Portland Luxury Travel Guide
Portland, Maine, is the perfect New England blend of fresh seafood, fantastic boutique shopping, comfortable accommodations, and outdoor adventures. Overlooking Casco Bay and dozens of small islands, it’s a wonderful place to visit. Every time we go, we eat, see, and do a handful of new things, and we always have a great time. If you’re planning a visit to Portland, flying into Maine’s largest city, or passing through on a road trip through the US’ most forested state, this Portland Luxury Travel Guide will help you plan the perfect stay.
How to Reach Portland
Portland has its own major airport (Portland International Jetport, aka Jetport and PWM). Be sure to triple-check all of your flights and reservations that you are flying into Portland, Maine, not Portland, Oregon, as each year thousands of people fly into the incorrect airport.
Portland is reachable by car from most of New England and Eastern Canada if you’re open to road tripping. Amtrak also has a train center in Portland, making it accessible by train.
Of course, sailing is always an option, too! Be sure to monitor docking time limits at public landings, as most in the region do not allow overnight docking.
How to Get Around Portland
Downtown Portland is very walkable. If you’re up for stretching your legs, you can see most of the city on foot. As Portland is an older city by US standards, the sidewalks and roads have settled, making them a bit uneven, which can be difficult to navigate for some. I also do not recommend wearing heels, as the cobblestoned streets and wooden docks are uneven and can be slick.
Best Time of Year to Visit Portland
There’s plenty to do in Portland all year long. Spring through autumn are busier, more expensive, and have bigger crowds, but the weather is always great if you carry a rain jacket and wear comfortable shoes. Flowers bloom from late April until the leaves turn, making it perfect for nature lovers.
Winter visits are fun, too. Budget more time for transportation delays brought about by common, sudden snowstorms. Pack warm layers, quality shoes with good traction, and enjoy Portland when it’s transformed into a winter wonderland.
Where to Stay in Portland
The Evalina Hotel was the perfect spot from which to explore Portland. The sprawling two-bedroom suite felt more like a spacious townhouse than a hotel. Complete with a full kitchen, living room, lounge area, balcony, and bathroom plus a washer and dryer, it had all of the perks of a hotel without any of the constraints. Read my full review of The Evalina Hotel.
Where to Eat in Portland
Honey Paw
New-England-influenced Asian food wasn’t something I’d heard put into words until hearing about Honey Paw. It’s incredible, and they have plenty of allergy-friendly options!
The Juicery
We loved having breakfast here. Using fresh, organic produce, they make fantastic fresh-pressed juices, smoothies, açai bowls, and so much more.
L.B. Kitchen
This bakery & café has a fantastic assortment of gluten-free and allergen-friendly pastries and snacks, plus their baristas can whip up just about anything.
Lady Fish
The perfect spot for seafood lovers seeking a beautiful atmosphere and fun spins on classic New England dishes.
Lucky Cheetah
Lucky Cheetah, an upscale Chinese restaurant, has fantastic dim sum, small plates, and shareable entrées. I’d love to see them expand their GF offerings, but the excellent flavors were well worth missing out on more classic dishes like dumplings, bao, and shumai.
Luke’s Lobster Portland Pier
Luke’s is a staple in New England and beyond, and their Portland Pier location is my favorite. Try their hot honey lobster rolls (which can be made GF!)
Mr. Tuna
If you love sushi, you can’t visit Portland without trying Mr. Tuna! Their otoro is out of this world.
Portland Food Co-op
We picked up some groceries here and were impressed by the variety of organic and allergy-friendly foods available. They also have a wonderful pay-it-forward program where you can pre-purchase food for those in need. If you do nothing else in this guide, please drop in and buy a few meals for those who need it. Community programs like this prevent the less fortunate among us from going hungry, and watching them hang up the meal vouchers we paid for felt wonderful!
Scales
Everyone we asked recommended Scales, and we were so glad to give it a try! Most of their menu can be made gluten-free– just ask!
Taj
We love Indian food, and this was some of the best we’ve ever had. They even have their dishes separated by gluten-free (about half of everything they serve!) and non-gluten-free, which made eating here a fantastic experience.
The Holy Donut
I hadn’t eaten a donut in nearly a decade, in part because being diagnosed with celiac made it impossible. When I learned they have gluten-free donuts at The Holy Donut, we made a beeline for them. And then, at the first bite of my honey lavender donut, I almost cried. It truly was that fantastic!
Twelve
Portland’s most beloved fine-dining experience would definitely have Michelin stars if the Michelin guide covered Portland.
Wildflours Gluten-Free Bakery
Another fantastic gluten-free bakery, Wildflours is perfect for those who want to support allergy-friendly businesses.
What to Do In & Around Portland
Build a Terrarium
We had SO much fun at Terrarium making our own terrariums! They also sell a fantastic assortment of houseplants!
Check Out the Cryptozoology Museum
I’ve never been to this museum about Bigfoot, mermaids, the Loch Ness Monster, and more, but it’s on my list!
Eat a Lobster Roll
It’s a New England classic for a reason, and there are plenty of great spots to grab one in Portland. Luke’s Lobster is my favorite because they have gluten-free rolls, but if you don’t have celiac disease, you have many more options.
Sunset Lighthouse Cruise
If you love lighthouses, this is a must-do in Portland during the warmer months.
Visit Portland Head Light
It’s one of my favorite lighthouses in North America!
Walk the Pier & Old Port
If you have any interest in sailing, seeing the water, and experiencing a different side of Portland, this is the place to do so.
Where to Shop
Blanche + Mimi
This cute vintage shop has everything a lovely home needs, plus a great assortment of jewelry and accessories.
The Lady in the Moon
If you like antiques and mysterious October vibes, The Lady in the Moon is the shop for you.
Little Pine General Store
This recently opened general store features a carefully curated selection of locally made goods.
Maxwell’s Pottery
Colorful pottery and fun, unique handmade dishware make Maxwell’s Pottery a must-visit in Portland.
Terrarium
We had a blast making our own terrariums at Terrarium. The knowledgeable staff will walk you through it so you can’t mess up, plus they have tons of houseplants to buy and bring home.
Destinations Near Portland
Acadia National Park
This gorgeous national park on Mount Desert Island is about three hours from Portland. It’s the perfect place to hike, swim, and enjoy the great outdoors.
Bar Harbor
The largest town on Mount Desert Island near Acadia National Park, Bar Harbor is my go-to place for lighthouse and puffin watching tours, great seafood, and cozy hotels.
Deer Isle
A gorgeous corner of Mount Desert Island, this secluded cove is a great spot for nature lovers.
Northeast Harbor
A beautiful seaside community, Northeast Harbor has small-town vibes with fantastic fine dining, hiking, and sailing opportunities. The coffee shops and boutiques in NE Harbor are fantastic, too.
Southwest Harbor
Yet another lovely spot on MDI, its secluded nature makes this a romantic escape.
Safety
Portland is a very safe city. Be safe around the water, be aware of weather conditions, and don’t leave valuables out in public places. We’ve never once felt uncomfortable here!
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