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Fresh oysters and authentic Italian.  It’s tough to beat a city with a food scene that does both of these flawlessly.  Here are some of my favorite spots in Boston:

Located inside Hotel Commonwealth near Fenway, Island Creek Oyster Bar is one of my go-to spots in in Boston.  Start off with a cocktail and some fresh oysters-- you'll have about a dozen to choose from.  Continue with some chowder, the ceviche, and choose from a variety of just-caught fish.  Whether you sit at the bar, the high top seats in the bar area, or in the dining room, the vibe is hip yet classy.  
B&G is another favorite spot in the South End.  It's perfect for lunch or dinner, especially during the summer when you can sit outside on the patio, strewn with lights and greenery.  The menu is simple, featuring New England favorites and yes, oysters.  The charred spanish octopus with salsa aji verde is a must.  Or the crispy soft shell crab which is lightly crispy on the outside, and infused with aoli.  Everything was on point-- even the playlist which I found myself Shazam'ing.
Neptune Oyster is a tiny North End restaurant that delivers big.  There are no reservations, so expect a wait-- a serious one.  As long as you put your name in 2 hours before you want to eat, you can grab a cappuccino and explore the North End while you wait.  Check out the daily specials on the chalkboard for the freshest picks.  The lobster cocktail and grilled octopus are delicious-- this place is famous for a reason!
Union Oyster House is a true landmark-- and claims to be the oldest restaurant on the Freedom Trail serving oysters since 1826.  When you walk inside, you'll feel transported back in time as not much has changed.  I recommend Union Oyster House for an afternoon snack: some oysters, clams, chowder, and a beverage.  To get the full experience, wait for a seat at the half-moon bar at the front.  It's the original bar, still slanted from decades of patrons leaning on the bar.  
Located in the Financial District, Fin Point is definitely has a classic "business chic" atmosphere.  So if you're downtown for business (or want to avoid weekend North End crowds) and need a seafood fix, this is the spot.  Whatever you do, get the lobster ceviche app:  fresh lobster, jonah crab, citrus segments, fresno chile, with crispy root vegetables chips.  This was my favorite dish of my Summer 2017 trip!
Another North End gem that doesn't disappoint.  If you're looking to avoid the 2+ hour line at Neptune, North Square Oyster Market is a great pick nearby.  The lobster roll was voted to one of the best in the city by my two Bostonite friends and my boyfriend (also an East Coast seafood snob).
Yes, Legal Sea Foods is a chain, but it's the iconic Boston-based chain.  I recommend the Harborside location for its third floor rooftop, which is open year-round with a retractable roof.  The rooftop is perfect for a cocktail, some oysters, and a view of of the harbor.
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