Union Oyster House on Union Street has shucked oysters in Boston since 1826, the oldest continuously operating restaurant in the United States. Daniel Webster's seat is still at the bar.
Signature dishes: Oysters on the half shell, Clam chowder
Must order: A dozen Wellfleets at the U-shaped bar and a cup of clam chowder.
Tip: Skip the dining-room tables and sit at the historic raw bar. The bar is the original 1826 plank.
Address: 41 Union St, Boston, MA 02108
Mamma Maria on North Square is the North End's fine-dining anchor in Boston, in a five-room brick townhouse since 1973. Northern Italian pastas, Tuscan game and a Barolo-heavy list.
Signature: Pappardelle with wild boar ragu, Veal osso buco
Order: The pappardelle bolognese; the kitchen makes the pasta in-house.
Tip: Book the upstairs Library room for a quiet conversation. The Sunday family menu at 17:00 is the easy walk-in seat.
Giacomo's on Hanover Street has run a no-reservations Italian-American room in Boston's North End since 1985. Cash-only, big portions, line around the block by 18:00 most nights.
Signature: Lobster ravioli, Fra diavolo
Order: Lobster ravioli with vodka sauce, the house signature.
Tip: Arrive by 17:30 to skip the longest wait. Cash only, BYOB welcomed from the wine shops on Salem Street.
Damien DiPaola named Carmelina's after his mother and runs it on Hanover Street as a regional Italian kitchen in Boston since 2012. Sicilian and Roman pastas, family-style portions.
Signature: Sunday gravy, Tortellini al pesto
Order: The carbonara pasta with smoked pancetta and pecorino.
Tip: Reservations open four weeks ahead on OpenTable. The bar is the easier walk-in seat at 17:30 weekdays.
Regina Pizzeria on Thacher Street has fired thin-crust pies in Boston's North End since 1926. The original location is the one that matters; brick oven, no slices, cash and card.
Signature: Margherita, Giambotta
Order: The Margherita pie, blistered crust, just-melted mozzarella.
Tip: Walk-ins only at the North End original. Lunch at 11:00 is the easy seat; dinner waits run 60 minutes weekends.
Mamma Maria on North Square is the North End's fine-dining anchor in Boston, in a five-room brick townhouse since 1973. Northern Italian pastas, Tuscan game and a Barolo-heavy list.
Signature: Pappardelle with wild boar ragu, Veal osso buco
Order: The pappardelle bolognese; the kitchen makes the pasta in-house.
Tip: Book the upstairs Library room for a quiet conversation. The Sunday family menu at 17:00 is the easy walk-in seat.
Giacomo's on Hanover Street has run a no-reservations Italian-American room in Boston's North End since 1985. Cash-only, big portions, line around the block by 18:00 most nights.
Signature: Lobster ravioli, Fra diavolo
Order: Lobster ravioli with vodka sauce, the house signature.
Tip: Arrive by 17:30 to skip the longest wait. Cash only, BYOB welcomed from the wine shops on Salem Street.
Damien DiPaola named Carmelina's after his mother and runs it on Hanover Street as a regional Italian kitchen in Boston since 2012. Sicilian and Roman pastas, family-style portions.
Signature: Sunday gravy, Tortellini al pesto
Order: The carbonara pasta with smoked pancetta and pecorino.
Tip: Reservations open four weeks ahead on OpenTable. The bar is the easier walk-in seat at 17:30 weekdays.
Regina Pizzeria on Thacher Street has fired thin-crust pies in Boston's North End since 1926. The original location is the one that matters; brick oven, no slices, cash and card.
Signature: Margherita, Giambotta
Order: The Margherita pie, blistered crust, just-melted mozzarella.
Tip: Walk-ins only at the North End original. Lunch at 11:00 is the easy seat; dinner waits run 60 minutes weekends.
Kathy Sidell's Back Bay seafood room on Dartmouth Street has run the tinned-fish-and-crudo agenda in Boston since 2016. Caviar service, lobster rolls and a rose-heavy list.
Signature: Tinned fish board, Lobster roll
Order: Tinned fish board with anchovies, mussels, sardines and butter on toast.
Tip: The window counter is the easier walk-in seat at 17:30. Brunch books two weeks out on weekends.
Demetri Tsolakis's Krasi on Gloucester Street has poured the country's largest all-Greek wine list in Boston's Back Bay since 2020. Regional Greek mezze, charcoal-grilled lamb and fish.
Signature: Spanakopita, Whole grilled fish
Order: The taramosalata with house pita and a glass of Assyrtiko.
Tip: Reservations open four weeks out on OpenTable. The bar serves the full menu for solo diners.
