Where should we eat on a date in Boston?

The tables our editors book for a date — read each entry for the dish to order and the best time to go.

How many places to eat on a date does this guide cover in Boston?

6 — hand-verified by editors and drawn from our full A-to-Z guide to Boston. Each one has a real address, the best time to go, and an editor's note.

Food Date Ideas in Boston — 6 Hand-Picked Spots

Kava Neo-Taverna

South End

$$
Dinner
Food

A pocket-sized Greek taverna in the South End where the octopus is charred just right and the tables are close enough to make any dinner feel intimate. Book ahead — everyone's in on the secret.

Tip A tiny Greek taverna on a brick South End corner — book ahead, because the dozen-odd tables fill fast and the room is the whole charm. Share a spread of mezze and the grilled octopus, and let them pour the Assyrtiko. The low light and close tables make it quietly one of the most romantic small rooms in the city.

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Legal Harborside

Seaport

$$$
Sunset dinner
Food

The flagship of Boston's most famous seafood name, three floors deep on the Seaport waterfront. Raw bar downstairs, a glass-roofed lounge up top — the splurge seafood date with the harbor at your feet.

Tip Three floors of seafood on the harbor's edge: come downstairs for a casual raw bar, or book the third-floor lounge with the retractable roof for the real splurge. Get a window or patio table at sunset and order the lobster and a raw-bar tower to share. The harbor lights doubling on the water do the work.

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Mike's Pastry

North End

$
After dinner
Food

The cannoli everyone tells you about, in the white box everyone carries through the North End. A cash-only, line-out-the-door institution — and the sweetest possible end to a date.

Tip The North End's most famous cannoli, and a Boston rite of passage — the line moves fast, it's cash-only, and you order at the counter, not by table. Get one ricotta and one chocolate-chip shell and settle the great Mike's-vs-Modern debate yourselves (Modern is two doors down, so you can do both). Eat them on a stoop or down by the harbor.

Full entry →Map ↗

Neptune Oyster

North End

$$$
Evening
Food

A jewel box of a raw bar where the lobster roll alone justifies the wait.

Tip There are no reservations and only a handful of seats, so put your name in early and stroll Hanover St while you wait. Split the warm-buttered lobster roll over the cold mayo version, and let the raw bar guy steer you to whatever oyster came in that morning. Counter seats are the move for two — you'll watch the whole shucking line work.

Full entry →Map ↗

Quincy Market

Downtown / Faneuil Hall

$
Evening
Food

A grand granite food hall where the move is to graze, not commit.

Tip Skip a sit-down dinner and split a dozen small things down the central colonnade — clam chowder in a bread bowl, a cannoli, a lobster roll. Catch the street magicians and buskers who set up outside in warmer months. It's touristy, yes, but the 1826 Greek Revival hall is genuinely gorgeous lit up at night.

Full entry →Map ↗

Union Oyster House

Downtown / Freedom Trail

$$$
Evening
Food

The oldest restaurant in America, creaking floorboards and all — order the lobster.

Tip Ask for the upstairs Kennedy booth — JFK's regular table is marked with a plaque — for the most romantic seat in the 1826 building. Sit at the original semicircular oyster bar downstairs first for a half-dozen and a chat with the shucker. Order the clam chowder and a whole steamed lobster and lean into the history.

Full entry →Map ↗Book ↗

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See the full A–Z guide to Boston — all 26 dates →

Boston places to eat on a date — FAQ

Where should we eat on a date in Boston?: The tables our editors book for a date — read each entry for the dish to order and the best time to go.
How many places to eat on a date does this guide cover in Boston?: 6 — hand-verified by editors and drawn from our full A-to-Z guide to Boston. Each one has a real address, the best time to go, and an editor's note.