Discovering the Best of Portland, Maine: Travel Tips and Culinary Adventures

Portland, Maine is a place that is often mixed up with Portland, Oregon-- while I'll admit that they do share a few similarities, what really differentiates Maine's Portland from its larger cousin are the quaint coastal vibes and lighthouses galore. You can experience beach life along the extensive stretches of coastline, island hop, and experience history in its offerings of several Victorian-era homes. Throughout my time in the city I couldn't help but exclaim how cute it is! I was also pleasantly surprised to notice a pretty large East African and African American presence in the city. Below I'll walk you through how best to enjoy Portland, where to stay and where to get the best lobster rolls!

*Several links below are of affiliate nature, meaning that a small commission may be received by myself when you purchase through them. This is in support of Black Girl Wanderer, to create more travel blogs for you to enjoy!

Contents

1. Accommodation

2. Transportation in the City

3. Things To Do

4. Where to Eat/Drink

5. Where to Get the Best Lobster Rolls

Accommodation

Portland Sheraton at Sable Oaks

Traveling to Maine during lobster season (June to December) can drive up hotel costs even higher than normal, and going in June meant already inflated summer prices. The Sheraton at Sable Oaks was one of the cheaper options during that time, and was of benefit as a Marriott-affiliated hotel for a friend and I to stay in comfortably during our trip. The hotel itself had everything we needed and was only about a 10-15 minute ride from the airport, and about 20 minutes to get to downtown Portland. A perfect fit!

Transportation in the City

Bus

Greater Portland Metro is a great option for getting around Portland and surrounding towns with its 10 routes including the newly effective BREEZE route and Husky Line that all come at an affordable price. Route 1 typically covers major tourist sites such as the Portland Observatory and Portland Museum of Art, etc.

Uber/Lyft

This was the method of travel my friend and I used while in Portland because car rental prices were too expensive for our liking. We used both Uber and Lyft, but throughout the trip we noticed that Uber is more widely available than Lyft drivers. I will note that Uber ride prices did fluctuate often and at times became pretty expensive, even for it being split between two people.

Car Rental

I would highly recommend getting a car rental if you're planning to travel outside of the Portland area or if you're traveling with a larger party. This is mainly for convenience of getting around although there is the option of public transport or Uber/Lyft, as mentioned above.

Ferry

Island hopping? You'll more than likely be taking one of the ferries on Portland's Casco Bay Lines, which is a ferry servicing all of the islands located in Casco Bay. Currently, peak season roundtrip adult fares range from $4.10-$11.55 depending on the island you plan to visit and peak vs. non-peak season. Children (over 5 years old), Senior and Disabled fares range from $2.00-$5.75. There are also separate fees for those traveling with bikes, and if you travel on the ferries often there are passes available that cover either a 5 round trip ticket book, monthly or annual pass.

Things to Do

Portland Head Light/ "Bug Light"

Portland Head Light is the iconic lighthouse in Cape Elizabeth, Maine who made its debut in 1791, making it the oldest lighthouse in the state. I actually didn't get to view it myself because of bad weather, but it HAD to make the list of things to do because it's a Portland staple! It'll be the first on my To-Do List whenever I come back. You can also swing a visit to the "Bug Light", another one of Portland's well-known lighthouses that is housed near a quaint park area where you can relax, take a stroll and enjoy expansive views of Portland Harbor. It's a great spot for dogs too!

Explore Old Port

This historic area of DownTown Portland serves up everything you'd need to for a good time; whether you're looking for specialty souvenir shops, boutique shopping or waterfront dining you won't be disappointed. I specifically remember walking through this part of town and shouting about how CUTE everything is! And if you're looking to have a fun night out with friends, you have more than enough options with the many breweries, cocktail bars and pubs on scene.

Visit Victoria Mansion

I'm not much of a history buff, and if you'd ask me whether or not I thought touring a Victorian home would be super interesting, I would probably tell you no. But Victoria Mansion was such a pleasant surprise! On a whim we decided to take a tour of this National Landmark and it was amazing! Our tour guide gave us a history lesson of the grounds and the families that lived there, and I have to say the design of the entryway was my absolute favorite. Tours run from 10am-4pm during the regular season for only $8.00 if you're a student (Tip: always carry your student ID with you, even if you haven't been a student in uhm...quite some time) and $19.25 for regular adult tickets.

Enjoy the Offerings at Portland's Local Wineries

While Portland is better known for their craft beers and breweries, there are a couple of traditional and urban wineries to interest any of you self-touted sommeliers. Check out Cellardoor Winery, eighteen twenty wines or the Blue Lobster Urban Winery, which not only has a Wine Bar/Taproom, but boasts unique offerings of canned wine so that you can enjoy on the go without compromising taste.

Take in a Sunset Kayak Experience

Looking for a little adventure? How about a 2-hour Kayak Tour around Casco Bay to get close up views of adorable seals, seabirds and all sorts of fish? Well, look no further than this $48 sunset kayak tour I experienced on my trip to Maine. Now I will warn you- kayaking for almost two hours straight is VERY tiring, even when paddling is being shared between two people (or maybe we needed to be in the gym for a bit before booking this excursion); but I think with the amazing guide we had (hey Whitney!), beautiful sunset views and getting to say hello to some adorably curious baby seals, it was well worth it.

Go For a Hike

If you have a car and you're looking for a more grounded outdoor activity, there are a few great hiking trails near Portland that you can check out. The Burnt Meadow Mountain Trail on Burnt Mead Mountain and the Tote Road Loop in Bradbury Mountain State Park are both highly recommended to enjoy some beautiful nature and panoramic views.

Lobstering or Sail Boat Tour

When you visit Maine, especially during Lobster season, you'll see that the people of Maine do NOT play about this delicious crustacean. A great way to learn about the process of how they're searched for, caught and sold is through lobstering boat tours, but from my prior research they do come at a pretty penny. Lobstering is serious business, and regulations are strict on when it can happen so if you're not in town during lobster season you can also try a fishing or sail boat excursion to learn about Maine's top-notch seafood (or avoid it all together, if that's not your thing).

Vibe Out at Reggae Sundays on Peaks Island

A unique experience outside of the city that I recommend are chill Sunday vibes at Jones Landings for their 'Reggae Sundays', starting from March through September 3-7pm and located on Peaks Island, which is about a 10 minute ferry ride from the dock in Downtown Portland. Ferry tickets cost around $7 during peak season and multiple ferries come and go from about 5AM to 11PM. If you're looking for good vibes, love reggae music and enjoy $5 rum punch then this is the spot for you! You can also take some time to explore; rent out a golf cart to get around easily and you're good to go!

Where to Eat/Drink

These are my picks for spots to enjoy that aren't necessarily focused on lobster dishes, although you'll be sure to find that much of the city's restaurants have at least one dish catering to the exemplary crustacean.

Hot Suppa

A great brunch spot with Southern comfort food and delicious cocktails. I went for the chicken and waffles and I enjoyed it! The waffle actually reminded me of Waffle House (if you know you know) and the chicken was well-seasoned and juicy. I also ordered a heaping of spinach on the side because of course that'll cancel out all of the artery-clogging goodness of everything else.

Black Cow

We only stopped at this burger joint for a few cocktails while waiting on our table at Highroller Lobster Company, but the vibes were immaculate (that could've also been because of the Pride parade that just finished earlier that day) and the burger menu looked appetizing as well. Try the Snowbird or the rotating Frozen Drink that they have for the day.

Beals Ice Cream

I love a good waffle cone, and Beals did not disappoint! Even though it was gray, cold and wet outside my friend and I couldn't help but to stop and see what Beals Ice Cream had to offer. I'm more of a classic vanilla/cookie dough girl myself, and it was just as sweet and creamy as I expected it to be. 10/10.

Rigby Yard

A great spot for a unique and more elevated breakfast or dinner experience; Rigby Yard on Wharf Street is actually located in what was once the historic train depot and now serves as a warm, comfortable space to enjoy New England fare. Whether you're in for a hot coffee and one of the assortment of handmade pastries, or looking to enjoy a juicy steak (or lobster roll!) you've got it made.

Nom Cafe

This breakfast/brunch cafe that offers meals with a slight Balkan and Middle Eastern flare is top-rated and I agree! I went for a typical Belgian-style waffle and egg dish but trust me, it did the job and the fresh berries topped it off perfectly. If you'd like something a bit more savory, I recommend the Shakshuka or the Kyufte and Eggs.

Where to get the Best Lobster Rolls

Luke's Lobsters - Luke's Portland Pier location is a beautiful way to enjoy nice, refreshing lobster meat stuffed into a buttery roll, and the berry salad was a perrrfect summer addition. A must try!

Highroller Lobster Company - For all of the lobster rolls and dishes I had on this trip, Highroller was definitely the winner for me! Idk what they did but the lobster was so fresh and has a bit of sweetness to it. Also the vibes in this place?! 10/10 (Also a warning that wait times get pretty long at this spot).

Gilbert's Chowder House - I was all lobster'd out at this point, so I actually opted for their crab roll instead, which I honestly feel could go toe-to-toe with their lobster equivalent, but my friend who did actually have it would disagree-- seeing as she rated Gilbert's as her absolute favorite of the three. We both also would've gone for the chowder, but we visited near the end of the day and as expected, everything was sold out.

Honorable mention: eventide - We unfortunately didn't get to try out their lobster roll, but literally every time I asked a local for recommendations, this was near the top of the list!

Happy Wandering!