South End tapas, a historic oyster bar and a walk through the Public Garden.
Valentine’s Day 2027 is a Sunday. These are the Boston rooms we’d book for a date any night of the year, plus a free walk through the Public Garden. Book early, since Valentine’s tables go fast.
Our top picks for Boston Valentine’s Day Date Nights are Toro, Union Oyster House and Boston Public Garden. The full map covers 5 stops across South End, Kenmore, Downtown and more, with 3 routes you can follow in order.
A lively South End tapas bar for sharing plates.
See the stop →One of America’s oldest restaurants, open since 1826. Sit at the oyster bar.
See the stop →A walk past the lagoon bridge, even in the snow.
See the stop →Map loading. The full list and location links work without it.
Approximate location pins. Follow current venue entrances and public-access rules. Map data © OpenStreetMap contributors.
A lively South End tapas bar for sharing plates.
Valentine’s Day is Sunday, February 14, 2027. Special menus and hours are not confirmed.
Check the Valentine’s menu and price when the venue posts it.
1704 Washington St, Boston MA
Pinned at the street address; follow the venue’s entrance directions.
A living-room-style cocktail bar in Kenmore Square.
Valentine’s Day is Sunday, February 14, 2027. Special menus and hours are not confirmed.
Check the current menu.
500A Commonwealth Ave, Boston MA
Pinned at the street address; follow the venue’s entrance directions.
One of America’s oldest restaurants, open since 1826. Sit at the oyster bar.
Valentine’s Day is Sunday, February 14, 2027. Special menus and hours are not confirmed.
Check the Valentine’s menu and price when the venue posts it.
41 Union St, Boston MA
Pinned at the street address; follow the venue’s entrance directions.
A bright South End spot for coastal Italian food and crudo.
Valentine’s Day is Sunday, February 14, 2027. Special menus and hours are not confirmed.
Check the Valentine’s menu and price when the venue posts it.
360 Harrison Ave, Boston MA
Pinned at the street address; follow the venue’s entrance directions.
A walk past the lagoon bridge, even in the snow.
Check current hours before you go.
Free.
Charles Street, Boston MA
Approximate venue, building or park location; follow the venue’s entrance directions.
These stops are close enough to walk between.
Stop order is editorial, not turn-by-turn navigation. Check current access, weather and transit.
These stops are close enough to walk between.
Stop order is editorial, not turn-by-turn navigation. Check current access, weather and transit.
Use transit or a rideshare between these stops.
Stop order is editorial, not turn-by-turn navigation. Check current access, weather and transit.
Researched November 9, 2026. Dates, menus, prices, access and availability can change. We have not checked tables or submitted any bookings.
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Open the guide →Get the plans before everyone else does.
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