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    The Chapman

    4.6 (146 reviews)
    Open 11:00 am - 10:00 pm
    Updated 3 months ago

    The Chapman Photos

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    THE CHAPMAN ATMOSPHERE

    What's the vibe?
    Moderate noise
    Trendy
    Intimate
    Romantic

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    Recommended Reviews - The Chapman

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    Reviews With Photos

    Espresso Martini
    Alessandra C.

    Second review, now after trying a different cocktail, an appetizer and an entree (coincidentally, both vegetarian). - Coco dancer: jalapeño infused tequila, coconut milk, elderflower, lime. A 3 step experience: first I tasted coconut with elderflower; then the punch of lime and tequila; then, the lingering spiciness of the jalapeño. 10/10. - Bang Bang Lion's Maine: an incredible vegetarian take of bang bang chicken. Extremely well executed. The Lion's Maine tasted just like and had the texture of chicken. - Involtini: I asked about the Portobello mushroom burger and the server recommended this one instead. So glad I followed her advice. The long ingredient list speaks for itself: eggplant, zucchini, raisins, pomegranate, crispy garbanzo, basmati rice, coconut curry, yogurt, pistachios, mint, house spices. I think I also saw and tasted some fine carrots slices in it. It was extremely flavorful and fun to eat. Who would have thought that an Indian Mediterranean vegetarian dish could deliver that much? The Chapman keeps delivering in all 3 Yelp elements (food, service and ambiance) and is my current favorite restaurant in WP.

    Amber S.

    This was probably one of the best meals I have ever had. Came here yo celebrate my spouses 40th. We ordered the facaccia rolls, wagu steak, and swordfish. Everything was delicious, the wagu melted in our mouths and the swordfish was cooked to perfection. The real winner though was the sweet potato mash that was served with the swordfish. I ate it so slowly hoping to pick up on the ingredients, but just ended up elongated my enjoyment of it.

    Juliemar R.

    Highly recommend working with The Chapman for a work event. We had our office holiday dinner here and MAN IT WAS AMAZING! Cocktails? 10/10. Salads? Delicious. Entrees? Juicy and perfectly cooked. Service? INCREDIBLE! I had never been here prior to coming for this event. Their private room was perfect for a party of about 15. It was intimate and of course, with the holidays, decorated beautifully. Even if it was a pre-fixed menu due to our party size, the options were great. I'm looking forward to coming back and trying the espresso martini among other cocktails on their menu.

    Christien B.

    Elegant spot on Park Ave, perfect for a brunch date! Everyone is super friendly and helpful in making recommendations. The weather was perfect for sitting outside and enjoying a few cocktails from the martini tower. You can choose two flavors, so we ended up doing the Spritz and the Espresso Martini. Both were delicious and not too sweet. By far my favorite salad in town, the Farmers LOL Chicken Salad. It's so full of veggies and perfectly cooked chicken, not dry at all! And ask for extra swicy bacon - it's a perfect blend of spicy and sweet. Also shared was the table side avocado toast which was a fun experience and topped with Hot Honey!

    Menu
    Madison L.

    We came in for Father's Day brunch and had a lovely experience. The restaurant is gorgeous. The service was absolutely fantastic. Our server Andres was very attentive and had great attention to detail. We shared the focaccia with citrus butter. It was fresh and fun. The bread was excellent. For my meal, I had the fish sandwich and a cup of corn soup. The fish was perfectly fried with a lovely zesty sauce and fluffy bun. The soup was delicious and very summery with a sweet corn and roasted jalapeño flavor. For my drink, I had the Game, Set, Matcha. It had lovely yuzu and paw paw flavor which mixed well with the grassy matcha. At the end of my meal, I enjoyed a rich cappuccino. Our waiter packed and labeled our leftovers for us and everyone wished my dad "happy Father's Day". We had a great time!

    Erin S.

    a MUST go in orlando. The chapman brings the ambiance vibes of elegance paired with taste! You have to stay for desert and get the cheesecake. They have a great patio as well. They have excellent service and it's always a good idea to go during magical dining. Extra point for their dog friendly patio

    Sydney W.

    Beautiful restaurant with great ambience! This restaurant has a super interesting menu and lots of references to Winter Park's history. We enjoyed the meal and strolling park avenue afterwards.

    Tini Tower
    Aimee P.

    We came to Chapman in Winter Park to celebrate a friend's birthday, and it did not disappoint! Chapman Avocado Tuna BOWL was a 10/10absolutely incredible. We also ordered the martini tree, which was super fun and really good. Great service, good music, and the perfect vibe for brunch. Can't wait to go back!

    Spicy Margarita and a mocktail
    Anna-Claire D.

    Great ambiance with multiple spaces to enjoy--full dining, a lounge area, and a seated full-service bar. They're especially known for their espresso martinis, which are a must-try. Each time we've gone, our waiter Derek has been incredibly knowledgeable about the entire menu. The food has always been excellent as well.

    The coco drink
    Gaby B.

    The vibe of this place was out of this world. Nice music, pretty decor, comfortable seating whether at the bar / lounge type of area or for dinner. Didn't get to eat here but the drinks were delicious and creative! The service was top notch for sure. I will be returning for their brunch and expresso martini tree.

    Valentine's day Prix fixe, Steak and scallops
    Hannah R.

    We went to the Chapman for the 3rd time this past weekend for Valentine's day. Always a good experience, good vibe, good service, and great food. Some of the drinks weren't our favorite, and they ran out of the crème brûlée when we already ordered the prix fixe, that was disappointing. Scallops and steak were great, LOVED the truffle mashed potatoes with the steak. We will return.

    Ribeye
    Breaunna S.

    I've been waiting to try this place for a while and I was more than impressed. Let's talk about the reason we're all here--the food. Exceptional. My party and I had a variety of appetizers and main courses and everyone more than enjoyed themselves. I had the bang bang mushrooms, the lobster flatbread and the ahi tuna for an appetizer--all of which I recommend. The ribeye was moist and flavorful, and the sides were all delicious. Portions can be seen as on the smaller side but I think they're just enough. With that being said, maybe don't share fries. My party enjoyed themselves drinks as well. The seemed to have a wide selection on wines as well as a whole section dedicated to different old fashions. The other mixed drinks were commented to be good as well. The service was also fantastic. Our servers were very attentive, even for a big party of ~20 on a weeknight. I can't wait to recommend this place to others and take some friends again.

    1882 Cuban Sandwich with  Black Bean Soup

    Located along the iconic stretch of the Avenue, The Chapman offers a delightful chic dining experience in the heart of Winter Park. From the moment we arrived, the warm welcome and service set the tone. Austin, our server, was an absolute gem--attentive, and flawlessly in sync, delivering hospitality that polished the entire experience. Service like this makes a lasting impression! The menu, created by chef Clifford Pleau, is locally sourced, delivering on flavor and plating, with fresh, vibrant Florida-centric (on the menu: 1882 Cuban sandwich and black bean soup) and modern American flavors--bright, high quality ingredients, perfectly suited to the snazzy setting. The wine and cocktail (mocktails included) selection is thoughtfully curated and exceptionally enjoyable. Must order: Finger Food Starter: Crispy Bang Bang Lion's Mane $19 Local lion's mane mushrooms, ssamjang chili aioli, toasted sesame, snipped chives Avocado Tuna Poke Bowl with Crispy Noodles $27 Chapman's Filet Mignon Wedge Salad $35 Cast iron seared angus filet, baby iceberg, Campari tomatoes, avocado, Cheshire Farm spicy bacon, blue cheese vinaigrette Worth Sharing: Pull-Apart Focaccia Rolls with Orange Butter, Tasman Sea Salt $8 What truly seals the deal is the ambiance. Inside the stylish dining room, guests are seated in large booths, banquettes, or tables on original Terrazzo floors (if you grew up in Florida, you understand the storied history here). We settled outside in the covered patio, (dog friendly) with the doors wide open and cool air flowing, it felt like the best of both worlds--al fresco dining without sacrificing comfort. It's that indoor-outdoor people watching high-energy vibe that defines dining on Park Avenue, especially on a perfect Florida day or evening. If you're someone who regularly dines at Boca or Atlantic Beer & Oyster, you'll be pleasantly surprised to learn The Chapman (named after Oliver Chapman, one of the three founders of Winter Park) is its sister Artistry restaurant--making it an easy choice when you're looking to try something new without straying too far from a trusted favorite. The Verdict: The Chapman isn't just another mainstay on the Avenue--it's a storied destination in its own right. Sophisticated yet comfortable, for those searching for the best restaurants in Winter Park or a new Park Avenue dining spot, The Chapman is worth adding to your list. The Plated Cappucino $15 Panna Cotta, coffee almond Crunch, Mascarpone Mousse with chocolate covered coffee beans (For more artistry, I would have loved more of the coffee beans, spilling out of the inverted coffee cup...) Worth the detour... even if it's just down the street, on the southern end of Park Avenue. The Chapman 500 South Park Avenue, Winter Park 407-635-1967 Parking tip: After 5 pm, you can park your car in the Winter Park City Hall parking lot across from the restaurant. Michi @worththedetour (Substack Review)

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    Ask the Community - The Chapman

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    The Courtesy - To go milk punch

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    The Courtesy is a cute cocktail bar, though this is my first time ever here and it's specifically…read morebecause I LOVE christmas so much and I couldn't pass up the opportunity to experience the holiday greatness this place offers. The decor speaks for itself, this place is absolutely decked out to the high heavens for Christmas and definitely worth a reservation and stop in ! but... be SURE to make a reservation because you may not be able to get in if you don't (best do it a couple days in advance if you can!) Rudolph's Replacement: 10/10 for cuteness (got it for the TRex cup) BUT this drink tasted like chocolate grass. if that's ur vibe, you'll love it. Christmapolitan: Not the cutest, average for looks just in a normal cute little glass, but guess what.... it was thebest drink we had!! 10/10 for flavor, loves it. Dancing Sugarplumb: Again not the cutest it's basic, BUT THE FLAVOR 9/10 The Krampus: the cup is killer. love it. drinks like a sippy cup, but for a Christmas demon. there is mezcal in this it's definitely on the smokier side, but even the mezcal haters at the table love it. 8/10 flavor if you like a little smoky and a tad bit of heat. All we had to eat was the pretzels with pimento - i was skeptical but wow, super good! All in all, would definitely recommend, you just have to plan to come here in advance and get that reservation!

    Always love to have festive drinks for the fall season and The Courtesy delivered! Made a…read morereservation for a birthday event for my bestie because we wanted an atmospheric themed spot with fun drinks for Halloween festivities after we had dinner nearby. Definitely make a reservation ahead because these themed pop ups that The Courtesy does book up quickly and you don't wanna miss out on it! Can't wait for the Christmas Holiday ones! Our first round of drinks were amazing and perfect choices of cup design or garnish. The only downside was when we ordered one drink there was confusing on whether it was up to the allergy request we had but it was fixed shortly after but I feel as if the server should have been more educated on it since it could have been avoided. Other than that the drinks were perfect, which my favorite was the Scream cocktail which came in its iconic Ghostface cup and went along with my outfit and Scream mask and knife I brought along with me. After another round of drinks we got their Trick or Treat shots which were definitely interesting and live up to their names for both shots! Definitely fit the vibe with the music, atmosphere and decorations around the bar which made an awesome spot for Halloween themed drinks to enjoy for the season!

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    We visited the trap on a Friday night around 8pm. A bunch of us had a reservation, but we had a…read morecouple no shows so we started without them. This place does a great job with getting everyone started and teaching you safety. We also added knives to the reservation. I love this place, everyone is there to have fun and they always have coaches around to help you improve your form if you have questions. Their bar is also great and they always make a good drink. It's got a nice sitting are to stick around and enjoy a drink after throwing too. I did dock one star because they wouldn't refund us for the 2 no shows, they said we could either take an extra half hour for the 4 of us or call the owner later, it just seemed more complicated that necessary. I would understand a non refundable deposit and then charging full for whoever shows up, but charging full for no shows seems odd. Either way I'd definitely recommend this place! It's great for friends or a date.

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    Visited on a weekday evening and it was pretty smooth from start to finish. Parking was easy, and…read morewe were seated right away. Service was consistent, and the food came out at a good pace. Everything tasted fresh and well-seasoned. Nothing over the top, just a really well-executed experience.

    We had family visiting from out of town, and we wanted to do a fun activity together. It was our…read morefirst time going to Jazz Tastings, and after our visit, it certainly will not be our last. This jazz lounge is tucked away in an unassuming shopping plaza. You're greeted by a red carpet at the entrance. When you enter, there are some nice round booths and other tables available with a view of the stage. The music was awesome. During our visit we saw a Grammy nominated trombonist along with a great drummer, bass player, and keyboardist. The music was great and had everyone dancing in their seat, with even a few dancing in the aisles. The food was also excellent. I wasn't sure what to expect and didn't have super high expectations, but the food beat my expectations. We shared some calamari, a spicy sautéed shrimp appetizer, and crab cake. They were all very tasty. Everyone ordered something different as their entree. We were all pleased with our meals. I ordered the Steak Frites. The steak was tender and juicy, and the truffle Parmesan shoestring fries were perfect. For dessert we shared the bread pudding à la mode and a slice of carrot cake. That banana bread pudding was phenomenal and the carrot cake was also really good. Our server was also very nice and did a great job handling our larger group. Overall, we were very pleased with our experience, and I would recommend giving this place a visit.

    The Chapman - lounges - Updated May 2026

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