Portland, a lively city by Maine’s Casco Bay, features historic red-brick buildings, cobbled streets, and century-old monuments. Along the shore, travelers embark on whale watching cruises, ferry tours, and fishing trips on Maine’s blue seas.
The city is brimming with shops, boutiques, cafes, restaurants, and rooftop bars. With a bustling atmosphere and vibrant nightlife, there’s a constant buzz of activity with people exploring the streets. Our time in Portland, filled with leisurely walks, shopping, and dining, was highly enjoyable.
Top Things to Do in and around Portland
Explore Cape Elizabeth
Just south of Portland lies a luscious green peninsula home to quintessential lighthouses, shoreside parks, and lobster shacks. Here you will find the iconic Portland Head Light, and three State Parks perfect for a day of relaxation on the Cape’s rocky shoreline.
Portland Head Light
Go on a Lobstering Tour
Participate in hauling and catching lobster in sight of picturesque lighthouses, forts, and coastline. If this sounds interesting, Lucky Catch Cruises offers the best hands-on experience to learn about lobstering and to try your hand at catching some marine life. Lucky Catch tours are offered from May-October and each tour lasts 90 minutes. For more detailed information, visit the official website.
Portland Discovery Land and Sea Tours
A great way to experience the beauty of Portland’s blue Casco Bay is via an ocean sail. Portland Discovery Land and Sea Tours offers two fully narrated cruises around Portland.
Their Harbor Lights and Sights Cruise is a 105-minute tour that gets up close to civil war era forts, lighthouses, and a common seal-sighting spot. The same company also offers a shorter 60-minute Lighthouse Lovers Cruise which travels to four lighthouses and provides a close view at the iconic Portland Head Light.
Find more information about Portland Discovery Land and Sea Tours on the official website.
Schooner Sail
For those who want to experience sailing on a decades old schooner, Schooner Company hosts a very relaxing and interactive sunset sail. The crew does an amazing job entertaining the passengers, allowing them to help hoist the sails, keeping the drinks flowing, and walking around chatting with everyone on board. Each sunset sail hosts around 25 people so prepare for a bit of a crowd. Long pants and lots of layers are also highly recommended, as it gets very chilly as the cruise goes on. We did a sunset sail with Schooner in Camden, Maine and loved the trip. Book a trip with Schooner here.
Schooner Sail in Camden, Maine
Take a Food Tour
Portland is the foodie capital of Maine, with fresh seafood, global cuisine, and sweet cafes dotting the city’s historic downtown. But to truly experience Portland’s local delights, you really need a guide to lead the way.
Portland’s highest rated food tour experience is the Old Port Culinary Walking Tour. On this trip, a guide will take guests to 7 different eateries, featuring a delightful mix of classic Maine, cultural, fancy foods, local seafood, and beverages. Along the way, your guide shares the unique history of the Old Port’s food scene and inspiring stories of culinary artisans.
Portland Freedom Trail
The Portland Freedom Trail is a self-guided tour that winds through 13 significant sites celebrating the Black Mariners who fought to end slavery.
By the early 19th century, many Black Mariners worked in the maritime trade as fishermen, sailors, and longshoremen. Amidst the nation’s tumult over the question of slavery, African Americans in Maine emerged as pioneers of the local Underground Railroad, directing enslaved men and women towards liberation in Canada.
On the Portland Freedom Trail, you’ll have the opportunity to discover how this stand played a pivotal role in the struggle for civil rights and pay tribute to those who were lost.
Download the walking guide and map here.
Wander the Old Port
A trip to Portland would be incomplete without walking around its historic Old Port area. Its 19th century brick buildings and cobblestone streets are lined with posh boutiques and some of the best restaurants in town. Sailboats line salty-aired wharves, recently returned from fishing trips and ferry tours around Casco Bay.
Portland Trolley Tour
Take a narrated trip through Portland’s historic district and neighborhoods. Portland Discovery Land and Sea Tours offers a 60-minute Peek at Portland Tour with an experienced guide on a whimsical trolley. This is a fun and relaxing way to view Portland’s iconic sights and learn its deep history.
Have a Night of Fun at Arcadia
With games, cocktails, food, special events, and a friendly vibe, Arcadia is the place to show off your pinball skills. You must be 21 to enter.
Day Trips from Portland
Kennebunkport
Kennebunkport is a very small coastal town on the southern end of Maine. Here visitors will find cute shops, a few restaurants, a very popular Clam Shack, and paddle boarding/ kayaking activities. From Portland, Kennebunkport is an hour drive away.
Just outside of Kennebunkport is Ocean Avenue, a scenic coastal drive that rides past large mansions and vacation homes. Most notably, the George Bush Family Compound is just off Ocean Avenue on a stretch of land called Walker’s Point. There is an overlook off Ocean Avenue where you can take photos of this famous property.
Kennebunkport is a good stop if you have the time, but there is not much to do here. If you already have a busy travel schedule, then making the trip to Kennebunkport is not worth the time.
Portsmouth NH
An hour south of Portland lies this small city filled with maritime history and coastal beauty. The city is lined with cobblestone streets and historic homes, and it is renowned for its vibrant arts scene, delectable seafood, and the iconic Strawberry Banke Museum. Portsmouth is a great addition to any New England road trip and can be seen in 1 to 3 days.
Boothbay Harbor Whale Watch Cruise
Boothbay Harbor is a small coastal town just an hour away with tons of souvenir shops, cafes, and restaurants. Public parking lots make visiting the town quick and easy, with parking costing just two dollars an hour.
You can expect to spend at least 4 to 5 hours if not more exploring the town, enjoying a cruise, and grabbing a quick bite to eat.
A tour we’d highly recommend is Cap’n Fish’s Cruises, a company that offers various boating excursions that will take you around the local waters to see a variety of wildlife. They offer everything from a one-hour harbor cruise to a 4 hour marine-sighting tour. We did the Whale and Puffin Combo Cruise and loved the experience.
How Much Time Do You Need in Portland?
How much time you need in Portland depends on how many activities you wish to do here. You only need one day to see the best of Cape Elizabeth and to walk around the Portland Old Port. This is what we did, and it worked great. But I wish we could have had more time to enjoy Portland. For this reason, I recommend spending at least two days here.
Best Restaurants in Portland
As the foodie capital of Maine, Portland has an array of delectable eateries and gourmet restaurants to choose from. Here are some of our recommendations for where to eat in Portland, but there are many other great restaurants that we did not consider during our short time here. Find more top restaurants here.
DeMillo’s On the Water
DiMillo’s On the Water offers a genuine maritime feel, located on a docked car ferry near Portland’s wharf. The interior looks like something out of the Titanic, and the ship’s multiple dining rooms can seat over 600 guests.
Despite the amount of seating, the restaurant is always bustling so I recommend you make a reservation ahead of time. This upscale seafood spot warmly welcomes families and casual diners. Prices, especially considering the generous portions, are reasonable. We greatly enjoyed the delicious food, the friendly service, and the unique ambiance of this restaurant.
Luke’s Lobster Portland Pier
Luke’s Lobster Portland Pier is continuously rated one of the best places to have a lobster dinner in town. The restaurant provides a diverse selection of freshly caught seafood dishes. Positioned conveniently on Portland Pier, it offers captivating vistas of the waterfront, enhancing the dining experience.
Portland Lobster Company
Nestled along the Portland marina’s edge, Portland Lobster Co. presents a delectable array of offerings, including lobster rolls, chowders, steamed lobster dinners, and a variety of non-seafood choices. With the option to dine outdoors, guests can enjoy their meal while overlooking Portland’s picturesque waterfront.
Highroller Lobster Company
The Highroller Lobster Company is a top-notch place in Portland to enjoy a delicious lobster roll. The restaurant’s red checkered décor and bar seating evoke a classic American diner vibe, which suits the sandwich-style meals they serve.
Fore Street
If you’re a traveler in search of an exceptional wood-fired dining experience, make your way to Fore Street. Here, you’ll find an unforgettable meal. The menu offers a variety of seafood, meats, game, and vegetable dishes, all crafted using ingredients sourced from local Maine farmers, fishermen, and foragers. Also check out Fore Street’s sister restaurants: Street and Co. and Scales for a gourmet seafood dining experience.
HiFi Donuts & Coffee
This is a cozy café located in the historic center of Portland. They offer coffee, breakfast, and lunch sandwiches, as well as incredibly unique and creative donuts. We thoroughly enjoyed everything we tried at this café.
Gelato Fiasco
This is an amazing gelato restaurant with a wide spread of creatively flavored gelatos and sorbets. The staff are friendly and encourage you to try as many flavors as you want, including some favorites like Netflix & Chill and Cookie Therapy.
Some other great restaurants to check out include Evo Kitchen + Bar, Solo Italiano, Duckfat, Honey Paw, and Crispy Gai.
Best Hotels in Portland
Courtyard by Marriott Portland Downtown/Waterfront
Situated right in the heart of downtown Portland, this hotel is conveniently close to many restaurants, shops, cafes, and the Old Port area. Its central location was a great advantage as we could easily explore the city on foot, without concerns about parking, taxis, or safety. The hotel staff was welcoming, and the rooms were tidy and cozy. Our experience staying here was highly enjoyable, and we felt that paying a bit more for the excellent location was definitely worthwhile.
Other great hotel locations in downtown Portland include:
- The Press Hotel, Autograph Collection
- Canopy by Hilton Portland Waterfront
- The Docent’s Collection
- The Chadwick Bed and Breakfast
- Hampton Inn Portland Downtown – Waterfront
- Portland Harbor Hotel
Inn By the Sea
Just a short distance from Crescent Beach State Park, at the southern edge of Cape Elizabeth, you’ll find Inn By the Sea, a high-end oceanfront resort. It’s a perfect choice for anyone seeking a tranquil vacation escape. The resort provides a variety of rooms, including beach suites, multi-bedroom options, and single-bedroom accommodations. Additionally, the resort offers convenient beach access, pet-friendly suites, a soothing spa, upscale dining, and enjoyable activities for families.
If you have any questions about the best things to do in Portland, Maine, let us know in the comment section below.
More Information for Your Trip to New England
NEW ENGLAND ROAD TRIP: Visit Cape Cod, coastal Maine, the White Mountains in New Hampshire, and more in this 12 Day New England Road Trip Itinerary.
CAPE ELIZABETH, MAINE: In this guide, we cover the best things to do in Cape Elizabeth, Maine with tips to help you have the best experience.
CAMDEN, MAINE: If you will be visiting the town of Camden on your trip to Maine, don’t miss our article Best Things to Do in Camden.
ACADIA NATIONAL PARK: Check out our Acadia National Park Travel Guide for important travel information, sample itineraries, and how to plan your visit. For a list of must-have experiences, read our article Best Things to Do in Acadia National Park. Go off the beaten path and explore Isle au Haut.
NEW HAMPSHIRE: Don’t miss our article about the best things to do in Franconia Notch State Park and how to hike the Franconia Ridge Loop. We also have a guide to 10 great stops along the Kancamagus Highway.
If this is part of a bigger road trip through the USA, visit our United States Travel Guide and our Maine Travel Guide for more inspiration and travel planning tips.
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