Last Updated on March 26, 2024
Looking for the best things to do in Winter Haven? Don’t miss this great collection of ideas.
Approximately 15 miles east of Lakeland, 50 miles east of Tampa, and a short drive away from Lake Wales (home of Bok Tower Gardens), this charming Central Florida town is located in Polk County.
Winter Haven is best known for its Chain of Lakes and for being the location of one of the original Florida roadside attractions, Cypress Gardens, which is still open and is now a part of LEGOLAND Florida Resort.
These are our recommendations on the best activities in Winter Haven, Florida, including places to eat, shop, and stay during your visit.
From exploring botanical gardens and freshwater lakes to riding roller coasters to eating delicious food and more, check out all the best places you can visit on a trip to this beautiful Florida town.
Fun Things to Do in Winter Haven FL
Table of Contents
Chain of Lakes
Visiting the Chain of Lakes is one of the best outdoor activities to do in the area. Once you see them, there’s no doubt as to why the city is the water ski capital of the world! There are many ways to explore these bodies of water.
You can relax on a scenic boat tour with The Living Water Boat Cruises or take control and rent a pontoon boat from Winter Haven Water Sports.
Nature lovers might prefer to rent a paddleboard or take a paddleboard tour with PaddleBoard Winter Haven.
Chain of Lakes is open daily.
For more information, visit the official Winter Haven Chain of Lakes website.
Chain of Lakes Address: 684 4th St NW, Winter Haven, FL 33881 (Chain of Lakes Downtown Trailhead Park)
LEGOLAND Florida Resort
LEGOLAND Florida Resort is the largest LEGOLAND Park in the world. There are tons of fun things to do at the LEGOLAND theme parks – including visiting their water park and the new Peppa Pig Theme Park.
The parks have many LEGO-themed rides, attractions, shows, and more, making this a great place to visit with the entire family.
LEGOLAND Florida Resort is open daily at 10:00 am. Closing times vary; please check the official website for current hours.
For more information, visit the official LEGOland Florida website.
Legoland Florida Address: 1 LEGOLAND Way, Winter Haven, FL 33884
Cypress Gardens
Though Cypress Gardens is technically now part of LEGOLAND Florida Resort, it has been in the city since way before LEGOLAND opened.
Cypress Gardens dates back to the 1930s. It was opened on January 2, 1936, by Dick Pope Sr. and his wife Julie.
Initially established as a botanical garden, it evolved into Florida’s first theme park.
The attraction quickly gained fame for its beautiful gardens, water ski shows, and the Southern Belles who became synonymous with the park’s image
The historical botanical gardens have plants and trees from all over the world.
Enjoy strolling through the walking paths and see a giant Banyan tree that was planted here as a seedling over 80 years ago.
Cypress Gardens is open during LEGOLAND Florida Resort operating hours and is part of the regular admission price.
They open daily at 10 am. Closing times vary; please check the official website for current hours.
For more information, visit the official LEGOLAND Florida (Cypress Gardens) website.
Cypress Gardens Address: 1 LEGOLAND Way, Winter Haven, FL 33884
Featured in: 9 Old Florida Attractions That Continue To Spark New Memories
Cypress Gardens Water Ski Team Free Show
On the third Saturday of each month, the Cypress Gardens Water Ski Team has a free water ski show on Lake Silver at Martin Luther King Jr. Park.
The Cypress Garden water ski shows started in 1943 and ran until 2009.
The water ski team helped Winter Haven earn its title of “Water Ski Capital of the World,” breaking many World Records in the decades the shows ran.
Now, the Cypress Gardens Water Ski Team hosts a free, family-friendly water ski show that continues to amaze Central Florida audiences.
In addition, it passes along the art of performative water skiing to future generations.
Make sure to get there early to find a great spot and see the impressive performances that the city is known for.
For more information, visit the official Cypress Gardens Water Ski Team website.
Cypress Gardens Water Ski Address: Lake Silver at Martin Luther King Jr. Park, 200 S Lake Silver Dr, Winter Haven, FL 33881
Marshall Hampton Reserve
Marshall Hampton Reserve is a Polk County reserve on the northeast section of Lake Hancock. The 1100-acre area includes flatwoods and hardwood forest wetlands.
Explore two loop trails that take you through different environments where you can see local flora and fauna.
Hiking and jogging are permitted on the trails. You might even be able to see native wildlife, such as alligators, Gopher Tortoises, and Barred Owls.
Marshall Hampton Reserve is open daily from 6 am to 6:30 pm Standard Time and daily from 5:30 am to 8 pm Daylight Saving Time.
For more information, visit the official Marshall Hampton Reserve website.
Marshall Hampton Reserve Address: 3115 Thornhill Rd, Winter Haven, FL 33880
Theatre Winter Haven
Theatre Winter Haven is a community theater that was established in 1970.
The theater is a nonprofit entity that puts on over 120 performances a year of shows like Hairspray and Little Shop of Horrors.
They produce a five-play MainStage subscription season, as well as other series.
Check out the show calendar to see what will be playing during your visit.
During a MainStage Production, the Theatre Winter Haven box office is open Tuesday through Friday from 1 pm to 4 pm.
For more information, visit the official Theatre Winter Haven website.
Theatre Winter Haven Address: 210 Cypress Gardens Blvd SW, Winter Haven, FL 33880
Additional Things to Do in Winter Haven
Willowbrook Golf Course
Willowbrook Golf Course Address: 4200 FL-544, Winter Haven, FL 33881
Incredibowl Entertainment
Incredibowl Entertainment Address: 2010 Dundee Rd, Winter Haven, FL 33884
Places to Eat in Winter Haven
Harborside Restaurant
Harborside Restaurant is a waterfront restaurant located next to Lake Shipp. This place offers beautiful views of one of the chain of lakes the city is known for.
The restaurant serves lunch and dinner, with a menu that includes many different seafood dishes, as well as steaks, ribs, and pasta.
For dessert, try their iconic Harborside Brownie Sundae, which comes with double chocolate fudge brownies, and Haggen-Dazs vanilla ice cream. It is topped with whipped cream, chocolate sauces, and cherries.
They also have a Florida favorite, key lime pie.
Harborside Restaurant is open Sunday through Thursday from 11:30 am to 8 pm, and Friday and Saturday from 11:30 am to 9 pm.
For more information, visit the official Harborside Restaurant website.
Harborside Address: 2435 7th St SW, Winter Haven, FL 33880
Harry’s Old Place
Harry’s Old Place is a fine seafood restaurant with lakefront dining.
Located beside Lake Ned, the restaurant has been open for over 30 years and is known as the best spot in the city to get seafood.
Their menu includes fresh fish and seafood entrees, as well as steak, chicken, and tasty sides like potatoes, grits, and rice.
Desserts include a delicious assortment of pies: key lime pie, peanut butter pie, and coconut cream pie, in addition to cheesecake and their brownie sundae.
Harry’s Old Place is open Tuesday through Thursday from 11:30 am to 8:30 pm, Friday from 11:30 am to 9 pm, Saturday from 4 pm to 9 pm, and Sunday from 11:30 pm to 8 pm.
For more information, visit the official Harry’s Old Place website.
Harry’s Old Place Address: 3751 Cypress Gardens Rd, Winter Haven, FL 33884
Ovation Bistro and Bar
Ovation Bistro & Bar is a local chain known for being the best smokehouse in Central Florida.
The restaurant menu includes classic grilled selections like steaks, ribs, and brisket – all boldly seasoned and smoked in-house daily.
Try their sweet selections like the moist Pineapple Upside Down Cake, served with a pineapple ring and a decadent brown sugar sauce.
They also have a bar menu of draft beers and specialty cocktails.
Ovation Bistro and Bar is open Sunday from 12:00 pm to 9:00 pm, Monday through Thursday from 11:00 am to 9:00 pm, and Friday and Saturday from 11:00 am to 10:00 pm.
For more information, visit the official Ovation Bistro & Bar website.
Ovation Bistro & Bar Address: 7130 Cypress Gardens Blvd, Winter Haven, FL 33884
Nutwood
Nutwood is led by chef and owner Steven Rojas, who has over 20 years of experience in the culinary industry.
He has worked in restaurants in Los Angeles, Chicago, San Francisco, and San Diego, to name a few.
The Nutwood dinner menu is a 3-course innovative experience, with a variety of options for starters, entrees, and desserts, which update frequently.
There is also a Sunday brunch menu with delicious options.
Nutwood is open Wednesday through Friday from 11:30 am to 2:00 pm and from 5 pm to 9 pm Saturday from 5:30 pm to 9:00 pm, and Sunday from 10:30 am to 2 pm.
For more information, visit the official Nutwood website.
Nutwood Address: 132 Avenue B SW, Winter Haven, FL 33880
Additional Places to Eat in Winter Haven
Andy’s Drive-In and Igloo
If you are looking for authentic Winter Haven, look no further than Andy’s Drive-In and Igloo. You can enjoy a variety of menu items at the indoor dining restaurant.
If you don’t want to dine inside, order a specialty frozen treat from the window.
Andy’s Drive-In Igloo Address: 703 3rd St. SW, Winter Haven, FL 33880
Arabellas
Dining isn’t just about the food. It’s also about the ambience and Arabellas offers just that. Enjoy a variety of delicious food items as well as a relaxing evening.
Arabellas Address: 346 W Central Ave, Winter Haven, FL 33880
The Fire Restaurant
The Fire Restaurant is well-known for its Cuban sandwiches. Locals also brag about their bottomless mimosas.
If you are looking for a delicious sit-down stop in Winter Haven, don’t miss this location. Not in the mood for dinner? No worries, they have an amazing breakfast menu.
The Fire Restaurant Address: 325 W Central Ave, Winter Haven, FL 33880
Manny’s Chophouse
If you are looking for an authentic steak dinner, look no further than Manny’s Chophouse. Enjoy delicious flavors and a location that is sure to make you happy.
Manny’s Chophouse Address: 1100 3rd St SW, Winter Haven, FL 33880
Places to Shop in Winter Haven
Downtown Winter Haven
Downtown Winter Haven is a great place to do some shopping!
The downtown area has plenty of retail stores to check out.
417 Boutique by Cate sells stylish clothes and accessories. Calypso’s on Central is a holistic health store.
Wander the quaint downtown streets and see what unique selections you can find at the shops in this cool district.
Downtown Winter Haven is open daily. Hours vary by store.
For more information, visit the official Main Street Winter Haven website.
Main Street Winter Haven Address: 254 W Central Avenue, FL 33881
Sherman’s Antiques
Sherman’s Antiques is a huge, 10,000-square-foot antique mall.
If you are looking for antique or vintage furniture and home décor, make sure this is on your list of places to stop in Winter Haven.
There are also tons of art and knickknacks spread out throughout the store. It’s always a fun adventure combing through these treasures.
You’ll more than likely find something that’s one-of-a-kind to take home with you.
Sherman’s Antiques is open Tuesday through Saturday from 10:00 am to 5:00 pm and Sunday from 12:00 pm to 5:00 pm.
For more information, visit the official Sherman’s Antiques Facebook page.
Sherman’s Antiques Address: 1103 6th St NW, Winter Haven, FL 33881
The Village Sampler
The Village Sampler is a shop in Downtown Winter Haven that sells a variety of vintage and antique items, as well as handcrafts.
The shop is ever-changing and a great place to find seasonal décor and gifts.
Check them out when you are in the area. You might happen upon some cool and unique items to take home with you!
The Village Sampler is open Monday through Friday from 10 am to 4:30 pm and Saturday from 10 am to 5 pm.
For more information, visit the official The Village Sampler Facebook page.
The Village Sampler Address: 155 Avenue B SW, Winter Haven, FL 33880
The Hippie Suitcase
The Hippie Suitcase sells a uniquely curated collection of items that are sure to be your next favorite. With jewelry, plants, vintage clothing, and more, you are sure to find something you’ll love.
Stop and talk for a while with the owner of the shop after shopping. She knows the area well and is happy to answer any questions you might have.
The Hippie Suitcase Address: 300 1st St S, Winter Haven, FL 33880
The Red Geranium
The Red Geranium is just down the street from Downtown Winter Haven.
The shop has been voted the #1 Gift Shop & Clothing Boutique in Winter Haven for three years in a row, according to Haven Magazine.
They sell everything from home décor to furniture to clothing, accessories, and gifts.
Visit this idyllic shop and see why they continue to be voted #1 in the city.
The Red Geranium is open Monday from 11 am to 5 pm and Tuesday through Saturday from 10 am to 5 pm.
For more information, visit the official Red Geranium Facebook page.
The Red Geranium Address: 605 E Central Ave, Winter Haven, FL 33880
Additional Places to Shop in Winter Haven
Curves Consignment
Curves Consignment is a plus-size-only consignment shop in Winter Haven. They offer a variety of beautiful clothing options for full-figure shoppers.
Curves Consigment Address: 251 Ave A SW, Winter Haven, FL 33880
Treasure House Antiques and Collectibles
Don’t skip Treasure House Antiques on your next shopping day. Every corner you turn will help you to discover something new.
Walking through the treasure house is like a little treasure hunt.
Treasure House Antiques & Collectibles Address: 232 6th St NW, FL 33881
Cool Places to Stay in Winter Haven
LEGOLAND Hotel
If you plan to visit LEGOLAND on your trip, it makes sense to stay at LEGOLAND Hotel. The resort has a lot of kid-friendly amenities.
The hotel has separate kids’ sleeping areas with different LEGO themes, entertainment, and workshops.
It is a short walk away from LEGOLAND Theme Park. The resort also offers a large heated pool, as well as free parking and a daily breakfast buffet.
LEGOLAND Hotel is open daily.
For more information, visit the official LEGOLAND Hotel website.
Legoland Hotel Address: 1 LEGOLAND Way, Winter Haven, FL 33884
Camp Margaritaville
Camp Margaritaville is another local area lodging option in the Winter Haven area.
Located on Lake Myrtle in the town of Auburndale, it’s only 17 miles from LEGOLAND Florida.
An RV and cabin oasis with plenty of options for the whole family, the property has spacious cabana cabins, motorhome suites, RV sites, and rental campers.
You get a scenic space with gorgeous views of the water and surrounding area. The camp has picnic tables, RV hookups, pools, parks, and more.
Camp Margaritaville is open daily.
For more information, visit the official Camp Margaritaville website.
Camp Margaritaville Address: 361 Denton Ave, Auburndale, FL 33823
Additional Places to Stay in Winter Haven
LEGOLAND Beach Retreat
Legoland Beach Retreat Address: 1 LEGOLAND Way, Winter Haven, FL 33884
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