A

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.

Don’t miss

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.