Are you looking for a beautiful weekend getaway? Close your eyes and imagine the fresh salty ocean air, the picture perfect lighthouses, and the oceanfront cobblestone downtown. If you can’t figure out where I am talking about, I am talking about Maine, particularly Portland, Maine. Maine is so underrated. It’s such a beautiful state, and it really brings me so much joy. Nick and I both consider Portland Maine as home. I want to take you on a tour of all things Portland, so you can start planning your weekend away. Whether this may be a romantic getaway, or for a girls weekend.
Getting around Portland, Maine
If you are arriving in Portland by plane, you most likely will be flying into Portland International Jetport. Make sure to catch a flight to jetport, and not airport, or you’ll be on the opposite side of the United States! Portland International Jetport is conveniently located only two miles from downtown Portland.
With the convenient location of the airport, renting a car, lyft/uber, and public transportation are both a great option to get from place to place in Portland. If you plan to stay mostly downtown, getting around by foot or uber/lyft is the better option. If you plan on venturing outside of downtown, a rental car is the best option. Honestly, I would suggest renting a car if you stay more than just a weekend. This gives you the opportunity to venture outside of downtown.
Where to Stay in Portland, Maine
Portland has so many good AirBnB’s, VRBO’s, and hotels. I definitely recommend staying in the Old Port if you are visiting for the weekend. The Old Port is considered downtown Portland. If the Old Port isn’t your scene, I would recommend staying near the Maine Mall. These are some of the places I suggest staying in Portland.
Near the Old Port
The Press Hotel, Autograph Collection
This hotel was built in the Old Portland Press Herald Newspaper building. If you are looking for luxury, look no further than the Press Hotel. The hotel restaurant and bar also have great reviews.
Price: Average USD $233.00
Portland Regency Hotel and Spa
This hotel is located in the heart of the cobblestones of Portland’s downtown. Portland locals go to the Regency for the espresso martinis. Trust me, I am a lover of espresso martinis… Check out the regency, whether you stay there or not.
Price: Average USD $229.00
Hampton Inn Portland Downtown- Waterfront
This hotel is located in the heart of downtown. The rooms overlook the ocean and its a prime location!
Price: Average USD $142.00
Holiday Inn Portland- by the bay
The Holiday inn Portland is a great hotel for your Portland getaway. It’s great for a relaxing weekend with the large pool or a happening weekend nestled in downtown.
Price: Average USD $116.00
Residence Inn by Marriott Portland downtown/waterfront
The residence inn is situated in Maine’s historic Old Port district. This hotel offers a free shuttle to the jetport.
Price: Average USD $152.00
Located outside of the Old Port
Home2Suites by Hilton Portland
Nick and I stayed at this extended stay when we were in town recently. It’s located near the jetport and the Maine Mall. It’s a cheap uber drive away to downtown portland. It’s located approximately 4 miles from downtown.
Price: Average USD $132.00
Portland Sheraton at Sable Oaks
I am definitely biased on this hotel. I used to work at this hotel for five years as a waitress, bartender, and restaurant manager. It was one of my favorite jobs I had. It’s a six story hotel adjacent to the Maine Mall. The restaurant and bar was just recently updated and has great food and drinks.
Price: Average USD $145.00
When’s the best time to visit Portland, Maine
Between the delicious lobster, lighthouses, and charming city, there’s so much to fall in love with Portland. It’s a beautiful destination for any time of the year. I definitely recommend going to Portland during the summer or the fall. If you are looking for foliage, I recommend going in October. A lot of the time, September is a little too soon. The only con of going to Portland during the summer and fall, is the hotel prices are typically a lot higher. Honestly the higher hotel prices are worth it! Let’s start talking about the fun things to do in Portland!
Activities in Portland, Maine
There are so many good things to do in Portland. It’s going to be hard talking about just a few!
- The Lighthouses
Maine is known for the lighthouses. Start exploring the beauty in Maine, and see the six lighthouses within 30 minutes of Portland. One of my favorite lighthouses is Portland Head Lighthouse. It’s located in a cute park. Nick and I actually had our engagement pictures here! Portland also offers lighthouse tours if that interests you!
- Explore the downtown Old Port
The Old Port is one of the most charming areas in New England. The
cobblestone streets, and scenic waterfront views are worth exploring.
- Walk the Eastern Promenade
The eastern promenade trail is a flat 2.1 mile scenic trail near downtown Portland. Besides the benefit of exercising, you also can have a picnic on the trail, visit the beach, go swimming, and hit up all the good food trucks. The best food truck is Muthah Truckah.
- Take a casco bay cruise
A weekend trip to Portland isn’t complete without a casco bay tour. Whether this may be one of their specialty tours, or a cruise to one of the casco bay islands. These cruises go to the six casco bay islands; Peaks Island, Little Diamond Island, Great Diamond Island, Cliff Island, and Chebeague Island. If you have to choose between the six casco bay islands, I’d choose Peaks Island. Nick and I love Peaks Island, actually we got engaged there!
Peaks island is a quaint casco bay island. People typically get around the island in a golf cart. You can rent a golf cart at Dyl’s Carts. The island is really beautiful, and honestly renting a bike/golf cart and exploring the island is a great day trip! During the summertime, Reggae Fest is a staple on the island. Jones Landing has the best rum buckets, and live music. Have a bite to eat at Peaks Island Lobster house before heading back on the ferry!
- Visit a local beach
A weekend trip to Portland should include visiting Old Orchard Beach. It’s a great beach town located 25 minutes away from Portland. Old Orchard beach has a great boardwalk, a sandy beach, and restaurants. One of my favorite summer favorites on Old Orchard Beach is the Brunswick. They have great drinks, and it overlooks the great scenery of the beach. Also, a trip to Old Orchard Beach isn’t complete without an ice cream at Fielder’s Choice, or pier fries.
- Visit the Portland’s Farmers Market
If you are looking to check out local vendors, Portland has a great farmers market! The farmers market has operated since 1768. If it can be grown, or produced in Maine, you will find it at this farmers market.
Restaurants to Check out in Portland, Maine area
Breakfast/Brunch
Mister Bagel
Bagels made with ingredients from local Maine Farms. This bagel shop is one of
the best breakfast spots in Maine. Order a super bagel, and you won’t be disappointed.
Address: 601 Forest Ave, Portland, Maine
Yelp Review: ⭐⭐⭐ 3.0/5.0
TravelingbeebryantRN’s review: ⭐⭐⭐⭐ 4.5/5.0
Flicks_with Nick’s Review:⭐⭐⭐⭐ 4.2/5.0
Becky’s Diner
There is always a line at Becky’s diner… it’s worth the wait!
Address: 390 Commercial Street, Portland, Maine
Yelp Review: ⭐⭐⭐⭐ 4.0/5.0
TravelingbeebryantRN’s review:⭐⭐⭐ 3.8 / 5.0
Flicks_withNick’s Review: ⭐⭐⭐ 3.7 / 5.0
Holy Donut
Maine potato made donuts from scratch
Address: 194 Park Ave, Portland, Maine
Yelp Review: ⭐⭐⭐⭐ 4.5/5.0
TravelingbeebryantRN’s review: ⭐⭐⭐⭐ 4.0 / 5.0
Flicks_withNick’s Review: ⭐⭐⭐⭐ 4.0 / 5.0
Lunch
The High Roller Lobster Co.
The controversial topic of who has the best lobster roll in Portland… is the High Roller Lobster company it?
Address: 104 Exchange Street, Portland, Maine
Yelp Review: ⭐⭐⭐⭐ 4.4 / 5.0
TravelingbeebryantRN’s review:⭐⭐⭐⭐ 4.0 / 5.0
Flicks_withNick’s Review:⭐⭐⭐⭐ 4.8 / 5.0
Duckfat
This little eatery in Portland is full of great surprises, poutine, sandwiches, and milkshakes. Did I say poutine?! The best poutine… I promise
Address: 43 Middle Street, Portland, Maine
Yelp Review: ⭐⭐⭐⭐ 4.5 / 5.0
TravelingbeebryantRN’s review: ⭐⭐⭐⭐ 4.5 / 5.0
Flicks_withNick’s Review: ⭐⭐⭐⭐ 4.4 / 5.0
Tuscan Table
A italian eatery located conveniently in South Portland on Maine Mall Road
Address: 390 Gorham Road, South Portland, Maine
Yelp Review: ⭐⭐⭐⭐ 4.0/5.0
TravelingbeebryantRN’s review: ⭐⭐⭐⭐ 4.0 / 5.0
Flicks_withNick’s Review: ⭐⭐⭐⭐ 4.0 / 5.0
Dinner
The High Roller Lobster Co.
The controversial topic of who has the best lobster roll in portland… is the High Roller Lobster company it?
Address: 104 Exchange Street, Portland, Maine
Yelp Review: ⭐⭐⭐⭐ 4.4 / 5.0
TravelingbeebryantRN’s review: ⭐⭐⭐⭐ 4.0 / 5.0
Flicks_withNick’s Review: ⭐⭐⭐⭐ 4.8 / 5.0
Street and Company
Mediterranean Bistro serving some of the local fresh seafood
Address: 33 Wharf Street, Portland, Maine
Yelp Review: ⭐⭐⭐⭐ 4.4 / 5.0
Tuscan Table
A italian eatery located conveniently in South Portland on Maine Mall Road
Address: 390 Gorham Road, South Portland, Maine
Yelp Review: ⭐⭐⭐⭐ 4.0/5.0
TravelingbeebryantRN’s review: ⭐⭐⭐⭐ 4.0 / 5.0
Flicks_withNick’s Review: ⭐⭐⭐⭐ 4.0 / 5.0
Scales
Elegant restaurant with views of the Casco Bay. One of the family restaurants that include Street & Company, Fore Street, and Standard Baking Company.
Address: 68 Commercial Street, Portland, Maine
Yelp Review: ⭐⭐⭐⭐ 4.3/5.0
TravelingbeebryantRN’s review: ⭐⭐⭐⭐ 4.4 / 5.0
Flicks_withNick’s Review: ⭐⭐⭐⭐ 4.4 / 5.0
Portland Lobster Company
Fresh seafood with waterfront views.
Address: 180 Commercial Street, Portland, Maine
Yelp Review: ⭐⭐⭐ 3.5/5.0
TravelingbeebryantRN’s review: ⭐⭐⭐ 3.9 / 5.0
Flicks_withNick’s Review:⭐⭐⭐⭐ 4.2 / 5.0
Duckfat
This little eatery in Portland is full of great surprises, poutine, sandwiches, and milkshakes. Did I say poutine?! The best poutine… I promise
Address: 43 Middle Street, Portland, Maine
Yelp Review: ⭐⭐⭐⭐ 4.5/5.0
TravelingbeebryantRN’s review: ⭐⭐⭐⭐ 4.5 / 5.0
Flicks_withNick’s Review: ⭐⭐⭐⭐ 4.4 / 5.0
Gilbert’s Chowder House
Casual restaurant serving award winning clam chowder. The outdoor patio overlooking the casco bay is the plus!
Address: 92 Commercial Street, Portland, Maine
Yelp Review: ⭐⭐⭐⭐ 4.0/5.0
TravelingbeebryantRN’s review: ⭐⭐⭐⭐ 4.5 / 5.0
Flicks_withNick’s Review: ⭐⭐⭐⭐ 4.1 / 5.0
Dessert
The Bar of Chocolate
Martini Wine Bar, specializing in desserts and dessert martinis
Address: 38 Wharf Street, Portland, Maine
Yelp Review: ⭐⭐⭐⭐ 4.0/5.0
TravelingbeebryantRN’s review: ⭐⭐⭐⭐ 4.5 / 5.0
Flicks_withNick’s Review: ⭐⭐⭐⭐ 4.2 / 5.0
Fielder’s Choice
Family owned business serving homemade ice cream
Address: 156 Saco Ave, Old Orchard Beach, Maine
Yelp Review:⭐⭐⭐⭐ 4.5/5.0
TravelingbeebryantRN’s review: ⭐⭐⭐⭐ 4.5 / 5.0
Flicks_withNick’s Review: ⭐⭐⭐⭐ 4.4 / 5.0
If you can’t decide between all these great places, Portland Maine offers many food tours! Check them out and taste your way around the coast.
Breweries, Distilleries, and Wineries to check out in Portland, Maine Area
Portland has the highest rate of breweries per capita than any other city in the country. Portland is full of great wineries and craft breweries. There’s too many breweries to choose our favorites, so I’ll just go over a bunch for you to visit. Portland, Maine also offers great brewery tours.
Shipyard Brewery Company
Yelp Review: ⭐⭐⭐⭐ 4.0/5.0
Address: 86 Newbury Street, Portland, Maine
Allagash Brewing Company
Yelp Review: ⭐⭐⭐⭐ 4.5/5.0
Address: 50 Industrial Way, Portland, Maine
Austin Street Brewery
Yelp Review: ⭐⭐⭐⭐ 4.0/5.0
Address: 1 Industrial Way, Portland, Maine
Bissell Brothers Brewing Company
Yelp Review: ⭐⭐⭐⭐ 4.5/5.0
Address: 38 Resurgam Place, Portland, Maine
Definitive Brewing Company
Yelp Review: ⭐⭐⭐⭐ 4.5/5.0
Address: 35 Industrial Way, Portland, Maine
Foundation Brewing Company
Yelp Review: ⭐⭐⭐⭐ 4.5/5.0
Address: 1 Industrial Way, Portland, Maine
Liquid Riot Distillery
Yelp Review: ⭐⭐⭐ 3.9/5.0
Address: 250 Commercial Street, Portland, Maine
Cellardoor Winery
Yelp Review: ⭐⭐⭐⭐⭐ 5.0/5.0
Address: 127 Middle Street, Portland, Maine
Portland, Maine Pro Tips
- Stay in the Old Port if you are a first timer.
- Book a day trip to one of the islands. You won’t regret it. Make sure to look at the right ferry schedule (Summer and winter schedule). Cough cough,I’ve made that mistake.
- Don’t wear heels in the Old Port. It’s not worth fighting with the cobblestone.
- The foliage cruise out of Portland is not just for old people… I myself have this on my bucket list, so should you.
- Eat at all the world class restaurants in Portland… don’t fall for the tourist trap, Dimillos. It’s good, but not worth the money.
- Be prepared to fall in love with New England.
Hopefully, I convinced you to plan a trip to Portland, Maine for the weekend! It’s a perfect New England weekend getaway. If you are planning a trip to Portland, Maine, drop a comment and I’ll help you start planning! Stay up to date with all things travel, nursing, and of course Flicks_withNick movie reviews. Give us a follow on instagram and subscribe to this blog.
TravelingbeebryantRN & Flicks_withNick 
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