If you love rugged coastlines, fresh seafood, and the charm of New England, this Boston to Portland road trip itinerary is just what you need. After starting in Boston and exploring Portland, I planned a few relaxing days in Kennebunkport on the way back. It’s the perfect place to unwind and take in those stunning coastal views.
As someone who loves discovering trendy restaurants and unique local spots, I handpicked the best spots that offer a mix of gorgeous scenery, top-notch dining, and unforgettable coastal experiences. This guide is your go-to for the best places to eat, stay, and explore, whether you’re a local or a visitor looking for the ultimate east coast escape.
Drive Times
The drive from Boston to Portland is just under two hours, but I highly recommend stopping along the way to eat some local seafood. Whether you’re taking your time to explore or simply curious about the journey, here’s a breakdown of the travel times between each destination—if you choose to skip the scenic detours:
- Boston to Portland: Just under 2 hours
- Portland to Kennebunkport: About 40 minutes
- Kennebunkport to Boston: Around 1 hour 45 minutes
If you’re up for a leisurely road trip, you’ll definitely want to break up these drives to fully embrace the New England experience.
Arrival
Night in Boston – Dinner & Cocktails
We landed in Boston around 8pm and stayed at the Aloft in the Seaport District, just a 10-minute drive from Boston Logan Airport. After checking in, we took an 8-minute Uber to The Nautilus at Pier 4, a lively spot with a beautiful waterfront patio and delicious Asian fusion dishes.
When it came time for after-dinner drinks, there were plenty of great options in the area, but I narrowed it down to two of my favorites:
- The Rooftop at the Envoy: Just an 8-minute walk from The Nautilus, this spot offers a fun, lively vibe (though it can get loud). If you come here, stick to classics like gin & tonic or Aperol Spritz.
- Wink and Nod: We chose this cozy speakeasy which is about 15 minute drive from The Nautilus. The cocktails here are incredible, and the ambiance is stylish and quiet—perfect for unwinding after a busy day.
Both spots are excellent ways to end the night, whether you’re looking to keep the energy up or enjoy a craft cocktail in a more laid-back setting.
Day 1
Drive to Portland
It was a hot July day, so we got an early start with coffee and a breakfast sandwich from Blue Bottle Coffee and walked around the Seaport area before checking out of the hotel and picking up our rental car.
Once we were on the road to Portland, we stopped at Frisbee’s Wharf in Pepperrell Cove, Kittery Point, Maine—about an hour from Boston. It’s right on the water, so it was the perfect spot to kick off our Maine road trip with fresh seafood. I had the lobster roll and seafood chowder, both of which were amazing. It was a great little detour before heading into Portland!
Check Into Your Portland Hotel
Once we arrived in downtown Portland, we checked into our hotel. Many places were priced around $700 a night, but the Holiday Inn was a great budget-friendly option, around $350 a night. It’s within walking distance to almost everywhere we went, has comfortable rooms and bikes available for exploring. We stayed there and were really happy with our choice—it was a pleasant surprise.
If you’re looking for something more upscale, The Press Hotel is a chic boutique in a former newspaper building. It’s stylish and artsy and right in the heart of Old Port, close to all the best shops, restaurants, and bars. Whether you want convenience or a bit of luxury, both are great options!
Explore Old Port and Have Lunch
After checking in, we wandered around Old Port, Portland’s historic waterfront district. The cobblestone streets, brick buildings, and mix of art galleries and boutiques make it a fun area to explore.
For lunch, we took an Uber to The Shop by Island Creek Oysters, the perfect spot for fresh oysters in a relaxed setting. If you’re craving something heartier, head to Eventide Oyster Co. for their famous brown butter lobster roll—it’s a must-try! Both spots offer a delicious taste of Portland’s amazing seafood scene.
Late Afternoon: Scenic Walks & Waterfront Views
After exploring Old Port, we walked along the Eastern Promenade to take in the views of Casco Bay. This waterfront park is perfect for relaxing and soaking in Portland’s coastline. If you have extra time, hop on the ferry to Peaks Island for a bike ride, more ocean views, and a taste of island life.
Dinner
I have two favorite dinner spots in Old Port: Via Vecchia and Scales. Both are popular, so be sure to make a reservation!
Via Vecchia has a lively vibe, with a gorgeous ivy-covered exterior and a dark, chic interior. The menu is full of delicious Italian dishes—my picks are the veal chop and the hot and dirty martini.
For seafood, Scales is perfect. It offers fresh catches, a fun atmosphere, and beautiful waterfront views. The tuna crudo and oysters are a must.
Post-Dinner Drinks
Old Port has two great spots for after-dinner drinks. Blyth & Burrows offers expertly crafted cocktails and a speakeasy vibe, while The Porthole has a laid-back atmosphere, waterfront views, and live music. We loved it so much, we went there both before and after dinner!
Looking for more tips on Portland, Maine? Be sure to check out my Ultimate Guide to Portland, Maine, for everything you need to know about the city.
Day 2
Portland Head Light & Kennebunkport
After checking out, we drove to Portland Head Light in Cape Elizabeth. The views were even more stunning than I expected, and I wished I had more time to explore. There are great walking paths, including a cliffside loop with amazing coastline views.
Check-In & Lunch
We drove to Kennebunkport and checked into the Grand Hotel, then walked over to Batson River Brewing & Distilling for a quick drink. The patio is perfect on sunny days, and when it gets chilly, the cozy, woodsy cabin vibe inside makes it easy to relax.
For lunch, we hit Boathouse Restaurant on the Kennebunk River. I’d heard a lot of hype, and honestly thought it might be overrated—but I was pleasantly surprised. The atmosphere is lively and the food is amazing. I had the shrimp tacos with a glass of rosé.
Shopping & Gooch’s Beach
After lunch, we explored Kennebunkport and popped into a few boutiques. My favorites were Bliss and 173 Mercantile. You can also grab one of the hotel’s complimentary bikes and ride over to Gooch’s Beach, just under a mile away. There’s a sandy spot to walk, relax in the sun, and take in views of Maine’s rocky coastline.
Pre-Dinner Appetizers, Dinner & Drinks
After exploring town and the beach, we stopped by The Spirit of Massachusetts for drinks and appetizers. This historic ship is on the Kennebunk River and has such a unique setting! The prawns and Sea Cucumber drink were my favorite—definitely try them!
For dinner, we went to Luca, the patio tucked in the woods at The Lost Fire. It’s one of the best places to eat in Kennebunkport! The boho vibe, with twinkling lights, a cozy fireplace, and drinks served from a little barn, made it feel magical. The food was amazing—had a burger and fries while Tim went for the filet. It’s about a ten-minute drive from town, but totally worth it.
Afterward, we walked over to Old Vines Wine Bar, just a short walk from the Grand Hotel. This wine bar has an outdoor patio is the perfect spot to wind down with a post-dinner drink.
Day 3
Morning Activities & Breakfast
We kicked off our day with the hotel’s complimentary breakfast, but if you’d prefer to venture out, Mornings in Paris and Dock Square Coffee House are great spots for an easy breakfast.
We walked back to Gooch’s Beach, but the Rugosa Lobster Tour sounds like a lot of fun! This lobster cruise offers a unique glimpse into Maine’s lobster industry. You can sit back and relax while the crew pulls traps, or get hands-on and help out. It’s both educational and scenic.
If you’re not up for a full tour, the hotel also offers complimentary kayaks, so you can explore the Kennebunk River at your own pace.
Lunch
For lunch, we headed to Casa Seventy-Seven in Cape Porpoise, a more laid-back part of Kennebunkport where you can watch the fishing boats come and go. The restaurant has a modern vibe inside, but we opted to sit at a bistro table outside, right by the water. I had the lobster roll with a limoncello spritz—honestly, it’s the perfect spot to soak in coastal Maine.
Live Music, Dinner & Drinks
Before dinner, we popped by the Kennebunkport Inn for a pre-dinner drink and sat on the patio to listen to the live music. It had this cozy vibe with twinkle lights and hydrangeas—just perfect for a relaxed evening.
After our drinks, we crossed the street to Chez Rosa for dinner. This French restaurant quickly became one of my favorite restaurants in Kennebunkport. The ambiance was amazing—greenery draped over the walls, French bistro chairs, and white marble tabletops. I started with a half-dozen oysters, but they were so fresh I couldn’t resist getting six more. We also had French onion soup, steak frites, and finished with crème brûlée.
Afterward, we wanted to go to Ryan’s Corner House Irish Pub, but it was closed for an event, so we ended up back at Old Vines Wine Bar. Still, if you’re in the area, I recommend checking out Ryan’s Corner House Irish Pub. It’s just across from the Grand Hotel, has an outdoor fireplace, and live music—such a great vibe!
For more insider advice on Kennebunkport, be sure to check out my Ultimate Guide to Kennebunkport, featuring the top things to do, dining spots, and local recommendations!
Day 4
Breakfast and Lunch
We started the day with breakfast at the hotel before heading back to Boston. I had hoped to stop in Ogunquit for lunch, but it was so crowded when we drove through, and we needed to get back to drop off the rental car. I’d planned to do the Marginal Way cliff walk and grab lunch at MC Perkins Cove, but in the end, we decided to go back to Frisbee’s Wharf for lunch instead. It was just as good as the first time!
Boston: Check-in and Drinks
We checked into The Cambria Hotel in Boston and Ubered to Terra in Eataly for an Aperol spritz. It was my first time in an Eataly, and I enjoyed wandering around the shops. After that, we walked over to Saltie Girl for a snack. I absolutely loved this place—the oysters and drinks were fantastic, and the vibe was so pretty and charming.
We then walked to the Cisco Brewers popup in Seaport. It’s a great outdoor spot to grab a drink, snack, listen to music, and play some games.
Departure
Our flight got canceled, so we ended up waking up early, grabbing a coffee at the hotel, renting a car, and driving home.
Looking back, I absolutely loved this Boston to Portland road trip—the charming towns, fresh seafood, and the laid-back atmosphere were just perfect. If I had more time, I definitely would’ve spent an extra day in Portland to really take it all in. Can’t wait to go back and explore more of Maine!
