When that summer heat rises, we Texans head North!
When you want to stay in the US and find some place cooler, you head to the northern most contiguous state – Maine. And why not start with the seaside town of Maine, Portland?
Portland is a beautiful city right on the coast of the Atlantic ocean. My friend Ashley and I had so much fun exploring the city! We stayed in the Old Port area, so restaurants, shopping, and excursions were all within walking distance! We had a great weekend exploring the city and I’m here to show you that you CAN see and do all the things in just two days.
A couple things you’ll want to keep in mind. Most places close early, so have a game plan in mind before you start down the road towards a destination. And you’ll also see that we rarely got several courses at one restaurant. I really recommend trying different things at different restaurants and enjoying the walk and the sights along the way. Each place has their own specialty, so don’t feel like you’re tied down to eating at just one place.
Are you ready for it? Here we go…
Day 1
Farmer’s Market. Hiking. Lighthouses. Lobstering.
Portland Farmer’s Market
If you’re visiting on a Wednesday or Saturday, you must stroll through the Portland Farmer’s Markets. I love living like a local for a day at farmers markets because it allows you to see and taste the local favorites. From home grown berries and homemade pies to freshly picked flowers and farm fresh eggs, this is THE place to visit. I ended up getting some fresh honeycomb and raspberries. The flavors are so robust and delicious!
Back Cove Trail
After we got our snacks, we headed to Back Cove Trail for a little hiking. This 3.5 mile loop is one of the oldest and most popular trails in Portland and provides great views of the skyline.
Tomaso’s Canteen (Lunch)
When a restaurant has something called the “bomb” on the menu, you know you’re in for some good food! If you happen to be in the area, I recommend heading to Tomaso’s and getting the fried pickles, chicken bomb, and the buffalo chicken mac n cheez.
Portland Head Light & Fort Williams Park
This beautiful lighthouse holds the title for the most photographed lighthouse in the country. Ever notice the lighthouse on Red Lobster’s logo? Yep. This is that same exact one. I could have stayed there for hours listening to the waves crash into the shore. If you’re feeling adventurous, you can walk down to the water along the jagged rocks and let the surf wash over your bare feet. I have to warn you – that water is little chilly! If you’re visiting earlier in the day, the lightkeeper’s home has been turned into a museum and you can tour the building to learn more about the history of the Portland Head Light.
Lucky Catch Cruises (Lobstering)
When you’re this close to the water, it would be a shame not to go out on it! And we didn’t just go out on it – we went lobstering! I cannot recommend Lucky Catch Cruises enough! We had the best time! I’ve always wanted to see how lobster were harvested and this blew my expectations out of the water (ba dum ching). Not only did we set traps with bait, but we also reeled in our own catches, saw different World War I forts, and learned about the sustainability the Maine fisherman adhere to.
With every lobster caught in Maine, the lobster is measured and checked for gender and eggs. One thing I thought was interesting was that not all female lobster reproduce. So if a fisherman catches a female lobster with eggs (little black dots) on her belly, the fisherman marks her tail and put her back in the ocean. This ensures that future fisherman won’t keep her and the lobster population will still be able to grow. Also, female lobster can reproduce until death, and since lobster can live to be up to 100 years old, that’s a lot of lobster babies she could produce.
Portland Lobster Co (Dinner)
Once we hauled in our catch, we walked our lobster next door to Portland Lobster Company. There, they steamed the lobster and we were able to eat what we caught. You can’t get much closer to sea to table than that!
Gross Confection Bar (Dessert)
Forget everything you know about desserts because this place is going to take all of the ingredients of a nostalgic favorite and reconstruct it into something completely different and utterly amazing.
LUNA (Cocktails)
This brand new cocktail bar on the rooftop of the Canopy by Hilton just opened about 3 weeks ago. This swanky, upscale bar features gorgeous fews of the harbor and specialty cocktails that are simply divine! If you’re a fan of tequila and a little heat, I recommend getting the Dioscuri.
Day 2
Shopping. Mansion Tour. Sailing.
Rigby Yard (Brunch)
Another big day of sightseeing means you’re going to need some sustenance to start your day off right. We loved having brunch at Rigby Yard. The breakfast charcuterie was the perfect way to mix and match the local ingredients.
Shopping
My friend Ashley loves to shop, so shop we must! The whole Old Port area has tons of shopping options to choose from and everything you could ever want! From housewares and kitchen gadgets to souvenirs and lobster hats, you can find it all. Start on Fore street. It’s got some great shops and cute items.
Then you’ll want to head over to Sea Bags Maine. I love this company’s mission! Instead of sailors throwing out old worn out sails, they can bring them to Sea Bags where the company makes the sails into bags and purses of all shapes and sizes. The vintage bags feature the number and symbol panels from the sails while the other bags have printed symbols on them (and are a bit cheaper than the vintage). They’re just so unique!
Anthony’s Italian Kitchen (Lunch)
If you’re tired of seafood already, do yourself a favor and head into Anthony’s. This family-run Italian restaurant features all the favorites with a red sauce that’s to die for! They have pizza, pasta, sandwiches, and salads, but you really can’t beat their lasagna! If you’re there on a Saturday night, they also have an all you can eat buffet and a dinner show.
Victoria Mansion
If you’re a lover of Downton Abbey and the early 1900s, then this is the place for you. Built in 1860, this beautiful home was one of the first in Maine to have indoor sewer and plumbing, hot and cold water, and a 25 foot skylight. The man who had it built, Ruggles Morse, was a self-made man only completing 2nd grade schooling and prospering through his own hard work. While I couldn’t video inside the home, I did want to show you a few photos I took inside. In every room, there are paintings of the owner, nods to his power and position, and even a full dinnerware set that was made just for him and his family that has their family name etched into the silverware. If you’d like to check out this beautiful home, make sure to make a reservation and get your tickets online before you visit because they sell out.
Portland Schooner Company
I have always wanted to go on a sailboat. This was my chance. When in Maine, right? We boarded the Timberwind and sailed out of the harbor. Once away from the dock, the passengers were able to volunteer to help hoist the sails, and let me tell you – they were heavy! I still know nothing about sailing or the commands they called out or the difference between port and starboard, but I totally enjoyed myself. Once out on the water, we floated along enjoying the breeze and watching the seals play in the water (we saw 3 that day which apparently was not common). The boat wasn’t packed and everyone was able to move around the ship freely. We also were able to bring snacks and drinks on board, so you could easily make a romantic date or family picnic on the water out of it. This cruise also requires reservations be made in advance.
Taco Escobarr (Dinner)
First of all, this Texas girl knows her Mexican food. So I was admittedly skeptical about a Mexican food joint so far away from the border. But let me say, I was pleasantly surprised! The infused tequila cocktails were refreshing (I recommend the pineapple one) and packed with flavor and the mix and match enchiladas were so freaking good. I got them filled with Bisteck (slow braised beef) and green verde sauce on top. It was amazing! The only thing I didn’t enjoy was the queso. It tasted like that cheese in can that sporting events buy in bulk and squeeze over some nachos. The service, the food, and the drinks were all great and definitely exceeded my expectations!
Captain Sam’s Ice Cream (Dessert)
I’ve never had bourbon in icecream, but I feel like I should have it more often now. We saw Captain Sam’s the day before and the line was out the door and down the street, so we decided not to stop in until later. I’m so glad we were able to come back because it was delicious! They had about 15 different flavors to choose from and I tried the Kentucky Derby (bourbon, molasses, pecans, chocolate chips). It was SO good. I wish I could take that stuff back to Texas with me.
Via Vecchia (Cocktails)
First of all, I’m in love with the look of this restaurant. It’s got a 1920’s flair about it and it perfectly sets the stage for some amazing cocktails. The bartenders are super friendly and knowledgeable as well, so it you don’t see something you like on the menu, they can craft something to your specific tastes.
I have definitely fallen in love with the East coast this summer! From my trip to Boston last month to this trip to Maine, I have been blessed to have seen some beautiful sights and east some amazing foods. If you liked this Portland itinerary, be sure to subscribe to my Youtube channel so you can get more vacation tips for your next trip.
