If you are up for an exciting, adventurous morning check out the Portland Schooner Co. for a schooner ride around the scenic coastline. This two-hour journey is an epic way to see the coast of Maine, as well as Portland from a different angle. They use historic wooden schooners called windjammers, and this is a very fun way to spend your morning!  

If two hours on a boat does not sound like your cup of tea, then we suggest a brisk morning walk around either the Western Promenade or the Eastern Promenade on either side of Portland for beautiful scenery. We love both of. these parks– the Western Promenade with its stately homes and views of the surrounding area, and the Eastern Promenade, a former rail corridor turned grassy city park. 

Next, head downtown to see the heart of Portland. The “main street” in town is Congress Street, and there are tons of cute shops for window shopping and cafés to pop into for a coffee or quick bite all up and down the whole drag. There is an old-school feel to much of Portland’s downtown, like the best parts of past decades are still flourishing here. While walking around downtown, be sure to spend some time in Monument Square and to snap some pictures of Portland City Hall.  

Possibly Portland’s most picturesque spot is its Old Port. With its cobblestone streets and abundance of shops, you could spend hours here exploring. Commercial Street down by the water has lovely waterside views, and lots of lunch options, such as . 

Whatever you do, do not leave the Old Port area without grabbing a gelato at Gelato Fiasco. This place is an institution in Portland, and for good reason. Our favorite flavor is the mascarpone pistachio caramel– absolutely mouth-watering (and those of you who have been with us for a while know we are major ice cream fans!) They have tons of flavors, though, let us know which ones you’ve tried in the comments!

After having lunch (and gelato) in the Old Port, a good option for some afternoon culture is to stop by the Portland Museum of Art.  Despite not being the region’s most-renowned museum, there is still much to see here and you will be impressed by the breadth on display.  We aren’t the biggest lovers of modern art, but even so this museum is worth your time.  

In the afternoon, for beer fans— just outside of Portland is one of the best breweries in the country, Allagash Brewing Company.  Known for their delicious take on the Belgian-style beer, Allagash has cemented itself in the top tier of craft breweries locally and nationally. Visiting their Portland brewery is always a treat, as you can take a tour of their taproom and have a drink in their tasting area.  Allagash White is one of Alex’s all-time favorite beers (a tough choice, to be sure), so coming to the brewery was like a dream come true!

While you may be getting a bit tired from this busy day out by now, don’t miss an opportunity to check out Portland’s culinary scene! There are so many restaurants to recommend here, but after much effort we have narrowed down a few favorites: Boda for its eclectic Thai food and chic interior; Eventide Oyster Co. for delicious lobster rolls and oysters (if you didn’t have that last night!); or Duckfat for truly excellent poutine and perhaps even a milkshake.

Topping your evening off with a nightcap is a welcome way to finish off a packed day, and there are more than a few good spots to head to after dinner.  We would suggest a drink or two at the classy yet understated North Point on Silver Street, for their excellent cocktails. If you are more interested in something a bit more casual, then Lincoln’s Lounge is your best bet– if you can find it, that is! The $5 beers (everything costs “a Lincoln,” or $5 USD, here!) are hard to beat, and the speakeasy style is really unique and memorable. 

As for nightlife or clubbing, the Old Port has the biggest concentration of nightlife in Portland, and Wharf Street is the closest to a “clubbing street” in the city.