JWTR đŸ©”

The Ultimate Recs for Visiting Portland, Maine

OKAY Y’ALL
 IT’S TIME!! HERE ARE MY ULTIMATE RECS FOR MY ALL TIME FAVORITE CITY: PORTLAND, MAINE!!!

Warning: this is not an overhype, for the hype is so real. Portland Maine is the cutest, vibiest, lil coastal New England town.

The food, the bev, the shopping, the people, the fresh air!! So much to obsess over. I wish I could keep this little token a secret forever, but hot girls don’t gate keep!!

I was lucky enough to spend both summer and fall seasons here in 2023 & it was the time of my life.

Summer and fall were both incredible for different reasons.

Summer is definitely the biggest tourist season, so plan ahead for your stay because it will be very expensive to stay in town. 

That Maine Summer vibe is well worth your money though. That chance to dress like a coastal grandma,  while eating a lobster roll and drinking a fresh Allagash White on the dock of a local restaurant. *Chef’s kiss*

If you feel like being a little different, might I recommend a fall trip to Portland? 🍁 It’s personally my favorite time of the year there.

Fall in New England is something to see!

Honestly, I highly recommend a roadtrip through New England in the fall & you could hit Portland on your way up to Acadia National Park. There are a lot of hiking opportunities near Portland. 

That Maine fall vibe gives you an opportunity to wear your cozy oversized sweaters & jackets while warming up in local coffee shops, surrounded by the fall leaves. 

You can trade in the Allagash White for A Shipyard Pumpkinhead Ale. đŸ»

Okay for stay recs:

So I lived in 3 different places in Portland during my short time there, and if you can afford it, STAY DOWNTOWN.  I say this because the city is SO walkable & you can really see around the whole city by foot in a few days.  

My favorite side of the peninsula is the East Side/Munjoy hill area because it’s quiet, very safe feeling and surrounded by the water. It’s underrated because most people think of staying in old port, but it is literally on a hill, so if that doesn’t sound fun to walk up daily, maybe avoid haha.

There are great businesses up this way, but most of the businesses are more on the West Side/in old port, so either way i think you’ll be happy in your stay 🙂

Just a little side note: **I would be cautious to stay in the west bayside area of the Portland if you plan to walk everywhere.** Over the years there has been an increasing “homelessness crisis” in the area as the mayor has referred to it. I wouldn’t normally mention it, but there’s also a drug issue amongst the population.

But ya know, just be aware of your surroundings 🙂

Alrightyyy now on to activities:

I would definitely find a way to get out on the water 🙂

I did a sailboat cruise more upstate Maine and it was one of the highlights of my time there. For sail cruise options in Portland I would look at 

Wine Wise: They hold upscale wine and food tastings and always sell out.

Portland Schooner Co. looks more laid back/affordable and they allow you to bring your own food and beverage.

Portland Paddle: Located on the East part of the city, we did a Kayak tour on Casco Bay & it was the perfect summer activity. Make sure you dress sporty for this & expect to get wet & need to change after lol. Highlight of it: we got to see seals!! <3 S/o Dan, he was a great guide.

Just go hang out on the East Promenade: at the very east point of downtown, up on Munjoy Hill, is the most beautiful view of the Casto Bay. Below the hill is East End beach, a quaint sandy beach with yummy food trucks.

The whole area is dog and family friendly (the beach area might be after 5 for dogs).

It was my favorite place to bring a blanket to picnic, read and relax.  

I loved being here for both sunrise and sunset. And of course, it’s the best place to take your insta-quality pictures 🙂

Other niche activities:

Catch a show at the State Theater downtown or at Thompson’s Point, which is a really cool venue on the water. 

If you have a rainy day on vacation,  Bayside Bowl is a really cute & fun Bowling Alley.

Catch a Portland Sea Dogs game! (minor league baseball)

If you’re more local & have access to a car:

Go to the Portland Head Light in Cape Elizabeth. This is the famous lighthouse built on a beautiful rocky coast line in Fort Williams Park. It really is gorgeous. According to the website, it is the most photographed lighthouse in America.

It’s not too far from the city center, so you could get an Uber and plan to have a little picnic in the park to make the Uber worth the price 🙂  They do have a lobster roll food truck parked there!

Maine is actually known for their blueberries and you can go blueberry picking locally in late June/ early July.

Or in the fall, go apple picking at Thompson’s Orchard (they also have fire apple cider donuts).

 

Day trips you can take from Portland:

Peaks Island: high on the recs list! Peaks Island is just a short ferry away from the heart of downtown Portland– so no car needed! It’s a very small and cute island, so you don’t need to devote a ton of time here. 

We rented a golf cart from Peaks Island Golf Carts for two hours, which was worth it! You can also rent bikes or you can just wander around on foot. For lunch we went to Il Leone where we ordered a lobster pizza.. OMG!! This place is only open seasonally.

Freeport: the birthplace of L.L.Bean. This is a hotspot to visit, as they have the huge L.L.bean store & outlet. It’s only about 25 minutes North of Portland. Gar & I spent a few days in Freeport because we loved walking in Wolfe’s Neck Woods State Park (sneakers are okay for this).

After, we would into town to Maine Beer Company for beers & pizza— their Lunch IPA is sold nationally, it’s bomb!

Boothbay Harbor: My mom and I went to Boothbay Harbor when she came to see me & I highly recommend going as a day trip or as a stop on your way up to Northern Maine. It’s another cute coastal town.

We split a HUGE lobster roll (leaving Portland for lobster rolls is the way to go— more bang for your buck) at Boothbay Lobster Warf. There are a few famous lobster roll places up this way. After lunch, we did a sail tour through Boothbay Harbor Schooners & it was incredible.

Shopping:

My favorite pastime in Portland was shopping! The thrift/consignment stores are incredible here! If you like to shop, you have to check them out for yourself.

They’re all amazing so I’ll just go in order of West to East side so you know what order to hit them in. 

Weekend Vintage: quaint with a smaller selection, so it’s easy to shop in. They sell vintage leather jackets for a great price.

Little Ghost: Authentic Vintage with trendy items. Def check this one out.

Portland Flea-for-All: love this flea market, only open on weekends!

Material Objects: Okay this may be my favorite because I found so many steals in here: L.LBean Vintage barn coat ($45), Ralph Lauren puffer coat ($35), practically new Blundstones ($60). They also have a lot of vintage chunky sweaters. 

Haberdashery: more designer consignment: Revolve, Reformation, Lulu, Agolde, etc. On the more expensive end for reused clothes.

& there are more, but those are the ones I most frequented 🙂

For souvenirs 

I always brought people to Shipwreck & Cargo: they sell good Comfort Colors printed tees.

The Maine Souvenir Store: Quirky, lots of goodies made by local artists. 

My favorite Portland Sweatshirt came from Cotton Garden, which is a grandma store lol, but they have very high quality sweatshirts in the back of the store. 

Pinecone & Chickadee: cute store with lots of art prints on stickers, pins, bags, etc.

Soleil: veryyy cute home goods store!!

Downtown there is also a great Madewell right downtown, as well as Anthropology, Free People and Athleta. 

Just go in all the shops! 🙂

Okayyyy why we are all really here: FOOD!! Holy Lobstah, the food scene in Portland is INSANE!

We’ll start with breakfast/brunch:

Tandem: for more of a quick grab and go option (despite the long line out the door). This is a MUST in Portland. They have great coffee and baked goods.

I love their breakfast biscuit with sausage, egg and cheese (limited quantity made daily) and loaded biscuit served with cream cheese and pepper jelly. 

Sit-down options:

Hot Suppa is always where I brought my guests that visited. The food and cocktails are so good, but also starting your day here puts you in the perfect location to start in the West part of the city and wander your way down into the old port for the later afternoon.

You can hit all the thrift/consignment stores I listed above in their order on the way in

🙂 It’s a small restaurant without reservations, so get there early to get on the list– it’s worth it.

Bayside American Cafe: also located on the west side, not taking reservations, so get there early to place your name. Their pancakes, specifically the cinnamon bun pancakes, should be world famous!!!

The Front Room: Located in a gorgeous neighborhood on the East side. Pricier, but great brunch! Takes resos

Other options I did not try, but were recommended to me:

Ocotilla Brunch: okay this place opened after we left, but it looks so good. They’re serving a Mexican style brunch.

Nom Cafe: Balkan (Turkish/Mediterranean) food– it looks really good!

 

Casual Lunch/Dinner:

Side note: Portland is a very casual town in general because the cobblestone & brick sidewalks make it pretty impossible to wear anything other than a flat shoe/ chunky low heeled boot.

Okay we know you want a lobster roll!! 

Let’s just go over casual seafood joints first:

The Highroller Lobster Co. is where you should go in town— you can just order at the counter, and they even have lobster roll flights oooo!

Gilbert’s Chowder House: honestly one of my biggest recs, because it is so under-rated.

The whole restaurant is just sit yourself, first come first serve, so we would just walk around the back & could always find a table on the deck looking to the water.  It’s so mom & pop here & the local hospitality will definitely have you feeling  like you’re in Maine.

You have to get the white wine mussels, non negotiable. 

The Lobster Co: Food is not as good as Gilbert’s, but they usually have good live music & a great big deck 😉 I usually just come here for drinks

Eventide Oyster Co.: So Eventide can def be casual, but the seafood is so high quality (and pricey) that you could make this a fancier dinner too! They don’t take resys, so show up early and place your name down, you don’t want to miss this joint on your Portland tour. Make sure to get oysters (obvi) and the brown butter lobster roll– yuppp đŸ”„

Yosaku: best place in Portland for casual sushi. 1. It is unreal affordable, like a damn steal! 2. Super fresh. 3. Lots of seating (unlike most Portland restaurants). 4. If you’re in a group & order a lot, request it on a boat! 🙂 

Mr. Tuna: Started out as a food truck, then opened a small brick & mortar and now are a full blown cutie restaurant!! Amazinggg quality, if you’re in the mood, get their sushi burrito
. Omg, life changing!!! Small enough to finish yourself!

Keg and Kraken: More asian food, more amazing sushi.

Not seafood:

Nura: super casual place serving Mediterranean food, they have the best falafel pita pocket sandwich I’ve ever had.

Duckfat: Great sandwiches & fries twice fried in duck fat. They have two locations, the sit-down OG location is closer to the middle of town & the Frites Shack has a limited menu outside Oxbow Brewery on the East side.

Taco Escobarr: Super yummy Mexican food with very healthy options. They soak their tequilas, making all unique flavored margaritas. 

Black Cow: great place to get a burger & beer. Butcher Burger has great reviews too.

Crispy Gai: I’ll put this one in casual, but again, could be fancy. It has more of a dinner vibe than lunch, but I’ve been for lunch too. 

If you like Asian food, do me a favor and GO HERE. It’s so vibey, the staff are so nice, and the food & cocktails are DELISH. You must get a version of their chicken wings because it’s what they’re known for (and the best wings ever) but I am also in love with their Cabbage Salad (needed to cool your mouth down from all the heat), and my #1, the Pad See Ew with mushrooms
 mmm, dreaming over here!

Empire Chinese Kitchen: BOMB Chinese food!! Cute ambiance.

Flatbread Company: serving great pizzas on the water!

Terlingua: for delicious Mexican/Texas bbq fusion.

Mami: Japanese street food, we came here for a few bites and it was so good! Only serving beer, wine & sake cocktails.

LB Kitchen: Great stop for a casual healthy meal (good vegan options).

Nicer dinner:

Izakaya Minato: Listen UP!!! Best restaurant in Portland, imo. I cannot imagine making it back to Portland, and not coming here.

First off, it just has a sexy vibe. Especially if you’re in town with your partner, don’t miss this place.

It’s very small and intimate, and only take resos for 4+ people, so go early, put your name down & get a drink across the street at Hardshore Distilling Company (great cocktails, for gin/bourbon lovers).

More importantly, the food is insane!! They do an increddddible Omakase for $42/ person. It’s a great option for first timers unsure on what to order.

If you do not do the Omakase be sure to get the oysters, garlic edamame, any/all of the raw fish options, mochi bacon, beef yukke, Japanese fried chicken. Just get the whole damn menu & thank me later!

Okay, as my close second fav, Crispy Gai, as mentioned above could be a considered a nicer dinner too! 

Via Vecchia: This place takes reservations & I suggest you book one, as it is very popular!! Incredible Italian food. Beautiful inside and out & in a killer location in Old Port.

Papi: Young, hip, Puerto Rican restaurant with unique cocktails and food. They won a bunch of local awards the first year they opened.

Scales: This is one of Portland’s fancier establishments. Went for my birthday, SO good!! Ya gotta get the butter rolls to start. 

Central Provisions: Tapas in a great location, they also have a bar around back serving the whole menu where seating is first comes first serve. 

Fore Street: Where a lot of older locals go to dine, so yeah check this place out if you’re in the mood for something fancy!! There menu is always rotating, but I had the scallop crudo when I went & it was one of the best things I’ve eaten!!

Twelve: Didn’t make it here, but great reviews on Google, if you’re looking for more fine-dining options. 

Truth is, I couldn’t make it to all the best restaurants in Portland, mostly because I revisited most restaurants above, but I am confident you won’t be disappointed anywhere you eat here. 

Bars: 

ooooo so many fun bars in Portland!

The Portland Hunt & Alpine Club: great place for cocktails & small bites before or after dinner!

Blyth and Burrows: another great spot for cocktails & small plates pre/post dinner. They have a speakeasy behind the bookshelf in the back. You have to ask the host if you want to sit there, and it’s only open Thurs-Sat I believe.

Papi: as mentioned above, cocktails are fire (literally they light their rum and coke cocktail on fire)

Room for Improvement: My personal fav for late night!! Best place to get a cocktail on Warf Street in Old Port, maybe all of Portland. The bartenders own the place as a group of friends, so the service here is awesome & you can tell the bartenders love their job.

Arcadia: I love this bar. It’s an adult arcade, with craft cocktails, so fun if you’re with a group!

The Porthole: Super popular on the weekends in the summer— they have a huge dock & live music! They also have food, but I just came here to drink. Def stop by around happy hour during peak season!

Lincoln’s: Okay this is IYKYK kinda joint. You’ll have to search for it & they’re cash only (they have an ATM)

Hardshore Distilling Company (great cocktails, for gin/bourbon lovers).

Late night partying: Just go down to Warf Street, you can find any vibe you’re looking for.

Bar of Chocolate: place on Warf to get a dessert cocktail. 

Dock Fore: Okay I love this dive bar because they serve one mean Guinness pour.

Munjoy Hill Tavern:  Don’t go out of you way for this lol, but if you find yourself staying on the East side of town, you should stop in for the dive vibe. We found ourselves here many nights on the way home.

Brewery scene:

Most of the breweries are on the East side of town, where you can brewery hop!

Rising Tide

Lone Pine

Austin street

Oxbow: specializing in farmhouse ales, love this place 

RootWild: Super refreshing kombucha bar, serving both spiked and NA options.

Apres: brew seltzers, also serving beer, great energy

Shipyard: A must stop during Pumpkinhead season— they serve them with a cinnamon sugar rim, nuff said!

Unfortunately, Allagash Brewing, serving my favorite Portland beer, the Allagash White, is not located downtown, but you can get a fresh one at any bar you go to in Portland. 

Pastries/Coffee/Dessert:

Tandem Coffee: mentioned above

Standard Baking Co.: Incredible baked goods. The locals line up here daily. The brownies are my favorite.

The Holy Donut: Famous donut shop in Portland— serving donuts made from potatoes. My favorite are anything cinnamon sugar.

Mt. Desert Ice Cream: mmmm my favorite local ice cream place!

Sticky Sweet: Serving delicious vegan ice cream.