You are currently viewing A Complete Guide To Visiting Winter Haven (After LEGOLAND)

A Complete Guide To Visiting Winter Haven (After LEGOLAND)

UPDATE: JUNE 2021: A sleepy bedroom community located in Central Florida, Winter Haven was awarded the “Number One Great Place in Florida” in 2019. I call Winter Haven home. In addition to boasting as the home of LEGOLAND Florida, what else is there to do? As a local, I can answer, “Plenty”! Here is my complete guide to visiting Winter Haven, Florida after LEGOLAND. Keep reading for tips on what to see, do, eat, and where to stay!

Nearby Attractions to LEGOLAND Florida:

What is there to do in the Winter Haven area after you have seen LEGOLAND? There is so much to do in the perfect Florida weather. 

Take a cruise through Winter Haven’s Chain of Lakes:

One of the best outdoor activities in Winter Haven is to cruise the Chain of Lakes.  Take in true Florida scenery aboard a pontoon boat. Enjoy the warm Florida sun all while seeing alligators, otters, turtles, bald eagles, Blue Herons, Pelicans,  Anhingas, White Ibis and much more! I recommend Living Water Cruises. This tour company provides several cruise options from 1 hour to full day tours. Several cruises include a stop for lunch or dinner. There is also an option for a romantic sunset cruise.  Have lunch on Lake Shipp at the Harborside Restaurant or take in the LEGOLAND fireworks from the water.  Cruise prices range from $24-$40.

Take a cruise on the Chain of Lakes

Tantalize your taste buds on a food tour:

Whether you are interested in brunch, happy hour, or sweet tooth food tour, Winter Haven Food Tours has a tour for every taste bud. Explore downtown Winter Haven on one of the 1.5 mile walking, outdoor food tours lasting approximately 2.5 hours. The “different food tasting locations fuse the elements of history, culture, and food.” All food tastings & drinks are included in the tour cost which range in price from $70-$139

Take Flight In a Bi-Plane

Waldo Wright’s flight service “offers a variety of vintage biplane experiences. Passengers can travel back to the 1930s to enjoy an authentic barnstorming ride in a New Standard D-25, or the 1940s for a more hands-on WWII adventure at the controls of a Boeing Stearman N2S-3.  Actually fly the plane. No flight experience needed! Flight costs range from $99 to $229 per person.

Get Out On The Water

If you are looking to rent a pontoon boat, jet ski, a kayak, or even a Craigcat, Winter Haven Water Sports can provide your entire family enjoyment on one of the chain of lakes in Winter Haven. In addition to renting a watercraft, you can partner with Winter Haven Water Sports for various types of tow-sports. Book a lesson and learn to waterski or wakeboard.

Paint a masterpiece to take home: 

Do you need a break from the Florida heat all while creating a beautiful masterpiece? Painting With a Twist Winter Haven provides step-by-step instructions to become the next Van Gogh. Led by skilled artist, classes provide the art supplies and instructions. Looking for a family activity, girls night out, or a date night? Painting with a Twist is fun for all ages.  Check their schedule to find the perfect art class for the occasion. Prices range from $25-$50.

Paint a Masterpiece at Painting With A Twist

Take in a show:

The Historic Ritz Theater located on Central Avenue in Downtown, Winter Haven, originally opened in 1925, is a venue for fantastic talent year-round.  See a Broadway play, musical act, comedy, and magic show. The Ritz has an array of shows that will thrill everyone.  Ticket prices range from $15-$50.

Theater Winter Haven, located on Cypress Gardens Boulevard, has been called “one of the best community theaters” and hosts over 120 performances per year. Check out a Broadway play, a young person performance, or a Tribute series at the newly renovated theater.

The Ritz Theater in Winter Haven, FL

Visit Historic Bok Tower Gardens:

Located outside Winter Haven, in Lake Wales, Bok Tower Gardens is a full day experience. Adult admission at $15 and child admission of $5 includes access to all Garden areas, entrance into the new children’s garden Hammock Hollow, and the 3.5 mile pine trail preserve hiking trail.

Their website describes historic Bok Tower Gardens as ” one of the greatest works of famed landscape by architect Frederick Law Olmsted, Jr. The meandering, historic landscape garden was designed to be a contemplative and informal woodland setting offering a series of romantic recesses and tranquil resting spots, picturesque vistas and breathtaking views of the Singing Tower.”

The highlight of a visit is to hear the beautiful carillon play its magical tunes while standing overlooking all of Lake Wales!

Free Things To Do Near LEGOLAND Florida:

Ready for fun but looking to save cash? Here are some ideas for adventure when visiting Winter Haven without having to spend any money.

Catch a free ski show: 

Did you know Winter Haven, Florida is the Ski Capitol of the World? While visiting, why not take in a free ski show by the famous Cypress Gardens Ski Team on Lake Silver? This free show is provided to the community on the third Saturday of each month. The show features water acrobatics and dare devil stunts. Check their website for a detailed schedule.

Visit the Splash Pad at the Trailhead Park:

The Trailhead Park is one of Winter Haven’s nicest parks for children. The splash pad, with newly equipped non-skid rubberized padding, is a hit to cool off this summer. Open daily from 10-7 p.m., come visit to cool off, bring a picnic lunch, and play on the amazing playground equipment.

The Splash Pad at Trailhead Park is free

Window Shop And Stroll Through Central Park:

Stroll the brick lined streets of downtown Winter Haven. Window shop at stores such as Little Studios Interiors or The Shop. Take in the beautiful Florida weather as well as eclectic art while meandering through Central Park. Many local bars and restaurants can be found in this area if you work up an appetite.

Take a Walk On The Wild Side At Circle B Bar Reserve:

Visit Circle B Bar Reserve located on Lake Hancock. This former cattle ranch, on over 1,200 acres, is now a nature reserve consisting of hiking trails and wildlife. Boasting nine hiking trails, you will be sure to see at least one Florida alligator, birds, and a variety of ecosystems. The trails are open every day of the week from 6:30 a.m. until 6:30 p.m. The Discovery Center provides educational resources for families as well as restrooms. It is open Tuesday-Saturday: 9 a.m. to 4 p.m. and Sunday: 12 p.m. to 4 p.m.  

Florida Alligator at Circle B Bar Reserve

RELATED: Five Family-Friendly Things To Do In Winter Haven, Florida

Best Restaurants in Winter Haven, Florida

There are so many great restaurants to try in Winter Haven.  Here are just a few:

Breakfast Restaurants

Egg Haven

Egg Haven is centrally located and offers affordable comfort food for breakfast and lunch. You will not leave the restaurant hungry with extremely large portions.

N + 1 Coffee Shop

Are you in need of a pick me up?  Check out the new N + 1 Coffee shop. Beautifully decorated in farmhouse décor, sit back and relax while sipping on a Rose or Chai Latte.

Haven Coffee Roasters

A new coffee shop located on 3rd Street in beautiful Downtown Winter haven, Haven Coffee Roasters will have you thinking of coffee as more than just a caffeinated beverage to get you through your day. Try a specialty coffee brew like a cookies and cream cold brew partnered with a pastries. Not a traditional coffee shop but instead an experience, you can enjoy live music or even a yoga class. Check their Facebook page for an updated schedule.

Lunch and Dinner Restaurants


Floridinos has delicious, affordable Italian dishes and pizzas. Try the pizza mufffins and the antipasto salad, you will not be disappointed!  Did you know Floridino’s holds the title for creating the largest calzone in 1991? The calzone was 409 feet, 1 inch!


Are you looking for a beautiful venue for lunch or dinner with view of Lake Shipp? Harborside is located right on the lake with large glass windows for a view of the perfect sunset.  The food is amazing with choices of fresh seafood, steaks, burgers, and pasta. I recommend Harborside’s Fish Sandwich.  It is massive so you can share it!

The Harborside Fish Sandwich


A farm to table restaurant located in downtown Winter Haven, Nutwood’s menu is like none other. This is not your typical restaurant. The entrees are made with fresh ingredients from local farms, ranches, and specialty food purveyors. Nutwood specializes in unique recipes such as mussels, grilled Spanish Octopus as well as Prime Culotte steaks and Potato Gnocchi Carbonara. They are open for Brunch on Saturdays from 10:30-1:30 p.m. Check out their website but beware you will probably begin to salivate.

Arabellas Ristorante

Arabellas Ristorante on Central Avenue in Downtown Winter Haven serves Italian and Mediterranean dishes for lunch or dinner. Have a cocktail at the Ave Bar or grab a slice of pizza at the Bistro located next door.

Tempo 1930

Do you love Blues and Jazz music? You must visit Tempo 1930 Friday through Sunday evenings for an array of jazz and blues music. The restaurant is named for the deep history of Blues and Jazz as well as the date when George Jenkins opened the first Publix in Winter Haven. Food choices are inspired by New Orleans with choices to include a muffuletta sandwich and etouffee.

Fire Restaurant

Fire Restaurant, located downtown on Central Avenue, is home to fresh food choices from steak, seafood, to smoked wings. They advertise they are a “mix of traditional and modern cuisine”. The restaurant was recently remodeled and there is a hip outdoor patio area if you just want to relax with a cocktail.

Hotels in Winter Haven

If you are looking for a budget-friendly place to stay while visiting Winter Haven, there are several chain hotels in Winter Haven to include a Courtyard Marriott and Holiday Inn.  LEGOLAND Florida has two hotels associated with the theme park: The LEGOLAND Florida Resort and the LEGOLAND Beach Retreat.  The LEGOLAND Florida resort, on the property of LEGOLAND, is rated a “5 Gazillion star hotel” housing over “two million LEGO bricks in the over 2,000 LEGO models throughout the hotel”.  The Beach Retreat, positioned on Lake Dexter, offers sun, sand, and fun for children and parents!

The LEGOLAND Hotel located in Winter Haven

RELATED: Are you looking for other Florida attractions? Check out our reviews of attractions and hotels in Florida.

Night Life in Winter Haven

The sleepy town awakens in the evening. Take a visit to downtown Winter Haven and visit several bars all within walking distance. Create your own pub crawl. Add dinner at one of the restaurants also within walking distance.

Grove Roots Brewery:

Started with a mission of “creating inventive, artisanal beers inspired by the traditions and tastes of Central Florida’s citrus past”, the brewery has grown to include a multitude of flagship beers and seasonal options which you can now find at local bars and pubs on tap as well. 

Grove Roots Brewing, Winter Haven, Fl

Some of our favorite beers are the Slanted Ladders White Pale Ale, Wakes of Grain Amber Ale, and the Rind and Shine Citrus Witbier.  My selection of choice is 6 a.m. Pickers Breakfast Stout, dark and full bodied with a mouthful of chocolate and coffee in every sip. 

Bring your kids and your dogs, this brewery is fun for all!

RELATED: 6 Of The Best Breweries in the United States

Barrel 239: 

Barrel 239 is Winter Haven’s first whiskey bar.  With specialty cocktails, a wide array of whiskeys and bourbon, as well as other spirits, Barrel 239 is the place to go for “liquid sunshine” in the Sunshine State.

Union Taproom:

Union Taproom is a self-pour bar featuring 40 taps with craft beer, cider, wine, cold brew, and Kombucha.  Pay by the ounce; try them all! The selection on tap changes frequently so every time you visit is a new experience.   Union Taproom is family and dog-friendly.  In 2021, they have opened they own pizza restaurant, Union Pizza, with some delectable and unique flavors. On Sundays, try a Brunch Pizza loaded with white sauce, breakfast sausage, bacon, hash browns, scallions, a fresh cracked egg and hollandaise sauce!

Union Taproom is a self pour bar in Winter Haven

Jensen’s Corner Bar:

Come in for a cocktail, a craft beer, and listen to live music on the back patio at Jensen’s Corner Bar. This laid-back, smoke free,  boutique bar is the perfect spot to chill with friends.  Grab a delicious burger at Adler’s.

Jesse’s Lounge:

Jesse’s Lounge is the sister bar to Jensen’s Corner Bar. Located right next door with a walkway between the two establishments, Jesse’s offers a more rock n roll feel if you are looking for a party! Looking to jam? Be part of “Jim and Judy’s Big Ass Jam” on Wednesdays where all musicians are welcome to participate.

Central Tavern:

Take in the game on televisions while drinking a beer at Central Tavern.  Grab a table in the outdoor patio and take in the sights of Winter Haven’s Central Avenue while enjoying a specialty cocktail.  If you are visiting on the first Sunday of the month, enjoy a free brunch buffet and pay only for a Mimosa and Bloody Mary bar.

The Bloody Mary at Central Tavern, Winter Haven

The Social Cocktail Lounge

Visit The Social Cocktail Lounge. With a speakeasy, piano bar vibe, this bar serves some amazing specialty cocktails. The vibe of the lounge is a combination between jazz bar and modern. Try a smoking old fashion and listen to live music.

What Is The Best time to Visit Winter Haven?

Any day is a great day to visit Winter Haven. With an average temperature between 70 and 90 degrees, Winter Haven is truly a haven from the winter cold.  Relax by a pool, take a cruise on the chain of lakes, or have a beer at Grove Roots!

Fun Facts about Winter Haven

Here are a few fun facts about Winter Haven, Florida:

  • In 1936, Winter Haven became the home of Cypress Garden Theme park, the first theme park in Florida
  • Winter Haven is the water ski capitol of the world.
  • Known as “The Chain of Lakes”, Winter Haven has 41 lakes in and around its limits.
  • George W. Jenkins opened the first Publix Supermarket in Winter Haven in 1930.
  • Kenny Brokenburr, Olympic Gold Medalist in 2000, was born and raised in Winter Haven.   

In Summary:

I have shared my favorite things to do, see, eat, and stay in this complete guide to visiting Winter Haven, Florida. Winter Haven has a host of fun things to do. Whether you are visiting Winter Haven for a day or a week, there is plenty to entertain you.  If you are looking for a haven from the harsh winter, look no further. Winter Haven is waiting to welcome you!  

Have you visited Winter Haven? If so, what was your favorite thing to do?

Locals, have I forgotten to mention anything amazing our town is known for?

Drop a comment!


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