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New Yorkers 1st Choice
Historic Kenwood's best

Cool spots

A spot with a genuine, standout personality changes the entire feel of the day.

Based on 530 Opinions
+527
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Updated May 2026
01
Ride’em Cowboy image 1
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Large outdoor space with games like Jenga and cornhole creates a fun vibe. Cool murals and a country theme inside add strong visual appeal. Diverse crowd enjoys live country music and themed events like karaoke and LGBTQ+ nights.

Cool murals cover the outside walls, adding a strong visual vibe. The country theme inside matches the friendly staff, making the bar feel genuinely cool.

People are saying

"The bartenders here are amazing, attentive, and super friendly."

"Karaoke nights here are so much fun, especially on Thursdays."

"This place is a really cool bar with a chill vibe."

Good to know

1

Karaoke happens every Thursday night, hosted by Brad.

2

Happy hour features $6 domestic beers and runs from 4-7pm on weekdays.

3

Drag Bingo is hosted every Monday night at the venue.

02
Gateway Subs image 1
Sandwich shop

Spacious dining and a chill, family-friendly vibe create a welcoming spot. Coffee beans roast on-site, filling the air with a rich aroma. Staff show a laid-back vibe and offer customized orders, while the Cool Ranch Ryder sandwich matches the cool atmosphere perfectly.

Staff show a laid-back vibe and are open to customizing orders. Sandwiches like the Cool Ranch Ryder stand out, matching the cool atmosphere on hot days.

People are saying

"I've never had a sub sandwich this good before."

"The staff here are so friendly and offer great suggestions."

"The staff here is super cool and friendly."

Good to know

1

Gateway Subs opens as early as 8am.

2

A whole sub costs $15-17.

3

There is limited on-site parking, but street parking is available.

03
Pepe's Cantina St. Petersburg image 1

Mexican restaurant shines with modern murals and a small outdoor patio perfect for dogs. Lively Mariachi band and Latin Pop music set a fun tone. Friendly crowd keeps the vibe cool and relaxed while tableside margaritas add flair.

Everyone here is nice and cool, creating a very cool atmosphere. The patio adds to the relaxed vibe.

People are saying

"I found the food here to be amazing and delicious."

"The service during dinner was amazing, with servers going above and beyond."

"I loved the cool vibe and atmosphere here."

Good to know

1

Monday is Margarita Monday, with house margaritas costing $6.25.

2

Happy hour runs all afternoon with great deals on drinks.

3

Taco Tuesday offers special pricing on tacos.

04
Cozy kava image 1
Coffee shop

Spacious coffee shop with comfortable seating and a pool table creates a chill vibe perfect for relaxing or studying. Warm lighting and an open layout add to the cozy feel. Cool TVs and plenty of board games make it a fun escape from the city's heat.

Cozy kava offers lots of board games, pool table, and TVs with cool displays. It feels like a comfortable spot to escape the city's heat.

People are saying

"Their coffee is amazing, bold, and flavorful."

"I found the kava and kratom drinks here to be the absolute best."

"The staff here is so friendly and makes you feel welcomed."

Good to know

1

Tonight, Cozy kava is hosting Karaoke and Trivia events.

2

There are plenty of places to sit and chill alone or with friends.

3

The WiFi is stable and suitable for studying.

05
Beau & Mo's Italian Steakhouse image 1

Old-school Chicago steakhouse offers an intimate, romantic vibe with soft jazz music and a lively bar serving craft cocktails. Steaks are the star, known for exceptional quality and flavor. Cozy space with complimentary cigars outside adds to the cool, offbeat charm.

Atmosphere feels old-school and reminiscent of Chicago steak houses. The spot sits off the beaten path with a cool vibe.

People are saying

"The food here is delicious, especially the French onion mac and cheese."

"The ribeye steak was off the charts delicious and tender."

"I found the atmosphere cool and old-school."

Good to know

1

Reservations are recommended, especially for special occasions like anniversaries or birthdays.

2

Happy hour runs from 5 PM to 7 PM with great deals on drinks and appetizers.

3

The restaurant has a minimum consumption requirement of $60 per person.

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Historic Kenwood, St. Petersburg

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