Located just 50 miles east of Tampa and about the same distance southwest of Orlando, Winter Haven is the perfect location for retirees who are looking to get away from the big cities but still be close enough to visit whenever they want.
Winter Haven is also home to exciting outdoors and water sports opportunities, an award-winning community theater program, some of the best antique shopping in Florida, and a wide range of excellent dining options for all occasions.
Winter Haven History
The area that would eventually become known as Winter Haven was originally home to the Timucua and Calusa tribes. It was also inhabited by various Seminole tribes throughout the 19th century. Railroad expansion in the middle of that century brought the first settlers to the area which was eventually named Winter Haven because of its comfortable year-round climate.
While there was some growth in the area during the early 1900s, things really began to take off in Winter Haven following World War II. During this century, the town welcomed the very first Publix supermarket, a large citrus packing plant, and the visually stunning Cypress Gardens, which would eventually become today’s Legoland.
Winter Haven Lifestyle
The Winter Haven lifestyle is all about getting out on the water and enjoying more than 55 lakes that you will find across the region. That means that everything from waterskiing and wakeboarding to kayaking and standup paddleboarding is available here throughout the year.
One of the best ways to get acquainted with some of the local waterways in Winter Haven is to head out on a guided tour with The Living Water Boat Cruises or Captain Fred’s Airboat Nature Tours. Not only will this get you out on the water, but it will also get you close to some of the fantastic Central Florida wildlife in the area as well.
Winter Haven Culture
Theatre Winter Haven has long been the heart of the cultural side of the community. Here you will find one of the most decorated community theatre organization in all of Florida, and just wait until you see what they have planned for their brand new Chain O’ Lakes Complex!
There is also the Polk Theatre located right down the road in Lakeland, which almost always has an old film or live musical performance on its calendar.
Nearby Lakeland is also the home of Florida Southern College, which houses the largest single-site collection of Frank Lloyd Wright designs, and you can find some exciting vintage aircraft restoration projects happening at The Fantasy of Flight.
Winter Haven Shopping
Shopping for antiques is an extremely popular way to spend an afternoon in Winter Haven, and there are more than a few great shops to keep your treasure hunt going for about as long as you’d like. Sherman’s Antiques, The Village Sampler, and Treasure House Antiques & Collectibles are all must-see attractions for antique lovers.
For your modern shopping needs, a quick trip up to Lakeland will open up the possibilities to include just about any store you might be looking for, and the first stop on most of those shopping trips is going to be the Lakeland Square Mall.
Winter Haven Dining
If delicious food in a casual environment is what you are looking for, Nutwood should be at the top of your bucket list for dining in Winter Haven. This modern American restaurant boasts some high-end menu items at mid-range prices that keep your palate coming back for more. And since the weather is always great in Winter Haven, you can usually make use of their lovely patio seating.
Another favorite restaurant in the area is Harry’s Old Place, which is the classic Florida seafood restaurant that offers the perfect combination of casual environment and stunning views of the water. Their fried fish “blackboard” changes every day, and you can get their fresh catches prepared just about any way you like.
When you are ready for a special meal in Winter Haven, Arabellas is the ultimate destination. This high-end Italian restaurant offers all of your favorite dishes prepared perfectly in an environment that just screams “special occasion.”
With everything that Winter Haven has to offer, it is no surprise that it has developed a reputation as one of the best destinations for retirees. If you are looking for an option just outside of Tampa or Orlando, this lovely town offers the unique hybrid combination of both.