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Portland, Maine punches well above its weight for such a small city. Think cobbled Old Port streets, a proper working harbour, and some of the best seafood you’ll eat anywhere.
On top of that, you get lighthouses that look like they’ve been lifted straight off a postcard. Here’s everything I’d actually recommend doing, based on my own visit. (Want it mapped out day by day instead? Here’s my full 4-Day Portland, Maine Itinerary.
The Best Things to Do in Portland, Maine
In This Guide
If you’re comparing US city breaks, I’ve also covered Best Things to Do in Chattanooga, TN.
1. Wander Old Port
Old Port doesn’t need much of a plan—cobblestone streets, old brick warehouses, and a working waterfront make it one of the most walkable, photogenic parts of the city. Give yourself a few unstructured hours here; it’s the kind of place best explored without an itinerary.
2. Explore the Arts District
Running alongside Old Port, the Arts District is worth slowing down for—galleries, independent shops, and a noticeably creative, laid-back energy that’s different from the more touristy stretch of Commercial Street.
3. Shop at Sea Bags
On Custom House Wharf, tucked between the fishing boats and lobster crates, is Sea Bags—a shop that makes totes and accessories out of genuinely recycled sails. You can watch the bags being sewn on-site, and every single one is one-of-a-kind since no two sails are the same. It’s the kind of proper, useful souvenir you’ll actually use for years.
4. Get a Lobster Roll at The Highroller Lobster Co.
The Highroller, on Exchange Street, is where I had my lobster roll—and it did not disappoint. They let you build your own with a choice of sauces (I’d go for the lime and jalapeño mayo if you like a bit of a kick), and the setting has a fun, retro diner feel with a genuinely lively atmosphere.
5. Try the Chowder at Gilbert’s Chowder House
For chowder, head to Gilbert’s Chowder House on Commercial Street. It’s a proper Old Port institution, and the clam chowder is rich, thick, and exactly what you want after a morning spent outdoors by the water.
6. Breakfast at Standard Baking Co.
Also on Commercial Street, don’t skip Standard Baking Co. I had what I thought was a biscuit and turned out to be a blueberry oatmeal scone—either way, it was excellent, and the smell alone as you walk past is enough to pull you in.
7. Take the Trolley Tour to Portland Head Light
The Trolley City Tour with Portland Head Light Stop is a relaxed way to see the city without worrying about driving or parking. It’s a fully narrated two-hour loop that takes you past the Arts District, the Victoria Mansion, and Longfellow’s childhood home, before heading out to Cape Elizabeth for a 30-minute stop at Portland Head Light—Maine’s oldest lighthouse, set inside Fort Williams Park.
Book Here: Trolley City Tour with Portland Head Light Stop
8. Get Out on the Water with a Lighthouse Cruise
The Best of Maine Lighthouse Scenic Cruise is a boat trip out on Casco Bay that takes in several lighthouses from the water—a completely different perspective from the trolley tour, and one I’d argue is just as worthwhile.
Book Here: Best of Maine Lighthouse Scenic Cruise
9. Consider a Windjammer, Puffin, or Sunset Cruise
If I went back, I’d want to try the windjammer sailing cruise—an old-school sailing trip along the coast that came highly recommended to me while I was there. A puffin-watching cruise and an evening/sunset cruise were both suggested too, and either would slot in nicely alongside the lighthouse trip if you have the extra time.
Book here: Coastal Windjammer Sailing Cruise, Puffin-watching cruise and Sunset cruise
FAQs
What is Portland, Maine known for? Fresh seafood (especially lobster), its historic Old Port waterfront district, and nearby lighthouses like Portland Head Light—one of the most photographed lighthouses in the US.
Is Old Port walkable? Yes, very. Old Port and the neighbouring Arts District are compact and easy to explore entirely on foot.
Do I need a boat tour to see Portland’s lighthouses? Not necessarily—Portland Head Light can be reached by trolley tour or car—but a scenic cruise gives you a completely different view of the coastline and multiple lighthouses at once.
Thanks so much for reading this far! If this guide helped you plan your trip to Portland, I’d love for you to follow along on instagram or Facebook for more honest, firsthand travel guides.
No pressure though – I’m just happy you’re here and hope you have an incredible adventure! 🙂
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