An Ideal Three-Day Getaway in Portland, Maine

Portland, Maine: a celebrated haven for lobster enthusiasts, where bustling waterfront activities, a vibrant local arts scene, and the fresh sea breeze combine to create one of the Northeast's premier escapes. Recently, the city has garnered much acclaim—and rightfully so. Portland is experiencing an exciting cosmopolitan renaissance, boasting an impressive array of restaurants, bars, and breweries while preserving its historic charm. If you're eager to indulge in exceptional seafood and local brews while enjoying the coastal atmosphere, venture north for a quintessential New England three-day weekend—itinerary provided!

Day One:

If you’re landing at Portland’s local airport, PWM, it’s just a five-mile trip to your accommodation at the Press Hotel, nestled in the historic Old Port district. Unpack your bags and take a moment to appreciate the hotel’s rich past—it once served as the headquarters for the Portland Press Herald, featuring rooms inspired by 1920s writing spaces and charming in-house venues like the Inkwell bar.

Once you’re settled, make your way to Commercial Street. Enjoy an early lunch by the waterfront at one of the city’s top chowder joints, Gilbert’s Chowder House—a local favorite known for its laid-back atmosphere and award-winning seafood chowders.

After lunch, visit the Portland Museum of Art at Congress Square, which boasts an impressive array of European, American, and contemporary art, along with a rotating selection of exhibitions from local Maine artists and renowned pieces from across the globe. Once you’ve soaked in the culture at PMOA, take time to explore the numerous art galleries, thrift stores, and boutiques that populate downtown. Don’t miss Longfellow Books and the Art Mart.

When you’ve had your fill of exploration, and if you have a car, take a short drive about eight miles south to Cape Elizabeth’s Crescent Beach to spend the afternoon basking in the sun and saltwater. If you’re on foot, stroll over to East End Beach on Casco Bay, a leisurely 20-minute walk from downtown Portland.

Return to your hotel for a glass or two of rosé at Inkwell, then enjoy a delightful dinner at the Press’s UNION Restaurant, led by Maine native chef Josh Berry. Indulge in dishes like pan-seared Maine salmon with summer corn fondue or seared local cod with Maine lobster, clams, and coconut nage.

Day Two:

Now that you’re comfortable in the city, it’s time to discover what Portland is famous for: its vibrant local beer culture. After a relaxing morning at the Press, take a 10-minute stroll down to Commercial Street and visit Standard Baking Co. to enjoy some organic pastries and coffee. Spend an hour exploring the shops along Commercial Street, recognized by the American Planning Association as one of the best streets in the U.S. in 2008. Don’t miss these must-visit spots: Portland Dry Goods, Browne Trading Market, Asia West, and Edgecomb Potters.

Next, it’s time for the beer! If you’re driving, you can easily tour various breweries in the greater Portland area (including the renowned Allagash Brewery and Bissell Brothers Brewing Company), but a convenient option is to board the Maine Brews Cruise bus, departing from the Portland Beer Hub on Fore Street. This bus takes beer enthusiasts on an all-inclusive, behind-the-scenes tour of Portland’s craft breweries. At $55 per person, the itinerary changes daily based on the theme of the tour, running midday on weekends and weekdays for several hours. Some breweries on the route include: Maine Mead Works, Oxbow Blending & Bottling, Geary’s Brewing Co., Rising Tide Brewing Co., Foulmouthed Brewing, Lone Pine Brewing Co., Maine Beer Company, and more.

If you can, try to find the High Roller Lobster truck, which visits several local breweries (like Bissell Brothers and Oxbow Blending) and serves up rolls packed with fresh Maine lobster on a soft brioche bun—don’t forget to add avocado and bacon for extra flavor.

When you return to Commercial Street in the afternoon, you might feel ready for a nap back at the hotel. However, if you’d like to walk off the brews, take a leisurely stroll along the Eastern Promenade Trail, which winds along the Casco Bay waterfront and connects to the Back Cove Trail.

Head back into town for a farm-to-table dinner at Fore Street (part of the same local restaurant family as Standard Baking Co.), conveniently located just a block from the waterfront. Savor a menu that changes daily, featuring fresh and foraged local ingredients. After your meal, treat yourself to a cone from Mount Desert Island Ice Cream on Exchange Street.

Day Three:

Take your time and relish your last morning with a leisurely breakfast at the hotel. Today is dedicated to enjoying Portland’s close proximity to the ocean. Be sure to dress in layers (it can get chilly by the water!), walk to Commercial Street, and look for Odyssey Whale Watch. Spend the day on the boat searching for humpback whales, potentially up to 20 miles off Portland's coast.

Upon returning to Commercial Street—if you’re still craving seafood—stop for a late lunch at Portland Lobster Company. Enjoy your meal on the outdoor deck with lobster rolls and fried clam baskets, or opt for takeout to enjoy a picnic at East End Beach.

Spend the rest of your day exploring Portland, browsing shops, galleries, and cafés. Begin your evening at a local favorite, Eventide, where fresh oysters on ice greet you as you enter. Come for the bivalves and cocktails, and stay for one of Portland’s top seafood menus—think battered Maine hake, lobster stew, and a classic New England clambake.

After indulging in seafood, make your way to Market Street for post-dinner drinks at Portland Hunt & Alpine Club, a contemporary Scandinavian bar with a cocktail menu split into four categories: Refreshing, Adventurous, Classics, and Wild Card. Choose your favorite and savor your final night in Portland with a crafted drink. From the bar, it’s only a two-block stroll back to your hotel.