The Most Fun Restaurants in Boston

Located in the heart of New England, Boston stands out as a historic American city, rich with culture and entertainment. A visit here offers all the benefits of a big metropolis without the intensity and fast pace of larger cities. Visitors can easily get around on the T or by bike to observe the many wide-open green spaces, trendy neighborhoods, and world-class museums. Plus, Boston has a culinary scene that foodies travel from near and far to enjoy. But where are the smartest, savviest diners eating out when looking for a good time? Welcome to the Tastemaker Lists. We’ve pulled data from thousands of restaurants to find the top spots among OpenTable's most expert, seasoned diners. If you’re looking for a dining spot where you can enjoy great food and an entertaining environment, check out our Tastemaker 20 List of the most fun restaurants in Boston.

The OpenTable Team
Restaurants:Brassica Kitchen, Table, Asta
Price Range:$$$ - $$$$
Cuisines:French American, Italian, Modern European
Neighborhoods:Jamaica Plain, North End, Back Bay
Party Size
For 2
Date
Time
7:00 PM

Brassica Kitchen

$$$$·French American·
Jamaica Plain
1,023 reviews
  • Neighborhood Gem
  • Fit for Foodies
  • Great for Outdoor Dining

Brassica Kitchen and Cafe is the brainchild of the Whisk pop-up team. It's a bustling coffeehouse by day and intimate bistro by night. The kitchen churns out amazing dinners at night with a focus on f...

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Best Overall in Boston
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Table

$$$$·Italian·
North End
335 reviews
  • Fit for Foodies
  • Good for a Date
  • Authentic

Table is definitely one of the most fun restaurants in Boston and locals love the family-style Italian dining. Located in the North End, the restaurant features a dining room that makes you feel like ...

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Fit for Foodies in Boston / New England
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Asta

$$$$·Modern European·
Back Bay
59 reviews
  • Fit for Foodies
  • Tasting Menu
  • Creative Cuisine

If you’re looking for a fun restaurant in Boston, Asta will not disappoint. This Modern European restaurant serves seasonally inspired tasting menus in a welcoming, open setting. It’s one of the best ...

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Season To Taste

$$$$·American·
Cambridge
1,059 reviews
  • Special Occasion
  • Neighborhood Gem
  • Fit for Foodies

Season To Taste is a funky twenty-seat restaurant featuring an open kitchen and warm, intimate environment. Wedged into an unassuming block in a quiet corner of Cambridge, it features local, seasonall...

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Healthy in Boston

Bondir Cambridge

$$$$·Contemporary American·
Cambridge
828 reviews
  • Fit for Foodies
  • Special Occasion
  • Romantic

Bondir Cambridge is a super small restaurant but they pack in a lot of fun! They offer a 5 course Tasting Menu in an elegant setting in the center of Cambridge. The cuisine uses expressive ingredients...

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Fat Hen Broadway East

$$$$·Italian·
Somerville
335 reviews
  • Fit for Foodies
  • Good for a Date
  • Creative Cuisine

The Fat Hen, located near Tufts University and Assembly Row in the Somerville neighborhood of Boston, is a casual elegant Italian restaurant. Diners love the sophisticated atmosphere and it’s perfect ...

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Forage

$$$$·Contemporary American·
Cambridge
1,037 reviews
  • Fit for Foodies
  • Creative Cuisine
  • Local Ingredients

If you’re looking for a super fun restaurant in Cambridge, head to Forage on Craigie Circle. It’s a farm-to-table neighborhood bistro right off Harvard Square that serves up casual, contemporary Ameri...

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Healthy in Boston / New England
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Dona Habana

$$$$·Cuban·
South End
944 reviews
  • Good for a Date
  • Good for Groups
  • Good for Birthdays

Dona Habana is definitely one of the most fun restaurants in Boston - ask any local! The space feels like a tropical paradise and you’ll feel like you’re in Old Havana, Cuba the second you step inside...

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Gustazo Cuban Kitchen & Bar - Cambridge

$$$$·Cuban·
Cambridge
624 reviews
  • Fit for Foodies
  • Special Occasion
  • Tapas

Gustazo is another lively and fun restaurant in Cambridge right on Massachusetts Ave. The word Gustavo means great pleasure and that is what you’re bound to find here. They aim to bring authentic Cuba...

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Darryl's Corner Bar and Kitchen

$$$$·Comfort Food·
South End
1,545 reviews
  • Neighborhood Gem
  • Hot Spot
  • Vibrant Bar Scene

If you’re looking for soul, spice and a little bit of jazz, head to Darryl’s Corner Bar and Kitchen, known as DCBK. They serve up great southern comfort food and signature cocktails and you can dine w...

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La Fabrica Central

$$$$·Spanish·
Cambridge
583 reviews
  • Great for Outdoor Dining
  • Good for Groups
  • Vibrant Bar Scene

Located right in the heart of Cambridge, La Fabrica Central is a fabulously fun Caribbean restaurant from celebrity chef Giovanna Huyke. She is a cookbook author and popular TV personality in Puerto R...

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Menton

$$$$·French·
Fort Point Channel
2,322 reviews
  • Special Occasion
  • Fit for Foodies
  • Good for a Date

Menton, located in Fort Point Channel, is the perfect stop for those looking for a fun night out in the neighborhood. The restaurant is Chef Barbara Lynch’s modern interpretation of fine dining and sh...

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Notable Wine List in Boston
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Loyal Nine

$$$$·American·
Cambridge
608 reviews
  • Fit for Foodies
  • Creative Cuisine
  • Handcrafted Cocktails

Another Cambridge favorite, Loyal Nine is consistently hailed as one of the most interesting and fun restaurants in Boston. Chef Marc Sheehan creates amazing seafood dishes that use fresh and seasonal...

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Dali

$$$$·Spanish·
Cambridge
926 reviews
  • Tapas
  • Fit for Foodies
  • Neighborhood Gem

For traditional Spanish cuisine in a fun setting that will spice up your night, head to Dali on Washington Street in Cambridge. The interior is bright and colorful with artwork on the walls, a tin cei...

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Best Ambiance in Boston
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Moonshine 152

$$$$·American·
South Boston
937 reviews
  • Neighborhood Gem
  • Fit for Foodies
  • Great for Outdoor Dining

Moonshine, located on Dorchester Ave in Boston, is a modern neighborhood restaurant that serves up creative American cuisine. It’s a popular late night spot in South Boston with a weekend brunch that ...

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American in Boston / New England

Shaking Crab - Boston Common

$$$$·Cajun·
Downtown Crossing
85 reviews
  • Spicy
  • Casual
  • Fun

Shaking Crab, located in Downtown Crossing, is one of the most fun restaurants in Boston for those who love to get messy! Their vision for messy eating started with the core belief that food can provi...

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Estragon

$$$$·Spanish·
South End
1,066 reviews
  • Tapas
  • Good for a Date
  • Fit for Foodies

Estragon Tapas Bar, established in 2008, offers a slice of Spain in the South End. Owned and operated by Julio de Haro and Laura Egger, the cuisine reflects their love of simplicity and tradition. The...

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Fire + Ice Boston

$$$$·American·
Back Bay
2,960 reviews
  • Kid-friendly
  • Good for Groups
  • Great for Lunch

Fire and Ice, located on Berkeley Street in the Back Bay, is a casual American place that is all about celebrating! They feature an interactive, all-you-can-eat experience in which every guest can cre...

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Kid Friendly in Boston
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Cuchi Cuchi

$$$$·International·
Cambridge
578 reviews
  • Good for a Date
  • Creative Cuisine
  • Tapas

Cuchi Cuchi, located right in the heart of Cambridge on Main Street, is one of the most popular small plates restaurants in town. Inspired by the Latin singer Charo, the decor evokes elements of Latin...

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