Travel Adventures: New England (Portsmouth, Portland, Boston)

Hi friends! Today I’m going to do a big long blog post all about our recent trip to New England! We flew in and out of Boston and stayed in three spots – Portsmouth, New Hampshire, Portland, Maine, and Boston, Massachusetts. We had heard THE BEST things about Portland so that was the main destination and where we spent the most time, but it was fun to stay in three distinctly different places and explore lots of places in between. We stayed two nights in

Stay tuned for another blog post about Maine beaches we loved. 🙂 I decided to put those photos and details in another blog post since this one is already so long! 🤪


Portsmouth was our first stop! We wanted to stay somewhere within an hour or so from the airport to make our travel day a little easier. We stayed here Wednesday afternoon until Friday morning. It was raining most of the time we were there, so we didn’t get to do *as much* as we’d like — but we loved how it was within 30 or so minutes of incredible beaches like Ogunquit and Kennebunkport. Here are the crowdsourced Portsmouth recommendations I got, with the places we visited italicized.

Coffee/Breakfast: The Friendly Toast (brunch)

Lunch/Dinner: Flatbread Pizza, Moxy (New American), Portsmouth Brewing, Chauncey Creek (lobsters, BYO drinks/sides), Street (international street food)

Drinks: Great Rhythm Brewery, Liars Bench Beer Co.

Sweets: Lickee’s & Chewy’s Candies & Creamery, Elephantine Bakery

Places to Go (parks, beaches, playgrounds, shops, etc): Splash Pad in Newmarket (15 min away), Great Island Common (park), Treehouse Toys (super cute toy store – we spent almost an hour here!), Gus and Ruby, Flower Kiosk (adorable flower + gift shop!)


I  knew we would love Portland, just because a ton of people I  love and trust love it and it just seemed so our vibe. And it was! It was incredible and I’m already itching to go back. Maine is absolutely stunning and Portland was such a fun city with great parks, food, and beer. We got to go to so many breweries, beaches, parks, and coffee shops. We were there from Friday mid-day to Monday morning! My cousin and her sweet daughter drove up to meet us one afternoon which was so fun — we hadn’t seen them in almost three years!

Here are the crowdsourced Portsmouth recommendations I got, with the places we visited italicized.

Coffee/Breakfast: Tandem Bakery, Rose Foods (bagels!), Bayside American Cafe, Coffee By Design, Speckled Axe, Caiola’s (brunch), Coveside Coffee, Two Fat Cats Bakery
Lunch/Dinner: Eventide Oyster Co., Fore Street, Hot Suppa (Southern), Bite Into Main Food Truck, Lukes’s Lobster (LOVED IT!), Street & Co, Emilitsa (Greek), The Highroller,  (lobster!), Central Provisions (tapas), Pai Men Miyake (ramen), Falafel Mafia Food Truck, Cong Tu Bot (Vietnamese), Duckfat (American), Otto (pizza) , Baharat (Middle Eastern), Bastion River (American)
Sweets: Dunnes Ice Cream, The Holy Donut, HiFi Donuts, Standard Baking Co., Belleville Bakery, Vena’s Fizz House (fancy soda shop)
Drinks: Allegash Brewery (so kid-friendly!), Rising Tide Brewery, Lone Pine, Tomaso’s Canteen (dive bar), Belleflower Brewery (loved their beer!), Liquid Riot Distillery, Portland Hunt + Alpine Club (cocktails), Austin Street Brewery, Urban Farm (kombucha), Root Wild (kombucha), Shipyard Brewery, Foundation Brewing
Places to Go (parks, beaches, playgrounds, shops, etc): Black Point Inn, Inn by the Sea, Crescent Beach, Eastern Promenade (good picnic spot and awesome playground overlooking the water!), Ferry to Peaks Island, Portland Observatory, Two Lights State Park (20 min drive), Fort Williams Park to see Portland Head Lighthouse, Mackworth Island State Park
Here’s photos from my favorite day – we went to Crescent Beach and also Fort Williams Park (and Portland Head Lighthouse) and it was just stunning!
Here’s a few more Portland photos!


We drove to Boston Monday and stayed until Wednesday (two nights). Outside of my horrendous experience driving a car in Boston (do not recommend!) we enjoyed Boston a lot! We tend to do a lot of walking to explore big cities and that’s really what we did! We walked a ton, through cute neighborhoods and parks (I think we did four playgrounds in one day!). The highlight of our trip was Neptune Oyster for dinner – so yummy! and then our trip to the Boston Children’s Museum. I included a ton of photos from that morning below!

Coffee/Breakfast: Jaho (get Iced Hanoi), Thinking Cup, Caffe Nero, Mike & Patty’s (breakfast sandwiches), Modern Pastry, Flour Bakery + Cafe
Lunch/Dinner:  Stephanie’s on Newbury (brunch/lunch), Lookout Farm (great for kids), Sarma (Mediterranean), Oleana (Mediterranean), Mamma Maria (Italian), Reelhouse (seafood), Buttermilk & Bourbon (Southern), Fox & Knife (rustic Italian), Roxys Grilled Cheese Food Truck, Bon Me Food Truck, Beehive (live music), Neptune Oyster (LOVED IT!), Felipe (burritos), Trattiro il Panino (Italian), Panza (Italian)
Sweets: Blackbird Donuts (get the everything bagel donut), Kane’s, Union Square Donuts, Cookie Monstah Food Truck
Drinks: Trillium Brewing, Night Shift Brewing (Everett location – so kid friendly!)
Places to Go (parks, beaches, playgrounds, shops, etc): Bostons Children Museum (LOVED IT!), Time Out Market Boston (great playground nearby), walk Beacon Hill and Acorn Street, walk the Charles River Esplanade, Boston Common (large central park), Christopher Columbus Playground, Olive and Grace shop
Here’s some photos from Boston!
Here’s some photos from our trip to the Boston Children’s Museum! This was a total highlight of our time in Boston – it was AWESOME and so covid conscious! 


Here’s a few other New England towns that were recommended to us! I italizied the ones we visited and will highlight those in my Maine beaches blog post soon. 💛

Rhode Island: Providence, Newport // Massachusetts: Bath, Plum Island, Newburyport, Salem, Gloucester // Maine:  Kennebunkport, Ogunquit, Booth Bay, Bar Harbor, York, Freeport, Westport // Vermont: Burlington // New Hampshire: Whites Mountain, Flume Gorge


Kennebunkport: Daytrip Society (cute shop), HB Provisions, Mornings in Paris, Goose Rocks Dairy (ice cream), The Tides Beach Club (early dinner + beach), The Clam Shack, Rococco (ice cream) // Newburyport, MA: Abraham’s Bagels // Cape Elizabeth, ME: Lobster Shack


Maine Beaches We Loved

Flying with Two Kids: Tips, Tricks and Recommendations

Share Your Thoughts:

Your email address will not be published. Required fields are marked *