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Calypso Bar & Grill

4.2 (29 reviews)
InexpensiveAmerican, Bars, Pizza
Open • 3:30 pm - 12:00 am (Next day)
Updated a few days ago

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Recommended Reviews - Calypso Bar & Grill

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Reviews are largely positive. People praise the food quality, generous portions, and welcoming atmosphere. The friendly service and good drink selection are also noted.

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8 months ago

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6 months ago

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8 months ago

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1 year ago

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11 months ago

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6 months ago

Food was amazing, staff was courteous, and honestly the music playlist was wonderful. Great night out.

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1 year ago

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11 months ago

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2 years ago

They don't know how to handle a rush... the service was good, the wait for the food an hour a half! When finally came it was frozen cold!

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1 year ago

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1 year ago

Incredible comedy show on Wednesday, so worth it and a great local spot. Food and drinks are one point

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2 years ago

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3 years ago

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2 years ago

Happy Hour at the bar! Great prices and the Calypso shrimp were delicious! Perfect spot to grab a drink when staying at the hotel.

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7 years ago

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7 years ago

Helpful 2
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4 years ago

Great service. Very accommodating. Good food. Shrimp tacos were very good. Beautiful breeze poolside.

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8 years ago

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8 years ago

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12 years ago

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12 years ago

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7 years ago

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8 years ago

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8 years ago

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9 years ago

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7 years ago

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8 years ago

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9 years ago

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10 years ago

Huge appetizer portion at fair price. Good bread. Had a filet with pasta that was fair for the price.

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I have been SO excited to try The Whiskey ever since I saw its amazing reviews here on Yelp, and…read morelet's just say i was definitely NOT let down!!! It was the perfect atmosphere for a quick stop on a Wednesday. We came at about 2:00pm and were greeted by the sweetest bar staff and asked to take a seat wherever we'd like! Choosing which burger was the hardest part. Everything sounded AMAZING!!! I ended up trying the Shroom N' Swiss which fulfilled my craving PERFECTLY!!! Such a flavorful burger that I didn't find too over the top. I had a few of my party's truffle fries and they were incredible as well. I will definitely be back here for some burgers and apps whenever I get the craving! So happy I was able to stop by and finally try!

We popped over here for lunch on a Saturday around two in the afternoon. We were very surprised…read morewith how busy it was as it's typically not that busy on Saturday afternoons. We chose seats at the bar and were greeted promptly by Brian and Rowan. Because there were a lot of people and just the two of them, they were running around taking orders from tables as well as servicing the bar so it did take a little bit to get our drink orders in, but we were enjoying looking through the whiskey library anyways. I started off with a Suncreek blonde ale. It is strawberry blonde ale and it's delicious. My husband started with the Yingling. He keeps hoping they will bring the Kentucky bourbon ale back on tap again. For lunch, I got the whiskey dip which is full of chopped beef with cheese and onions. Served with an herb, dipping sauce, and your choice of side. I opted for the sweet potato waffle fries because they are delicious. My husband got a burger with fries cooked perfectly. Once we are done with our food, we did opt for a taster. My husband had to go through several different bottles before he found one they actually had in stock. That is one of the downside is the whiskey library that is online is not always reflective of what they actually have in stock as he was really looking forward to trying the old Fitzgerald birthday, but alas, they did not have it in stock. He ended up going with the jack Daniels 12 year and really enjoyed it. I opted for the widow Jane 14 year very sweet easy to drink. Great service from Bryan and Rowan always enjoy seeing them behind the bar

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The Whiskey - Bar Ambience

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The Whiskey - S & S Potatoes

S & S Potatoes

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PBR Cowboy Bar - Outdoor entertainment near PBR

PBR Cowboy Bar

3.4(28 reviews)
2.3 mi•International Drive / I-Drive

A last-minute dinner turned into an all-nighter…read more THE PUB / POINTE ORLANDO NIGHT/ and other Pointe Orlando Venues -- 09.2026 Saturday night started simple. My wife and I decided at the last minute to go out for dinner -- more of a go out, dress flashy, wine-and-dine type of evening. We love music, so the original plan was dinner, then maybe spend an hour at PBR Cowboy Bar listening to the music before heading home. Well... according to the timestamp, we left the next day -- early morning! Ha! My wife enjoyed the complimentary offers through Live! at The Pointe Orlando, and we ended up checking out several venues we had never experienced before. The Palm Tree Club had a completely different look and energy. The skyline was beautiful, and there was something pretty cool about being able to see the moon while dancing. So, one can say it's open style venue. The music leaned toward dance/EDM/rave-style music, at least from what I understood. We stepped into Shark Bar for the first time and enjoyed the Spanish music and reggaeton. Then we visited Still Lounge by Dr. Dre and Snoop Dogg. I could honestly sit there and chill all night. There's just something about old-school music that makes you bob your head, sing along, and relax. Definitely take time to check out the memorabilia inside. And finally -- PBR. Yes, the line was LONG. Out of every venue we visited, PBR was clearly one of the places everyone wanted to be. The music was fantastic. Hearing everything from Michael Jackson and Journey to Toby Keith -- and then hearing the entire crowd singing along -- gave the place a completely different energy. What I especially appreciate is the recognition shown to military members, law enforcement, first responders, and others who serve. The crowd is fun, the energy is high, the drinks are reasonable, and the atmosphere makes it very easy to lose track of time. I wanted to mash up all the photos from every venue we visited that night because the pictures really tell the story -- one stop turned into another, and before we knew it, we had experienced an entire night across Pointe Orlando. A huge thank-you to Kyle for the invitation and hospitality. It was greatly appreciated and helped turn a last-minute dinner into an unforgettable night for my wife and me. Love the VIP bands Highly recommend PBR Cowboy Bar Orlando. At this point, I honestly don't know why people feel the need to drive downtown when there is this much nightlife, music, food, and entertainment all in one place at Pointe Orlando. I wish after 8pm, metropolis stop charging for parking. #Salute

I came here after having dinner downstairs at a Brazilian steakhouse we weren't quite ready to turn…read morein so we decided to check this place out. It was definitely an interesting crowd. We were 40s and up, but you could tell there were some 20-year-olds there which was fine. They played an array of music, including Country and rap. There is a mechanical bull there however it was not in service when we went. I did visit the restrooms and they were very clean. I don't believe they serve any food here. We did come on a Tuesday night, so it really was not that busy. I'm sure the weekends has quite a crowd.

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PBR Cowboy Bar - Bar area.

Bar area.

PBR Cowboy Bar - Dining area. Saddle seats were mostly taken by other patrons, so I just sat on a regular seat in the bar.

Dining area. Saddle seats were mostly taken by other patrons, so I just sat on a regular seat in the bar.

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Calypso Bar & Grill - tradamerican - Updated October 2026

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