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Best Live Music Restaurants in Wildwood

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4 restaurants available nearby

A photo of McGrady’s Pub restaurant
4.4
Awesome(238)
Price: Moderate
• Scottish • The Villages
Booked 1 time 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!
A photo of Boosters Bar & Grill restaurant
4.3
Awesome(36)
Price: Moderate
• American • Wildwood
Booked 30 times today
We are a premium sports bar located at Shallow Creek Golf Club in The Villages! With over 30 TV's, a great sound system, live entertainment, a delicious menu, craft cocktails and great service, you will have an awesome experience!
A photo of Prime 3 restaurant
4.8
Exceptional(540)
Price: Expensive
• Steakhouse • Leesburg
Booked 8 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 Calypso restaurant
3.6
Very Good(11)
Price: Expensive
• American • The Villages
Booked 5 times today
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.

See what locals rave about

From verified diners like you
From verified diners like you
  • Robert
    Orlando / Central Florida East •13 reviews
    5.0
    Dined 1 day ago
    What a great restaurant. When we were first seated we were put at a table near where a live band was playing. I asked to be moved to a quieter area so i would be able to enjoy dinner conversation. This was promptly and courteously undertaken. We were met by Jenna who was an outstanding server. She was efficient, friendly and very accommodating. The meal was great and the desserts were even better. I was able to hear the band and still easily have a conversation without yelling. A great experience and a place I will go back to again.
    More info
    The EdisonPrice: Expensive• American• Lake Buena Vista
    4.4
  • Beatrice
    Orlando / Central Florida East •1 review
    5.0
    Dined 2 days ago
    Our waitress Sue was amazing and went above and beyond to give us a special experience for our one year wedding anniversary! Very much enjoyed the food and atmosphere!
    More info
    Hard Rock Cafe - OrlandoPrice: Moderate• American• I Drive / Sand Lake
    4.5
  • Linda
    Orlando / Central Florida East •1 review
    5.0
    Dined 3 days ago
    Wonderful experience, thoroughly enjoyed the Irish Dancers, as well as the Dingers. Food was plentiful and very tasty, I had the fish and chips and booth done to perfection. My husband had the shepherds pit and it was equally done. Jack was our waiter and he was very attentive and friendly. We couldn't have asked for a better experience.
    More info
    Raglan Road Irish PubPrice: Moderate• Irish• Lake Buena Vista
    4.7
  • Barry
    Orlando / Central Florida East •1 review
    5.0
    Dined 7 days ago
    The food was great, server was attentive and friendly. We have eaten at Boosters before and it has always been excellent.
    More info
    Boosters Bar & GrillPrice: Moderate• American• Wildwood
    4.3
  • ElkeVIP
    Orlando / Central Florida East •15 reviews
    5.0
    Dined on Jan 10, 2025
    We were in a rush on a cool evening and made Open Table reservation. We were seated promptly on a busy Friday night with an open air concert on the band stand outside the Scottish themed pub. Nice menu selections, something for everyone. Our excellent waitress recommended chowder, sandwiches and fish &chips, all were delicious. Portions were generous. The chowder was piping hot, just as we had requested. We enjoyed a nice pint of Guinness along with our meal. Restaurant is very clean and spacious, architecture is a modern take on Scottish pub with traditional touches, with a cozy ambiance. Recommend McGrady’s for a casual meal with family and friends.
    More info
    McGrady’s PubPrice: Moderate• Scottish• The Villages
    4.4
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