8 Best Things to do in Portland, Maine

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Planning a trip to Portland, Maine? You’ve landed in the right spot!

We’ve strolled the Old Port’s cobblestone streets, tracked down the city’s best lobster rolls (tough job, but someone had to do it), and seen Portland from every angle—on foot, by boat, by bike, and even from the seat of a vintage fire truck. After a few visits, it’s safe to say we’re hooked on this coastal gem.

Whether it’s your first time in town or you’re coming back for another dose of sea air and small-city charm, we’ve rounded up the absolute best things to do in Portland. These tours and experiences go way beyond the guidebook and show off what makes Maine’s coolest little city so unforgettable.

Things to do in Portland, Maine

1. Discover Portland’s history on a harbor sightseeing cruise

• Duration: 1 hour and 45 minutes
• Time: 10:30 am, 1 pm, 2:15 pm, 3:30 pm
• Highlights: Maritime adventure and sightseeing exploration, discover Portland Harbor, see Maine’s oldest lighthouse, the Casco Bay Islands, Fort Gorges, and more
• Inclusions: Guide, restroom, drinks, and snack bar on board
• Rating: 4.8 stars (check 440+ reviews here)
• Free cancellation: Yes
• Price: Check price here!

We made the classic mistake of thinking a stroll through the Old Port would reveal the city’s story. It didn’t. The forts, lighthouses, and maritime past barely registered. That’s why we took this Portland Harbor boat tour the second time around and finally saw Portland for what it really is—a city shaped by the sea.

We cruised through Diamond Pass with a cold drink in hand, catching sight of lobster boats bobbing in the bay and seals lounging on Halfway Rock. Our guide, Mark, was wildly knowledgeable and genuinely hilarious. He brought every historic fort and lighthouse to life and peppered the tour with wild local legends and stories we’d never read in any guidebook.

We even spotted a bald eagle soaring overhead and drifted past the iconic Portland Head Light, which we learned was commissioned by George Washington himself. It felt like the bay was putting on a show just for us. Between the seals, the sea birds, and the crisp ocean breeze, it was hard to know where to look.

Passing Fort Gorges, Spring Point Ledge Light, and the classic white homes tucked into the cliffs made us appreciate just how layered Portland’s history really is. There’s no better way to get a sense of the city than floating through its salty, storied harbor!

Check out the HUNDREDS of 5-star reviews and book this tour here!

2. Visit historic lighthouses with a local

• Duration: 1 hour and 45 minutes
• Time: 10 am, 12 pm, and 2 pm
• Highlights: Historian-guided sightseeing tour through Portland, visit three lighthouses, see some of the area’s hidden gems and less-visited spots, learn about local lore along the way
• Inclusions: Born-and-raised Portlander guide, air-conditioned vehicle, small-group tour
• Rating: 5 stars (check 1,200+ reviews here)
• Free cancellation: Yes
• Price: Check price here!

Portland might be small, but figuring out what’s actually worth seeing can be surprisingly overwhelming. You hear about lighthouses, seafood joints, cobblestone streets—but how do you fit it all in and learn something along the way? This small-group city and lighthouse tour solved that for us in one smooth, incredibly fun ride.

Our guide, Derek, didn’t just know Portland. He was Portland! His family has been here for generations, and it showed in the way he told stories. He effortlessly blended history, humor, and personal anecdotes as he drove us through the neighborhoods and out to three of the area’s most scenic lighthouses. 

He made the whole trip fun, casual, and packed with local flavor (plus, his food recommendations were spot on). We followed his advice later that day and ended up devouring lobster rolls so good we considered ordering a second round just to delay leaving.

We stopped to explore Fort Williams Park and walked right up to Portland Head Light, happily joining the ranks of visitors snapping selfies with the most photographed lighthouse in the world. From there, it was on to Spring Point Ledge and tiny-but-mighty Bug Light, with panoramic views of the city skyline in the distance. 

Out of everything we did in Portland, this was hands-down our favorite tour, and we clearly weren’t the only ones who felt that way. Check out over a thousand five-star reviews here to see why travelers rave about this experience!

This lighthouse tour sells out fast—grab your spot here so you don’t miss out!

3. Taste fresh seafood in Portland

• Duration: 2.5 hours
• Time: 11 am (dates vary)
• Highlights: Seafood lovers walking tour experiencing Portland restaurants, markets, and artisanal shops, visit Old Port and Waterfront District areas, learn all about the industry, sample local delicacies
• Inclusions: Small-group guided tour, food and beverage tastings, souvenir gift
• Rating: 4.7 stars (check 120+ reviews here)
• Free cancellation: Yes
• Price: Check price here!

You can’t come to Portland and not eat seafood, but choosing where to go can feel like a gamble. The “best chowder” claims are endless, and there are more lobster roll signs than you can count. That’s why we booked this small-group seafood walking tour, and we couldn’t have found a better way to eat our way through the Old Port.

Our guide, AJ, was the best kind of local—warm, funny, and bursting with food and fishing knowledge. We started with a snack and a refreshing Maine-made soda, then made our way through the cobblestone streets, stopping for haddock tacos, creamy chowder, and a fresh lobster roll that ruined all others for us going forward. 

AJ knew all the neighborhood food secrets and sprinkled in fun facts between bites, like which spots serve scallops right off the boat and how to tell a soft-shell lobster from a hard one. Everything was wicked good, as the locals say!

We toured the Harbor Fish Market and learned everything from how lobsters are harvested to the surprising life cycle of scallops. Between the bites, the history, and the behind-the-scenes seafood intel, we left full, happy, and a little more Maine-savvy.

This tour will likely sell out, so book it early if you want a seat at the table. Trust us—you don’t want to miss this one!

Reserve this tour now and pay later when you book in advance here!

4. See Portland in a vintage fire truck

• Duration: 50 minutes
• Time: Multiple times available from 9 am to 4 pm
• Highlights: Go sightseeing in Portland on a classic fire engine, get great views of lighthouses and architecture, learn about the city’s maritime past, explore cobblestone streets, browse souvenir shops, and sample local foods
• Inclusions: Driver/guide, small-group tour
• Rating: 4.8 stars (check 720+ reviews here)
• Free cancellation: Yes
• Price: Check price here!

Walking tours are great until your feet start to hate you! After a few days of pounding Portland’s cobblestones, we were ready for a break that still let us see the best of the city. Cue this sightseeing tour aboard a bright red vintage fire engine. It was the most fun we had getting off our feet, and a surprisingly awesome way to soak up the city’s history and scenery.

We settled into the elevated seats and rolled through the Old Port, up to the Eastern Promenade, and past some of the city’s most iconic landmarks. The view from the top was unbeatable—picture-perfect lighthouses, harbor vistas, and blocks of beautifully preserved architecture. 

Every time we turned a corner, it felt like we were part of the scene—waving to people on sidewalks, catching the scent of salt air and wood-fired pizza drifting from nearby shops.

Our guide narrated the ride, weaving together quirky stories and fun facts as we cruised by everything from the Portland Observatory to Victoria Mansion. The whole thing felt equal parts informative and delightfully offbeat. Plus, we had time to hop off and browse some local shops after the ride wrapped up downtown.

If you’re looking for a memorable and low-effort way to explore the city, this tour’s got you covered. But don’t wait too long to book—it’s a popular one that fills up fast. And if you still need convincing, just read the glowing 5-star reviews from travelers who loved it as much as we did!

Reserve this walking tour here and get FREE 24-hour cancellation before you go!

5. Enjoy Portland’s sights on a tall ship cruise

• Duration: 2 hours
• Time: 10:30 am, 12 pm, and 1 pm
• Highlights: Enjoy a relaxing excursion out on Casco Bay aboard a traditional, Maine-built windjammer, soak up the sea breezes, look out for seals, take a turn hoisting the sails or behind the ship’s wheel
• Inclusions: Two-hour cruise, life jackets, private tour (if option selected)
• Rating: 4.5 stars (check 220+ reviews here)
• Free cancellation: Yes
• Price: Check price here!

Portland’s waterfront is beautiful from land, but nothing compares to seeing it from the deck of a tall ship, sails full, and sea breeze in your hair. After a packed couple of days on foot, we were ready for a slower pace, and this two-hour cruise aboard a traditional Maine-built schooner was exactly what we needed.

The whole experience felt timeless from the moment we stepped aboard. Our boat, built in the 1920s, glided smoothly through Casco Bay as we kicked back and relaxed into the sea breeze and soaked up the view. We even brought our own food and drinks, making it feel like a floating picnic with front-row views. 

The views were unreal—seals sunning on rocks, seabirds swooping low over the water, and a string of coastal lighthouses dotting the horizon. At one point, we even spotted a seal bobbing right alongside the boat like it was part of the crew.

What really made it special was the chance to get hands-on. A few people helped hoist the sails, and one brave soul even took a turn at the ship’s wheel. For a more personal experience, there’s also the option to book a private sailing tour, which we’re seriously considering for next time.

Whether you want to relax or feel like part of the crew, this cruise delivers. It’s one of the most peaceful, scenic, and uniquely authentic ways to experience Portland’s coastline!

Book this windjammer cruise and experience the bay from a whole new perspective!

6. Bicycle to Portland’s lighthouses and enjoy a lobster roll lunch

• Duration: 5 hours
• Time: 9:30 am 
• Highlights: Small-group biking tour discovering the lighthouses and coastal landmarks of Portland, learn about Maine’s history, get an overview of the city’s waterfront attractions, enjoy a traditional extra-large lobster roll for lunch
• Inclusions: Guide, use of bicycle, lunch (extra-large lobster roll, chips, local soda, and dessert)
• Rating: 4.8 stars (check 100+ reviews here)
• Free cancellation: Yes
• Price: Check price here!

After a few days of walking tours and boat rides, we were craving something active but still easygoing. This small-group bike tour struck the perfect balance with smooth trails, coastal views, and a lobster roll lunch that’s honestly reason enough to sign up.

Our guide, Mackenzie, was laid-back, upbeat, and full of local stories that made each stop way more than just a photo op. We pedaled out from the Old Port and made our way to five lighthouses in total, including Bug Light, Spring Point Ledge, and the grand finale—Portland Head Light. 

A small group of just eight of us made everything feel friendly and unrushed. We had space to ride, time to ask questions, and lots of opportunities to just enjoy the crashing waves, candy-colored cottages, and cliffs that made us want to stop and stare every five minutes.

Lunch was a total highlight. An extra-large lobster roll from an award-winning food truck, with chips, dessert, and a local soda to wash it all down? Perfection on a park bench!

From Liberty Ship Memorial to Cape Elizabeth’s coastline, this ride covered so much of what makes Portland unique, and we never felt like we were racing to the next thing.

For a refreshing way to explore the coast, book this lighthouse biking tour and cruise your way through Portland’s best views—and best lobster roll!

Check prices and availability and book this tour here!

7. Find Portland’s hidden gems on a donut walking tour

• Duration: 1.5 hours
• Time: 9:30 am and 11:30 am
• Highlights: Guided walking tour around the Old Port to three of downtown’s donut shops, try six unique samples, learn how the first ever donut was created in Maine, skip the line at The Holy Donut shop
• Inclusions: Small-group tour, guide, all samples, fees, and taxes
• Rating: 4.7 stars (check 120+ reviews here)
• Free cancellation: Yes
• Price: Check price here!

Donuts were already on our Portland to-do list, but choosing just one shop was impossible. That’s why we signed up for this small-group donut tour, and it ended up being one of the most fun, flavor-packed ways to explore the Old Port.

Our guide, Chris, had the whole experience dialed in. He was sharp, hilarious, and full of random city history that made the stroll between donut stops just as enjoyable as the treats themselves. He even filled us in on the wild legend that the donut was actually invented in Maine. Who knew?

Over the course of a mile, we hit three of downtown’s best donut shops, tasting six delicious samples along the way. 

At The Holy Donut—a Portland institution known for its potato-based donuts and notoriously long lines—we got to skip the wait and go straight for the good stuff. Their dark chocolate potato donut was rich, dense, and easily our favorite of the day!

We also stopped at a local shop serving warm, just-fried mini donuts—some dusted in cinnamon sugar, others topped with cereal and cookie crumbles. They were light, crispy, and totally addictive. And then there were the old-world-style crullers, so buttery, eggy, and soft they practically melted in our mouths.

This was one of our favorite Portland tours because it paired city history with something everyone loves—dessert for breakfast! Whether you’re visiting for the first time or just looking for an excuse to eat six donuts before noon, this tour delivers.

Reserve this donut tour here and snack your way through Portland’s history!

8. Explore Casco Bay on a sunset sea kayaking tour

• Duration: 2 hours
• Time: Multiple times available from 4 pm–6:15 pm
• Highlights: Small-group kayaking tour from the waters of Portland’s Casco Bay, see phenomenal vistas of Portland harbor and cityscape, great for first-time or experienced kayakers
• Inclusions: Professional Maine sea kayak guide, dry bag, all necessary equipment
• Rating: 4.9 stars (check 90+ reviews here)
• Free cancellation: Yes
• Price: Check price here!

We wanted to end our Portland trip on a high note—and this small-group sunset kayaking tour over Casco Bay delivered in the dreamiest way possible. After a few days of buzzing around the city, gliding across calm water with the golden light hitting the harbor was exactly the kind of peaceful adventure we were looking for.

This two-hour paddle is great for beginners and experienced kayakers alike. The friendly crew gave us a quick, confidence-boosting lesson and set us up with everything we needed, including dry bags for our phones and cameras.

From there, we followed our guide, Joe, past lobster boats and schooners, spotting seals bobbing in the distance and seabirds cutting across the horizon like clockwork. We passed Fort Gorges and took in views of Spring Point Ledge Lighthouse, all bathed in a soft, honey-colored light that made everything look magical.

Joe clearly loved being on the water, and by the end of the tour, we did too. His stories about Portland’s harbor history gave the whole experience even more depth and made us see the coastline in an entirely new way.

As the sun dipped below the horizon and the sky turned shades of peach and lavender, we floated quietly, taking it all in. It felt like the whole city had slowed down just for us.

Ending our trip away from the crowds, out on the water, watching the harbor fade into twilight was everything we didn’t know we needed. Peaceful, beautiful, and completely unforgettable!

Read 5-star reviews and reserve this incredible sunset kayak tour here!

Related Read: Follow our 3-day Portland itinerary to maximize your time and seamlessly check off nearly all of these activities!

Where to Stay in Portland, Maine

Now that you’ve sorted your Portland itinerary, it’s time to find the perfect place to stay. This vibrant coastal city offers something for every kind of traveler—whether you’re looking for a stylish boutique hotel, a cozy mid-range stay, or a budget-friendly option, Portland has you covered.

To make your planning easier, we’ve put together the best places to stay in Portland so you can spend less time researching and more time soaking up the city’s cobblestone streets, fresh seafood, and salty sea breeze.

Luxury – $$$

Perched on Portland’s charming Congress Street, the Longfellow Hotel is a refined 5-star retreat where elegance meets thoughtful design. With a warm, inviting atmosphere, this boutique stay offers beautifully curated rooms, a full-service spa, a serene café, and a cozy lobby that guests rave about. It’s the kind of place where every detail feels considered, making it ideal for a relaxing escape just minutes from the waterfront and local landmarks.

Nightly rates generally range from $400–$1,000+ USD. See room rates and book your luxury stay on Booking.com.

Mid-range – $$

Embassy Suites by Hilton Portland Maine is a top mid-range choice near the Portland International Jetport, offering spacious two-room suites with separate living areas, microwaves, and fridges—great for families or business travelers. Guests rave about the free made-to-order breakfast, evening happy hour, indoor pool, and free airport shuttle. It’s also just a short drive to the Old Port and Maine Mall, making it a convenient and comfortable stay.

Prices range from around $150–$350 USD per night. Check Booking.com for room rates today!

Budget – $

For a cozy and affordable stay, the Best Western Merry Manor Inn is a solid pick! Located in South Portland just off I-95, this family-friendly hotel offers spacious rooms with comfy beds, free Wi-Fi, and a complimentary continental breakfast. Guests love the year-round heated indoor/outdoor pool and on-site restaurant—plus, the location makes it easy to explore local beaches, lighthouses, and downtown Portland.

Rooms start around $130 USD per night. Head to Booking.com to check availability and reserve your stay!

For more options, see all of Portland’s hotels listed here!

Renting a Car in the USA

The United States is a vast country with diverse landscapes, from bustling cities to scenic national parks. While public transportation exists in major cities, renting a car is often the best way to explore the country’s wide-open spaces and hidden gems.

We always book with Discover Cars and can’t recommend them enough. It’s super easy to compare prices, check company ratings, find the right vehicle for your needs, and add affordable full coverage insurance. If you want a full breakdown, check out our Discover Cars review here.

Tips for Renting a Car in the USA

• Drive on the right: In the U.S., vehicles drive on the right-hand side of the road, and the driver’s seat is on the left. If this is different than your home country, take some time to adjust before hitting busy streets!
• Know the local rules: Speed limits, road signs, and driving laws can differ between states. For example, turning right on red is generally allowed after a complete stop, unless a sign indicates otherwise. Always check the specific rules for the states you’ll be driving in.
• Add full insurance: We always recommend full coverage rental insurance, especially in the U.S., where long distances, varying road conditions, and unpredictable weather can lead to unexpected situations. Discover Cars makes it easy (and affordable!) to add this peace of mind when you book.
• Choose the right car: Consider the nature of your trip. For city driving, a compact car is convenient, while for road trips or national park visits, an SUV might be more comfortable. With Discover Cars, it’s easy to filter by vehicle type, transmission, fuel efficiency, and more to find the perfect fit.

What You Need to Rent a Car in the USA

• A valid driver’s license from your home country.
• An International Driving Permit (IDP) is recommended if your license is not in English or uses a non-Roman alphabet. Some rental companies may require it, so it’s best to check in advance.
• A credit card in the driver’s name is typically required for the security deposit.
• Most rental companies require drivers to be at least 21 years old, with a young driver surcharge applicable for those under 25. Some companies may have higher age requirements, so make sure you double-check.

Ready to hit the road? Book your car with Discover Cars here and discover the freedom of exploring the USA on your own terms!

Thanks for reading!

If you love history, charming cities, and a sea breeze, Portland is the place to be! We had so much fun exploring the northeastern corner of the United States, it was so unlike any other city we’ve explored in the country. Follow this list and I know you’ll see the absolute best of Portland!

Before you go, check out our other USA blogs! We love sharing our favorite places and experiences with fellow travelers. Here are a few related blogs that might be helpful as you plan your next great adventure – cheers!

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