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If you’re trying to work out how to spend 4 days in Portland, Maine, here’s the short version: split your time between wandering Old Port on foot and getting out on the water. That’s really the rhythm of this city, and four days is enough to do both properly without rushing.
My 4-Day Portland, Maine Itinerary
Contents
Here’s exactly how I spent mine.
Day 1: Settle In and Wander Old Port
I started my stay at the Inn at St John Portland In-Town, a historic Victorian B&B on Congress Street in the West End—a lovely, characterful base with an easy walk (or short drive) into Old Port.
Book here – Inn at St John Portland In-Town
First afternoon was all about getting my bearings on foot. Old Port’s cobbled streets and old brick warehouses are made for wandering, and the neighbouring Arts District is worth slowing down for too—galleries, independent shops, and a much more laid-back energy than the touristy stretch of Commercial Street.
Down on Custom House Wharf, right among the fishing boats, I stopped into Sea Bags, a shop that makes totes and accessories out of genuinely recycled sails. You can watch them being sewn on-site, and since no two sails are alike, every bag is one of a kind.
For dinner, I headed to The Highroller Lobster Co. on Exchange Street for my first Maine lobster roll—built to order with your choice of sauce (I went for lime and jalapeño mayo). Great atmosphere, retro diner vibe, and a properly good introduction to Portland’s food scene.
Day 2: Breakfast, Chowder, and More Old Port
Day two started with breakfast at Standard Baking Co. on Commercial Street—I had what I thought was a biscuit and turned out to be a blueberry oatmeal scone. Either way, excellent, and the smell alone pulls you in off the street.
For lunch, Gilbert’s Chowder House, also on Commercial Street, is an Old Port institution—thick, rich clam chowder that’s exactly what you want after a morning outdoors. I spent the rest of the day continuing to explore Old Port at a slower pace, ducking into the shops and galleries I hadn’t got to the day before.
Day 3: Lighthouses, By Land and By Sea
This was my big “get out on the water” day, and honestly the highlight of the trip.
In the morning, I did the Trolley City Tour with Portland Head Light Stop—a relaxed, fully narrated two-hour loop past the Arts District, the Victoria Mansion, and Longfellow’s childhood home, finishing with a 30-minute stop at Portland Head Light in Fort Williams Park. It’s Maine’s oldest lighthouse, and it’s every bit as photogenic as it looks in photos.
Book here: Trolley City Tour with Portland Head Light Stop
In the afternoon, I did the Best of Maine Lighthouse Scenic Cruise, taking in several lighthouses from the water on Casco Bay—a completely different perspective from the trolley tour, and just as worthwhile.
Book here – Best of Maine Lighthouse Scenic Cruise
If you have the extra time, I’d also seriously consider a windjammer sailing cruise—an old-school sailing trip that came highly recommended to me while I was there. A puffin-watching cruise or an evening/sunset cruise would also slot in well here if lighthouses and boats are your thing (they clearly were mine).
Book Here: Coastal Windjammer Sailing Cruise
Day 4: One Last Wander, Then On to the Airport
For my last night, I moved over to the Clarion Hotel Portland Airport ME. It’s also on Congress Street, but don’t let that fool you—it’s about two miles further out, closer to the Jetport than to Old Port. It made sense for an easy departure, but it’s not a walk-to-everything base the way the Inn at St John is, so I wouldn’t plan on wandering from here.
Book here: Clarion Hotel Portland Airport ME
I used the morning for one last loop through Old Port before heading to the airport—there’s always another gallery or shopfront you didn’t quite get to.
FAQs
Is 4 days enough time in Portland, Maine? Yes—four days is a comfortable amount of time to explore Old Port on foot, fit in a lighthouse tour and a boat trip, and eat your way through the city’s best seafood without feeling rushed.
Where should I stay for a Portland, Maine itinerary like this? Somewhere in or near the West End or Old Port keeps everything walkable. Save an airport-adjacent hotel for your last night if you have an early flight, rather than basing yourself there for the whole trip.
Do I need a car for this itinerary? Not really. Old Port and the Arts District are walkable, and the trolley and boat tours handle transport to the lighthouses for you.
Thanks for taking the time to read this article. I hope this post has given you the information you need. If you have any recommendations, tips or advice, I would love for you to share them in the comment section below!
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