1. arrive (and get around) in style

If you’re coming from New England, the Amtrak Downeaster is a relaxed, scenic, and cost-effective way to travel—plus it drops you just 10 minutes from downtown. Flying in? Portland International Jetport (PWM) is also minutes from the city and serves nearly 30 direct flights to major hubs like: New York (JFK, LaGuardia, Newark), Washington, D.C. (Dulles and National), Chicago (O’Hare and Midway), Atlanta, Philadelphia, Charlotte, Baltimore and more. Once you’re here, Portland is wonderfully walkable (under 4 miles end-to-end) and local transit plus bike rentals/tours or ferries make exploring a breeze.

Once you’re here, skip the car. Portland is walkable, bikeable, and well-connected by the METRO bus system, which reaches key neighborhoods and nearby towns. For coastal adventures, visit one of the Calendar Islands dotting Portland’s coastline.

They are also called the Casco Bay Islands, but locals know they are nicknamed Calendar Islands because it is said you could visit one 365 days of the year and never run out of new ones to see. Hopping our downtown ferry makes island hopping easy—all without needing to sit in traffic. Start here.

2. Hop the Ferry and daytrip the Casco Bay Islands

Once you’re settled in Portland, don’t stop at the city limits—book a ticket on the Casco Bay Lines ferry and set your sights on the islands. Craving a leisurely cruise? The Mailboat Run is a beloved local experience. This three-hour narrated cruise loops through the Bay, delivering mail and passengers to the inhabited islands—giving you a glimpse into everyday life on the water. It runs twice daily (year-round). You’ll enjoy lighthouse views, bobbing lobster buoys, seabirds, and a kind of peaceful rhythm you only get offshore.

For a reasonable round-trip fare, ride out to islands that feel a world away. Long Island is a 40-minute ferry ride and perfect for a quick, laid-back day trip. Walk to some of the hidden beaches and coves in New England, then swing by Buyers & Sons Long Island Bakehouse for everything from pizza pies and whoopie pies to a classic lobster roll and craft brew. There you can sit seaside and watch the boats drift by with a mimosa or bloody mary (complete with bloody mary ice cubes).

For something active, head to East End Beach and rent a kayak or stand-up paddleboard with Portland Paddle. It’s an affordable way to explore the coast at your own pace—with the added bonus of seals, schooners, and sea spray right in front of your eyes. Start here.

3. Affordable Places to Stay close to portland, maine

For a smart and affordable accommodation, look just off the peninsula in neighborhoods like Deering Center, Rosemont, or East Deering, where local budget-friendly stays and suite rentals offer low nightly rates and an immersive, local feel. Nearby towns like South Portland, Westbrook, and Falmouth have convenient lodging options with easy access to the city as well.

Booking midweek or during the shoulder seasons can help you find even better rates, while early reservations ensure the best availability. Uncover hidden local gems like the McKernan Inn on the SMCC campus where you’ll find student-run rooms lighthouse-side. Whether you’re after comfort, convenience, or a place to unwind between adventures, Greater Portland offers a wide range of accommodations to fit your summer plans—without breaking your budget. Start here.

4. find Nature Escapes + Outdoor Adventure

Whether you’re a casual hiker, beach stroller, or picnic enthusiast, there are plenty of nature escapes near Portland, Maine that deliver big on views and small on cost. Portland is perfectly positioned for affordable outdoor adventures that don’t require a long drive or expensive gear. In under 20 minutes you could be at the largest saltwater marsh in Scarborough or try out fly-fishing or archery with L.L.Bean Discovery School in Freeport, Maine.

Just 30 minutes from downtown, Bradbury Mountain State Park in Pownal is a local favorite for quick hikes with panoramic summit views. The trails are beginner-friendly and open year-round, with picnic areas and shaded forest loops that make it perfect for a half-day getaway.

For something closer to Portland, check out the Presumpscot River Trail in Falmouth, offering riverside views and gentle woodland paths—great for walking, birdwatching, or biking. South Portland’s Greenbelt Walkway is another hidden gem, connecting neighborhoods and waterfront parks with scenic, easy-to-navigate trails. Start here.

5. Uncover the Best Beaches Near Portland, Maine

With more than 3,000 miles of coastline, Maine offers no shortage of seaside escapes—and some of the best are just minutes from downtown Portland. From long, sandy state parks to hidden local coves, you’ll find a Maine beach for every mood and budget. Willard Beach in South Portland is a small but beloved local hangout, while Crescent Beach State Park and Ferry Beach offer more space to spread out, swim, or picnic in view of the surf. These spots are accessible by car, bike, or foot with free public access.

Higgins Beach in Scarborough is known for its charming mix of surfers, families, and salt-splashed cottages, it’s a low-key favorite just 20 minutes from Portland. After a dip, order lunch from Higgins Beach Inn‘s seasonal takeout Shade Shack—delivered beachside by bike. The menu is all about summer favorites: loaded glizzys, crispy fries, and casual coastal fare just steps from the waves. Start here.

6. Discover the Best New England Lighthouses

There’s something timeless about a lighthouse—part postcard, part legend, part story from a forgotten era. Along the coast of Greater Portland, you’ll find some of the United States most photographed and iconic lighthouses, all easy to visit in an afternoon (just 10 minutes from downtown Portland) and free to enjoy.

Can’t start a Maine bucketlist without Portland Head Light in Cape Elizabeth. It’s the oldest lighthouse in Maine and easily one of the most breathtaking. Set on the banks of Fort Williams Park, it offers profound ocean views, plenty of grassy space for outdoor games, and even a lobster roll food truck, Bite Into Maine, to subside any midday cravings.

Stop by the onsite Museum at Portland Head Light or just watch the waves crash against this larger-than-life landmark—it’s peak Maine. Catch even more area lighthouses just minutes from Downtown such as: Bug Light and Spring Point Ledge Light. Start here.

7. get more for less tasting your way through portland, maine

Portland’s food scene is well-known—and yes, the seafood is absolutely worth the splurge, but whether you’re building your own picnic or taste-testing your way through farmer’s markets and food trucks, you don’t need a big budget to get big flavor in Portland, Maine.

Start with casual neighborhood favorites like South Portland’s A&C Soda Shop, where you’ll find craveable shakes, floats, burgers, and fries. For something sweet, The Holy Donut is a must—famous for its Maine potato donuts in both classic and creative flavors. And for your morning (or afternoon) caffeine fix, grab a cup from Coffee By Design, pouring thoughtfully-curated, hand-roasted sips of the world’s best beans.

To mix and match your own meal, visit the Portland Farmers’ Market—held Saturdays in Deering Oaks Park and midweek at Monument Square. You’ll find seasonal produce, hand pies, local cheeses, and baked goods perfect for a picnic. It’s one of the most affordable and authentic ways to experience the city’s culinary spirit—no reservations required. For budget-friendly eats Start here.

8. Enjoy Free Events, Outdoor Concerts, and Movies in the Park

Summer in Portland is full of energy—and some of the best experiences are completely free. Throughout the season, local parks and public spaces come alive with concerts, movies, festivals, and community gatherings that invite you to slow down, settle in, and enjoy the city like a local with locals.

There’s no better way to end a Maine summer day than with live music and a golden-hour view—and Portland’s surrounding scene is full of it. At Summer Sunsets at Thompson’s Point local bands take the stage, food trucks line the Fore River, drinks are available over at their covered beer garden. It’s a laid-back and free local favorite where the vibe is high as the sun starts to set.

Want to see what’s happening while you’re in town? From live shows and markets to festivals, films, and family events, there’s something happening every week across the region. Start here.

9. Catch a Happy Hour (or other deal/promotion)

In some places—Massachusetts, for example—happy hour deals are off the table. But in Portland, Maine, they’re very much alive and well. Many local restaurants and bars offer early evening specials and late-night menus that make it easy to enjoy craft cocktails, local brews, oysters, and shareable plates without stretching your budget.

From dollar oysters to discounted snacks and drinks, this city knows how to do casual dining with a side of savings. Some spots advertise their specials online, while others keep things quiet—locals love a good unlisted deal—so it’s always worth asking. And if you’re out after hours, plenty of places offer cozy, late-night menus that go well beyond fries and wings.

Want to know where the best deals are happening while you’re in town? We round up happy hour specials, packages, and seasonal promotions regularly—find more on our site and plan your perfect Portland night out. Start here.

10. Take some Maine souvenirs Home With You

Portland is full of small shops, markets, and makers where you can shop smart and save on souvenirs that actually mean something. From locally crafted home goods to handmade soaps, candles, or art, you’ll find thoughtful pieces that bring a little bit of Maine back with you.

Sometimes it’s the experience itself that stays with you. Try a local tasting, book a hands-on class, or simply spend a little extra on a shared moment—something delicious, creative, or just a little indulgent. These are the kinds of things that become the stories you tell long after summer ends. Start here.

Ready to Soak Up More Summer in Portland?

Start Planning Your Trip to Maine | Greater Portland + Casco bay Islands

From scenic ferry rides and lighthouses to fresh local eats and free outdoor concerts, Portland, Maine proves that unforgettable summer adventures don’t have to come with a high price tag. Whether you’re planning a long weekend or just passing through, this coastal city makes it easy to do more, explore more, and enjoy more—for less.

So pack your tote bag, bring your appetite, and get ready to wander. Summer in Portland is on the line—it’s time to answer the call. Start here.