and occasional live music

• Dimillios On The Water: Waterfront dining with local seafood options including fresh Maine lobster or clam chowder.

• Becky’s Diner: Right in Old Port on the water known for seafood, lobster, and great breakfast options

• Eventide: A popular spot for seafood and oysters and other New England fare!

• Standard Baking Co: Highly rated spot for fresh baked goods from a family-owned business

• Breweries: Bissel Brothers, Lone Pine Brewing (for gluten-free friends, the Oh J Seltzer was super refreshing), and Austin Street Brewing…to name a few! Portland is also home to Allagash Brewing Company, a few miles outside of downtown.

Interactive Map

When planning your Portland Maine itinerary, it can be helpful to be flexible! Weather, long lines or wait times at restaurants, or other factors can cause there to be a change of plans… and as RVers we have quickly learned to always keep our plans carved in jello.

This map includes all of the amazing Portland points of interest from this article, as well as some honorable mentions, so that you can stop at all of the area’s best places and plan the adventure that works best for you!

Example 1, 3, & 5 Day Itineraries

If the idea of not having a game plan sounds stressful, here are a few example itineraries based on our experience in Portland and what we learned about the area and getting around!

1 Day Portland Maine Itinerary

If you have time for 1 perfect full day in this small city in Southern Maine with a big appetite, here is what we recommend:

• Start the morning out with some donuts from Holy Donut and head to the iconic Portland Head Lighthouse to beat the crowds and spend some time taking in the views at Fort Williams Park
• Head up to Bug Light Park to see Bug Light and Spring Point Ledge Lighthouse, watch the ferries going over to Peaks Island, and get a glimpse of the busy nature of Old Port while watching it across the water.
• Grab lunch at the Eastern Prom Food Truck Park or walk the trail into Old Port and check out a local spot there. Or if you prefer lunch to be more of a snack and a treat, consider hitting up Duckfat and Sticky Sweet before going out for a bigger dinner!
• Check out a brewery, local dining spot, and perhaps some live music in downtown to cap off the evening

3 Day Portland Maine Itinerary

Heading to Portland for a long weekend and have a bit more time? This is how you might want to divide up your time:

Day 1:

• Morning: Start the day out with some donuts from Holy Donut and head to the iconic Portland Head Lighthouse to beat the crowds and spend some time taking in the views at Fort Williams Park. Then head up to Bug Light Park to see Bug Light and Spring Point Ledge Lighthouse, watch the ferries going over to Peaks Island, and get a glimpse of the busy nature of Old Port while watching it across the water.
• Afternoon: Visit local museums, such as the Portland Observatory or Portland Museum of Art or reserve time for a food or brewery tour or a unique excursion like a lobstering tour
• Evening: Experience Portland’s vibrant food scene by dining at one of the many excellent restaurants, focusing on local and seasonal ingredients.

Day 2:

• Spend part of the day at one of the Casco Bay Islands, taking a ferry to Peaks Island or one of the other nearby islands. Enjoy a bike ride or stroll along the island’s scenic trails.
• Return later in the day and have a low-key picnic, take-out, or meal from a local food truck at one of the parks along the Eastern Promenade Trail
• Enjoy a casual drink or cocktail and maybe some live music at a local brewery or maybe even a hidden speakeasy…

Day 3:

• Have breakfast at a local favorite like Becky’s Diner (best if you are staying in and around downtown) or head right out to On the Rocks at Two Lights to see the two Cape Elizabeth Lighthouses near Dyer Cove. Explore the rocky coast and tide pools.
• If you are up for it, consider grabbing a bite at The Lobster Shack at Two Lights or exploring one of the local state parks or beaches
• End the day with a sunset cruise on the Portland Harbor or another great meal downtown!

5 Day Portland Maine Itinerary

With 5 days in Portland Maine, there is so much you could see, do, learn, and eat! You might even consider branching out to see some other iconic Maine sights if this will be your only stop in the state during your trip

Day 1: Spend part of the day at one of the Casco Bay Islands, taking a ferry to Peaks Island or one of the other nearby islands. Enjoy a bike ride or stroll along the island’s scenic trails. Finish the day back in Old Port with a casual bite to eat or snacks and beverages at a local brewery

Day 2:

• Make a day of lighthouses! Start with some Holy Donut treats or other local breakfast, head down at Two Lights, make your way up to Portland Head Lighthouse and explore Fort Williams Park, and then head to Bug Light Park and Spring Point Ledge Lighthouse.
• For the afternoon, visit local museums, such as the Portland Observatory or Portland Museum of Art, or reserve time for a food or brewery tour or a unique excursion like a lobstering tour
• Cap the day off with a local bite to eat in downtown!

Day 3: Reserve a day and overnight to head up and explore Acadia National Park and Bar Harbor 3 hours north* (see more about this day trip below)

Day 4: After returning from Acadia, use this as a free day to explore as you see fit. Head to the Farmers Market for local bites, do some shopping, check out a local beach to state park or simply stroll the Eastern Promenade and enjoy some fresh air and sunshine

Day 5: Consider taking your final day to take on some more outdoor adventures! Take a guided tour or rent equipment from Portland Paddle and head out onto Casco Bay or over to Fort Gorges for a full or part-day exploration! End with a local lobster roll, some Duckfat fries, or a local beverage to cap off your trip!

* Portland is about a 3-hour drive from Bar Harbor and Acadia National Park, a picturesque park with more great local seafood options, iconic trails, lighthouses, and more. Acadia National Park was the next stop on our journey north, and we highly recommend adding it to an extended road trip to the area if possible!

We believe Acadia deserves AT LEAST a few days, but if you only have time for a day trip up from Portland we would still recommend it. You could stay in Bar Harbor or grab an overnight campsite in the National Park and see the main sights along the scenic Park Loop Road.

Check out our Acadia National Park Guides for more help planning your trip!:

• Best Things To Do in Acadia National Park
• Reserving a Spot for Cadillac Mountain Sunrise
• Best Things To Do on Acadia’s Schoodic Peninsula

Guided Activities & Tours

If you are looking for a more hands-on experience from a local tour guide that allows you to experience even more of what Portland has to offer in unique and exciting ways, consider one of the area’s great tours! Get Your Guide is a great site that allows you to compare tour prices and availability and find the perfect match for your trip!

Fulfilling Travel Tips

Whether you have time for a day trip to Maine’s largest city, or have more time to dive into the local eats and rich history, Portland Maine provides you with plenty to see, do, and experience.

As you stroll through downtown’s brick buildings and cobblestone streets you are transported back in time and it is easy to see the charm and appeal of this waterfront city (even for us, who tend to be less city-minded).

What we loved most was how easy it was to forget you were in a city and become immersed in large green natural spaces and stretches of coast with uninhibited views of blue out to the horizon. This is a very walkable city with ample opportunities to connect with nature and experience gratitude for the special features of these hardy maritime communities of the Northeast.

When planning your Portland Maine itinerary, our biggest tip is to leave room for free exploration so that you can find your own hidden gems and take a few moments to slow down and soak it all in.

It can be easy to get wrapped up in checking off places and items and forget to really experience them and lean into the joy, adventure, and fulfillment that can come from discovering things for yourself along the way and leaning in to your own sense of wonder and curiosity!

Tips For Getting Around Downtown

Finally, as RVers, getting around in cities with our large dually can be a source of stress. So here is what you need to know about navigating in Portland Maine:

• Bicycles: Portland is a bike-friendly city with various bike lanes and paths. You can rent bicycles from local shops or make use of bike-sharing programs available in the city.

• Greater Portland Metro Buses: Greater Portland Metro operates bus services that connect various neighborhoods, including downtown. Metro Buses offer an affordable and convenient way to travel within the city. You can check their schedules and routes to plan your journeys.

• Taxis and Ride-Sharing: Taxis and ride-sharing services like Uber and Lyft are available in Portland.

• Parking: If you have a personal vehicle or rental, there are parking lots and on-street parking available in downtown Portland. However, be aware that parking spaces can be limited, especially during peak times or events. We were able to find street parking for our large dually in downtown on a weekday night (which was free), and found parking further from downtown at the Eastern Prom Food Truck Park on a Saturday afternoon (free). This city is very walkable so if you are an RVer with a larger vehicle you may want to opt for parking a bit further from your destination… the streets can be tight and busy!

Ready to explore more of the East Coast?

READ: Ultimate Guide To RV Trips on the East Coast

Some of the links on Fulfilling Travel are affiliate links. We may earn a small commission at no additional cost to you if you make a purchase, contributing to the site's upkeep while ensuring our travel recommendations remain freely accessible. Read our disclosure policy to learn more.