Welcome to Backpacker’s Boutique. Every Sunday, this spot will feature a new travel blogger. Some weeks it will be a really fun interview about packing, fashion, and fitness so you can snoop inside their bags & lives a little bit and other weeks it’ll be a detailed luxury guide to a city the featured blogger/expat knows very well. E-mail me if you’d like to be featured.

A Luxury Guide to Portland, Maine

Tell us a little about yourself and tell us why you’re an expert on luxury travel in Portland, Maine.

I’m a born and raised Mainah (we prefer not to use our “r’s”). After 28 years in the beautiful state of Maine, I just left to begin my “Great Escape” around the world. I spent almost a decade in Maine working for biotechnology and healthcare information technology companies which was interesting but not my passion. Now I’m a freelance writer and virtual assistant traveling the world in pursue of great stories and fun adventures. In my spare time I enjoy competing in triathlons (I completed Ironman Lake Placid in 2013), hiking, and good glass of red wine.   

What makes Portland, Maine a perfect destination for travelers seeking a glamorous trip?

When most people think of Portland they think of the other Portland. Portland, Maine is the original Portland first settled by the English in 1623. And we’re way cooler. I mean… we have lobster.

Fun Fact: Two men, Asa Lovejoy and Francis Pettygrove, founded Portland, Oregon. Lovejoy was from Massachusetts thus he wanted to call the new settlement “Boston.” Pettygrove, a native Mainah, wanted to call it “Portland.” The two men flipped a coin and Pettygrove won. So, obviously, we are cooler than Boston too. Wicked cool.

Portland is the perfect travel destination for a wide range of travelers. We have something for everyone. Portland is a foodie town. In fact Portland constantly ranks as one of the best food cities in America because of its restaurant scene. Many chefs have left cities like New York and San Francisco to open a restaurant in Maine.

Not to mention we have lighthouses, sandy beaches, beautiful mountains, and more L.L. Bean boots than you can want just a short drive outside the city.

luxury guide to portland maine

What 5 star hotel is the best in Portland Maine?

Up until a few years ago Portland had a hotel crisis. The city didn’t have enough hotel rooms to accommodate the number of visitors. Several new hotels have been recently built in the Old Port, the city’s historic commercial center.

The hot new hotel in town is the Press Hotel, a hotel built in the former Portland Press Herald building. The hotel opened last May as a luxury hotel with a newspaper theme. You’ll find vintage-looking desks, typewriters, and newspapers throughout the hotel and even the hotel logo is designed to resemble typewriter keys.

What about boutique hotels in Portland Maine, of them all, which would you send your friends or family to stay at?

If you’re coming for the true Maine coast experience then Black Point Inn, located just 15-minutes from downtown Portland is a luxurious option. Each of its 25 rooms is quintessentially Maine and the perfect romantic getaway. While you’re there, check out American painter Winslow Homer’s artist studio just steps away.

The Gulf of Maine contains 365 islands, which are often called the calendar islands. Remember that for Jeopardy, okay? Over 100 of those are located close to Portland. Peaks Island is the most popular island destination that is just a quick ferry ride away. If you’re looking for a true boutique Maine experience, stay at the Inn on Peaks.   

Are there any fun activities for the adventurous traveler in Portland?

Portland is a great city for food, craft beer, and the arts, but if you’re looking to for true adventure then you need to head outside the city.

Maine has some great hiking within an hour of Portland. Pack the car with a picnic basket and head for the local mountains to spend some time in nature and enjoy our state tree, the pine tree. Maybe you’ll be lucky and see a moose!

Looking for even more adventure? Mount Katahdin, Maine’s tallest mountain and the end of the Appalachian Trail, is about a 6 hour drive north from Portland. Trust me, it’s worth the drive!

During the winter months both nordic and alpine skiing and snowboarding is very popular at Sunday River and Sugarloaf Mountain. Head to Pineland Farms for the best local cross-country skiing.

Curious where exactly our famed lobster comes from? Take a Maine Lobster Tour through Lucky Catch for a unique Maine experience.   

luxury guide to portland maine

Where are the best hangouts during the day in Portland Maine?

If you are in town on a Saturday you need to walk through the weekly Farmer’s Market in Deering Oaks Park. Farmers from all over Maine come to sell their fresh produce, meats, cheeses, and berries.

Next, take a short drive to Cape Elizabeth to Fort Williams Park. Here you can see Portland Head Light, the most photographed lighthouse in America that was commissioned by George Washington. Grab a lobster roll at the Bite into Maine food truck and finish it off with our famous whoopie-pies.

There are many beaches located just outside of Portland. Scarborough Beach is a wide family-friendly sandy beach popular with locals and tourists alike. Get there early, as parking is limited. If you’re looking for the true tourist experience, head to Old Orchard Beach, a favorite summer spot for French Canadians. Hop on the roller coaster, play games at the arcade, work on your tan on the beach, and stuff your face silly with pier fries and fried dough.

If you have a big date night, what are the most delicious restaurants in Portland Maine and what are their best dishes?

Portland has it all – from our world-famous lobster to Thai to fine French and Italian restaurants. We have a bit of everything at everyone’s budget.

My favorite restaurant is Boda, an authentic Thai restaurant. The place is popular so expect to wait for a table, but the food is worth the wait. From delicious pad thai to quail eggs to sticky rice, you can’t go wrong.

If you’re looking for something upscale then head to Fore Street of Street & Co, but make sure you make a reservation in advance. Vinland is a popular restaurant that only makes food from local Maine ingredients so you can bet lobster is on the menu.

luxury guide to portland maine

Let’s talk desserts- what place makes the best?

Portland has some great cafes with yummy pastries, but if you’re looking for dessert, either gelato or donuts are the way to go. Check out either the Holy Donut or Tony’ Donut. Definitely try the Maple donut at Tony’s. Yum!

Gorgeous Gelato and Gelato Fiasco are located across from each other on Fore Street and both have delicious and rich gelato. Some people prefer one to the other, but personally I believe any gelato is good gelato. Give them both a try.

Tell us all the hot shopping spots; who’s carrying the trendy local designers in Portland Maine?

The Old Port is full of cute shops containing anything from clothes to housewares to trinkets. Bliss Boutique is my favorite shop where you can find labels like Citizens of Humanity, Prairie Underground and Frye.

Looking for something local – check out Sea Bags and Alaina Marie for fashionable Maine bags. Kennebunkport is also a charming seaside town located about 30 minutes south of Portland with great shopping.

Of course, if you come to Portland you need to drive the 20 minutes north to Freeport to visit the L.L. Bean flagship store and the amazing outlet shops like J. Crew, Ralph Lauren, and more. 

luxury guide to portland maine

What are a couple of the best salons and spas in Portland?

Nine Stones Spa has some of the best massage and ski care packages north of Boston. Their staff is friendly, helpful, and very professional. The spa itself is very tranquil making it the perfect spot to relax and unwind.

Portland has many salons, but my favorites have always been Head games, Akari, and J. Kelley Salon.

Time for a great sunset view… where would you go?

For the best view of Portland head to the Top of the East for a cocktail and enjoy the views of the city and Casco Bay.

However, the best sunrise in Maine is a top Cadillac Mountain in Bar Harbor, which is about 3 hours north of Portland. Acadia National Park is one of the oldest national parks in the country and a great place to spend some time. So after Portland head north.

luxury guide to portland maine

Now that the sun’s gone down, fill us on the best places to go for some evening drinks or a great pre-gaming spot.

Not only is Portland a very foodie city, it is ranks as the top city for the number of breweries per capita beating out even the other Portland. If craft beer is your thing then Portland, Maine should be at the top of your list.

You can easily spend the day brewery hopping on your own or take the brewery tour through the Maine Brew Bus. My favorite local brew is Allagash Belgian White. And definitely check out Maine Mead Works for delicious mead. You can beat the lavender lemonade!

Portland has a wide range of bars from total dive bars to upscale cocktail bars. Most of the bars are concentrated in the Old Port, but several are located up the Peninsula. If you’re looking for a cool laid-back vibe then head straight to Novare Res, the local beer garden showcasing local Maine brews and European beers, or Bramhall Pub, where Maine’s best bartender mixes and stirs all sorts of fabulous concoctions.

Looking to relive your early 20s? Head to Amigos or Bonfire. The best cocktails can be found at either the Portland Hunt + Alpine Club or the North Point.   

If you end the night at a fancy club, which one do you head towards?

Well, Portland doesn’t really have fancy clubs, which is one of the many things I love about Portland. You won’t find us wearing expensive heels and designer dresses. We prefer jeans and a flannel shirt.

But, if you insist…. The Pearl is popular amongst the newly minted 21 year olds and has a bit of a dress code. My favorite is the Oasis. It’s totally down-to-earth and you can order bucket size drinks and play giant jenga. Oh, and the music is pretty good too. 

luxury guide to portland maineKatelyn is a freelance writer traveling the world on her “Great Escape.” Hailing from the great state of Maine, she spent most of her 20s working in the biotechnology and health IT industries, but decided to follow her true passion in life – writing and traveling. She enjoys hiking, watersports, triathlons, and a good glass of red wine. Preferably from South America. You can follow her journey on Diaries of a Wandering Lobster. Katelyn is also found on Twitter, Facebook, and Instagram