Had a nice visit to The Tipsy Skipper earlier this summer. I was first introduced to this place a few years ago when I visited Ocala for the first time. My fiancé has been coming here since the opening weekend, and takes me here each time we visit Florida and Ocala. The Tipsy Skipper is located near The Square in downtown Ocala. There is street parking nearby, and some various parking lots. The establishment does not have a designated parking area, but I had no trouble finding a spot nearby on this day. If you visit on a weekend or during a particularly busy time, you might have to spend a few more minutes finding a spot. We visited as a group of four on a Monday evening in July around 9 PM. Not a lot of places in this area are open on Mondays, but luckily this business is! There were a couple groups at the bar, but it was no way at all crowded. There is bar seating, as well as tables and chairs throughout the space. There is a more isolated front room, and then the main area where the bar is. The atmosphere is unique in this place. It is decorated like a beach/tiki bar, and the lighting is kept dim. The tables have candles, along with appropriate decor for the theme. They have several cocktails that go with the theme of the bar. This was my first time sitting at a non-bar seat in this place, and given that it was a Monday, I am not sure if this is typical or if at times they provide table service. However, we had to go up to the bar to order the drinks. Not a huge deal, but something to note regarding table service, especially on a slower weekday. There is no food here, it is strictly a bar. They have themed cocktails, as well as some beer, wine, non-alcoholic options, and various specials. I ordered directly from the menu this time, but I have visited before where the bartender can essentially make you a unique drink according to what you like. So, the possibilities for drinks here are really endless. I typically like to get a "fancier" drink when I come here, since it is such a fun experience to accompany the atmosphere of the place. This time, I enjoyed the O'ahu Skies, which was a cocktail of gin, lavender, and lemonade. Truthfully, I did not read the menu closely and did not realize the drink contained gin. I am not the biggest fan of gin, but I did enjoy this drink! It was perfect for a summer night. Another member of my party really enjoyed the Ciderboys Pineapple Hula Hard Cider. Everyone enjoyed their selections overall. I find the staff here to be consistently friendly and kind. This visit in particular, there was a female bartender who was sweet and courteous to both myself and our entire group. I have had other positive experiences with different bartenders on other visits. I would dare to say the staff here is top-notch and will take care of you! In terms of pricing, I believe it is fair for a speciality cocktail bar. The speciality drinks that come in the fun glasses cost, I would say $15 on average. There were specific $10 drinks, Happy Hours, and discounts if you bring the theater ticket from your show next door, so not every drink is that much. Additionally, beer and wine were priced as you would expect, so you could very well come here to enjoy the space and only spend a few dollars. I enjoyed this trip to The Tipsy Skipper, as I have enjoyed all my others previously. It is a spot I look forward to visiting each time we come to Ocala for an evening. I will most certainly return again on our next trip to the Sunshine State. read more

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Another review I swore I wrote years ago! It took us a while before we made it here when we first moved to the area. It was super busy when we went our first time and it was not during happy hour on several occasions we have visited. We live close and visited here a bunch the first 2 years we moved to Ocala and have visited less and less since then. There have been several occasions we have stood at the bar waiting not only to be greeted but also waited very long times to receive our drinks. In their defense, many times the bartenders were busy attending to patrons or making drinks. However, there were several times some bartenders were just talking to friends or messing around. The drinks here are super detailed so they take some time and TLC. I will say, most times our drinks taste delicious and the presentations are magnificent! The decor is so cozy and the ambiance is consistent. Hubs and I absolutely love Tiki themed bars and fell in love with Hawaii after our visit years ago so this place is perfect for us. We also like this place because they are open later than most places in town. We recently visited for a nightcap and it was definitely different. I recently had referred someone here because she was looking for Hawaii themed food (they used to serve food) and she informed me they did not serve food. That sucks because we always meant to try it but never did. Looked good. When we recently visited, they did not have physical menus and were referred to QR code cards on the bar. Our bartender was attentive and helpful with choosing a drink during our recent visit. He actually went out of his way to make the orange peel twist in a perfect manner. I appreciated that! I was going to suggest to hubs we have another drink and then a roach crawled across the bar. I discreetly informed the bartender of the dead roach I killed when we closed out and he took it away. Usually this place is clean and tidy so I was surprised to witness the roach. They do have seating outside as well but we usually sit inside to listen to the themed music. read more

Def like tiki adjacent in deco but the drinks are pretty good and they use the legit items. It was karaoke night so low on tiki vibes but I had a Saturn and a tropical itch. Tasty balanced and I would go back. Good deal for Ocala read more

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A fun spot for original tropical cocktails. Our bartender was attentive and walked us through our options. A great before or after dinner spot conveniently located a block from the Ocala Square. It was fun and the drinks were delicious. read more

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Was super excited to find that Ocala now has a legit real tiki bar. Amazing cocktails and amazing atmosphere. Definitely coming back next trip to Ocala read more

This place was so great! Me and my cousins all went out to downtown Ocala. It was the first time we all have been out together as we all live in different places. We stopped in the Tipsy Skipper and my cousin asked if he could DJ for free in there, and the bartenders said yes, which was so nice of them. We all had such a great time dancing to the music and buying drinks all night. The staff was so nice, I don't drink alcohol, so they were kind enough to make me mocktails and they were delicious! The rest of my family had pain killers and they said they were pretty good. It's a very cute place, it's cozy and such a great vibe. We stayed for probably 2 or 3 hours up until they closed. I would definitely come back here! read more

The Tipsy Skipper - Tiki Bars Near Me - Ocala, Florida

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Our absolutely favorite bar in central Florida!! The tiki cocktails are always so delicious and creative. A must stop!! read more

The Tipsy Skipper - Tiki Bars Near Me - Ocala, Florida

The drinks we had there were very tasty but pricey. Each specialty drink is about $15 bucks. The decor is very nice and the bartenders were friendly. Heads up--there are menus on the tables, but you have to order at the bar. Nice cozy place to enjoy tropical drinks. read more

The Tipsy Skipper - Nice decor - Tiki Bars Near Me - Ocala, Florida

If youre in Ocala visiting family, as I was, I can't recommend this enough. Got me through a family trip. On the craft cocktail side of tiki with a good local vibe. Nice tiki decor. Decor is a work in progress. If you're looking for a destination bar, some theater lighting will improve decor a bit. But as a local bar with very good tiki drinks, good company and nice tropical decor, it was exactly what I needed! read more

The Tipsy Skipper - Legit Mai Tai. If not a 44 Mai Tai, it was close enough for government work. - Tiki Bars Near Me - Ocala, Florida

Excellent, thank you. Google: DJ LB Young Chyna Hill. Will be back soon. Food, is a yes. read more

I'm a tiki afficionado and was delighted to discover the Tipsy Skipper on our last trip to Florida - this place is legit! If you're a rum nerd like me, you'll appreciate the selection of hard to find rums on the back bar that are available for neat pours. The tiki cocktails are top flight as well. Daniel was a mensch. We will be back as soon as possible. read more

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What an amazing little hole in the wall in Ocala. Absolutely amazing service and the ambience was to die for. The drinks were super good and it was an absolute amazing time. They have some bar snacks to nibble on but not a full menu. Such a good stop. My new favorite place! read more

The Tipsy Skipper - Tiki Bars Near Me - Ocala, Florida

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Cute tiki bar. We had half alcohol drinkers and have non-drinkers, but everybody found some thing on the menu for them.

My daughter and I had drinks there. The krafted drinks are amazing!!! We have been going there for years.

The least hipster bar in all of Ocala. Super laid back Hawaiian vibe. Mixologist, Sam, was superior to other bartenders on the square. Top Drink suggestions: pina coloda, Juan Mcclane and Miracle on Magnolia. Drinks are super flavorful and distinctly unique. Good times. good vibes. Great drinks. read more

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Avoid all drinks here-$15 drink -3sips of drink the rest was ice!!!! AVOID Standard snacks were OK read more

The Tipsy Skipper is a fantastic vacation away within Downtown Ocala! The entire experience is a vacation away to the islands for an exotic getaway. I ventured away with my wife and friend for an afternoon experience. The bar is truly an immersive experience. We sat at the bar where we were treated like royalty the entire time. We all grabbed multiple drinks each of them fantastic! I would absolutely recommend The Tipsy Skipper if you are looking for a great drink with great service! read more

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Super fun atmosphere. Step up from the usual tacky tiki bar. I was impressed with our bartender's knowledge of tiki culture and tiki bar industry in general. Beautiful glassware! The evening we were there, it was empty but it was a weeknight around 9pm. I would definitely return if I were in the area. Of the several bars we explored along that stretch of downtown this was by far my favorite. read more

The Tipsy Skipper is our neighborhood rum/tiki bar. I wouldn't say it's a dive bar but it has that familiar regular feel. Sam the bartender is awesome and Buck the owner is one of those few people that you find who is genuinely excited that you are at his bar. Their rum selection is solid and the food is great. The drink menu always has the standard tiki drinks but they also have seasonal drinks that are creative and delicious. read more

Nice little bar in downtown Ocala. Great for a date night, cozy little tiki style bar. Drinks were top notch and service is fast and friendly. read more

Drinks are exquisite! Fresh ingredients, awesome atmosphere and the perfect location. Bartender was super nice also!!! Highly recommend. Best drinks I've had around. read more

Love this place! Every single time it's top Notch service, thanks to Amy at Ivy on the square for telling us about this! read more

This bar is one of a kind! Sam made the best drinks and was so personable and happy to help us find drinks that suited our tastes. Each drink is unique and different, and the quality is well above average! Craft cocktails did not disappoint! The inside of the bar is a great atmosphere, friendly staff and such a great motif throughout. I would highly recommend stopping for a drink any day! I've seen that they have a good menu too! Haven't tried it but it looks great! And not just your average bar food for sure. I regret not taking pictures of our drinks because they were in the cutest glasses as well, definitely adds to the overall mood that is set when you walk in. read more

I am an Elite Yelper and have been a serious slacker this year. This was the spot that inspired me to write a dang review for 2021 on December 29th. This spot? It's a unique gem amongst the revitalized downtown Ocala. Also, these bartenders are the real deal and a drink is a piece of art to them. I reside in eclectic, St. Petersburg, FL. so I know a cool bar when I see one. I couldn't stop looking around at the cool decor. The fun, creative vibes and the first thing you notice when you walk in. I felt like Austin Powers or Elton John could come waltzing through the doors at any moment while I sipped on my Banana Bread Old Fashioned (order this!!!!) and I would be like, "Yes, it makes sense. This is my current reality and I like it here." You won't regret stopping in for a drink here. read more

Seem to have something for everyone's taste, not just funky strong rum-forward tiki options. Bartenders are knowledgeable and willing to tailor a cocktail to your taste. Nice dim classic tiki bar atmosphere read more

Just what Downtown Ocala needed, a tiki bar with the vibe and flavor of the islands. From the second you walk in, you are taken to your favorite beach bar and welcomed with big smiles, cold drinks, and wonderful decor. I can't wait to go back to The Tipsy Skipper! read more

The Tipsy Skipper - Craft Cocktail Menu - Tiki Bars Near Me - Ocala, Florida

Love this place. Great atmosphere and IPA's on tap. Great service. I see this bar becoming a very big part of the downtown nightlife scene.

Favorite bar in Ocala! Amazing drinks, moderate prices, and great ambience. I really love the theme and the service is always great. Highly recommend for folks visiting Ocala or anyone 21+ really. read more

Great staff, great cocktails and the decor, we'll come check it out for yourself it's amazing! read more

The Tipsy Skipper - Zombie! - Tiki Bars Near Me - Ocala, Florida

Don't know if it was the way we were dressed (after a wedding) or if it was because we're Latinos (everyone was very white) but the bartenders literally would look at us and serve every single person around us BUT us. After waiting 15 minutes to be served, we decided to go elsewhere. read more

Must have been an off night, or they simply do not want " old folks" in their place, but on Friday 12/9 I had the worst drink I have ever had.After waiting around 10 minutes to place our order in a nearly empty bar, I ordered the painkiller.Chock full of ice, barely any liquid in it. Really bad, worse than Chilis cocktails. Very dissapointed, it looked promising, As they say, one and done. read more

They change the menu often with lots of cool drinks, reasonably priced, friendly staff. Located in the middle of everything right downtown. I'm glad the replaced the barstools they're much more comfortable. This is a family owned business. They will be adding food soon. This place is great for hanging with friends, it's casual, unpretentious. And not so loud you can't have a conversation. Def read more

Bartender is lacking in customer care. We were there for Friday art fest. It wasn't sundown and had time to kill and place was only 1/2 occupied. So we decided to give it a go and enjoy a drink at the cute bar we'd found several months back. Drinks were top notch then and fish dip was tasty then as well. Fast forward to this second visit. Pitiful! You delivered our fish dip first, no napkins, stale crackers. As if that wasn't enough you preceded to chat with those at the bar who already had drinks. You delivered ours 1/2 hour later. You could have at least dropped off water to go with the stale crackers. Stating that you didn't have napkins and silverware because you shared a kitchen with the establishment next door is unacceptable. Get it together or you'll keep loosing customers. Never again. Save your money and go elsewhere. read more

Excellent selection of mixed drinks. Great, personable bartender. Stop off here before dining on the Square.

Absolutely 10/10, AMAZING hand crafted drinks. Gf had the o'ahu skies I had the guava overboard, I never like cocktails really but I'm still reeling over this drink. Bartender is awesome nice guy too, definitely going to be back often! read more

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This place is amazing amazing decor and rum drinks. With a very chill dark atmosphere!

One of my absolute favorite places to have a pre-dinner cocktail. And all of them are fabulous!

cutest drinks that also taste amazing, the vibe in there is also unmatched! the drinks are all the same price but well worth it! they also have the cutest cups and garnish's read more

All I can say is I enjoyed 2 of the best 'classic'Daiquiris I have ever been served....anywhere! Whether this level of taste/quality/effort will be consistent here....well, that could be doubtful....but mine were beyond great. Only the 'happy hour' price of $5.00 each keeps me from returning often...a little above my personal pay scale for a cocktail, but forgive me for living in the past...!! read more