A Noteworthy 72 hours in Portland, Maine
A love letter to my favorite place on earth. From the most delicious pastry to start your morning, shops to peruse, and all the summer bliss to the most relaxing weekend you didn't know you needed.
Portland, Maine feels like the place where you can take a breath of fresh air and never have a bad meal. The vibes are relaxing, the town is walkable, and it has quickly turned into my favorite weekend getaway! I have way more recs than a quick 72 hours but if I were to curate the perfect 72hr itinerary it would look something like this…
THE NOTEWORTHY 72HR ITINERARY
THURSDAY!
Arrive by noon to soak in an afternoon at Portland Head Light, grab a lobster roll from Bite Into Maine (food truck) sit along the water at one of the picnic tables and bask in the sun, enjoy the breeze, and breathtaking views.
Take a short hike along the trail that overlooks the water, maybe even dip your toes at the finish line where you’ll find some people taking a swim or scuba diving!
Grab a gelato from Gorgeous Gelato to cool off!
Check into your Air BnB or hotel, I loved staying at the Inn at Parkspring but if you’re a boutique hotel lover check out Blind Tiger!
Street + Co for dinner- order the tuna tartare, branzino, + lobster linguini!
Peruse the shops along the water: shipwreck & cargo, blanche + mimi, and mexicali blues
Head over to Portland Lobster Co. on the water for a blueberry beer + live music! If you’re still hungry- calamari + lobster :)
FRIDAY!
The second you open your eyes, walk to Tandem Coffee + Bakery (they open at 8a), I beg you to order the Kimchi Cheddar Scone (sounds weird, but it is to die for) and the savory biscuit! You honestly can’t go wrong with anything here. The iced cold brew is delish too, V potent.
Get your steps in, bring a picnic blanket and walk to the Eastern Promenade to sit on the hill overlooking the water and peruse all the food trucks that line up! I personally love the Mr. Tuna truck for handrolls!
Next, head to The Post Supply (loved this store so much)!
A couple doors down head to Onggi that has the cutest market, but also has an amazing matcha cafe. If you’re in need of a mid day matcha pick me up (this trip was a sober venture for me)! Or head to Oxbow Brewing if you’re looking to day drink (they also have duck fat fries)!
While you’re at it- The Shop at Island Creek is next door so you might as well get cozy at their picnic style spot and snack on a dozen oysters!
For a snack- head to Highroller for a lobster roll (was V impressed)
For dinner- Crispy Gai is an absolute MUST! Order: Hat Yai Fried Chicken, sauce party, som tom (papaya salad), crying tiger ribeye, and all the dessert. ALL the cocktails are freaking delicious, it’s a must (Same, Same but Different). If you’re pregnant, don’t skip the mocktails, they are also DELISH! I loved the Thai Herb Tonic!
SATURDAY!
Brunch at Smalls which doubles as a cutie store and cafe! Order the iced dirty chai (they use DONA!) and a breakfast sandwich!
If you’re a sushi lover, you’re going to head over to ISF Trading which is a hidden gem! You order on the first floor then take your lunch up the the staff cafeteria to enjoy. You can make your own handrolls! It is SO affordable because you are buying directly from the fishermen! This is where restaurants get their fish from to serve!
Oyster HH at Lil Chippy’s from 3-5pm
Head to Cong Tut Bot across the street for their HH from 5-6pm! Vietnamese street food + their cocktails/mocktails are super yummy!
Dinner at Scales- it’s iconic for a reason. Grilled octo for an app is a must, it was the best octo we had. You can never go wrong with Lobster here and definitely order a cocktail.
For a late night bite- you’re going to head to Roasty’s for the best roast beef sandwich of your life (I love the Boston style).
SUNDAY!
Breakfast at Bread + Friends, it’s a must. They make all their bread in house, the sourdough is out of this world. Must order: crab omelette, smoked bacon, and pastries for the table. I also ordered a side of sourdough with butter + jam. Simplicity at its finest.
You’re probably getting ready to get all packed up so stop by MatchaMood (I loved this matcha better than Onggi) for a caffeine boost + get your bags packed! Order: Iced coconut water matcha!
Ramona’s for a hoagie to go for your journey home! It’s a Philly sandwich shop so you know.. it is to die for :) However, if you order the Italian tell them to hold the olive spread! Yuck!
Honorable Mentions:
CAFES/BREKKIE
Speckled Ax (wood fired beans)
Night Moves Bread (sourdough bread)
Belleville
Forage Woodfired Bagels
LUNCH/DINNER/COCKTAILS
Friend’s + Family (pizza + salad)
Cutie’s (cocktail bar + small bites)
Fore Street Restaurant
Lamb’s
Boda (Thai street food)
Mr. Tuna (sushi)
SoPo Seafood
Via Vecchia (italian + bomb cocktails)
Blythe + Burrows (cocktails!!)
The Portland Hunt & Alpine Club (cocktails + snacks)
ISLANDS
Crown Jewel on Diamond Cove Island *take ferry ($14 roundtrip)* lobster papaya salad is a must
Island Lobster Co at Peaks Island: love the low key vibes and sitting at the picnic tables overlooking the water! Amazing views!
Rent a golf cart and explore the island! ($100 for 2 hours)
BREWERIES
Allagash Brewing
Belleflower Brewing
Shipyard Brewing
Oxbow Brewing
Lone Pine
SHOPPING
The Post Supply
Blanche + Mimi
Viand Mercantile
Frankie Lane
Sunday Town
Fitz + Bennett Home
Pinecone + Chickadee
Soleil