Pizza on a date? Absolutely. Regina's Pizza Fenway is an absolute classic. Share a large pie (extra cheese = extra love), sip some beer, and soak in the casual, no-pressure atmosphere. It's perfect for a first date or a chill hang with your person.  

Pro tip: Go early if there's a game—this place fills up fast.  

Where?  

• 1330 Boylston St – Just a 5-minute walk from Fenway Park and close to the Landmark Center.  

• Nearest T stop: Fenway Station (Green Line – D branch)  

If you're aiming to impress, hit up a Fenway sushi spot. With good atmosphere and melt-in-your-mouth sashimi, it's a great way to show you've got taste. Grab a sake flight and toast to good company and even better rolls.  

Try Hojoko, a funky Japanese izakaya with next-level sushi and sake. Or try Umai, a cosy spot steps from the park. It's ideal for a vibe-y dinner date.  

Where?  

• Hojoko: 1271 Boylston St (inside The Verb Hotel)  

• Umai: 1302 Boylston St  

• Both are a 6-minute walk from Fenway Station  

Right by the ballpark, Fenway Tasty Burger is a must. This spot is iconic for a reason. Burgers, milkshakes, and fries—what more could you ask for after a game or a show at the House of Blues. It's casual, delicious, and super date-night friendly.  

Where?  

• 1301 Boylston St – Right behind Fenway Park, steps from the bleachers.  

• A 3-minute walk from Kenmore Station or Fenway Station  

Live music, Southern eats, and cowboy boots? Count us in. Loretta's Fenway brings honky-tonk flair right to the heart of Boston. It's one of the most fun bars in Fenway for dancing, drinking, and maybe a little karaoke. Date night just got interesting. 

Where?  

• Lansdowne St – Right next to House of Blues and across from the ballpark's iconic Green Monster.  

• Less than 5 minutes from Kenmore Station  

Sunday morning brunch Fenway style hits differently. Think mimosas, warm pancakes, and a chilled environment. Plenty of Fenway dining gems offer brunch menus—perfect for a low-key yet charming daytime date. Look out for patios when the weather is nice! Try the Friendly Toast or Audubon for funky vibes and fabulous French toast. Discover more delicious brunch places.  

Where?  

• The Friendly Toast: 35 Stanhope St (right off Boylston)  

If you want to step it up a notch, Fenway restaurants bring serious flavour. Whether it's farm-to-table, Italian comfort food, or rooftop views, the food in Fenway goes beyond just ballpark franks (though we love those, too). It's a dining scene made for sharing plates and sharing stories. Whether Italian at Caffè Nero, American comfort food at Sweet Cheeks Q, or rooftop views at Bleacher Bar, Fenway, dining has serious game.  

Where?  

• Sweet Cheeks Q: 1381 Boylston St  

• Bleacher Bar: 82A Lansdowne St (under the stadium!)  

• Each of these are within a 5–7-minute walk of Fenway or Kenmore Stations  

There's no shortage of bars near Fenway to keep the night going. Cosy wine bars, Irish pubs, rooftop cocktails—you name it. Start somewhere mellow, then pick up the pace if the night calls for dancing or just one more round. Start with wine at Time Out Market, head to Game On! for some sporty fun or end with views and vibes at Roofdeck at Game On.  

Where?  

• Time Out Market Boston: 401 Park Dr (inside the Landmark Center)  

• Game On! 82 Lansdowne St  

• All spots are walkable from either Fenway Station or Kenmore