Portland, Maine Travel Guide

It should come as no surprise that a city in Maine is first on my list of destinations. Maine is truly my happy place. I believe some places you’re simply meant to find. Maine had been calling to me since I was a little girl, when the pages of Miss Rumphius and Blueberries for Sal planted dreams of fields covered in lupines and wild blueberries. I didn’t make it here until my late twenties, but when I finally did, it felt like being reunited with an old friend.

There’s so much to see and do in Maine, it’s easy to understand why it’s known as Vacationland. Whether it’s the rocky coastlines, the mossy forests filled with the scent of balsam, or the charm of its small lobstering villages, Maine has a way of making you feel like you’ve arrived exactly where you’re meant to be.

Portland is Maine’s largest city and, in my opinion, one of the best food cities in the country. Located around two hours north of Boston and three hours south of Bar Harbor/Acadia National Park, this charming seaside “city” features cobblestone streets, a bustling food scene, and a quintessential New England vibe.

To Eat/Drink

Tandem Coffee and Bakery – Lattes are consistently great and the sweet loaded biscuit is life-changing. Dan loves the breakfast sandwiches too! Get there early, line gets long on weekends after 9:00am. Note: If you just need coffee and a pastry to-go, you can also check out there second, smaller location on Anderson St.
Standard Baking Co. – Another one of my favorite bakeries in Maine. We always get morning buns, anything with Maine wild blueberries (lowbush), and/or so many baguettes.
Bite Into Maine – Our favorite lobster roll in the Portland area. We personally prefer it Connecticut style (hot butter, cold lobster) but the mayo-based Maine style is a favorite too.
Izakaya Minato – An intimate Japanese restaurant with a super creative menu. We always get the chef’s choice / omakase dinner and have loved every single thing we have been served. Their signature fried chicken is… chef’s kiss!
Island Creek Oysters – This colorful spot is right across the street from Izakaya Minato, so it’s perfect for pre-dinner oysters or post-dinner soft serve. Amazing patio and huge selection of local oysters!
Street & Co. – Super romantic spot with delicious pasta. Split the Lobster Fra Diavolo!
Eventide Oyster Co. – You have to try the Bao bun–style lobster roll and any of the oysters. The oysters rotate often so ask the server for recs!
Duckfat – Famous for their fries cooked in duck fat. No notes.
Twelve – A fine dining vibe with delicious cocktails. The parker house rolls, croissant lobster roll (I mean come on) and the birthday honey cake were the highlights for us. (Note: the honeycake is off-menu and only available for special occasions).
Via Vecchia – Popular Italian spot serving authentic dishes with great patio vibes and people-watching. Also to note, their spritzes come with a side car.
Bread and Friends – There’s no shortage of amazing bakeries in Portland and this one is no exception.
Bahn Appetite – The absolute best bahn mi’s in a very casual, no frills, take-out only spot. Bonus points for punny restaurant name.
Central Provisions – Famous for small plates, we loved their popovers, but you can’t go wrong here!
Holy Donut – Delicious donuts made from potatoes. Honestly, cake donuts aren’t my thing, but it felt blasphemous leaving off this list.
Allagash Brewing Company – This place is famous for their Allagash White, a.k.a. the only beer I actually love. Their brewery tour is really fun and the brewery is home to one of our favorite food trucks, Bite Into Maine.
Blyth & Burrows – A chic cocktail bar that’s worth a stop. Also, there’s a hidden speakeasy inside!

To Stay

AC Hotel Downtown Waterfront
The Press Hotel, Autograph
Hilton Garden Inn Downtown Waterfront
Longfellow Hotel
There are also tons of amazing Airbnb’s in the Portland area.

To Do/See

Old Port – Cobblestone streets, historic brick buildings, tons of shopping, restaurants, and harbor views, what more could you ask for?
Munjoy Hill – Watch the sunrise from the top of Munjoy Hill at East End Promenade/ Fort Allen Park and don’t sleep on the cafes, restaurants, distilleries, and shops in this neighborhood.
Thompson Point – Check to see if anyone is playing at Thompson Point State Theater.
Peaks Island – You can hop on the Casco Bay Ferry and take a scenic ride to Peaks Island or one of the other Casco Bay islands. You’ll get beautiful views of the Portland waterfront and nearby lighthouses from the water. Note: The Casco Bay ferries are commuter ferries, not tourist boats, which means they’re cheap and a very local way to see the islands. BYO drinks/snacks and enjoy a floating happy hour.
SoPo – South Portland is a more residential community just over the bridge and home to several more iconic Maine Lighthouses, Bug Light and Spring Point.
Cape Elizabeth – Portland is surrounded by iconic lighthouses. We found the Portland Head Light in Cape Elizabeth to be by far the most picturesque. It’s a great place to enjoy the view and scarf down a lobster roll and yet another Bite Into Maine location.
Freeport – On your way north from Portland, make a quick stop to browse the L.L. Bean flagship store and explore the other outlet shops. If you’re hungry or thirsty, we love the Maine Beer Co. and the Freeport Oyster Bar. Freeport also has the fanciest McDonalds ever, if you’re into that kinda thing.

To Procure

To Explore

Mackworth Island State Park
Gisland Farm Audubon Center
Presumpscot River Preserve

To Know

Best Time to Visit – Summer is peak lobster, blueberries, patios, and festival season, but it’s also the busiest. Fall brings that perfectly crisp air and beautiful foliage with fewer crowds, while winter is quiet and cozy.
Reservations – Many of Portland’s top restaurants (Eventide, Central Provisions, Izakaya Minato, Twelve) book up fast, be sure to plan ahead or be ready to wait.
Parking – Street parking, especially downtown is limited. Consider a garage or leave the car at your hotel/Airbnb and explore on foot, Portland is very walkable.
Weather – It’s basically San Francisco of the East. Always bring a sweater or light jacket, even in summer. Fog and sea breezes can make it chilly any time of year.
Oysters – Maine is the Napa Valley of oysters so don’t be surprised to see an abundance of options on menus. We personally prefer larger, sweeter, more crisp, and less briny oysters. Our favorite oysters are Glidden Point, John’s River, Eros, and Love Point.
Lobster Rolls- Locals will debate lobster roll style (Maine vs. Connecticut). Maine is more of a mayo based lobster salad, while Connecticut is lobster meat served with hot butter. As noted above, we personally prefer CT style, but it’s worth trying both.