72 hrs in Greater Portland, ME
Must: Stay + Do – Activities + Attractions
IPW Sample Itinerary
Embark on a coastal odyssey through Greater Portland, Maine – a world-class destination that has earned it’s stripes gaining accolades like “Coolest Small Cities in the U.S” by Thrillist and “Best Foodie Cities in the U.S. to Chow Down In” by Redbook in 2023. Nestled along the Atlantic shoreline, the Greater Portland region offers unrivaled New England charm with a cosmopolitan flair.
With its picturesque lighthouses, serene parks, cultural richness, and mouthwatering cuisine, Greater Portland, Maine offers a diverse range of experiences. This adventure promises to leave you with lasting memories of this coastal treasure.
Day One – Arrival in Portland
Your adventure begins as you touch down in picturesque Maine. Staying at the in Portland, Maine, is an invitation to embrace the city’s vibrant spirit. The hotel’s contemporary design and lively atmosphere set the stage for a memorable experience. Comfortable rooms offer a stylish retreat, and the welcoming lobby bar, Explore the Old Port’s cobblestone streets, savor fresh lobster rolls, or take a scenic harbor cruise. The Aloft immerses you in the essence of Portland, making your leisure trip an unforgettable adventure.
Check into the Blind Tiger, a truly special stay that blends historic character with modern boutique comfort. Housed in an 1823 Federal-style mansion in the charming West End, it offers just nine uniquely themed rooms—each curated by a local creative, featuring antique furniture, bold artwork, and original architectural details. Guests love the seamless combination of cozy “stay-at-a-friend’s-house” ambiance with thoughtful amenities like a complimentary artisanal breakfast bar, an open pantry stocked with snacks, and a speakeasy-style billiards room in the basement. Cozy fireplaces, high-end linens, and distinctive décor make the Blind Tiger feel intimate yet refined. Tucked just steps from galleries, restaurants, and the Old Port, it’s the perfect base to experience Portland like a local—relaxed, stylish, and steeped in stories.
Afternoon: No 72-hour visit to Portland, Maine, is complete without experiencing a Wine Wise sail is a one-of-a-kind event that perfectly captures the city’s coastal charm and culinary sophistication. Set aboard a traditional Maine windjammer, this immersive sailing experience combines stunning views of Casco Bay with expertly curated wine tastings and gourmet food pairings. Led by sommelier Erica Archer, the sail offers a chance to sip, savor, and learn while gliding past lighthouses, islands, and working lobster boats. It’s not just a wine tasting—it’s an unforgettable afternoon on the water that blends Maine’s maritime heritage with its dynamic food scene. Whether you’re a seasoned wine lover or just looking for a unique way to enjoy the coast, a Wine Wise sail is a must-do experience during any short stay in Portland.
Evening: As the sun sets over the Atlantic, indulge in a quintessential Maine experience with a seafood dinner…
Dining at Boone’s Fish House & Oyster Room is a delightful coastal experience. The restaurant, overlooking Casco Bay, offers a relaxed and nautical ambiance with rustic wooden décor and stunning waterfront views. Known for its fresh seafood, patrons can savor a variety of dishes, from lobster to clam chowder, expertly prepared and bursting with flavors. The menu reflects the region’s maritime traditions, with an emphasis on locally sourced ingredients. The friendly staff and laid-back atmosphere make it a perfect spot for enjoying classic Maine cuisine while watching the boats go by. Boone’s Fish House offers an authentic taste of Maine’s coastal charm.
After Dinner – enjoy a nightcap at a cozy bar or pub, while taking in the stunning views of the Casco Bay. The dining scene comes to life as the lights go down. Get in on the happy hours and late night eats.
Day Two – Must Do Attractions
Morning/Afternoon: For a truly unforgettable perspective on coastal Maine, a Pine Tree Helicopter Tour is a must-do during your 48 hours in Portland. This exhilarating experience offers a bird’s-eye view of the region’s dramatic coastline, iconic lighthouses, rugged islands, and bustling harbors—all from the comfort of a private helicopter. Whether you’re soaring over Portland Head Light, tracing the curve of Casco Bay, or catching a glimpse of seals sunning on the rocks, the tour delivers breathtaking views you simply can’t get from the ground. With experienced pilots who double as knowledgeable guides, you’ll gain a deeper appreciation for Maine’s geography and natural beauty. Perfect for photography lovers, adventure seekers, or anyone looking to make their visit truly memorable, a Pine Tree Helicopter Tour turns a quick getaway into a once-in-a-lifetime experience.
Or embark on the Lucky Catch Lobster Cruise, where coastal adventure and culinary delight come together in perfect harmony. This picturesque journey begins with a hands‑on lobster-fishing experience led by seasoned lobstermen, who will teach you how to haul traps and introduce you to the region’s iconic crustaceans. As you glide through shimmering waters toward Peaks Island, the cruise culminates in a rustic lobster bake at Island Lobster Co.—think fresh Maine lobster, clams, sweet corn, and hearty side dishes, all served seaside with panoramic island views. It’s an immersive taste of Maine’s maritime heritage: from deck to table, the Lucky Catch offers an authentic, deliciously memorable afternoon on the water.
Day Three: Shops, Sights and Savory Delights
Morning: Portland’s vibrant shopping scene is a delightful mix of coastal flair, sustainable style, and local artistry—perfect for a leisurely afternoon of browsing. Sea Bags, with its iconic tote bags crafted from recycled sailcloth, offers a snap-into-Portland piece of nautical charm and functional design. Over at Toad&Co, you’ll discover refreshing, eco-conscious apparel that balances comfort and style—ideal for both town and trail. And don’t miss Angela Adams, a local design standout whose bold, colorful home goods—from rugs and pillows to tableware—infuse everyday living with vibrant Maine-inspired patterns. Whether you’re hunting for unique gifts, stylish essentials, or something truly one-of-a-kind, Portland delivers a curated, design-driven shopping experience you won’t forget.
Afternoon: Immerse yourself in the world of art and culture as you explore the vibrant arts district of Portland (and beyond). Visiting renowned art galleries, studios, and shops that showcase Maine’s creative spirit is all apart of getting to know the destination. Admire diverse artistic expressions, from contemporary works to traditional crafts, while engaging with local artists and their stories. From there make sure to shop local downtown and get one of a kind items sure to please any recipient, or if you’re just looking to obtain a memorable souvenir. To round out the experience, Portland’s thriving performing arts scene—including institutions like the State Theatre and Portland Ballet—adds even more depth to the city’s cultural offerings, making it a true hub for art, creativity, and inspiration in every form.
Explore the outdoor sculpture garden at Portland Museum of Art or explore the streets uncovering public art along the way. Find murals, sculptures, and statues nestled around every corner. Visiting Portland is all about experiencing its rich cultural tapestry, and two standout gems are the Portland Museum of Art (PMA) and the Children’s Museum & Theatre—each offering a unique and rewarding experience for travelers of all ages.
Photo by Capshore Photography
The PMA is Maine’s largest and oldest public art museum, showcasing an impressive collection that spans centuries—from European masters to contemporary New England artists, including iconic works by Winslow Homer and Andrew Wyeth. The museum’s thoughtfully curated exhibitions and rotating programming provide insight into both local heritage and global art trends, making it a must-stop for culture lovers and curious minds alike.
Just a short drive away, the Children’s Museum & Theatre creates an environment brimming with hands-on discovery. With interactive exhibits on science, art, and the world around us, it sparks curiosity in children and invites adults to join in playful exploration. Whether you’re enjoying imaginative playhouses, quirky art installations, or dynamic performances, the museum is a joyful and engaging destination designed to delight families and multi-generational travelers.
Together, these two museums offer the perfect balance of reflective inspiration and spirited discovery—making your Portland visit not just a feast for your taste buds, but a celebration of creativity, imagination, and cultural richness.
Evening: Time for another amazing meal and with Portland’s robust dining scene – you’ll have plenty of options to choose from. Portland’s food scene is nothing short of legendary—vibrant, diverse, and deeply rooted in Maine’s natural bounty. From award-winning chefs to hidden neighborhood gems, the city offers something for every palate, whether you’re craving freshly shucked oysters, hand-crafted pasta, or inventive farm-to-table fare. Known for its dedication to local ingredients and bold creativity, Portland has earned its place on the national culinary map, blending New England tradition with global inspiration. Whether you’re dining in a cozy bistro, a historic waterfront pub, or a sleek modern eatery, choosing dinner in Portland means indulging in thoughtful, seasonal cuisine made with passion and purpose. With so many standout options, the hardest part is choosing just one. We recommend Paper Tiger, Luke’s Lobster or a delicious Lobster Roll (for a light bite) from Bite Into Maine.
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