Ultimate Friends Weekend in Portland, Maine
Fun-Filled Friends Weekend Exploring Greater Portland
Shopping Sprees, World-Class Eats, and Beachy Breeze
It’s time to get the squad back together. Look no further than Portland, Maine with easy access by train, plane, bus, or car – get here from anywhere, so you can start spending time together sooner. Check our weekend guide on how to get started planning the ultimate Friends Weekend filled with craft brews, waterfront views, and endless fun.
Photo Credits: Capshore Photography
Morning Arrivals
DAY ONE
Every stay starts with a home away from home. Greater Portland offers the best of both worlds when it comes to accommodations. You’ll find both chain and boutique hotels as well as local Bed and Breakfasts. Cabins and campgrounds, like Pride Motel & Cottages, to provide a tranquil retreat for those who want to get closer to nature.
You’ll find South Portland hotels and local boutiques just minutes from downtown – near the Portland jetport and the hustle and bustle of the city. Whitehall Manor offers a rental that will make you feel like a true Mainer. If you’re interested in outdoor adventures, hotels in South Portland are just a stone’s throw from our area towns, where you’ll find lighthouses, parks + trails, and Casco Bay all waiting to be explored.
Get out and enjoy the fun, sun, and sea breezes walking downtown in the Old Port. Laugh and catch-up while canvassing the cobblestone streets, popping into local shops for souvenirs and snacks as you make your way to the Working Waterfront. Gather the group downtown at one of our Portland, Maine hotels.
Residence Inn Portland Downtown Waterfront offers spacious all-suite accommodations, ideal for group gatherings. Start each morning with a complimentary hot breakfast, and stay active in the on-site fitness center. In the evening, unwind with craft brews and cocktails at their cozy Shipyard Lounge, making it the perfect spot to relax after exploring Portland’s waterfront.
The heart of Portland’s Downtown District is along Commercial St. Where our area fishers and lobsterers weave in and out of Casco Bay with their catches. Lose yourselves in the slow, peaceful pace of the schooners, fishing boats, and ferry carving their way across the water. While you’re at it – snap a new group photo! The opportunities are endless to find a picturesque photo spot downtown.
Lunchtime
DAY ONE
Imagine this: it’s a bright, summer day on the waterfront in Portland, Maine. Your favorite people are finally together and you’re ready to grab a bite. As you take in the picturesque views of the harbor, you find countless restaurants and feel a sense of community with your friends as you explore the serene landscape together. All food types are represented whether there’s a member of the party who is vegetarian, vegan, gluten-free, or has a food sensitivity – we take care of your crew as if they are our own.
Brimming with fresh seafood options like lobster rolls, clam chowder, and fish and chips. Maine is known for its abundance of fresh seafood, and there’s no better place to experience it than off our rocky coast in Greater Portland, Maine. A group lunch downtown on the waterfront is the perfect way to enjoy the best of Portland’s cuisine and atmosphere with your besties.
Afternoon
DAY ONE
No trip to the region is complete without some brewery hopping. With over 20 breweries to choose from, each offering something unique, you just can’t go wrong. Get off peninsula and explore where Maine’s beer journey started at some of our classic establishments below. Diversify your palette and explore even more of our craft beverages–you’ll find local wine, spirits, kombucha, and flavored sodas all across the region.
Tasting flight with folks; Photos by Mat Trogner c/o Allagash Brewing Co. 
Wine Tastings. Photo Credit: Vine Nirvana 
Work For Your Beer | Mel Fox, Photo Courtesy of Geary Brewing 
Food/Drink from Bite Into Maine + Orange Bike Brewing. Photo Credit: Bite Into Maine 
Group at Brewery. Photo Credit: Maine Brews Cruise
Allagash Brewing
Known for its easy-to-sip and enjoyable flagship beer, Allagash White, Allagash is one of our brewery staples. Enjoy drink options that can please everyone in your group, from house-made cider, to blueberry wine- or a refreshing Belgian-style golden ale, Tripel. If you’re looking for a snack to soak up some of those suds – Bite into Maine’s airstream trailer serves-up some of the best lobster rolls you’ll ever taste, or if you’re not into lobster rolls, there’s pulled pork sandwiches, lobster grilled cheese, and burgers.
Geary Brewing Co.
After you’ve had your fill of the brews and bites at Allagash, get ready to do a little walking to your next stop. It’s close because Geary’s is about a half mile from Allagash, meaning it’s easy to walk to. Once you get to Geary’s tasting room, you’ll find plenty of classic beers, like their Razzle Dazzle Raspberry Tart, Original Pale Ale, or Off Trail Brown Ale. Settle in outside at the Beer Garden, where you can play a game of cornhole or sit and chat for a bit. Geary’s was New England’s first craft brewery and is a superb spot for an afternoon of casual drinking with your friends!
Don’t think we forgot your pals who prefer wine, spirits, or even a non-alcoholic option. For those who prefer wine, look to Vine Nirvana wine tastings. This unique experience offers all the benefits of a wine tasting, brought to you! Choose your choice of five Italian wines to impress your friends with. Then, you can sit back, relax, and learn something new.
Evening
DAY ONE
You may have heard about Portland’s unbelievable food and drink scene, but it’s also a hub for the performing arts. Many of your favorite stand-up comedians now have stops on their tours here, making it an excellent activity for friends to do together. Make a night of it by grabbing a bite and head to one of our venues like Merrill Auditorium, State Theatre, or Cross Insurance Arena.
Morning
DAY TWO
When you wake up refreshed on the first full day of your trip – you’re going to want to get out and go exploring. Our outdoor adventures can take you all over town. So, ask yourselves – what does level of recreation is the group looking for? Find everything from hiking trails to scenic walks in the park over the bridge at our lighthouses in Cape Elizabeth and South Portland.
How about getting out on the water? Take a cruise or ferry over to a local island for frozen cocktails and sandy beaches. If your friends want to explore more of Casco Bay, what’s more fun than sea kayaking? Sea kayaking with your favorite people while enjoying the salt air and scenic views.
Portland Paddle has everything you and your besties need for a good time. Don’t worry about equipment or gear because you can rent it right from them conveniently at their East End Beach location. You can also take lessons to help you and your group get your sea legs. Once you feel comfortable, you can paddle and kayak around the East End beach waters. There’s nothing better than a soft breeze on your face on a warm spring day while you paddle with a group!
Afternoon
DAY TWO
Take a trip to one of our area towns for the afternoon. Getting away doesn’t have to mean going far away – in 10 minutes you can arrive on a sandy beach or rocky coast featuring lighthouses and parks. Or visit the shopping capital of Maine. Portland to Freeport is about 25 minutes by car, making it a convenient day trip destination. If you get peckish, Linda Bean’s Perfect Maine is a fun stop for a lobster roll. After all, there’s no such thing as too much lobster in Maine. While you’re perusing the outlets, remember to check out the 24/7 flagship LL Bean store and the iconic Bean Boot to take group selfies with.
Evening
DAY TWO
Gather your squad and head back to the city to indulge in an unforgettable culinary adventure. Experience the unique blend of flavors and aromas that make Portland’s restaurants stand out from the crowd. The culinary scene is a testament to the chefs’ passion for using local ingredients and farm-to-table (or often ocean-to-plate) dining, making it a must-do destination for your foodie friends. From upscale seafood to rustic Italian and beyond, Portland offers a mouth-watering experience for every palate.
From the first bite to the last sip, you and your friends will discover the magic of Portland’s food scene and make memories that will last a lifetime. For a nightcap – grab a crafty cocktail downtown and bask in the late-night nightlife and entertainment at locals bars and pubs around the city. Trust us, it’s the musical send-off your friends trip needs.
