Mini Guide: Portland, Maine

The way life should be

Maine is a great state to explore the outdoors, and apparently beer as well. Portland, Maine is just under two hours from Boston and can make for a great day trip or long weekend. The Amtrak goes right into town so even those without a car can take advantage. They have endless breweries, waterfront activities, and the city was recently voted the 2018 Restaurant City of the Year by Bon Appetit.

Here’s a guide on how to eat, drink and be merry in the north, with some of my favorite things to do in Portland.

Breweries:

My top pick is Allagash; great tour with a full flight of samples along the way. And did I mention it’s free? It’s also near Foundation Brewing Company, Austin Street Brewery, Battery Steele Brewing, and Definitive Brewing Company, so it’s easy for an afternoon of brewery hopping.

Shipyard, Bissell Brothers, Gritty McDuffs, Sebago Brewing Company, Bunker Brewing are also great spots to hit closer to downtown. Batson River has the coolest vibes (and their holiday decorations are unreal) with lots of good brews and bites.

Non-breweries for drinking: Lincolns is a cool (and cheap) speakeasy, Apres has amazing hard seltzer, and if you feel like dancing among antiques (yes, this is a thing) head to Bubba's.

Dining:

There is no shortage of seafood in Portland. Any spot on the water can guarantee fresh catches and New England fare. The city is also becoming a restaurant hot spot and there are so many “top” restaurants to find with a Google search.

Hot Suppa and Local 188 have great brunch, The Holy Donut and Tandem Coffee Roasters have great sweets, and Duckfat absolutely cannot be missed if you like poutine.

Taco Escobarr is a fun, casual Mexican spot, and Via Vecchia has great Italian food and stunning vibes.

Things to do in Portland, Maine:

Peaks Island is a short boat ride from downtown and a great day trip, especially in the summer. Arcadia National Bar has drinks and old school video games for late night fun. Old Port has cobblestone streets and great shops. Cape Elizabeth is a short ride away from Portland with a beautiful cliff walk and the Portland Head Lighthouse.

Portland is the perfect place to go year round to take in beers, bites and beautiful landscapes.

Mini Guide: Chicago.

Pizza is a meal that I find hard to improve, but deep dish brings it to a level I never knew I needed. Chicago is home of the deep dish pizza, a stunning blue lake and so much more. I’ve been twice and am itching to go again to enjoy all my Chicago food favorites and to hop around all their amazing rooftop bars. Here are some of the best things to do in Chicago.

Where to eat:

Lou Malnati’s: Home of the best deep dish in Chicago. Buttery crust, gooey cheese, pure deliciousness.

Garrett Popcorn: While their classic combo of cheese and caramel corn may sound unappealing, I found this to be one of the best snack’s I’ve ever tasted. Whenever I have a layover in Chicago I make the trek to the airport store because it is just that good.

RPM Italian: Fine dining and great pasta in the heart of the city.

Portillo’s: While I have yet to make it on my trips, my Chicago native friend tells me this is the place to go in Chicago. Also a great place to try a classic Chicago hot dog.

Where to drink:

Cindy’s Rooftop: Right above the Chicago Athletic Association, this trendy spot overlooks Millenium Park.

The Signature Room: Forget the Sears Tower, this is where you can get the best views of the city from 96 stories up. Go at sunset for the best views.

London House Rooftop Bar: While being outside that high up gave me slight vertigo, this was my favorite rooftop we went to as it was outdoors and overlooked the downtown architecture and river.

Things to do in Chicago:

Sears Tower, now known as the Willis Tower: The classic spot for a full view of the city and getting in your basic photo op sitting on glass and looking down at the street.

Navy Pier: This is a great place to walk around the water and you can take the Centennial Wheel for a spin to view the city.

Bus Tour with Boat Ride: If you’ve read my travel guides before you know I’m an advocate for the hop-on hop-off bus tours. It’s an easy way to see the city and forgo paying for public transit. The one in Chicago includes the option to add on an architecture river cruise, which I loved.

Visit the Zoo: The zoo is free and in Lincoln Park, which is a great place to walk around and spend the day.

Bike or walk around the river: You can rent a city bike or just stroll around the riverfront area.

Where to stay:

I’ve stayed at both the Chicago Marriott Downtown Magnificent Mile and the W Chicago City Center. Both have great locations that are close to shopping, bars and restaurants, and allow you to walk pretty much everywhere you want to go.