A waterfront town par excellence, Portland sums up what the American East Coast truly means; lobster and oysters by the bucketful followed by long walks (in this case along the Eastern Promenade), the sea breeze on your face and a picturesque lighthouse in the distance. Once you've had enough crisp air, cosy up in a cheap and cheerful waterfront pub with a pint.
Make the most of Portland by spending as much time as possible drinking in the salty surroundings. Amble between rows of red-brick houses in the Old Port, pop between old-fashioned shops and L.L. Bean and watch wooden sailboats float by the fishing wharves. If you're lucky enough to snag a boat ride yourself, jet over to Peaks Island for an afternoon. Drizzly days are great for visiting the Roux & Cyr International Fine Art Gallery.
Eventide Oyster Co. is a bright and airy space that's brimming with same-day catches for lunch and dinner. Book in here for a buzzy Saturday evening spent sampling cold-water Belon oysters and fresh-as-can-be Maine lobster - either whole or in a brioche roll.
An autumnal American pilgrimage also wouldn't be complete without some sweet treats - and we're not talking about pumpkin-spice lattes. Check out The Holy Donut for potato delights in flavours ranging from maple bacon to toasted coconut with ginger glaze. For an all-American excursion worthy of Grease and Riverdale, make a pit stop at Beal's Old-Fashioned Ice Cream.
Who to take with you
A sailor at heart.
When to go
The autumnal months are perfect for catching the vibrant colours of the northeast while avoiding peak summer season.
Most likely to bump into
Doppelgängers of Gossip Girl's Nate Archibald.
Essentials to bring with you
Button-ups and Fair Isle everything - this is the place to go preppy or go home.
How to get there
Cruise into Portland International Jetport just two miles from downtown.