How to Make the Most of Your First Trip to Portland, Maine: A guide to the best attractions, restaurants, and hotels!

Portland, Maine is a perfect weekend getaway for a change of scenery and pace. It is closer than you think. You can fly from DCA to Portland, Maine in less than 2 hours with American Airlines. You can also take a train from Philadelphia to Portland, Maine in about 7 hours with Amtrak. Portland has a rich and diverse history. Explore the Old Port district, which dates back to the 17th century and features cobblestone streets, brick buildings, and waterfront views.

When to visit:

  • Summer in Portland runs from June to August and is a great time to visit as all the flowers are in full bloom. This being said, if you don’t like crowds, it’s best to stay well away from Portland during this time.
  • Spring in Portland runs from March to May, during this time the temperatures rise, however you can still expect scattered rain showers throughout your trip. Spring is a great time to visit if you’d like to enjoy some warm weather and stay away from the crowds!
  • From September to November, Portland experiences Autumn. The temperatures drop and so does the price of accommodation. If you’re on a budgeted trip, this is a great time to visit this beautiful city.

Attractions:

Victoria Mansion is a landmark example of American residential architecture from the 19th century, built as a summer home for Ruggles Sylvester Morse and his wife Olive. The mansion features original interiors, furniture, and artworks that showcase the opulence and elegance of the Victorian era. It is two blocks from the Blind Tiger Inn where we stayed. Purchase your tickets in advance and get the guided tour. The mansion is open from May 1 to October 31, 10 a.m. to 4 p.m. daily except for major holidays.

Wine Wise Sails from Casco Bay is a unique and memorable way to enjoy fine wines while sailing in the beautiful scenery of Maine. You will join Sommelier Erica Archer for a wine education experience that will teach you how to see, swirl, sniff and taste wines from different regions and styles. You will also learn about the history, culture and cuisine of the places where the wines come from. You can choose from a variety of wine sails that suit your preferences and interests, such as Mediterranean wines, California wines, French wines, Italian wines, Greek wines, Champagne and oysters, and more. You can also book a private sail for your clients, friends or family. Wine Wise Sails are available from June to October on Fridays, Saturdays and Sundays. Tickets are on sale now and they sell out fast, so don’t miss this opportunity to have a fun and educational wine adventure on Casco Bay.

Portland Saturday Market -One may also discover the local talent and craftsmanship at the Portland Saturday Market, where you can find handmade goods, food and entertainment.

Portland Harbor Museum– If maritime traditions speak to you, be sure to check out the Portland, Maine at the Maritime Museum, or the Portland Observatory, the last remaining maritime signal tower in the USA.

Portland Museum of Art– is a must-see museum.  PMA is the oldest public art institution in the United States, located in the downtown area known as The Arts District. You will recognize the SEVEN Sculpture outside the entrance. The Artist is Robert Indiana. Yes, he is the same artist responsible for the LOVE sculpture in downtown Philly. PMA was perfect  – it is manageable: four floors, a gift shop and a café. Their mission is Art for All–Accessible to all.

SOAKOLOGY is an extraordinary spa experience for an ordinary day. You should try it because it will make you feel refreshed, rejuvenated, and happy. It is a unique and relaxing spa and tea lounge that offers a variety of services and products to pamper yourself or a loved one. You will love the copper tubs for soaking.

Food Scene

Central Provisions is a restaurant that offers creative and delicious dishes made with fresh and local ingredients. The menu changes daily according to the availability and seasonality of the products, but you can always expect to find a variety of small plates, salads, sandwiches, soups, charcuterie, cheese, seafood, meat and desserts. You can also enjoy a selection of craft cocktails, beers and wines that complement the food. Central Provisions Restaurant has a cozy and rustic atmosphere with exposed brick walls, wooden tables and an open kitchen where you can watch the chefs at work. The restaurant is in the heart of the Old Port district, close to many shops, galleries and attractions. Central Provisions is open for lunch and dinner from Tuesday to Sunday, and brunch on Sunday. Reservations are recommended as the place is very popular and busy. Yes, it was our favorite restaurant in Portland!

Duckfat is a small sandwich shop that serves classic Belgian fries made with local Maine potatoes fried in duck fat, as well as panini, soups, salads, charcuterie, sodas and milkshakes. They also have a great beer and wine list, and is a fun and unique dining destination while in Portland.

Via Vecchia is a small plates Italian inspired restaurant in Portland, Maine. It is in the heart of the Old Port in a historic brick and ivy covered building overlooking cobblestone streets. The restaurant offers a variety of dishes, such as fried artichokes, buffalo mozzarella, homemade pasta, risotto, pork Milanese, and pizzette. The restaurant also has a large wrap around 20 seat bar that serves craft cocktails and Italian wines. The atmosphere is warm, energetic, and sophisticated.

Accommodations

Blind Tiger Inn: Unique guest house on Danforth Street – about a 15-minute walk from the Old Port district.

The Francis Boutique Hotel – free parking and close to the Old Port.

The Westin Portland Harbor Hotel offers stunning views of Casco Bay and near popular attractions.

The Press Hotel: known for its uniqu3e decor that celebrates art in all forms – near the Old Port district.

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Portland is a city that has something for everyone, whether you are looking for culture, nature, food, or fun. You can easily get around the city by public transit and enjoy the many attractions and activities that the city offers. You can also indulge in the diverse and delicious culinary scene that Portland is famous for. Portland is a city that will surprise you, delight you, and make you want to come back again and again.

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