Discover the Spirit of Maine With 5-Day Coastal Itinerary
Your Ultimate 5-Day Maine Summer Itinerary:
From Greater Portland to The Maine Beaches
Journey Through Maine’s Coastline of Culture, Cuisine, and Community
Take a New England dream vacation across two vibrant regions of Maine that go beyond the surface—digging into the flavors, stories, and multicultural experiences that make Maine a singular experience.
Summer starts here. From the cobblestone streets of Portland to the sun-drenched sandy shores of Ogunquit, this weeklong Maine itinerary isn’t just about scenic views and seaside relaxation—it’s about getting gritty and learning about the local culture and our greater connection to the world.
Through hands-on international cooking demos, immersive art walks, heritage tours, and culinary tastings that celebrate global influence, this journey invites you to connect deeply with the people and places that shape Maine’s coastal spirit.
DAY 1: Historic Charm Meets Seaside Opulence
Arrive in Portland and check into your home base: the elegant Portland Regency Hotel & Spa, set in one of the city’s most iconic historic buildings in the heart of the Old Port. With timeless architecture, classic New England charm, and a reputation for warm, attentive service, the Regency offers a perfect blend of heritage and comfort. Guests can enjoy complimentary shuttle service from the jetport, convenient valet parking, and walkable access to Portland’s scenic waterfront, shops, and top dining spots—making it an ideal launch point for your stay.
Spend the early afternoon exploring Portland’s working waterfront and charming cobblestone streets at your leisure while fellow travelers arrive. Gather at the cozy Armory Lounge or their outdoor Garden Cafe for a welcome toast.
If you’re coming with a group consider hosting a an opening party or reception just steps away at Ballast, a downtown venue steeped in history and old world charm with modern touches and flair. Work with a local catering that cares about curating the perfect Maine meal like Experience Maine Culinary. Your first taste of Portland could be their lobster nori, blueberry chicken, or a maine-made charcuterie with local meats and cheeses.
Dinner brings you to the harbor for a quintessential Maine seafood feast at Boone’s Fish House & Oyster Room, where the oysters are as fresh as the salty breeze. Stick around and you can enjoy their after hours happy hour outfitted with unique twists of classic staples, a can’t miss late night treat.
Wrap up the night with a short stroll back to the hotel for a restful evening or some late nights in the Old Port exploring the lounges, pubs, and nightlife scene or explore the rooftop dining and craft cocktails across the city.
DAY 2: Art, Ocean Breezes & Hands-On Flavors
Begin your day with a relaxed breakfast at the elegant Eighteen95 Restaurant, located right at the Regency Hotel & Spa. Savor classic morning fare in a cozy, refined setting that reflects Portland’s timeless charm—complete with fresh avocado toast, fluffy wild Maine blueberry pancakes, and crisp mimosas to start your day on the perfect note.
From there, dive into the city’s vibrant Arts District for a curated art walk. Browse masterpieces at the Portland Museum of Art and explore local culture and public installations with guidance from Creative Portland’s art app.
Next, walk along the spine of the Art’s District and spot local murals and sculptures and cultural landmarks on your self-guided art tour with the app in hand to explore and learn more about the behind-the-scenes stories of art that makes our region shine. Head over cobblestone streets and a thriving downtown, with architecture that’s been likened to some of the most popular European destinations abroad.
Here, craft beer meets coastal fare at one of Portland’s most iconic breweries. Shipyard Brewing Co. has long been a staple of the city’s beer scene, known for its classic Maine brews and innovation in craft beer. Grab a flight to sample a variety of their small-batch ales and seasonal selections, or pair a frosty pint with one of their crowd-favorite flatbreads—crispy, creative, and made to complement the pour.
Afterward, head to the Maine State Pier to climb aboard a traditional schooner for a two-hour sail with Portland Schooner Co. This beloved maritime experience is more than a sightseeing cruise—it’s a step back in time aboard historic wooden vessels like the Bagheera and Wendameen, both listed on the National Register of Historic Places.
The crew invites you to take the helm or simply relax as the wind fills the sails and you glide past lighthouses, rocky shores, and harbor islands. With panoramic views and the scent of saltwater in the air, this unforgettable Windjammer sail is a celebration of Maine’s nautical legacy—and a highlight of any trip to the coast.
Take a short drive to Fork Food Lab for a hands-on cooking experience with EN-NOBLE. This is a rare opportunity to learn from a chef who now calls Maine home, but whose roots reach across borders and oceans. As you slice, stir, and plate dishes inspired by their heritage, you’ll also hear the personal stories that shaped them—bringing cultural traditions to new life in Maine.
This shared table experience isn’t just about food; it’s about learning and celebrating the flavor of home, wherever that may be.
DAY 3: Hidden Histories + Coastal Transitions
Start the day with a sweet twist on tradition at Eighty8 Donut Cafe, where gourmet mini donuts are served hot and fresh to order. Taste test every flavor from boston cream to bamm bamm (fruity pebbles). This breakfast spot in Portland, Maine offers a light, cheerful send-off as you transition from city streets to coastal scenes.
After breakfast, peel back the layers of the city with a Hidden Histories Walking Tour by Portland By the Foot. These expert-led strolls offer deeper insight into the stories, struggles, and voices that helped shape this historic seaport city—this experience invites you to explore the communities that shaped Portland—and the historic fires that nearly burned it to the ground…more than once. It’s a deep dive into the city’s resilience, character, and untold stories.
For one last taste of Portland: a hands-on seafood shucking and tasting experience with Maine Oyster Co. Learn to shuck oysters like a local with all the toppings whether you like it: hot sauce, lemon, or house made mignonette. Of course, you’ll enjoy Maine’s most iconic dish—lobster rolls—just before you journey south.
By mid-afternoon, depart for the Maine Beaches region—a scenic and seamless ride along the coast 30 minutes away. A whole new chapter of your Maine adventure awaits, just down the road.
Step into the stories of Southern Maine with a guided visit to the Old York Historical Society, where centuries of preserved buildings, archives, and exhibits bring the region’s colonial and maritime heritage to life. This immersive stop roots your beach getaway in the deep, layered history of the people and port towns that came before us.
Shift into relaxation mode as you arrive at the serene Dunes on the Waterfront. Nestled just beyond the hustle and bustle, this cottage hotel in Maine delivers postcard-worthy views and peaceful moments by the tidal river. The property is a true hidden gem—private, tranquil, and beloved by repeat visitors for its unbeatable access to the shore and timeless New England charm.
Enjoy a meal at Jonathan’s, a beloved institution where dinner is an experience as much as a meal. With menus that highlight both land and sea, Jonathan’s offers a welcoming atmosphere and a commitment to locally sourced ingredients. Expect coastal classics with gourmet flair in a setting that feels like home.
Cap the night with a dazzling performance of Guys and Dolls at the legendary Ogunquit Playhouse. Regarded to as Broadway’s perfect musical, Guys and Dolls follows gambler Sky Masterson as he sets his heart on Salvation Army reformer Sarah Brown. With hits like “Luck Be a Lady” and “Sit Down You’re Rockin’ the Boat,” this Tony-winning classic charms audiences of all ages.
DAY 4: Summer Events + Luxe Local Goods
Ease into the day with a rich roast and a warm croissant from Mornings in Paris-Ogunquit, a café that feels like a French escape tucked right into Ogunquit Village. It’s a perfect place to reflect on the journey so far, and set the tone for a day filled with coastal wonder and creative discovery.
Hop in a vehicle and head to Wells Reserve at Laudholm, where the salt marshes and walking trails offer a peaceful counterbalance to the cultural immersion of earlier days. This National Estuarine Research Reserve isn’t just scenic—it’s a living classroom where conservation and coastal ecology come to life. The reserve also showcases the history of the property and has an art gallery on site.
Next, head to the lower village of Kennebunkport for lunch. Whether you grab a quick and classic lobster roll from The Clam Shack or enjoy a relaxed waterfront bite at The Boathouse, both options celebrate local seafood and small-town hospitality. Fun Fact: The Clam Shack is the go-to place for celebrities of all stripes; Seth Rogen has been spotted there and the Bush Family only gets lobster meat and meals from this restaurant!
In the afternoon, tap into your senses at Sea Love with a scent-diffuser experience. Choose your scent and create a souvenir that’s both personal and aromatic—a keepsake that smells like summer in Maine.
Later, stroll through the mill towns of Downtown Biddeford & Saco, where old brick buildings have been transformed into a vibrant arts and food scene. It’s a community defined by its creative reinvention. Below is a photo from the Biddeford Mills Museum.
As the sun sets, take a walk through the nostalgic boardwalk of Old Orchard Beach. Home to one of New England’s last oceanfront amusement parks, Palace Playland. Not to mention it has seven miles of serene, sandy shoreline. Come for the taffy and fudge, but don’t forget to get a side of pier fries.
Head to Joseph’s by the Sea for dinner—an upscale yet cozy spot that offers sweeping views and a fresh-from-the-ocean menu. End your day with a sweet scoop from Fielder’s Choice Ice Cream, where local flavor meets big portions. This is the Maine you came to experience—welcoming, inspired, and full of soul.
DAY 5: Explore Iconic Maine
Rise early to greet the sun at Marginal Way, one of Ogunquit’s most iconic seaside paths. The morning sunrise paints the sky with colors worthy of a postcard—offering a moment of quiet reflection as the waves roll in below. Afterward, enjoy a peaceful morning walk along the winding cliffs, breathing in the salt air and the last notes of your coastal retreat.
Cozy up at Crew Ogt for breakfast and one final browse through their collection of locally inspired apparel, accessories, and beach gear. It’s more than a café—it’s a send-off with character, rooted in community pride.
Departure and transportation is made easy when paired with a local drive service like SP+ / Metropolis that provides seamless and reliable transfers for groups of different sizes, and makes traveling around Maine easy, so the return to the Portland International Jetport is stress-free, giving you time to reflect on the stories, flavors, and connections that made this journey truly unforgettable.
Plan Your Journey to Greater Portland & Casco Bay + The Maine Beaches
We hope this itinerary offers more than just a getaway—but an invitation to connect. To explore through taste, art, and community. To meet the people who shape this region and share its soul.
Let this be your starting point. Plan your trip to Greater Portland for cultural immersion, culinary brilliance, and a walkable city that welcomes curiosity. Pair it with a retreat to The Maine Beaches, where sun, sand, and small-town charm deliver the perfect balance of inspiration and relaxation.
Maine is calling—come discover what sets it apart.
Where to Start Planning A Trip to Vacationland
Visit Portland
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The Maine Beaches
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Want more? Visit Maine
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