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. When Floridians see my lobster posts, they hit me up for the places to go for their first visit to Maine. Since I always recommend the same places, I figured I’d do this itinerary of the way to spend a day in Portland.

• Maine in Autumn

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  Plan a visit at the right time of year. Get out of the Florida heat and visit in summer or fall. Winter (except for Christmas) and spring are miserable in New England. Snow looks great on postcards, but it's a nightmare to drive in. If you want to see the fall foliage, early to mid October is when the trees change color so you can go "leaf peeping."

• On second thought…

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  Listen I hate snow and cold. But you're a Floridian so these scenes probably appeal to you. Go in December. But just know that after a few days, frozen toes get old quick.

• Have a Bennie for Breakfast

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  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

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  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…

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  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 $15 Cruise around Portland’s Calendar Islands

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  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. Here are more pics from just the cruise.
• Head to Portland Headlight.

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  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

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

• Seafood… finally!

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  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.
• Be a kid. Go sledding.

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  That was a busy day. I'll give you a few honorable mention alternate options. Listen, as a former Mainer, I moved to Florida for a reason. I hate snow and cold. But to you, it'll probably be fun for a few days. Grab a sled and knock yourself out. I'll stay inside where it's warm.

• If you get a chance…

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  Get an Italian sandwich. Much like Tampa loves their Cubans, 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.

• Find a Whoopie Pie too.

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  Few Floridians know about them... but it's just two chocolate cakes with a vanilla frosting in the middle. They usually have them at Lobster Shack where I had you go for dinner. If they're out, any sandwich shop will have them. Amato's is probably the most popular one you'll see all over the Portland area. You can also get your Italian there.
• If you must, go to LL Bean

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  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

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  Listen... don't count calories when you go to New England. 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.

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  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.
• Good night Maine…

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  For more tips on food in Maine and Boston, I have 2 hashtags for you on Instagram that'll give you loads of advice: #genoatemaine and #genoateboston. Look those up on Instagram and you'll eat very well. Enjoy!

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