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Dining on the patio at Calypso - Calypso, The Villages, FL

Calypso

3.8
3.8
29 Reviews
$31 to $50
American

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2 people
10:30 pm
Booked 11 times today
  • Great for scenic views
  • Great for outdoor dining
  • Great for creative cocktails
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.

Order delivery or takeout

Additional information

  • Dining style
    Casual Dining
  • Price
    $31 to $50
  • Cuisines
    American
  • Hours of Operation
    Mon–Thu, Sun 11:30–21:00 Fri, Sat 11:30–22:00
  • Phone number
    (352) 750-8265
  • Payment Options
    AMEX, Discover, Mastercard, Visa
  • Dress code
    Casual Dress
  • Area
    The Villages
  • Parking details
    Public Parking
  • Additional
    Bar/Lounge, Beer, Cocktails, Entertainment, Full Bar, Happy Hour, Indoor Fireplace, Non-Smoking, Patio/Outdoor Dining, Takeaway, View, Wheelchair Access, Wine

What 29 people are saying

Overall ratings and reviews

Reviews can only be made by diners who have eaten at this restaurant

3.8
3.8 based on recent ratings
  • 3.7Food
  • 4.3Service
  • 4Ambience
  • 3.4Value

NoiseModerate

Review summary

AI-generated from verified diner reviews
Calypso offers a "beautiful waterfront view" and "awesome service" with standout dishes like the "crispy shrimp appetizer." While some guests note high prices and occasional service delays, the ambiance and the friendliness of staff, like servers Jay and Tammy, make dining here a memorable experience. "Definitely recommend!"

29 Reviews
  1. Michael

    Chicago13 reviews

    3.0

    Dined on 2 March 2025

    1. Overall 3
    2. Food 3
    3. Service 4
    4. Ambience 2
    Service very good. Food was good. Nothing exceptional at all. Convenient more than anything else

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  2. Judy

    Minneapolis5 reviews

    1.0

    Dined on 1 March 2025

    1. Overall 1
    2. Food 1
    3. Service 1
    4. Ambience 1
    Horribly expensive from the drinks to the food. Wrong dish delivered and not resolved. Short ribs dish inedible. Sent back to kitchen. Unbearably cold in dining room. We stopped earlier in day for cocktails. Ignored by both bartenders, took over 20 minutes to get a drink. Should have seen writing on the wall.
    CalypsoResponded on 1 March 2025
    Thank you for taking the time to share your feedback. We're genuinely sorry to hear that your experience didn't meet your expectations. We strive to offer both great food and service, so it’s disappointing to learn that there were issues with your order, the temperature, and your experience at the bar. We take your comments seriously and will review the concerns with our team to ensure that all are addressed. Our goal is to create a welcoming and comfortable environment, and we regret that we didn’t deliver that for you. We hope you'll consider giving us another chance to provide the quality service and experience that we aim for. Thank you again for your feedback.

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  3. Holly

    Orlando1 review

    5.0

    Dined on 28 February 2025

    1. Overall 5
    2. Food 5
    3. Service 5
    4. Ambience 5
    Food was amazing! Sad outside, beautiful view of the lake and lighthouse. Waiter was super friendly and helpful.
    CalypsoResponded on 1 March 2025
    Thank you so much for your kind words! We're thrilled to hear you enjoyed the food and had a great time with the beautiful view of the lake and lighthouse. Our team will be happy to know that the service was friendly and helpful — we always strive to make every experience memorable. We hope to welcome you back soon for another amazing visit!

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  4. Toni VIP

    Orlando29 reviews

    4.0

    Dined on 28 February 2025

    1. Overall 4
    2. Food 5
    3. Service 5
    4. Ambience 4
    Had no problem making a same-day reservation. They were very busy at 6pm. Still, server Jay was terrific and timely. The food was good, the pork sliders and shrimp tacos were excellent! The bar drinks were good. All guests looked happy. The view is awesome!! Overall, I found it relatively pricey for the locals, but it's a hotel, sooooo... It will be interesting to see if the prices hold up during the off-season. Even so, I heartily recommend that you try Calypso. I know I'll be back.
    CalypsoResponded on 1 March 2025
    Thank you so much for your wonderful review! We're thrilled to hear that you had a great experience with us, from the easy reservation process to enjoying the food and drinks. Jay will be especially pleased to know you appreciated his service! We agree, the view is pretty special, and we're glad you enjoyed it.

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  5. Debbie

    Greater Boston2 reviews

    5.0

    Dined on 28 February 2025

    1. Overall 5
    2. Food 4
    3. Service 5
    4. Ambience 5
    We had such a great time at Calypso! From the moment we walked in, the hostess made us feel right at home, and our waitress, Bianca, was absolutely fantastic. She wore a smile the entire night and made sure every little detail was just right. The food was delicious, the service was top-notch, and sitting outside by the water was the perfect touch. We’ll definitely be back—probably sooner than we should, but hey, good food calls!

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  6. James

    Kansas City3 reviews

    5.0

    Dined on 23 February 2025

    1. Overall 5
    2. Food 5
    3. Service 5
    4. Ambience 5
    I had Grouper, Island style. It was delicious. My companion had a chicken dish that she also liked. We dined outside, great views and great weather. No music, so don't know how loud it will be on nights with music. Not inexpensive, but good food & service make it worthwhile.
    CalypsoResponded on 25 February 2025
    Thank you for your review! We're so glad you enjoyed the Grouper Island Style and that your companion liked her dish as well. Dining with a great view and perfect weather makes for a wonderful experience! We appreciate your feedback and hope to welcome you back soon—maybe on a night with music!

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  7. Diane

    New York City4 reviews

    4.0

    Dined on 18 February 2025

    1. Overall 4
    2. Food 4
    3. Service 5
    4. Ambience 5
    The Waterfront recently remodeled the entire restaurant and the ambiance is so much nicer now. We sat outside with a lovely view of the water. Our server, Jason was the best! All we ordered was delivered in a very timely manner and we will definitely be back.
    CalypsoResponded on 20 February 2025
    Thank you so much for your kind words and for taking the time to share your experience with us! We’re thrilled to hear that you had such a wonderful time at Calypso. It’s always our goal to provide excellent service and delicious food, and it’s rewarding to know we succeeded. Kudos to Jason for taking great care of you! We will be sure to pass the great review along to him.

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  8. Jeffrey

    Indiana4 reviews

    1.0

    Dined on 14 February 2025

    1. Overall 1
    2. Food 1
    3. Service 1
    4. Ambience 1
    This was a terrible experience. We had reservations for Valentines and they couldn't seat us until 20 minutes after our reservation time. Then they were so backed up that they didn't take our drink order for another 15 minutes. The table of 4 next to us ended up leaving because they'd been waiting over 2 hours for their food. Our food finally came out and in less than 2 hours, however the burger was medium rare - not good for a hamburger. The fries were cold. And the other dish (grouper) was cold and over cooked (very dry). The crazy thing is that they had several empty tables, so not sure how they were so "slammed". It's not as if they didn't expect a good turnout, with reservations and all. Whoever is running this restaurant seems to be in over their head.
    CalypsoResponded on 15 February 2025
    Thank you for taking the time to share your feedback with us. We truly appreciate your visit on Valentine’s Day, and we deeply apologize that your experience did not meet expectations. We understand how frustrating long wait times can be, especially during a special occasion, and we sincerely apologize for the delay in service and food delivery. While Valentine’s Day is one of our busiest nights, this is not an excuse for the wait, and we are actively working to improve our processes so that we can better accommodate our guests during peak times. We value your feedback and hope you’ll consider giving us another chance to provide the experience you deserve. We would love to have the opportunity to make it right.

    1 person found this helpful

  9. Thomas

    Jacksonville1 review

    4.0

    Dined on 14 February 2025

    1. Overall 4
    2. Food 5
    3. Service 4
    4. Ambience 5
    My wife and I were pleased and appreciated that the concierge changed our reservation to an outside table due to the excessive loud noise inside, which would have made conversation extremely challenging for our special Valentine's Day dinner. Our server was wonderful, and she apologized for the 30+ minute delay to receive our deserts after she picked up our dinner plates. The food quality was excellent, and we enjoyed the outside ambiance. Calypso, in our respectful opinion, is better suited to being a bar & grille because of its large and open bar area coupled with the small inside seating area adjacent to the open lobby. These factors combined with the problematic acoustics, utilitarian tables, and kitchen delays make the inside unsuitable for a finer dinner experience.
    CalypsoResponded on 20 February 2025
    Thank you so much for your review! We're thrilled that you appreciated the option to move tables and that it made your experience more enjoyable. We apologize for the delay in food service and truly appreciate your patience. We do have solutions to the noise level in progress as well, as we are always working to improve the guest experience and your feedback helps us ensure we’re providing the best possible experience for all our guests. We hope to have the pleasure of serving you again soon!

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  10. John

    New York City1 review

    1.0

    Dined on 14 February 2025

    1. Overall 1
    2. Food 2
    3. Service 1
    4. Ambience 2
    Thought we would have a wonderful Valentine’s night at the Calypso. But not even close!’ Drinks took 25 minutes to get. Dinner an hour later. Everyone around us had the same miserable service. For some reason our server had a table of 18 and was assigned at least four other tables that suffered the same fate. We did get two red roses for our wives.
    CalypsoResponded on 17 February 2025
    Thank you for your feedback. I do understand the frustration. Unfortunately, as we have learned, sometimes high volume can cause delays that we don’t anticipate, but we are committed to improving this so it doesn’t happen again. However, we sincerely apologize for the experience and service that you received. Please know that this is not the level of service we aim to provide, especially on a special evening like Valentine’s Day. We would love the opportunity to make this right if you can give us a chance to give you a better experience in the future.

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FAQs

Calypso offers takeout which you can order by calling the restaurant at (352) 750-8265.

Calypso is rated 3.8 stars by 29 OpenTable diners.

Yes, you can generally book this restaurant by choosing the date, time and party size on OpenTable.

Make a booking

2 people
10:30 pm
Booked 11 times today

Order delivery or takeout

Google Map for Calypso

1105 Lake Shore Dr, The Villages, FL 32162-1698

Additional information

  • Area
    The Villages
  • Hours of Operation
    Mon–Thu, Sun 11:30–21:00 Fri, Sat 11:30–22:00
  • Price
    $31 to $50
  • Cuisines
    American
  • Dining style
    Casual Dining
  • Dress code
    Casual Dress
  • Parking details
    Public Parking
  • Payment Options
    AMEX, Discover, Mastercard, Visa
  • Additional
    Bar/Lounge, Beer, Cocktails, Entertainment, Full Bar, Happy Hour, Indoor Fireplace, Non-Smoking, Patio/Outdoor Dining, Takeaway, View, Wheelchair Access, Wine
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