Grape Expectations
Wine store · Cypress Gardens ·

Grape Expectations

Wine store · Cypress Gardens ·

Wine bar offering large pours, happy hour, and pizza delivery

Grape Expectations by null
Grape Expectations by null
Grape Expectations by null
Grape Expectations by null
Grape Expectations by null
Grape Expectations by null
Grape Expectations by null
Grape Expectations by null
Grape Expectations by null
Grape Expectations by null
Grape Expectations by null
Grape Expectations by null
Grape Expectations by null
Grape Expectations by null
Grape Expectations by null

Information

5535 Cypress Gardens Blvd #150, Winter Haven, FL 33884 Get directions

$

Information

Static Map

5535 Cypress Gardens Blvd #150, Winter Haven, FL 33884 Get directions

+1 863 318 8800

$

Features

payment credit card
Tap to pay
wifi

Last updated

Dec 13, 2025

Powered By

You might also like

Terms of Use • Privacy Policy • Cookie Policy
 © 2025 Postcard Technologies, Inc.
@eater
390,870 Postcards · 10,986 Cities

Two new happy hours to check out bring cheese boards and cocktail classes | Eater Vegas

"Is one of the businesses featured in the Booze District Passport, a $18 passport offering specials, freebies and incentives to visit participating wine and beverage spots through June 15; passports can be purchased online." - Susan Stapleton

https://vegas.eater.com/2021/3/19/22339458/valley-wine-cheese-legacy-club-happy-hours
Grape Expectations

Megan A.

Google
I enjoy getting wine for my mani & pedi next door. Usually I come back for my second one afterwards. New owner seems nice, but kind of lost? I hope it's just me but.......

Mike B P.

Google
Great little wine tasting bar with good selection of tasty wines at reasonable prices. Manager was warm friendly and super efficient. Generous pours and little nibbles or pizza delivered from across the way completes a nice evening!

Sue C.

Google
This is a delightful little hole in the wall wine bar in a Winter haven strip mall. We absolutely loved it! Waitress was friendly and explained that our first wine choice was full price, but the second glass was half price. If we chose the house wine it was two for one. The wine pours were very healthy. We went on a Thursday and they had free meatballs, cheese, and crackers appetizers. If you want a pizza, you can run next-door and order it and they will deliver it to you while you’re drinking your wine. This was a very enjoyable experience and we will be back.

Chris N.

Google
One of my favorite places to sit and relax with friends. They have seating both inside and outside. Service is usually good, and they always have specials on their wine by the glass. An added benefit is you can also step next door and order a pizza over at J Burn's to eat while you have your wine 🙂

Yolanda P.

Google
Local wine bar in Winter Haven has great wine selection not far from Legoland. Everyday special buy one get one 50% off red and white wines 🍷

Stacy C.

Google
We come here fairly often and love this place! All the bartenders are so friendly and knowledgeable, and make for a really nice casual atmosphere. They have a great selection of wines to choose from, and the pours are very healthy! Love the BOGO1/2off and the punch cards that get you a free glass! This is such a little gem of a place and a great spot to bring friends!

Carla L.

Google
We have been loyal customers of the wine bar for years, enjoying conversations with the loyal patrons along with Madison, Chole, and Taren. This evening was a huge disappointment. I am pretty sure if Randy reviewed the cameras from this evening at 9:30 pm to observe he would not be pleased. First, the bartender was eating pizza and drinking “something out of a cup” at a table with a large group of her friends. As they left, which we were glad since the noise level was absurd, she started to socialize with her drunk friends that were at the end of the bar. She did not engage with any customers, continued to socialize with friends, and poured extremely large pours that were almost to the rim. We have always supported small businesses and continued to support Randy, even though the wine is WAY overpriced, because of the level of service and atmosphere. I do not agree with a business that is paying their employee to turn, what was a special place for us, into a hang out with her friends while getting paid. Tonight took the cake. We will never be back. I would recommend reviewing the receipt journal and cameras to see if those “customers” paid for their drinks. I do not want to support a business that allows their bartenders to ignore their customers and pay $12,00 for a glass of wine. You lost several loyal customers tonight and several hundreds of dollars a week.

Donald S.

Google
Always a great time. Good friends and great service. Awesome wine selection. Usually have buy one get one half price. Also on Monday evenings they have chair massage available for a dollar a minute.
google avatar

Christopher N.

Yelp
Excellent wine bar. House wine was BOGO and it was really good. Service was top notch. Will be a regular here. Like the laid back atmosphere.
google avatar

WP S.

Yelp
This place is great. More of a social place to bring a friend or 7 kind of atmosphere. Had 1 tv so solos may awkwardly look awkward. Best selection of wines found down here to date but every city and block is different in Florida. The ladies there that day were super nice and knowledgeable whenever someone had a question before getting their pour. Also there is a nice nail spa next door, a pizza place that is great, and a paddy's all on this half of the center. 10/10
google avatar

Laura W.

Yelp
I love this place! Great selection of wines and snacks. The atmosphere is both cozy and relaxing. I highly recommend!
google avatar

Mike F.

Yelp
Wine bars aren't just for those snooty types! I'm sorry - I totally jumped to conclusions. Let me start off by saying, I know NOTHING about wine. The "tannins" and all that other jargon ... yeah, no idea. I sometimes mumble that word to sound smart, but I have no idea what it means. When my family wanted to hit up Grape Expectations, I thought, "Oh, HELL NO!" Sure, the name is awesome (props to you, Charles Dickens), but me? At a wine bar? Uh, me and wine bars are like pairing a white wine with steak - IT JUST AIN'T HAPPENING! Ok, so I was wrong. This place was so laid back. They actually had trivia during the day. I love trivia. Again, it's not something I'm good at, but I can play along. Trivia and alcohol is actually not a great combination for me, as I end up shouting out the wrong answers - very loudly and confidently, no less. There were tons of wines to try out - and get this - FOR FREE! You could probably sample wines all day and not even buy a single drink. As an added bonus, they even had complimentary Chex Mix! All in all, what a great little spot. I wish all wine bars could be this welcoming to the everyman like me who knows little to nothing about the sophisticated lifestyle.

Sara G.

Yelp
Love it! We don't usually out this far, but this wine bar was totally worth it! Amazing selection and the bar tender was great! Small cozy venue, but warm atmosphere, definitely coming back!
google avatar

Jenni C.

Yelp
cute little wine bar with great prices and happy hour specials. Extremely nice and welcoming staff, very crowded, but they do have outdoor seating. Plus, you can order and take next door to nail salon, or order from nail salon and they'll bring it to you. Lots of wines to choose from as well!
google avatar

Sally G.

Yelp
The best sangria and the best service! Free appetizers also! Outside and inside tables! Can't beat it!!

Tyrone C.

Yelp
One of a kind in Winter Haven! A great, cozy place with a big variety of wine choices and nice service. If you're a wine or beer fan, I would say that this place has one of the best selections in Winter Haven. You can also get some finger foods here too. This would be a nice place to meet up with friends for before or after dinner drinks.
google avatar

Mallory B.

Yelp
Love this place! Love their wine selection! Wonderful staff. I even love that they let your order wine and take it to the nail salon next door!

Greg R.

Yelp
OMGosh!!!! We were told about the "wine bar" near our hotel in Winter Haven . It was a marvelous experience. Friendly hosts, huge crowd, and pets outside to please all. Reasonably price wines, hors d'oeuvres, and a very friendly crowd. We'll definitely be back.
google avatar

Julie H.

Yelp
Great place, with a friendly staff. Their wine down is outstanding. I had 2 glasses of wine and complimentary buffet for just under $7.00. This place is a great value and the perk is how inviting you feel.
google avatar

Amy J.

Yelp
Wine bar in Winter Haven? I wasnt sure what to expect after the multiple wineries and wine bars I've been to. I was pleasently suprised. This is a pretty cool little place, definately not what i expected. Cool decor with a large player piano and a cool vintage chandelier. They also have a couple TV'S for games. Good wine selection and decent prices. They have happy hour everyday from 12-7 and all day Monday. We got the cheese and sausage plate. It was pretty good. I got a reisling and my so got a pinot noir. Both were good. They also have wine for purchase by the bottle. Service was good. Looks like they have special events different times during the month as well. Will be back again.
google avatar

Dan G.

Yelp
Two for ones until 7pm on weekdays. Friendly bartenders. A bit of an older crowd but I actually prefer that most of the time. I'll be back.
google avatar

Bryan T.

Yelp
The wine selection was solid. The happy hour was great! The added was the bar snacks and hor d'oeurves. what actually made the night was the staff of one for the whole place, Amanda. She didn't skip a beat with serving, knowledge of wine, and a smile the whole time!
google avatar

Edward P.

Yelp
Very nice wine bar, in a small plaza near Legoland. Definitely recommended for any couples around Winter Haven, my girlfriend loves wine so I brought her here. Food selection isn't the greatest, but wine is pretty good for options. The service wasn't 5 stars, our bartender kept talking to a friend at the bar rather than attending everyone equally but the wine we had made our experience worth it.

Noelle C.

Yelp
Grape expectations has a great atmosphere and friendly service. I would suggest trying the dessert wine called dragons blood. I wasn't a fan of their food but the wine was great.