We started our trip in Boston, but honestly, I couldn’t wait to get to Portland, Maine. Next time, I’ll skip the drive and fly straight in—because the moment we drove into town, I felt it: that unmistakable summer-on-the-water energy.
Cobblestone streets, charming boutiques, cozy restaurants, the salty harbor breeze, and fishermen unloading their morning catch—it was the kind of place that immediately makes you slow down and stay awhile.
And July? It couldn’t have been more perfect. Warm sun, soft coastal breezes, and the kind of weather that practically demands a lobster roll in one hand and a glass of rosé in the other. I couldn’t get enough.
It didn’t take long to realize that Portland is the kind of place you could come back to again and again—but even with just a couple of days, you can experience so much of what makes this coastal Maine city special.
So if you’re wondering how to spend a weekend in Portland, Maine, you’re in exactly the right place. This ultimate Portland, Maine weekend guide covers everything you need to plan your trip—from where to stay and how to get around, to the best restaurants in Portland, Maine, can’t-miss bars, and the top things to do (including lighthouses, lobster cruises, and a few easy day trips).
Whether you’re visiting Portland, Maine for the first time or planning a quick coastal getaway, this itinerary will help you make the most of every moment.
Getting Around Portland, Maine
We had a rental car since we flew into Boston, but getting around Portland itself is surprisingly easy without one. If you’re planning to explore nearby towns, having a car definitely helps—but if you’re sticking to downtown, everything is walkable, and Uber or Lyft are always easy options. Many hotels also offer bikes, which is such a fun way to see the city.
If you have a little extra time, I highly recommend a day trip to Kennebunkport—it’s just a short drive away and full of charm. You can read all about our Kennebunkport adventure here.
Where to Stay in Portland, Maine (Best Hotels for Every Budget)
Portland’s hotels can get pricey, especially in summer. When we visited in July, rooms were around $700 a night—so I booked the Holiday Inn by the Bay for about half that. I wasn’t expecting much, but it ended up being such a great find: comfy beds, a location perfect for walking almost anywhere, plus on-site parking and bikes to explore the city. Definitely a place I’d stay again.
If you’re in the mood to splurge a little, Canopy is worth it. It’s within walking distance to most restaurants and shops, has waterfront views, a rooftop bar, Luna, and bikes to cruise around town- basically everything you want in a Portland home base. The Press Hotel is a luxury boutique hotel in town worth checking out.
Arrival: Exploring Old Port & the Waterfront
Check into your hotel, then head straight out to explore Old Port and the waterfront. With its cobblestone streets, boutique shops, art galleries, and seafood restaurants, this area is full of energy and perfect for easing into the weekend.
I usually like to have a plan, but this is one of those places where it’s more fun to wander and see what catches your eye for dinner. Afterward, head to Luna, the rooftop bar at the Canopy hotel- even if you’re not staying there. With harbor views and a cocktail in hand, it’s the perfect way to wrap up your first night in Portland.
Day 1 in Portland, Maine: Lighthouses & Dinner in Town
Morning: Visit Portland Head Light (Maine’s Most Iconic Lighthouse)
Located in Cape Elizabeth, Portland Head Light is one of Maine’s most famous lighthouses- and somehow even more beautiful in person. I went early in the morning to beat the crowds, and it was totally worth it- we were able to walk around and take photos without anyone else in the background.
There are plenty of walking paths, and I wish I’d had more time to do the cliffside loop that winds along the rocky coast. The park is open year-round from sunrise to sunset.
Want to see more lighthouses? Sign up for a lighthouse bike tour—you’ll ride along the coast and get to see a handful of Maine’s most picturesque lighthouses in one go.
Lighthouse Bikes has 2 hour, 3 hour and 5 hour bike tours available.
Lunch: Island Creek Oysters
After exploring the lighthouse, head back into town for lunch at The Shop by Island Creek Oysters, a casual little spot that’s perfect for an easy afternoon. We grabbed a table, ordered a round of Palomas, and split a dozen oysters. It’s casual, unfussy, and perfect for a relaxed lunch before heading back out to explore.
Dinner: Via Vecchia (A Must-Visit Restaurant in Old Port)
For dinner, treat yourself to Via Vecchia in Old Port. The restaurant’s atmosphere is stunning—dark, moody, and full of character. We sat at the back bar, which was nice, but next time I’ll request a table in the front room for that lively night-out energy.
I’m still dreaming about their hot and dirty martini and the veal chop, which might just be the best I’ve ever had. The pasta was good- but honestly, I’d go back in a heartbeat just for that martini and veal chop.
Reservations are recommended—it fills up fast.
After-Dinner Drinks: The Porthole (Waterfront Bar with Live Music)
After dinner, head to The Porthole, a lively dive bar right on the water. It’s casual, waterfront, and perfect for a drink while enjoying some live music. We loved it so much that we actually stopped by both before and after dinner—the great energy of the place kept drawing us back.
For anyone looking for a true Portland, Maine night-out experience, The Porthole is a must-visit.
Day 2 in Portland, Maine
Morning and Afternoon: Lobster Cruise or Peaks Island
For a unique Portland experience, a lobster catch cruise is a fun way to learn about Maine’s lobster industry while spending time on Casco Bay. You head out with local fishermen, get hands-on pulling up traps, and even have the chance to buy the lobster you catch and have a local restaurant prepare it.
I had to cancel my cruise last minute and was honestly so disappointed—but it’s at the top of my list for next time. I can’t wait to go and experience it firsthand.
Lucky Catch Cruises is based in Portland and offers an 80–90 minute excursion for $50 per person. You can also book a private charter for $550.
If you’re looking for something a little different, you could swap the lobster cruise for a trip to Peaks Island. Just a quick 15-minute ferry ride from Portland, the island is perfect for renting a bike and exploring at a leisurely pace. Cruise along quiet roads, check out the beaches, and visit the historic forts scattered around—it’s a peaceful escape and a great way to see another side of Portland.
Dinner: Scales (Fresh Seafood on the Portland Waterfront)
Scales is a vibrant waterfront spot in Old Port, known for fresh seafood and a lively, upbeat atmosphere. We stopped by for a late afternoon snack instead of a full dinner—an Aperol Spritz and the tuna crudo, which were light, fresh, and perfectly refreshing. I really wish we had another night to have a full meal here.
The restaurant was buzzing with energy, and I overheard someone mention that some of their fish comes from the boat docked right outside—talk about fresh and local! Definitely make a reservation in advance—it’s a popular spot for a reason.
After-Dinner Drinks: Blyth and Burrows (Craft Cocktails in Old Port)
End the night by walking over to Blyth & Burrows for a craft cocktail. The cozy, intimate bar is perfect for winding down after dinner, and their expertly made drinks are worth the stroll. It’s a great way to cap off your evening in Portland.
Departure
On your last morning, I recommend stopping by The Holy Donut. I’d heard so much about their famous potato donuts, so I had to try one—but honestly, I didn’t quite get the hype. It was good, just not my personal favorite. That said, it’s such a local favorite that it’s still worth trying for yourself- you might love it more than I did!
Portland, Maine is full of amazing places to stay, unforgettable meals, and one-of-a-kind experiences that really capture the spirit of this coastal city. Whether you’re planning a quick weekend getaway or a longer trip, this guide gives you everything you need to make the most of your time by the water.
Want to plan your perfect trip? Check out my complete Portland, Maine guide for even more hotel, restaurants, and activity recommendations here!
