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Calling all lovers of lobster rolls, lighthouses, and L.L. Bean! This picturesque foodie paradise is only a 2.5 train ride from Boston, making Portland the perfect long weekend trip to check off of your bucket list. 

Here's your plan for a delightful weekend in Portland filled with food, exploration, and relaxation

Perfect Long Weekend Getaway to Portland 

Hop on the Amtrak Downeaster at Boston North Station for a scenic 2.5-hour train ride to Portland, enjoying a hassle-free start to your weekend getaway.

Train Travel

✅ Before you go
• Don’t stress too much about booking in advance! Tickets for your train ride between Boston and Portland are almost always <$50, no matter when you book: 

💪 Pro tips
•  Use code V814 for 15% off your Amtrak ticket if you’re between 17-24!

Take the Amtrak Downeaster out of North Station 

Check into the luxurious The Longfellow Hotel, offering beautiful views of Back Cove. Ideal for a picturesque and relaxing stay in Portland.

Hotel Check-in

✅ Before you go
• Learn more about the hotel + book your stay here: https://www.longfellowhotel.com

💪 Pro tips
• If you like what you see, look for The Grand Standard Room with Back Cove Views when booking!

Check into The Longfellow Hotel

Start your Portland getaway right with lounge vibes and delightful snacks at Five of Clubs in the Longfellow Hotel. Happy Hour offers daily deals that can't be missed.

Lounge and Snacks

✅ Before you go
• Walk in from 3 pm onwards, any day of the week!
💪 Pro tips
•  Happy Hour is 4 pm - 6 pm every day except Monday… when Happy Hour is all day!  

Head down to the lobby to lounge + enjoy sips & snacks at Five of Clubs

At Tandem Coffee and Bakery, start your day with top-notch breakfast sandwiches, coffee, and scones, but be early to avoid sold-out items!

Breakfast Dining

✅ Before you go
•  Arrive early before they sell out… 

💪 Pro tips
• … or order ahead from 7:45 am - 10:15 am to ensure you snag a sandwich!!! They’re that good: https://pickup.tandemcoffee.com

Dig into breakfast sandwiches, coffee, and scones at Tandem

At Open House, discover a treasure trove of vintage clothing and unique antiques in Portland's Downtown, perfect for weekend browsing.

Antique Shopping

✅ Before you go
• Only open Friday - Sunday! 

💪 Pro tips
• Don’t skip the racks of vintage clothing in the back of the store! 

Sift through antiques & hidden gems at Open House 

Discover artisan pieces and New England-inspired goods at Viand Mercantile.

Artisan Shopping

✅ Before you go
• Keep an eye out for vintage pieces sprinkled throughout the store! 

💪 Pro tips
• If you see something you like but don’t have room in your weekend bag, check their website to see if it’s available online! Shop here: https://www.viandmercantile.com

Shop small for artisan, New England-inspired pieces at Viand Mercantile

Indulge in an eclectic mix at Crispy Gai with $1 oysters and $5 mimosas during happy hour, featuring a range of Thai and American dishes and tropical cocktails.

Adult Happy Meal

✅ Before you go
• Walk ins only, unless you’re a party of 6-10. 

💪 Pro tips
• $1 oysters + $5 mimosas from 1-3 pm!!!

Enjoy an adult happy meal at Crispy Gai

Explore the magic of Allagash Brewing Co. with a behind-the-scenes tour. Enjoy ample beer tasting in the brewery and barrel room.

Beer Tasting Tour

✅ Before you go
•Book your tour here, starting at $28: https://www.allagash.com/visit/events-tours/

💪 Pro tips
• Start your art print collection with Ana Inciardi’s print vending at the Allagash Brewing Co. gift shop! 
• Grab a lobster roll from Bite into Maine’s food truck on the premises… though this won’t be your last chance to! 

Go behind the scenes at Allagash Brewing Co. to enjoy beer tasting amongst the barrels

Dine at Bread & Friends for a memorable meal featuring pasta, oysters, pork chops, and more. A perfect spot for dinner or an exceptional brunch.

Diverse Dining

✅ Before you go
• Make a res here: http://resy.com/link?venue_id=84231

💪 Pro tips
• If you can’t make it in for dinner, don’t sleep on their killer brunch! 

Enjoy pasta, oysters, pork chops, and more at Bread & Friends 

At Twinflower Café, enjoy a leisurely breakfast either in your room or in the cozy café environment downstairs.

✅ Before you go
• Twinflower Café can be ordered up to your room, or enjoyed downstairs

💪 Pro tips
• 

Start your morning off slow with breakfast in bed (or downstairs) at Twinflower Café

Revitalize at Astraea Wellness Spa, equipped with unique meditation loungers and a private infrared sauna suite for ultimate relaxation and a nervous system reset.

Spa Treatment

✅ Before you go
• Explore the spa menu + book your wellness services here: https://www.longfellowhotel.com/spa/

💪 Pro tips
• Try out the meditation loungers + private infrared sauna suite with your partner!

Head next door to Astraea Wellness Spa for TLC of your choice

Visit Portland Head Light, Maine's oldest lighthouse, for breathtaking views of Casco Bay and a stroll in Fort Williams Park.

Lighthouse Visit

✅ Before you go
• This is a little out of bounds for Longfellow’s complimentary luxury car service, so schedule an Uber in advance! 

💪 Pro tips
•  Head over early to avoid too much foot traffic
• Wear comfy shoes if you want to spend some time exploring Fort Williams Park afterwards

Visit the Portland Head Light for Panoramic Casco Bay Views

At Bite into Maine, enjoy a picturesque picnic with their famous lobster rolls, available in various unique flavors, at a scenic location with views of Portland.

Lobster Roll Feast

✅ Before you go
• Snag a picnic table and eat your lobster roll with a picture-perfect Portland view. 

💪 Pro tips
• Even if you have a personal preference on how you like your lobster rolls (hot vs cold, butter vs mayo), each style here is worth trying at least once. Especially the more unconventional flavors, like wasabi! 
• If you don’t make it out to one of their food trucks, Bite into Maine has a brick & mortar location in East Bayside.
• Craving the rolls even after you’ve left Portland? They ship on Goldbelly! Order a lobster care package here: https://www.goldbelly.com/restaurants/bite-into-maine?ref=gs

??? at Bite Into Maine

At Rabelais, explore an eclectic collection of vintage cookbooks and culinary delights, and watch out for the resident kitty while shopping.

Vintage Cookbook Browsing

✅ Before you go
•

💪 Pro tips
• Keep an eye out for a very cute kitty that loves to hang out in the shop! 

Browse vintage cookbooks & other quirky culinary delights at Rabelais 

Browse The Post Supply for a thoughtfully curated selection of home goods and artwork in Portland's East End neighborhood. Discover ceramics, candles, and local crafts.

Home Goods Shopping

✅ Before you go
• 

💪 Pro tips
• You can also shop online, here: https://www.thepostsupply.com

Peruse The Post Supply for a thoughtfully curated collection of home goods   

Experience a lively evening at Papi Portland with an array of fiery cocktails and small plates, perfect for a fun night out.

Small Plates & Drinks

✅ Before you go
• Walk ins welcome, or make a res here: http://resy.com/link?venue_id=68424

💪 Pro tips
• Their extensive drink menu is not to be missed!!Order one that comes on fire if you really want to get the party started. 

Pop in to Papi for fiery sips & small plates 

At Twelve, indulge in an exceptional prix fixe meal, ideally at the chef’s counter with a wine pairing, for a dining experience that rivals the finest.

Prix Fixe Dining

✅ Before you go
• Make a res here: https://www.sevenrooms.com/explore/twelvemaine/reservations/create/search/?venues=twelvemaine%2Cevokitchenbar%2Cthegoodtable

💪 Pro tips
•  Sit at the chef’s counter, and spring for the laminated lobster + wine pairing if possible!!! 

Prepare for the prix fixe meal of a lifetime at Twelve

Start your day at Hot Suppa in Portland with delicious waffles and seasonal Eggs Benedict, perfect for any breakfast lover.

✅ Before you go
• It’s walk in only, so prepare for a potential wait.

💪 Pro tips
•  

Wake up with classic waffles & eggs Benedicts at Hot Suppa

At Soleil, dive into a treasure trove of viral trinkets and TikTok-worthy souvenirs, and don't forget to snap up a Maine-made bag if yours is full!

Souvenir Shopping

✅ Before you go
• Still no more room in your bag? Just buy a new, Maine-made one here!

💪 Pro tips
• Make sure to save up the last of your quarters for the print vending machine, of course! 
• Continue spreading the love by shopping small online: https://soleilmaine.com

Finish up souvenir shopping at Soleil, home of all of the viral trinkets from your TikTok feed!

Visitors can enjoy a unique NeoLifting©️ Facial Massage exclusively offered by Astraea Wellness Spa, promoting lymphatic drainage and facial relaxation.

Facial Massage

✅ Before you go
• This is Maine’s first and only spa that has a licensed massage therapist certified in performing NeoLifting©️ Facial Massage, so make sure to try it while you’re here: https://psmsspa-northcentral.azurewebsites.net/#/en-US/Longfellow/SPA

💪 Pro tips
• 

Put your best face forward with facial massage from Astraea 

Celebrate your visit with a last-round of oysters and a tiny ‘tini during the all-day Happy Hour at Five of Clubs, right before departing from Portland.

Happy Hour

✅ Before you go
• Guzzle down one last dozen oysters, sip on a tiny ‘tini, and cheers to a weekend well spent!

💪 Pro tips
• Don’t be scared to book your trip to Portland outside of the summer seasons! The city is truly gorgeous year round, with SO much to do. More on that in the next Perfect Portland Itinerary… 

One last hurrah at the Five of Clubs Happy Hour 

this is your itinerary for the perfect long weekend getaway to

that will most definitely have you feeling like the main character.

This picturesque foodie paradise is exactly a 

with the Downeaster depositing you just a few minutes away

from your accommodations at The Longfellow Hotel, 

a newly opened boutique hotel with beautiful Back Cove views.

Your first stop is down in the lobby for cocktails 

(or functional mocktails) at the Five of Clubs,

you can opt for another round of sips paired with some caviar service 

Portland’s arguably best baked goods and coffee are

just a stone's throw away from where you're sleeping.

Though there is always a line here at Tandem,

this is a breakfast spread well worth waking up early for.

With biscuit sandwiches and scones secured,

Open House is a sprawling store filled with antiques and hidden gems,

while Viand Mercantile features a mixture of thoughtfully curated

vintage and new artisan pieces inspired by New England.

meaning there's a little something for everybody.

Between Crispy Gai’s selection of traditional Thai dishes,

delightful takes on American staples like the McMuffin and crab rangoons,

there's not a single bad bite to be had here.

Plus, the $1 oysters + $5 mimosas make a hell of a happy (hour) meal.

Portland is the birthplace of Allagash White,

so any beer lovers would be remiss to miss out on a

chance to go behind the scenes of where the magic happens.

Just a short drive out of the city will bring you to HQ

where tickets to one of their tours will allow you to witness where

with both having ample tasting opportunities throughout the brewery and barrel room.

So, it's definitely best to come with a full stomach, and some room in

your weekender bag for any six packs or souvenirs you pick up afterwards.

My personal favorites are the mini prints from local artist Ana Inciardi,

whose art vending machines can be found in major cities across the country,

(Let me know if you want to see a separate video on where to find all of those!)

and these are truly a perfect bite into Maine.

But, if you're positively stuffed from the day of eats and sips so far,

This won't be your last chance to try those lobster rolls-

check out Henry’s Study if you need a cozy place to catch up on some work,

or enjoy a hot shower in your spacious bathroom that you’ll want to hog all night 

in The Longfellow's complimentary luxury car service,

Though Bread and Friends is known for their killer brunch,

their recently launched dinner service is just as good

…or the pastas and pork chop, for that matter.

it's time to start off the next morning with some much needed TLC.

The Longfellow not only has Twinflower Cafe attached to the

lobby for all of your caffeine and breakfast food needs,

but also a fully equipped wellness spa with offerings that

I’m willing to bet you've never seen at a hotel spa before.

Astraea has a meditation room with zero gravity,

and weighted accessories that act as an amazing nervous system reset-

especially when followed by a stint in the private infrared sauna suite.

with temperature and chromatherapy control,

and can be enjoyed solo or with a partner.

Your cold shower directly after is made a bit more comfortable

Check out this video for a summer day trip! 

Here's your plan for a day trip: explore Rockport's views, shops, food, and galleries

Beach Town Day Trip

Visit Rockport for a quaint day trip—enjoy window shopping, snacks, and exploring bookstores and art galleries, plus don't miss the lobster roll!

💪 Pro tips
• save room for a lobster roll!

Rockport

Here's an idea for a weekend adventure filled with views,

Head to Rockport about one hour north of Boston.

This is a cute little beach town but not overwhelmed with tourists.

looked at some knickknacks and beautiful jewelry,

stopped for a quick snack and then visited the bookstores and art galleries.

So head to Rockport for your next quick weekend getaway.

Get on a tiki-themed boat and sail around the Boston harbor. 

Here's your plan for a fun day sailing on a tiki boat in Boston harbor

Tiki-ing Around the Harbor

Start your tiki-themed harbor adventure at The Landing at Long Wharf with a punch bowl for a spirited beginning.

Boat Party

💪 Pro tips
• Watch out for those punch bowls!

Landing at Long Wharf

Hop aboard Tiki Boat Boston for a tiki-themed cruise around the harbor. Enjoy a DJ, drinks by the onboard bartender, and bring your own food.

Harbor Boat Party

✅ Before you go
• Book a boat for 2 or for a whole crew: https://tikiboatboston.com/
• They have options of public and private cruises and they last either 90 minutes or 3 hours. 

💪 Pro tips
•  You can bring your own food, but not your own drinks. But don’t worry there is an awesome bartender on board!
• There is also a DJ on board so you can sit back, relax, and enjoy sailing. 

Tiki Boat Boston 

Get excited for summer in Boston and get on a boat

because you can't miss sailing around in the harbor this summer.

but before that we headed to The Landing at Long

Wharf for a punch bowl to start things off.

our lovely bartender and DJ playing the best tunes.

We partied until the sun went down and caught this beautiful Boston skyline.

So check out Tiki Boat Boston and book your next adventure on the Boston Harbor.

Check out this beer garden and surrounding pizza and sake bar for a sunny day out!

Here's your plan for a sunny day at a beer garden with pizza and sake

Outdoor Beer Garden 🌞 

Visit Notch Brewery at The Charles River Speedway in Brighton for a German-style beer experience with both indoor and outdoor seating options.

Beer Garden

✅ Before you go
• Check out their hours here: https://charlesriverspeedway.com/community/notch-brewing/

Notch Brewery

At Pizza Project, enjoy tasty pizzas in a casual setting. Order online or onsite and savor your meal in the bustling Brighton neighborhood.

Eating Pizza

💪 Pro tips
• Order online or at the food stall: https://order.toasttab.com/online/pizzaprojectboston

Pizza Project

Enjoy a night at The Koji Club in Brighton. Make a reservation for sake tasting, cocktails, and unique events like 'Chocolate & Sake Tasting.'

Sake and Cocktails

✅ Before you go
• Make a reservation or put your name on their waitlist: https://resy.com/cities/boston-ma/venues/the-koji-club?date=2025-05-17&seats=2

💪 Pro tips
• They also have fun events ongoing, like “Chocolate & Sake Tasting”: https://www.thekojiclub.com

The Koji Club

Check out this beer garden with German style beers galore,

An awesome place for a sunny Friday evening with friends.

Either do some dog watching or grab a board game.

The beers here are also low in ABV percentage if you're trying to go low alcohol.

You can also grab a pizza to have in the courtyard,

Beacon Hill Books and Cafe & walk around beacon hill!

Here's your plan for enjoying coffee, exploring a bookstore, and strolling through charming Beacon Hill

Beacon Hill Books & Cafe

Explore Charles Street, Beacon Hill, wearing sturdy shoes to navigate cobblestones. Ideal for those who relish historic ambiances and unique local boutiques.

Books and Cafe

✅ Before you go
• wear walking shoes! Cobblestones & bricks are not for the faint of heart

💪 Pro tips
• You can take the T or uber right there to Charles Street!

Head over to beacon hill

Explore Beacon Hill by walking through charming streets and visiting local boutiques, immersing yourself in the unique allure of this historic Boston neighborhood.

Beacon Hill Walk

💪 Pro tips
• make sure to stop in all of the cute boutiques! 

Walk through Beacon Hill

Visit Beacon Hill Books & Cafe for a delightful time with books and treats. Reserve in the cafe and explore each book-filled level, featuring a pressing button activated train.

💪 Pro tips
• make sure you make a reservation in the cafe (they book out in advance) we went for tea and cookies! Check out every level of the book store! The train goes off when you press the button to the left of the entryway :)