Portland Maine Ultimate guide

Your Ultimate Guide to Exploring Portland, Maine

If you’re looking for a charming destination brimming with activities, delicious food, and breathtaking scenery, then Portland, Maine should be at the top of your list. This small city perfectly blends urban sophistication with laid-back coastal charm. Its compact size makes it easy to navigate, and the friendly locals add a layer of warmth to your visit. Let’s explore things to do, places to stay and of course, what to eat in Portland!

Getting There and Getting Around

Portland International Jetport (PWM) is the main gateway, and it’s located just a short drive from downtown. Once you land, consider using the METRO bus system, which is affordable and efficient. METRO Bus fare is $2.00 per ride, with a $6.00 day pass available. 

Portland's compact downtown area is very walkable, with historic buildings and waterfront views. There are plenty of bike rentals available if you prefer to explore on two wheels.


Where to Stay

The Press Hotel

For a touch of luxury with a nod to local history, The Press Hotel is a fantastic choice. Located in the former headquarters of the Portland Press Herald, this boutique hotel offers stylish rooms with a literary theme. It's also within walking distance of many downtown attractions.

Blind Tiger

For a unique and luxurious stay, consider Blind Tiger, a boutique hotel that perfectly captures the essence of Portland's charm. The hotel offers beautifully decorated rooms that blend vintage elegance with modern amenities. Guests can enjoy a cozy library, a billiards room, and a lovely garden. It's an ideal spot for travelers seeking a distinctive lodging experience in the heart of Portland.

Hidden Gem: Pomegranate Inn

For a more intimate and quirky experience, check out the Pomegranate Inn. This colorful bed and breakfast in the West End is known for its eclectic decor and cozy atmosphere. Plus, the homemade breakfasts are a delightful way to start your day.


Things to Do

Explore the Old Port

The Old Port district is the heart of Portland. It's known for its charming cobblestone streets lined with 19th-century brick buildings. Spend a day wandering through the boutique shops, art galleries, and cafes. Don’t miss out on the chance to try some local lobster rolls – they're a must!

Visit the Portland Museum of Art

Art enthusiasts will love the Portland Museum of Art, which houses an impressive collection of American and European works. The museum frequently hosts special exhibitions, so there's always something new to see. The Adult admission is $20. If you happen to visit the museum on Friday, the Admission is FREE to all every Friday from 4-8 p.m.

Take a Ferry to the Casco Bay Islands

For a relaxing day trip, hop on a ferry to the Casco Bay Islands. Peaks Island is a favorite for its beautiful beaches and quaint village feel. Rent a bike and explore the island’s scenic trails, or simply unwind on the sandy shores. Ferry rates to Casco Bay Islands: $14.00 for a round trip, $7.20 off season.

Hidden Gem: Southworth Planetarium

Located at the University of Southern Maine, this planetarium offers immersive cosmic shows. It's one of the largest and most technologically advanced planetariums in New England.


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Siedah’s wayre pick: the Flow Short and Shift & Snap Tank in Fern Green.


            Wayre Flow Short in Fern Green



Food and Drink

Portland, Maine is well known for its incredible seafood and farm-to-table cuisine. With its coastal location and dedication to local sourcing, Portland offers an amazing array of fresh seafood and farm-fresh cuisine. Here are some of the best local foods to try in Portland:

  • Lobster - Being a coastal city, lobster is a must-try in Portland. You'll find it served in various ways like steamed whole lobsters, lobster rolls, lobster stews, and even lobster ice cream! Some top spots for lobster include Eventide Oyster Co., Highroller Lobster Co., and J's Oyster.
  • Oysters - Portland has access to some of the best oyster farms in the region. You can sample fresh, briny oysters from places like Eventide, Scales, and Highroller Lobster Co. Many restaurants offer oyster happy hours.

                                         Oysters are a must try in Portland, Maine


  • Farm-to-Table Cuisine - Portland's thriving farm-to-table movement means that you can enjoy fresh local produce, meats, cheeses and more. Restaurants like Fore Street, Piccolo, and Tipo make excellent use of ingredients from local farms and purveyors.
  • Breweries and Distilleries - Portland has emerged as a craft beer and spirits destination, with many award-winning breweries like Allagash, Shipyard, and Rising Tide offering tours and tastings. Maine Craft Distilling and Hardshore Distilling are top spots for craft cocktails.
  • Donuts and Pastries - For a sweet treat, don't miss the donuts and pastries from beloved local spots like Holy Donut, Scratch Baking Co., and Tandem Bakery


Where to Eat:
Bite Into Maine
Hidden gem alert! This unassuming food truck serves up some of the best lobster rolls in Portland. Look for their bright red truck parked on Fort Allen Park or track them down at local breweries

Eventide Oyster Co.

Seafood lovers, rejoice! Eventide Oyster Co. is renowned for its fresh oysters and inventive dishes.

Fore Street

For a memorable dining experience, book a table at Fore Street. This farm-to-table restaurant focuses on locally sourced ingredients and has a menu that changes with the seasons.

Sur Lie

For a unique dining experience, visit Sur Lie. This tapas-style restaurant offers a creative menu with locally sourced ingredients. Their small plates are perfect for sharing, making it a great spot for a group of friends or a solo traveler looking to try a variety of dishes.

The Holy Donut

For a sweet treat, head to The Holy Donut. These potato-based donuts come in a variety of flavors, from classic chocolate glazed to unique combinations like maple bacon.

Tandem Coffee + Bakery

While Portland has no shortage of great coffee shops, Tandem Coffee + Bakery stands out for its delicious pastries and cozy ambiance. It’s a bit off the beaten path, making it a perfect spot to relax with a book or catch up on some journaling.


Travel Tip: If you’re dining out, look for restaurants that focus on local and sustainable ingredients. It’s a great way to support the community and enjoy the freshest flavors.


Portland Flea-for-All

If you love unique finds, Portland Flea-for-All is a treasure trove of vintage and handmade goods. Located in the Arts District, this shop offers a selection of mid-century furniture, jewelry, vintage clothing, and unique collectibles. It's the perfect place to find one-of-a-kind treasures.

Venn + Maker

This unique shop features locally made furniture, jewelry, clothing, leather goods, and home decor items crafted by Maine artisans. You'll find repurposed vintage pieces alongside modern designs, all made with high-quality materials.

Campfire Studios

This husband-and-wife team handcrafts stunning, minimalist pottery designed at their Westbrook studio. Their heirloom-quality pieces make perfect gifts for weddings, housewarmings, or treating yourself

With its thriving community of local makers and vintage shops, Portland is a great place to find plenty of unique, high-quality items.

Outdoor Activities

Kayaking on Casco Bay

Get out on the water and explore Casco Bay by kayak. Several local outfitters offer rentals and guided tours, providing a fantastic way to see the coastline and its wildlife up close.

Hiking at Mackworth Island

A short drive from downtown, Mackworth Island offers a scenic hiking trail with stunning views of Casco Bay. It’s an easy hike suitable for all skill levels and a great spot for a picnic.

Hidden Gem: Jewell Falls

For a more secluded nature experience, visit Jewell Falls, the only natural waterfall in Portland. It’s located in the Fore River Sanctuary, a peaceful spot perfect for a quiet hike.

wayre destination guide to portland maine, jewell falls

Fun Facts About Portland, Maine

  • Lighthouse Capital: Portland is home to six historic lighthouses, each with its own unique charm. The most famous, Portland Head Light, is the oldest lighthouse in Maine and offers spectacular ocean views.
  • Birthplace of Prohibition: Portland was the first dry city in the U.S. thanks to Neal Dow, a staunch prohibitionist and former mayor. You can learn more about this intriguing history at the Neal Dow House.
  • Stephen King Connection: Maine's famous horror author, Stephen King, is a native of Portland. Fans can visit sites that inspired his novels, like the Eastern Cemetery.


Portland, Maine, is a fantastic destination for all travelers who appreciate good food, beautiful scenery, and memorable experiences. With its welcoming atmosphere and plenty of activities, it’s a place where you can truly unwind and immerse yourself in the local culture. So pack your bags, lace up your walking shoes, and get ready to explore all that Portland has to offer. 


Happy travels!


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