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Best Live Music Restaurants in The Villages

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4 restaurants available nearby

A photo of Calypso restaurant
4.3
Awesome(1)
Price: Expensive
• American • The Villages
Welcome to Calypso, a bold Caribbean-inspired dining haven that brings the vibrant, sun-soaked flavors of the islands to the lakeside shores of Lake Sumter. With a warm, inviting atmosphere, we offer guests an immersive island escape through a playful mix of tropical décor, radiant evening beats, and breezy dining delights. The indoor-outdoor bar lets you sip on taste-forward, rum-infused cocktails as you feel the lakeside breeze & gaze across the water. Our lively menu takes you on an adventurous, bold taste journey, with zesty island bites and flavorful dishes that celebrate Caribbean flair & global influences. Expect exotic ingredients, sunkissed atmosphere, and an enlivening dining experience crafted to satisfy all the senses.At Calypso, every bite, sip, & beat is a celebration of Caribbean-inspired, lakeside bliss.Please Note: Calypso is currently offering a sneak peak menu only as well as our full cocktail menu, we look forward to announcing our full menu availability soon.
A photo of Whispering Oaks Winery restaurant
4.4
Awesome(969)
Price: Expensive
• Steak • Ocala
Whispering Oaks Winery, with Steak Nights Friday - Saturday Choose From a Choice of Steaks, Surf N Turf, Chicken or Fresh Fish Choice of Soup or Salad Fresh Vegetables Chef's Choice of Potato or Rice AND Freshly-baked BreadDinner is served in our tasting room or outdoors on our patio next to our open wood grill. We have live music every Friday, 5:30-8:30 and Saturday 5:30-8:30. Come enjoy our Award winning wines and great food under the oak trees of Whispering Oaks Winery!
A photo of Prime 3 restaurant
4.8
Exceptional(524)
Price: Expensive
• Steakhouse • Leesburg
Booked 4 times today
We are a 2023 & 2024 Wine Spectator Award of Excellence Winner.If you’re in the mood for an evening of good food and elevated ambiance, pull up a seat at Prime 3 Steakhouse, in Historic Downtown Leesburg, FL, with flair. By serving premium steaks and fine wines, we hope to provide an elegant and family-friendly dining experience for everyone in our community. Try our mouth-watering prime rib or seared scallops or our Norwegian Salmon. Pair it with a fine wine and treat yourself to a top-notch meal.Don't forget to try our creme Brulee or Craft-Made Ice Cream for dessert. Now open for Lunch Mon-Friday 11am to 2pm. No reservations are required for lunch.Not sure what wine goes with your dinner? Ask your server for a recommendation. One of the Prime 3 Steakhouse owners hand-picked all our wines. If you cannot make your reservation, please call us so we may offer your seats to additional customers. 352-314-0015.See our wine list at https://www.prime3steakhouse.com/wines
A photo of McGrady’s Pub restaurant
4.6
Exceptional(235)
Price: Moderate
• Scottish • The Villages
Booked 5 times today
McGrady's Pub, a Scottish culinary experience at Sawgrass Grove, located in Florida's Friendliest hometown, The Villages. Come enjoy a pint of Guinness, Craft Cocktails, Shepherd's Pie, Bangers & Mash, Fish & Chips, Leg of Lamb and Scotch Eggs while listening to Live Music on our Patio or overlooking the Boxcar Stage at Sawgrass Grove. Our friendly staff will make you feel at home, while you dine in our comfortable, new Celtic-themed pub! Don't forget to check out our Wine Down Wednesdays where bottles of wine $60 or less are half price all day! Our Happy Hour every day features half priced domestic drafts and house wine. Don't forget to visit our bar in the middle of the Sawgrass Marketplace and enjoy the view from the festive Grove Bar in Sawgrass Grove. Stop by and cool off after your round of golf at Southern Oaks Championship Golf Course. Our pub is the perfect place to catch up with all of your friends and plan your next adventure!

See what locals rave about

From verified diners like you
From verified diners like you
  • Clarissa
    Fort Lauderdale •6 reviews
    5.0
    Dined 1 day ago
    I love coming here. The food is so good we booked another dinner reservation for the next day. Great vibes, great food and drinks, and great music. This is a cool dining experience!
    More info
    The EdisonPrice: Expensive• American• Lake Buena Vista
    4.3
  • Rob
    Jacksonville / Northeast Florida •2 reviews
    5.0
    Dined 4 days ago
    Omar made the experience great! Give that guy a raise.
    More info
    The Boheme at Grand Bohemian Hotel OrlandoPrice: Expensive• Modern European• Downtown Orlando
    4.3
  • Madisen
    Nashville •1 review
    5.0
    Dined 4 days ago
    Amazing place!!! We could not recommend it more, especially if you have a gluten allergy! They have gluten free fish and chips and gluten free onion rings!! They also have amazing entertainment! You get to listen to authentic Irish music as well as watch Irish Step Dancing! The server was knowledgeable and so attentive and the manager came and talked to us multiple times about what we ordered to make sure we knew it was going to be gluten free!
    More info
    Raglan Road Irish PubPrice: Moderate• Irish• Lake Buena Vista
    4.8
  • Etienne
    Orlando / Central Florida East •1 review
    5.0
    Dined 6 days ago
    Our waitress, Sassy, was extremely helpful and friendly! Great displays and vibe! A must see!
    More info
    Hard Rock Cafe - OrlandoPrice: Moderate• American• I Drive / Sand Lake
    4.4
  • RuthVIP
    Philadelphia County •8 reviews
    4.0
    Dined on Dec 11, 2024
    To be fair, we ate there as hotel guests and because it just opened, they did not have a full menu yet. We started with crab soup and Ahi tuna which were both very good. My husband had stir fried rice and shrimp, which was fine but overpriced in my opinion and his as well, $32 for basically some Chinese food with a little bit of tropical flare, using roasted pineapple. I had a wedge salad and had I been thinking I would’ve asked to have the dressing on the side because that’s what I typically do. Not a huge fan of wedge salads, but that’s the only salad they had and I Was not hungry enough for an entrée. The wasabi dressing was so hot, I finally had to just give up continuing to eat it because it was becoming actually rather painful when my sinuses were burning with every bite. As far as ambience, we were expecting a bit more since this has been newly redone, but it’s very contemporary with a bit of an island feel. Nothing to drowned out noise so while it wasn’t too bad since there were only maybe six tables occupied, I would think it could become much noisier. We had a 20% discount as guests, and it ended up for the aforementioned food and two glasses of wine, I believe including tip we spent close to $120 which is a fairly good price overall
    More info
    CalypsoPrice: Expensive• American• The Villages
    4.3
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