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Best Fun Restaurants in Old San Juan

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9 restaurants available nearby

How are Featured results ranked

A photo of Al Fresco Rooftop Wine & Tapas restaurant
3.2
Good(15)
Price: Moderate
• Tapas / Small Plates • San Juan
Booked 1 time today
At Alfresco Rooftop we offer a variety of Tapas Criollas (Puerto Rican delicacies) with vegan and vegetarian options. Nestled in an intimate setting its perfect for date night or even large parties we cater to all needs.We are located on the 3rd floor of a historic building which was the location of the Puerto Rico Nationalist Party headquarters and apartment for Puerto Rican Freedom Fighter and party president Pedro Albizu Campos. Rated by Tripadvisor as one of the best gastronomic destinations in Old San Juan 2021 to present. Rated Tripadvisor's Best rooftop wine & Tapas Bar 2019-2020Try our signature cocktails or choose from our wine lists, and even local craft beers, there is something for everyone here at the Rooftop.
A photo of Denko Asian Eatery restaurant
4.7
Exceptional(727)
Price: Moderate
• Asian • San Juan
Booked 17 times today
Standard seating reservations are for our "Rocket Experience", your food will be delivered right to the table. Las mesas Convencionales son estilo booth para la "Experiencia de Cohete" donde la comida le llega directo a la mesas.
A photo of Nonna Cucina Rustica restaurant
4.6
Exceptional(677)
Price: Moderate
• Italian • San Juan
Booked 7 times today
Nonna Cucina Rustica is a fun place because it offers a unique Italian gastronomic experience with dishes made from scratch, fresh vegetables, assorted cheeses, and unfiltered olive oil. It's like stepping back in time to a traditional and rustic Italian home, where everything is made with love and care. Reviews rave about the fantastic food, excellent service, and cool ambience. As one reviewer put it, it's a 'real gem' with 'exquisite Italian cuisine'.
A photo of Arena Medalla restaurant
4.7
Exceptional(80)
Price: Moderate
• Sports Bar • San Juan
Bienvenidos to La Casa del Triunfo Boricua, a celebration of Puerto Rico’s sports’ heritage past, present and future!Immerse yourself in action and watch your favorite teams play their A-game in the latest 30-ft panoramic, multi-view LED screen technology where you can enjoy a game or two from every corner; you are guaranteed never to miss a home run, knock out, or grand slam!
A photo of Piccolino Cucina Italiana restaurant
4.3
Awesome(244)
Price: Moderate
• Italian • San Juan
Booked 9 times today
Italian cuisine restaurant, homemade pasta, meat and fish in the heart of Guaynabo.
A photo of Tekka Bar at La Concha restaurant
4.5
Awesome(9)
Price: Moderate
• Sushi • San Juan
Booked 2 times today
Concepted from Las Vegas Restaurateur Takashi Segawa, Tekka Bar: Handroll & Sake now opens in San Juan, Puerto Rico. Handrolls are prepared counter-side and made to order for guests, highlighting the freshest seafood, featuring the restaurant’s notable spicy sauce, alongside an eclectic sake program.
A photo of Aguardiente Bar restaurant
4.1
Excellent(6)
Price: Moderate
• Bar / Lounge / Bottle Service • Condado
Aguardiente Bar is the place to hang out all night when visiting San Juan. Located in the most popular and socially thriving area our capital city; La Placita de Santurce. Great atmosphere, DJ's mixing the hottest hits, Bottle service and Hookah available. Recommend it by the official Discover Puerto Rico tourism page as one of the top places to dance the night away. Everyone is welcome but only good vibes allowed. Opened from Monday to Sunday.
A photo of CHICO CABARET - Fairmont El San Juan Hotel restaurant
4.6
Exceptional(84)
Price: Expensive
• Bar / Lounge / Bottle Service • Isla Verde / Carolina
In 1958 Chico was the hotel’s speakeasy, a cozy secluded lounge hidden from the lobby. In fact, Chico Cabaret was originally designed and named after a famous speakeasy in Manhattan. It is our intention to recreate that era with an emphasis on curated live entertainment where seasoned performers are featured, be it burlesque, DJs, live musicians and singers or comedy.$45 minimum consumption per person Sushi and Tapas available from Monday to Sunday starting at 5:00pm.
A photo of Aglio E Olio restaurant
3.3
Good(17)
Price: Moderate
• Italian • Guaynabo
Booked 2 times today
Wood-Fired Italian Restaurant & Brick Oven Pizzeria

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See what locals rave about

From verified diners like you
From verified diners like you
  • Marta
    Caribbean •1 review
    5.0
    Dined 5 days ago
    Service was really outstanding! They took effort in creating an experience for me and my family
    More info
    Denko Asian EateryPrice: Moderate• Asian• San Juan
    4.7
  • RafaelVIP
    New York City •16 reviews
    5.0
    Dined on May 26, 2025
    We had a great family dinner and loved the decor,ambience,food and specially the service.I believe our waiter’s name was Shirley and she was fantastic! Knowledgeable of the menu and wines with a very nice and welcoming attitude! This place has a great bistro feeling-warm and comfortable! We will definitely be back!
    More info
    Piccolino Cucina ItalianaPrice: Moderate• Italian• San Juan
    4.3
  • Sandra
    New York City •1 review
    4.0
    Dined on May 24, 2025
    The waitress was very nice and polite. She recognized a kitchen error on a gluten free meal and took immediate corrective action. She was very attentive to our needs. The food was delicious. I would certainly come back.
    More info
    Nonna Cucina RusticaPrice: Moderate• Italian• San Juan
    4.6
  • RobertVIP
    Nashville •31 reviews
    4.0
    Dined on Mar 29, 2025
    The food and service were great. Sadly they ran out of several dishes in the early evening
    More info
    Al Fresco Rooftop Wine & TapasPrice: Moderate• Tapas / Small Plates• San Juan
    3.2
  • Mark
    Fort Lauderdale •1 review
    5.0
    Dined on Feb 9, 2025
    The Venue was amazing, service was awesome. The Medalla staff made us feel very welcomed. The party planner Ana Suarez did an amazing job accommodate our groups so we could all sit together. Our server Ozuna was on point with the drinks. We would love to come back next year. We came in a large group of over 20. The commercials are a big part of watching the superbowl. But Medalla decided to do raffles and quizzes instead. For the money we paid for premium seats we would like to have the full experience and enjoy the commercials as well.
    More info
    Arena MedallaPrice: Moderate• Sports Bar• San Juan
    4.7

Discover best fun restaurants in Old San Juan

Discover the vibrant dining scene in Old San Juan, Caribbean, Puerto Rico, where the keyword "fun" truly comes to life in its array of restaurants. Each venue encapsulates the lively spirit of this historic location, offering not just meals, but memorable experiences. From the lively local music that echoes through the walls to the creative culinary delights inspired by both local and international cuisines, these eateries make every meal an adventure. Patrons can expect a diverse range of atmospheres, from cozy and intimate settings to bustling, energetic spots perfect for a group outing. The restaurants here are known for their engaging environments where the fun continues long after the meal is done. Whether you're a local or a traveler, the fusion of exquisite flavors with an upbeat ambiance ensures that dining out in Old San Juan is always a joyous occasion. This destination is a treasure trove of culinary delights that promises to enhance your dining experience with every visit.

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