The Perfect 3 Days in Portland, Maine Itinerary

Planning a trip to Maine and wondering how to spend 3 days in Portland? This Portland, Maine itinerary covers all the highlights, including scenic lighthouses, historic neighborhoods, local eats, waterfront walks, and easy coastal day trips.

From tasting Holy Donuts to biking around Peaks Island and exploring nearby towns like Kennebunkport, this 3 day Portland, Maine itinerary is packed with fun and practical ideas to help make the most of your visit.

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Day 1: Discover Portland’s Highlights

Holy Donut

There’s no better way to kick off a Portland, Maine itinerary than with donuts, and Holy Donut is the go-to spot!

Known for their signature potato-based dough, these donuts are soft, rich, and come in unique flavors like maple bacon, dark chocolate sea salt, and Maine blueberry.

The shop has multiple locations, but the one on Exchange Street in the Old Port is the most central for sightseeing. Get there early if you’re visiting on a weekend. Lines can get long and popular flavors often sell out by midday!

Seating is limited inside, so consider grabbing your donuts to go and walking a few blocks to Monument Square or the waterfront.

Portland Museum of Art

After breakfast, head over to the Portland Museum of Art. It’s one of the best things to do in Portland, Maine if you enjoy art, architecture, or just a peaceful indoor break.

The museum’s collection includes everything from American and European paintings to modern and contemporary works, plus rotating exhibits that often feature New England artists.

The building itself is worth seeing, with a clean and airy design that makes it easy to explore at your own pace. You can walk through in about an hour, or linger longer if you’re into the details. It’s small enough not to feel overwhelming, but still has plenty to see.

The museum is closed on Mondays, so be sure to plan your 3 days in Portland, Maine accordingly.

Wadsworth-Longfellow House

Just a short walk from the museum, the Wadsworth-Longfellow House offers a quiet peek into Portland’s past.

This was the childhood home of poet Henry Wadsworth Longfellow, and it’s the oldest standing structure on the Portland peninsula.

The house is preserved with original 19th-century furnishings and gives a real sense of what life was like in the city during that era.

If it’s open during your visit, guided tours are available seasonally and include access to the home and a small on-site museum.

The adjacent garden is open to the public and makes a peaceful spot to rest for a few minutes, even if you’re not doing the full tour.

Old Port District

No Portland, Maine itinerary would be complete without some time in the Old Port District! This is the city’s most iconic neighborhood, known for its cobblestone streets, historic brick buildings, and working waterfront.

Spend the early afternoon exploring the shops, grabbing a coffee, or just strolling along the piers. The area is packed with local boutiques, galleries, and great lunch spots.

If you’re in the mood for something casual, try a lobster roll or fish sandwich from one of the seafood shacks. For a sit-down meal, there are plenty of cozy restaurants tucked into the side streets just off Commercial Street.

It’s an easygoing part of the day, perfect for soaking up the local vibe before heading out for a walk along the water.

Victoria Mansion

After exploring the Old Port, walk over to Victoria Mansion, an ornate 19th-century home just a few blocks away.

It’s one of the best-preserved historic houses in the Northeast, with original furnishings, elaborate wall paintings, and plenty of architectural detail to take in.

The mansion is open seasonally from May through late October, and it closes at 4:00 pm most days, so it’s best to plan this stop earlier in the afternoon. Guided tours are available, but you can also explore at your own pace if you prefer.

Even if you’re not usually into house museums, this one is impressive. The outside is striking too, so if you’re short on time or visiting off-season, it’s still worth walking by for a quick look.

Portland Observatory

Next, make your way up to Munjoy Hill to visit the Portland Observatory. Built in 1807, this wooden tower was used to spot ships approaching the harbor, and today you can climb to the top for views over the city and Casco Bay.

It’s open seasonally from late May through early October, but the opening hours vary depending on the day.

Sometimes it closes as early as 3:30 pm, and other days it stays open until 7:00 pm, so it’s worth checking ahead if you want to go inside.

If it’s open, a guided tour is included with admission and takes you up through the tower. If it’s closed during your visit, you can still stop by to see the outside and enjoy a quick walk around Munjoy Hill.

Eastern Promenade

End the afternoon with a relaxing walk along the Eastern Promenade. This waterfront path runs along Casco Bay and offers great views of the harbor, nearby islands, and passing boats.

You’ll find benches, green space, and access to East End Beach if you want to dip your toes in.

It’s a short, easy walk from the observatory and a nice way to wind down after a full day of sightseeing. From here, you can either head straight to dinner or find a quiet spot to sit and take in the view for a bit longer.

Dinner & Drinks in the Old Port

Wrap up your first day with dinner back in the Old Port. This neighborhood has a wide range of restaurants within walking distance so you can easily find something that fits your mood.

For something upscale, try Fore Street. If you want casual but still excellent, Duckfat is great for paninis and fries, and Eventide Oyster Co. is a top pick for seafood.

Boone’s Fish House & Oyster Room is another solid choice, especially if you want oysters or lobster with a waterfront view.

After dinner, grab a drink at Liquid Riot or Blyth & Burrows, both just a short walk away. It’s an easy and relaxing way to wrap up the first of your 3 days in Portland, Maine.

Day 2: Lighthouses + Casco Bay

Portland Head Light & Fort Williams Park

Start your second day with a short drive or rideshare to Cape Elizabeth to visit Portland Head Light. It’s one of the most iconic lighthouses in New England and sits inside Fort Williams Park on a rocky stretch of coastline.

You can walk the grounds around the lighthouse, explore a short cliffside trail, and check out the remains of old military batteries in the park. There’s also a small museum inside the former keeper’s house that’s open seasonally.

Parking is available inside the park, and food trucks are often around during the warmer months. Plan to spend about an hour here before heading to the next lighthouse.

If you’d rather join a guided tour instead of driving, consider The Real Portland Tour. It includes Portland Head Light and two other lighthouses, along with local insights and stories about the city. The tour starts downtown and usually lasts just under two hours.

Spring Point Ledge Lighthouse

From Portland Head Light, it’s a short drive over to Spring Point Ledge Lighthouse in South Portland. This one is unique because you can actually walk out to it on a granite breakwater that stretches into the harbor.

The walk is less than a quarter mile each way, but the uneven stones require a bit of balance, so wear decent shoes. Once you reach the end, you’ll be right at the base of the lighthouse with open views of Casco Bay.

There’s also a small beach and the remains of Fort Preble nearby if you want to explore a little more. Parking is free and usually easy to find near Southern Maine Community College.

Bug Light Park

Next, head over to nearby Bug Light Park, home to one of the smallest and most charming lighthouses in the area. It’s an easy addition to any Portland, Maine itinerary that includes multiple lighthouse visits.

The park has a wide open lawn, walking paths, and great views of the Portland skyline across the harbor. The lighthouse itself, officially called Portland Breakwater Light, is small but beautifully designed and easy to access.

There’s free parking at the park, and it’s a nice place to take a short walk or sit by the water before heading into the afternoon portion of your day.

Casco Bay Cruise or Peaks Island

For the afternoon, you have two great options depending on your energy level and the kind of experience you’re after.

Both offer a chance to get out on the water and see a different side of the city, and they’re perfect choices when planning how to spend 3 days in Portland, Maine.

If you’d rather keep things easy, the Harbor Lights and Sights Cruise is a great pick. It’s a 1-hour and 45-minute narrated cruise that passes by several lighthouses, historic forts, and Casco Bay islands. There’s a bar and indoor seating on board, so it’s a good option even if the weather is a bit off.

If you’re up for a bit more exploring, hop on the ferry to Peaks Island. It’s just a 20-minute ride and easy to do without a car. Once you arrive, you can rent bikes, grab ice cream, walk the quiet back roads, or head to the rocky shoreline for views back toward the mainland.

Both the cruise and the ferry leave from the same terminal near the Old Port.

Dinner with a View

After a day by the water, keep the coastal vibe going with dinner at one of Portland’s waterfront restaurants.

If you haven’t been yet, Boone’s Fish House & Oyster Room is a solid pick for fresh seafood and harbor views. They have two outdoor decks and a menu full of New England classics, including lobster, oysters, and clam chowder.

For something a bit more casual, head to Portland Lobster Company. It’s right on the wharf and has a laid-back vibe with picnic tables, live music in the summer, and classic seafood baskets.

Both spots are popular in the evenings, especially during high season, so it’s worth arriving a little early or checking if reservations are available.

Day 3: Day Trip to the Southern Coast

Morning in Ogunquit

Start the final day of your 3 day Portland, Maine itinerary with a drive down to Ogunquit, a charming seaside town about 45 minutes south of Portland.

It’s one of the most charming small towns in Maine, known for its long sandy beach, relaxed atmosphere, and one of the prettiest coastal walks in the state.

Head straight to the Marginal Way, a paved cliffside path that runs just over a mile between Ogunquit Beach and Perkins Cove. It’s an easy walk with ocean views the entire way, plus benches and side trails if you want to take a break or explore the rocks below.

Once you reach Perkins Cove, you’ll find a small harbor, a footbridge, and a few shops and cafés. It’s a great spot to grab coffee or a light breakfast before continuing on to Kennebunkport.

Afternoon in Kennebunkport

From Ogunquit, it’s about a 25-minute drive to Kennebunkport, another one of the prettiest places to visit in Maine.

Start in Dock Square, the main shopping and dining area filled with boutiques, art galleries, and local cafés. It’s a nice place to wander, pick up souvenirs, or stop for lunch.

After exploring the center, take a drive or a walk along Ocean Avenue. This scenic road winds past stately homes, boats bobbing in the harbor, and lookout points with views of the rocky coast.

You’ll also pass by Walker’s Point, the Bush family’s summer compound, which you can see from a public pull-off just beyond town.

If you have time before heading back to Portland, consider grabbing a drink or dessert at one of the spots near the water. The town quiets down in the late afternoon, and it’s a peaceful way to end your visit.

Evening back in Portland

After a full day on the coast, head back to Portland for one last evening in the city. Depending on when you return, you can either go out for a relaxed dinner or stop by a brewery to wind down before your trip ends.

If you didn’t make it to Eventide, Fore Street, or Duckfat earlier in your trip, this is a good chance to fit one in. For something more casual, Highroller Lobster Co. is a fun spot with a creative take on seafood and a laid-back atmosphere.

If you’re in the mood for a drink, check out one of the local breweries or cocktail bars. Austin Street Brewery and Oxbow Blending & Bottling are both solid options with a neighborhood feel.

It’s a great way to cap off your 3 days in Portland and end the trip on a relaxed note!

Where to Stay in Portland, Maine

Portland is a compact, walkable city, and most visitors choose to stay near the Old Port or the Arts District for easy access to restaurants, shops, and the waterfront.

If you’re planning to explore mostly on foot, look for hotels in the downtown area so you can leave the car behind.

There are plenty of options depending on your budget and style, from boutique hotels to modern waterfront stays. Here are some great options to consider:

• Canopy by Hilton Portland Waterfront – Modern, upscale option with harbor views and a great location near the Old Port
• The Press Hotel – Stylish boutique hotel in a former newspaper building, right near City Hall
• Hampton Inn Portland Downtown Waterfront – Comfortable chain hotel just steps from the harbor and Old Port
• Inn at St. John – Budget-friendly with a bit of historic charm, located just outside downtown