Travel Guide: Portland, Maine

Portland, Maine

Today I am going to be sharing my most recent travel adventure to Maine. I had never been before and  it’s been on my bucket list for a while! I love small town New England charm and was ready to feast on lobster rolls for the entire four days I was there. Maine did not disappoint. In fact, I felt as though I had stepped into a Nicholas Sparks movie and I never wanted to leave!

I spent long weekend in Portland and Cape Elizabeth walking into the local shops and farmer’s markets, whale watching, exploring landmarks like the Portland Headlight and museums and sunset walks on the beach (no joke, it was cheesy and perfect and had The Last Song written all over it!)

Where to Stay:

First things first, we booked the flight and now needed a hotel, having never been I was solely going off anything I could find on the internet. After lots of research, texting all my friends who went to school in Maine and grew up in New England, we decided we wanted to see as much of Maine as possible. There are lots of options in downtown Portland but we stayed at The Black Point Inn, a charming bed and breakfast, about 20 minutes from downtown. The inn is right next to the water, it has bikes to rent and ride along the shore, a mile long hiking trail and pathways to walk and view the beautiful residential mansions! The staff was super accommodating and told as all the things to do around the inn. We had breakfast and lunch on the patio but never ended up getting to the main dining room for dinner. The food is great, the bike rides and hiking trails are refreshing after being in New York City all summer and it’s a quick ride into town.

Where to Eat:

We flew in early on Friday morning to Portland, rented a car, threw our luggage in the truck and drove right to downtown, stopping for donuts on the way at Holy Donut. I didn’t realize there were two locations! We went to the location driving into downtown instead of  the one on Exchange Street. Regardless, it’s perfect for an Instagram photo and yummy if you like unique flavor combinations. I definitely tried the Maple Bacon and Chai Glazed donuts… Oh and also the Pomegranate flavor, well worth it! In case I forgot to mention that this trip was almost solely food based, I will now!

Once we got into downtown, I wanted to look around Commercial Street. This the main drag where you can check out the local shops and then wonder your way around on the cobblestone streets to see the rest of the stores. For lunch, we went and got Fries/Burger at Duckfat to go! There are hours wait time at Duckfat, Eventide and Honeypaw. These are all within the same area so get there early if you want to sit down. We went into East Ender and had a raspberry and basil cocktail called The Ricky as we waited for our truffle fries and Cubano sandwiches from Duckfat. YUM!

Things to Do:

After we finished lunch we drove over to see the Portland HeadLight, the Maine Historical Society & Wadsworth-Longfellow House. Then in was time to eat again, we went to dinner at a tiny Italian restaurant called Piccolo. If you decide to stay downtown, ForeStreet is supposed to be incredible but its packed a lot of the time so if a reservation isn’t avail you can eat at the bar for dinner. Street and Co and Central Provisions are also fantastic!

On Saturday, the alarm woke us up bright and early for coffee and a 9 am call time to go whale watching! We spend four hours trying to track down whales… we failed! We didn’t see one whale. However, ended up seeing a school of more than 500 dolphins! The tour guides of Odyssey Whale Watch were beyond ecstatic because the dolphin sightings apparently only happen a few times a year and no one had seen them this season yet.

Sitting on a boat for four hours, you really can work up an appetite, so naturally we went to find the famous Maine lobster roll. We were pleasantly surprised when the boat dropped us off next to Portland Lobster Co. The lobster was everything you would expect and more! Delicious, fresh and satisfying.

By the late afternoon, we drove back to The Black Point Inn, went on a bike ride and then got ready for dinner at The Earth at Hidden Pond. The food was good, the ambiance was romantic with the room lit completely by candlelight!

With an early flight on Sunday morning, we headed back to NYC. The trip was short but sweet and filled with lots of New England activities.

love that look:


Brixton Hat // Green Windbreaker // Mansur Gavriel Purse // Earrings // Ray Ban Sunglasses // Grey Tank // Suitcase

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