I grew up in Westbrook, Maine which is just outside Portland so I thought I’d show you around. Portland is a short 2 hour $25 bus ride to Boston so you could knock out 2 cities in one trip easily. Since I always recommend the same places, I figured I’d do this itinerary of the way to spend a day in Portland.

  • Start the day with a Bennie

    Up early enough for breakfast? Have a “bennie” at St. Joe’s Cafe not far from the Maine Mall in South Portland. The breakfast sandwiches and coffee were good, but it’s all about the beignets with maple cinnamon dip that’ll stick in your memory for weeks. Save room.

  • Head to Portland’s Old Port

    Walk off the bennies in Portland’s Old Port. It’s on the waterfront so you’ll see lobster boats dropping off their catch at seafood vendors. There are tons of touristy shops and bars. Skip DiMillo’s. It’s nice. The food is good, but it’s a tourist trap that really isn’t all that amazing. Every tourist book will tell you to go. Don’t. It’s just a decent restaurant with overpriced seafood on a big boat that doesn’t go anywhere. You’ll be on a real boat a little later.

  • Pizza for lunch

    Head toward India Street and get a pizza slab at Micucci’s. It’s close to Portland’s Old Port. It’s a scaled down version of Mazzaro’s… lots of wine, cheese, pasta, etc. But the star of the show is the pizza slab which you need to go to the back and up the stairs to find. They don’t make them custom to how you like so don’t ask. If there’s a slab available, grab it. If they’re sold out, too bad. You’ll have to wait til the next batch is ready.


  • Take a Cheap $15 Cruise around Portland’s Calendar Islands

    They’re called the Calendar Islands because there are about 300 of them. I grew up in Maine and never went on one of these boats. Now I’ll jump on one every time I go back. Do a cruise around the Portland islands. It’s pretty cheap… about $15/person and lasts a little over 2 hours. Bring a sweatshirt just in case – Portland can even be cold in the summer when you’re on the water. It’s walking distance from Micucci’s where you’ll get that slab of pizza. Just walk toward the water and look for Casco Bay Lines. Do the mailboat run if you can.


  • Head to Portland Headlight

    It’s the lighthouse that’s pretty much on 99% of Maine postcards. It’s about a 15 minute drive from Portland. If you have time 2 Lights State Park is worth a visit too. But Portland Headlight is an easy spot to visit and get some good “I really did visit Maine” pictures.

  • Explore the coast

    There’s Two Lights State Park and plenty of other spots nearby to get some great pics of Maine’s coast.


  • Seafood… finally

    After Portland Headlight, grab dinner at The Lobster Shack. I always go with the fried shrimp. But there’s probably no bad choice. Avoid going during the peak hours around 5 or 6pm if you can. The line can get long and the picnic tables outside fill up fast. But it’s worth the wait. And the views of the rocky coast will entertain you while you wait.

  • If you get a chance, eat an Italian

    Mainers love their Italians. Nothing fancy, just ham, cheese, tomatoes, onion, peppers, olives on some Italian bread with oil. Just order a “regulah” and pick off what you don’t like.


  • If you must, go to LL Bean

    I guess I should also mention Freeport, Maine as a side stop. It’s super touristy so I usually avoid it, but it’s home to the famous outdoor life megastore LL Bean. Freeport is overpriced but stinkin’ cute so if that’s your thing, go for it. It’s particularly nice around the holidays since they want to ruin your credit card.



  • Pier Fries at Old Orchard Beach

    Another honorable mention is a visit to Old Orchard Beach. If you go, look for the famous pier fries. And do NOT put ketchup on them. It’s all about drowning them in salt and vinegar as the locals do.

  • Or just drive around and skip all my tips

    You’ll definitely need a rental car when you get to Maine. Nobody really uses the public transport and it won’t get you to the good stuff anyway. Just rent a car and drive around. You’ll find lots of ooooh ahhhh moments.


Sign me up for the 105.7 WROR email newsletter!

Make sure you're in the know on the latest music and entertainment news, plus exclusive prizes, trips, and more!

By clicking "Subscribe" I agree to the website's terms of Service and Privacy Policy. I understand I can unsubscribe at any time.