How To Spend The Perfect Weekend In Portland, Maine
If you’re dreaming of fresh lobster, charming cobblestone streets, and the salty breeze of the Atlantic, Portland, Maine is calling. This coastal gem is the perfect spot for a weekend getaway filled with food, views, and unforgettable vibes. Whether it’s a couples getaway, a friends trip, or a quick recharge by the water, here’s exactly how to spend a weekend in Portland, Maine.
Weekend In Portland, Maine
Stay: The Portland Press Hotel
For a boutique hotel stay that feels quintessentially Portland, check into The Portland Press Hotel. Housed in a former newspaper building, this hotel blends historic charm with modern luxury. It’s ideally located within walking distance of the harbor, Old Port, and tons of amazing restaurants and shops.
Allure Travel Co. Tip: At Allure Travel Co., we have partnerships with thousands of hotels around the world. Booking a stay through us is a complimentary service-meaning no extra cost to you! Not only will you save valuable time, but you’ll also unlock exclusive perks (like hotel credits and complimentary room upgrades, if available) and experience VIP treatment throughout your stay.
Weekend In Portland, Maine
Day 1:
Breakfast at Tandem Coffee + Bakery
Kick off your first day with a cozy breakfast at Tandem Coffee + Bakery. Known for strong coffee and flaky pastries, it’s the perfect start to your Portland itinerary. Don’t miss their loaded biscuit or the malt iced coffee.
Explore Old Port & the Waterfront
Stroll through Portland’s Old Port district, filled with cobblestone streets, waterfront views, and charming shops. Spend time browsing boutiques or grab a bench and enjoy the harbor views.
Lunch At Bite Into Maine (at Fort Williams Park)
Head to Fort Williams Park in Cape Elizabeth for lunch with a view. The Bite Into Maine food truck serves some of the best lobster rolls in Portland - and that’s saying a lot considering the city is known for lobster rolls. Choose from Maine-style with mayo or Connecticut-style with warm butter. Both equally delicious.
Portland Head Light & Fort Williams Park
Snap the ultimate coastal photo at Portland Head Light, one of the most photographed lighthouses in the country. Wander the walking trails or enjoy a seaside picnic - it’s a must-do stop just minutes from downtown Portland.
Dinner At Central Provisions
For dinner, head to Central Provisions, one of Portland’s most-loved restaurants serving creative small plates. Must-tries include the bluefin tuna crudo, peekytoe crab, and bone marrow toast.
Dessert At Gross Confection Bar
End the evening at Gross Confection Bar, a moody, dessert-focused spot with imaginative sweets and dessert cocktails. Be sure to try the warm brown butter cake with aged Parmigiano Reggiano - it’s a must!
Day 2:
Breakfast at UNION
Located inside The Portland Press Hotel, UNION serves breakfast classics with locally sourced ingredients. Order the Crab Benedict or fresh pastries to start the day off right.
Ferry to Peaks Island
Catch the ferry to Peaks Island for peaceful vibes and pretty coastal views. The 20-minute ride across Casco Bay feels like a mini escape. Rent a bike to explore the island or take a relaxing walk along the shoreline.
Lunch At The Highroller Lobster Co.
Back on the mainland, head to The Highroller for lobster rolls with a twist. Customize yours with options like charred pineapple relish or lime mayo. Their lobster grilled cheese and craft sodas are also worth a try.
Eastern Promenade
Walk off lunch with a visit to the Eastern Promenade, a waterfront park with beautiful views of Casco Bay. Relax on the grassy hills or go for a bike ride. You can even rent a kayak if you’re feeling adventurous.
Dinner At Eventide Oyster Co.
End your weekend in Portland with dinner at Eventide Oyster Co., known for its oysters, crudos, and steamed bun lobster rolls. They do not take reservations, so head over during off-hours and explore the area while you wait for a table.
Allure Travel Co. Tip: Eventide sends a text when your table is ready, so put your name down and plan on exploring while you wait.
Interested in booking a trip to Portland, Maine?
At Allure Travel Co., we don’t just plan trips-we curate experiences. We offer bespoke travel planning, luxury hotel bookings, and travel concierge services. If you’re looking for full-service planning or to simply elevate your experience, we’d love to work with you!
