Hotel: The Press Hotel. Located in the heart of downtown Portland, it offers easy walking to major attractions and all the best dining and shopping. Expect to see lots of cool design touches, as The Press Hotel was built in the former Portland Press Herald building, so you’ll find nods to journalism everywhere. The hotel has its own art gallery, free Wi-Fi, bicycles for guests, and free airport transportation.
Friday: Head out to the Eastern Promenade, a 2.1 mile trail along the waterfront which offers amazing views and cool breezes. There’s a public beach out here if you feel like taking a dip in the (cold even in summer) ocean. Later in the evening, venture down to Andy’s Old Port Pub, a popular locals spot which has live music every night of the week.
Saturday: Go shopping (or just people-watching) at the Portland Flea-for-All, a market that attracts vendors shilling everything from handmade clothing to antique furniture. Keep the shopping going by strolling up and down Commercial Street, which is lined with unique local stores. When you’re ready to sit down and put your feet up, grab a cocktail at one of the many waterside bars, before heading to UNION (one of Portland’s hottest new restaurants) for dinner. The cuisine highlights fresh local Maine ingredients, and vegetarians will be pleased to find that almost anything on the menu can be made meatless.
Sunday: Take advantage of The Press Hotel’s late check-out (12 pm), but don’t sleep too late—you’ll want to grab one of the famous potato donuts at the Holy Donut before they sell out. The sugar should fuel you while you drive around and explore the six lighthouses located within a 20-minute radius of downtown.
Extra Day: If you want to see what’s beyond the city, hop on one of the ferries that depart from the harbor and call at the many small islands just off the coast, like Peaks Island, Great Diamond Island, or Little Diamond Island.
Bar & Restaurant Recommendations:
- UNION Restaurant, Old Port
- Novare Res, Downtown
- Gorgeous Gelato, Old Port
- Hot Suppa, West End
- Central Provisions, Downtown
- Inkwell, Old Port
- Maps, Old Port
More from SmarterTravel:
- The World’s Most Hipster ‘Hoods
- Penobscot Bay, Maine: From the Land to the Sea (in Photos)
- Where to Score New England’s Best Cider Donuts
(Photos: The Press Hotel/Irvin Serrano; UNION/Kari Herer)