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New Yorkers 1st Choice
Dunedin's best

Cool date spots

A date spot that feels genuinely cool without the pretension that usually comes with the label.

Based on 505 Opinions
+502
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Updated May 2026
01
Caledonia Brewing image 1
Caledonia Brewing image 2
Caledonia Brewing image 3
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Historic building houses a brewery with plenty of indoor and outdoor seating and a pub vibe. Live music from local bands and bar games create a laid-back, friendly atmosphere. The space offers diverse, unique beers including hard cider and hazy IPAs.

This spot offers a casual brewery vibe that has served as a backdrop for multiple couples' visits. It features a relaxed atmosphere suitable for sharing a few beers and catching up.

A cool vibe sets the tone with a solid selection of awesome drinks. They also offer cool merchandise to check out.

People are saying

"I loved their IPAs and other unique craft beers."

"It's a great spot for Date Spots with friendly staff and great beer."

"I loved the cool brewery with awesome choices for drinks."

Good to know

1

Trivia night happens every Wednesday at 7pm with a $5 entry fee.

2

Happy hour runs from 4-5pm on weekdays with discounted drinks.

3

The brewery hosts themed bingo nights every Thursday at 8pm.

02
Jardin De Pollos image 1
Barbecue restaurant

Outdoor garden seating blends tribal decor and Bolivian artisan wood furniture with lush plants, creating a natural vibe. Live music and a pet-friendly patio add to the relaxed, friendly atmosphere. Sangria with fresh fruit complements the setting without overpowering it.

Smoked chicken and crispy empanadas make for a solid meal on date night. The food competes well with authentic Puerto Rican cooking, adding a genuine touch to the experience.

Outdoor seating offers a mix of shade and sunshine with cool wood furniture surrounded by various greenery. The atmosphere feels friendly and relaxed, creating a consistently cool vibe.

People are saying

"The food here is so juicy and flavorful."

"The chicken here is simple, delicious, and perfectly cooked."

"The chicken here is phenomenal and cooked perfectly."

Good to know

1

Jardin De Pollos offers a $5.99 lunch special with amazing food.

2

The restaurant has outdoor seating only, which can be warm in summer.

3

They ran out of food by 8:00 pm on a Friday night, so arrive early.

03
Pineapple Jacks image 1
Restaurant

Small restaurant blends Old Florida vibe with tiki and diner/pub styles inside and out. Live music plays at a comfortable volume, creating a fun and relaxed atmosphere. Bar seating opens to a cool outdoor area with fans, offering a beachy feel and dog-friendly space.

Seafood dishes come in ample portions with a blackened seafood platter standing out. The menu features pineapple-inspired flavors that add a unique touch to the dinner experience.

Outdoor seating features fans that keep the area cool while maintaining a beachy Florida vibe. The overall atmosphere is welcoming and relaxed.

People are saying

"The seafood here is amazing, truly great food."

"The pineapple painkillers and coconut shrimp are amazing Date Spots."

"The clam strips and crab cakes here are so good!"

Good to know

1

Happy hour runs daily from 2 PM to 7 PM with 2-for-1 Tito’s vodka.

2

BOGO burger night occurs every Wednesday, offering two burgers for the price of one.

3

Parking is available behind and on the right side of the building.

04
Salty Soul Island Kitchen image 1

Restaurant offers tropical decor with open-air seating and a beachy, relaxed vibe. Live reggae music plays on select days, enhancing the family-friendly atmosphere. Multiple seating areas provide varied views and a breezy, island oasis feel.

Seafood dishes like the seafood platter and shrimp-loaded salad stand out. Tacos offer a tasty option. Meals and drinks come at a budget-friendly price.

Atmosphere feels very relaxing with a beach environment vibe. Outside seating adds to the cool breeze island ambience.

People are saying

"The fish tacos here are the best I ever had."

"Our server Holly was great and very friendly."

"It's a cool little spot for a quick meal."

Good to know

1

Happy hour features $2 bottle beers, making it a great deal.

2

The restaurant is dog friendly, allowing pets on the patio.

3

Weekend brunch menu is available with unique offerings.

05
The West End Market image 1

Open-air food court with a roof and open ends hosts a slowly spinning carousel bar at its center. Live music and bubble machines create a lively, fun atmosphere filled with diverse food options. Murals and unique decor like book-themed stairs add to the vibrant, engaging vibe.

Enjoyable for date nights with a relaxed vibe for drinks. Some food orders come out quickly, but others may have a long wait.

Open air seating with fans keeps the atmosphere cool. A 360-degree slow rotating carousel bar adds a unique vibe alongside multiple order-at-the-counter food vendors and TVs with heaters.

People are saying

"I found lots of great food choices here."

"The bar is a really cool 360-degree slow rotating carousel."

"The carousel bar is a fun spot for drinks."

Good to know

1

Parking is very limited, so arrive early to secure a spot.

2

The market features a variety of food options and drinks.

3

Live entertainment occurs regularly, enhancing the market experience.

06
Eddie's Bar & Grill image 1

Sports bar with multiple dining rooms, three bars, and tons of big screen TVs showing all NFL games creates an immersive experience. Atmosphere stays family- and dog-friendly with a casual, lively vibe and no loud music. Outdoor patio offers pet-friendly seating with fans and a game room entertains kids and adults alike.

Long drives happen for date nights here because the food quality stands out. Sandwiches and loaded skins get special mention, and staff handle meal issues quickly, making it a solid spot for couples.

A shaded, breezy patio with fans keeps the space cool even in hot weather. A small video game area and various fun games add to the cool, seaside vibe.

People are saying

"You can get great food while watching live sports here."

"You'll love the food here; the grouper sandwich is terrific."

"It's a cool place with fun games and good drinks."

Good to know

1

Eddie's Bar & Grill has a Monday trivia night that starts at 6:30 PM.

2

Happy hour runs all day with discounted drinks and appetizers.

3

The bar is family-friendly and has a game room for kids.

07
Señor Rita's Tequilería & Margarita Factory image 1

Rooftop bar with swings at booths and live salsa music creates a lively, trendy atmosphere. Guests enjoy handcrafted margaritas and flavorful Mexican dishes like Birria tacos and steak quesadillas. The space offers free sunset views and a fun, social vibe.

Charcoal old fashioned stands out with a unique twist that even surprises whiskey lovers. The spot offers cold beer with free chips and salsa, making it a relaxed choice for a double date or casual drinks.

A cool vibe fills the space with a Cabo feel and rooftop cabanas that stand out. The atmosphere is very Instagram-worthy and the staff are super nice.

People are saying

"The bar service was friendly and with a smile."

"The rooftop atmosphere here is fantastic and fun."

"The food here is so flavorful, even the chips and salsa."

Good to know

1

Happy hour drinks are under $10, making it a budget-friendly option.

2

The DJ performs every Friday and Saturday starting at 11 pm.

3

The restaurant charges a mandatory 20% gratuity on all bills.

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Dunedin, Florida

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