I don’t know about you, but I like to pick my vacation destinations by what I’m hungry for at that particular stage in my life. “There are places I’ll remember” … for the food I ate while I was there. Mussels in the Canadian Maritimes, all the pasta and gelato in Italy, spicy Szechuan and soup dumplings in China. You get the idea.

I woke up one morning a couple months ago hungry for seafood – and not the standard Mid-Atlantic variety crab cake or steamed shrimp I can get at my neighborhood grocery. No, I needed some lobster rolls. Several lobster rolls. I wanted to eat legit New England lobster rolls until I was sure I could safely return home without even thinking about another lobster for at least a year. So, where was I going to go to fulfill this sudden urge?

Why, Portland, Maine, ayuh.

It’s a fairly inexpensive two-hour flight from Baltimore/Washington International Thurgood Marshall Airport, rooms right in the middle of the action on Fore Street in the Old Port District can be had for less than $200 a night and — as I discovered within hours of landing — it’s very accommodating to solo travelers (i.e. me).

Here are my suggestions for how to spend a long weekend in Portland, Maine:

  1. J’s Oyster
J's Oyster
J’s Oyster was the author’s favorite spot during a recent long weekend in Portland, Maine. (Photo by Amanda Krotki, Jmore)

After I checked into my room, I wandered down to the waterfront where I happily came across just the thing I was looking for — J’s Oyster, a seat-yourself, unassuming, no-frills oyster shack consisting mainly of a stool-cluttered, four-sided bar. An hour in Portland and I’d already arrived at a place where locals congregate, seemingly for years.

As I grabbed an available bar stool, I found myself seated between two very salty career seamen — one in his 60s, the other in his 80s. They were sharing heavily accented sea stories as I imagine boat captains do, and I asked if they would prefer my switching places so they could talk more easily. “No,” Bryan “with a Y” told me, “It’s good for yah to heeyah this.” And so I sat a while, slurping up a variety of Maine oysters with a side of fish tales — music to my ears.

J's lobster roll
J’s serves a plain, but heavily packed, lobster roll with the diner’s choice of mayo (Maine-style) or hot butter (Connecticut-style). (Photo by Amanda Krotki, Jmore)

J’s serves a plain, but heavily packed, lobster roll with the diner’s choice of mayo (Maine-style) or hot butter (Connecticut-style). I hate to say it, given my environs, but I prefer mine with butter. There’s actually a big debate about this, so don’t get Bryan “with a Y” started. (Speaking of debates, never ever try to order Manhattan clam chowder anywhere in New England. Manhattan is tomato-based and not served within city limits as far as I could tell. New England is cream-based, hearty and delicious.)

I became immediately enamored of J’s thanks to the interactions with the locals, the fresh-caught seafood and the ease in which I was accepted at that bar as a solo traveler.

Of course, I returned to J’s for one last fix just hours before my departing flight.

2. Take a ferry ride or the mailboat

Casco Bay Island Ferry
The Casco Bay Island Ferry is a cheap and easy way to cruise the Casco Bay. (Photo by Amanda Krotki, Jmore)

The Casco Bay Island Ferry is a cheap and easy way to cruise the Casco Bay. I opted for the 17-minute ride to residential Peaks Island, home to the forgotten World War II fort Battery Steele, where you can rent a golf cart or bike and go exploring for the day. I walked around the island until I discovered the “beach.”

By “beach,” I mean lots of rocks and not much sand. You can see a couple lighthouses and forts (including Fort Gorges) from your Peaks Island vantage point.

Peaks Island
Take the ferry to Peaks Island to enjoy the scenery and the “beach.” (Photo by Amanda Krotki, Jmore)

There are several ferry trips available daily to various islands for between approximately $8 and $12 per passenger. The more romantic-inclined may opt for specialty cruises like the 2.5-hour roundtrip sunset or sunrise runs or the 2.5- to 3.5-hour roundtrip mailboat run, which takes mail and freight to Little Diamond, Great Diamond, Long, Cliff and Chebeague Islands.

After a couple hours enjoying the Peaks Island scenery, I hopped on the return ferry and started plotting my dinner.

3. Take a foodie walking tour

Lobster handroll
Trying the lobster handroll at the Public Market House during the Foodie Tour. (Photo by Amanda Krotki, Jmore)

I wanted to get the lay of the land and sample as much of the local offerings as early in my trip as possible, so I signed up for the Old Port Culinary Walking Tour from Maine Foodie Tours.

Lobster roll
Sampling the lobster roll at David’s Opus Ten during the Foodie Tour. (Photo by Amanda Krotki, Jmore)

The three-hour tour (where have I heard that before?) highlights some of what has put Portland on the foodie map in recent years. It includes stops along the way for a sample of a blueberry microbrew from Gritty’s, a detour to Public Market House (a food hall akin to R. House or Mount Vernon Marketplace, if a little rougher around the edges) for a lobster handroll, and a taste of some excellent chowdah and pizza at David’s from Chef David Turin with a sneak peek into David’s Opus Ten, which only seats 18 guests a night for 40 nights a year. Make your reservations now!

The tour ends on a sweet note with a stop at Dean’s Sweets to nibble some truffles made the regional way with mashed potatoes. (Ayuh.)

4. Go on a Trolley Tour

Portland Head Light
Portland Head Light is Maine’s oldest and most photographed lighthouse. (Photo by Amanda Krotki, Jmore)

The 21-mile peninsula of Portland is immensely walkable and easily navigated, but after three days of trekking about 8 miles each, I was ready for some sit-down action. This lead me to Portland Discovery Land & Sea Tours. The weather was gnarly, so I decided to stick to terra firma, but there are lighthouse lovers and sunset cruises available.

I opted for the 105-minute, fully narrated Portland City and Lighthouse Tour, mainly because I thought I’d better go see the famous cliff-hugging Portland Head Light, Maine’s oldest and most photographed lighthouse, which everyone seems to be all in a froth about.

The tour included some historical and pop culture points of interest along the way. There’s the house Judd Nelson grew up in! Who knew? There’s the tallest building in Maine! Franklin Towers. 16 stories. There’s the Etz Chaim Synagogue and Maine Jewish Museum! Hmm.

Fort Williams Park
Henry Wadsworth Longfellow was a fan of Fort Williams Park. (Photo by Amanda Krotki, Jmore)

Portland Head Light and Fort Williams Park is indeed stunning and everything you’d want out of a picturesque lighthouse, if you’re into lighthouses. However, the 15-to-30-minute trolley stop offers plenty of time to walk around, take a bunch of selfies and say you’ve seen it. You probably don’t need to schedule an entire day to explore the iconic Head Light, which was first lit in 1791. It is even said that the poet and Portland native Henry Wadsworth Longfellow enjoyed taking long walks on the lighthouse grounds.

[See more things to do in Portland, Maine]

5. Visit the Wadsworth-Longfellow House & Gardens and Maine Historical Society

Wadsworth-Longfellow House
The Wadsworth-Longfellow House & Gardens and Maine Historical Society are worth a quick visit for history buffs. (Photo by Amanda Krotki, Jmore)

Speaking of the author of “Paul Revere’s Ride” and “Evangeline,” this is a good place for history buffs to pick up some knowledge on the city’s most famous son. The house, built from 1785-86, is known as the first all-brick dwelling in Portland. The garden is Colonial Revival style. The Maine Historical Society, founded in 1822, is the third oldest in the country. The Museum Store offers some unique souvenirs.

Speaking of souvenirs, Portland is a town blessed with multiple indie bookstores. I stopped in at both Sherman’s, where I found a bunch of treasures in the bargain bins, and Longfellow Books, where I ducked in for some browsing during a downpour.

6. Try a Holy Donut … or two … or three

Holy Donuts
Holy Donuts are made from potatoes and are a favorite among Portland locals. (Photo by Amanda Krotki, Jmore)

If you prefer to do less learning and more eating, wake up early and get in line for a locally made Holy Donut. I didn’t know these were a thing until I was walking up Exchange Street and spotted a bunch of really eager-looking people wrapped in a line out the door.

So, I did what any good stranger in a strange land would do. I queued up. These aren’t just any doughnuts, these are spectacular Maine potato doughnuts only available until sell-out. Yes, they do a lot of things in Maine with potatoes. (They also do a lot of things with blueberries, but I was hard-pressed to get my hands on a slice of homemade blueberry pie and, believe me, I tried.)

Back to these cakey doughnuts. Holy Donut offers really unusual flavors like the two I tried: honey lavender glazed and sweet potato ginger. Other varieties include fresh lemon, maple bacon, dark chocolate sea salt (the store’s most popular flavor) and, alas, blueberry with blueberry glaze. These were very good, but I wouldn’t make a habit of them.

7. Eat some more. No, really.

A Maine oyster selection at Eventide Oyster Co. (Photo by Amanda Krotki, Jmore)

Portland is a foodie destination, after all, and I was there to eat. So enough with the sightseeing and the history lessons. Here are a few of my other favorite eateries.

Becky’s – A diner for breakfast. Cheap and good. Opens at 4 a.m., I’m presuming for the fisherman to fuel up before they hit the open seas.

Eventide Oyster Co. – There’s a highfalutin’ brown butter lobster roll on the menu. I didn’t get that because I was trying to remain a purist. I did get some more excellent oysters and a quivering tuna crudo that practically swam down my throat.

Gilbert’s Chowder House – So freakin’ good. I had one of my many lobster rolls here (Maine-style) and tried the seafood chowdah. I think there was an entire lobster claw in there. It was also brimming with shrimp, clams and haddock. Additionally, Gilbert’s has haddock chowder, clam chowder, lobster stew and haddock stew. Try them all. Actually, I wish there was a chowder sampler available. I liked this place second only to J’s.

Standard Baking Co. – The locals really like lining up for their baked goods. This place is more traditional, but the chocolate croissant I had was flaky, buttery goodness. There’s also baguettes, focaccia, brioche and scones. Get ’em while they’re hot and fresh.

Vena’s Fizz House
Check out Vena’s Fizz House when you’re parched — for alcoholic and non-alcoholic concoctions. (Photo by Amanda Krotki, Jmore)

Vena’s Fizz House– Tinctures, fizzes, rickeys, spritzers, phosphates, shrubs. It’s all here at Vena’s – another place where I just pulled up a bar stool and settled in for some deliciousness — mocktails in this case (though it’s worth noting, Vena’s has an impressive list of “with spirits” drinks as well.) I wanted one of everything, so I opted for the small orange cardamom spritzer and the blueberry phosphate. Vena’s also has bar supplies and mixers to go and if they weren’t packaged in adorable glass jars, I would have brought several home for gifts.

[Things to Eat and Drink in Portland, Maine]

So, that’s the gist. Portland, Maine, is an easy, non-judgmental, entirely casual, hassle-free long-weekend getaway from the Baltimore-area. Just remember to find your sea legs and eat at least three lobster rolls and you’ll have a wicked good time, ayuh.