Winter Haven is the second largest city in Polk County, Florida. The city was formerly an agricultural center, but over the past 1-2 decades has transformed into a largely residential and manufacturing city. Winter Haven is home to Legoland and the world-famous "Chain of Lakes". Visitor information can be obtained at the "Polk Outpost 27" (, 863-828-7655) on US 27 just south of I-4 if you're coming from Orlando, while the Winter Haven Chamber of Commerce is located at 401 Avenue B NW (, 863-293-2138).
The city celebrated its centennial in 2011. Settled in the 1880s, Winter Haven became a transport hub for the citrus industry in the early 20th century. Eastern Polk county has long been among the top citrus-producing regions in the country. Since there are a few dozen lakes in and around the city, the Chain of Lakes project to link many of them by canals was begun in 1915. Most of the current canals were built during the Great Depression by the Civilian Conservation Corps, although the original wood seawalls have rotted and been replaced by metal ones in recent years. In 1936, Cypress Gardens opened as the first commercial theme park in Florida. Cypress Gardens was famed for its water ski shows, Southern atmosphere, and lush gardens traversed by canals. The city was also home to Spring Training baseball, home to the Philadelphia Phillies (1928–1937), Boston Red Sox (1966–1992) and the Cleveland Indians (1993–2008). Cypress Gardens struggled financially and closed in 2003. Several successive owners added roller coasters and a water park, but it closed again in 2009 and was transformed into Legoland Florida, which opened in October 2011. The original botanical gardens (owned/protected by the county) and the water ski show (a pirate-based one) have been incorporated into the new park and Southern belles—made of Legos, of course—have kept the memories of the original Cypress Gardens alive. Winter Haven remains a small suburban city, but Legoland, the Chain of Lakes, and the many other nearby attractions make it a nice destination.
Winter Haven was named for its temperate climate. The climate is much the same as the rest of Central Florida (except coasts). Winters are mild, with highs in the 70s and lows in the 50s. Lows in the 30s are common after cold fronts and there are usually a handful of lows below freezing each winter, although that requires clear skies, so it usually warms very rapidly after sunrise (30 at 6am, 55 by noon is typical). Cold fronts occasionally pass by as squall lines, so tornadoes in December or January are not unusual. Snow is rare; the last measurable snowfall was in 1977, although sleet/wintry mix fell in an unusually cold January 2010. Summers are hot and humid, with highs around 95 and lows in the mid-70s. During the summer, onshore winds from both coasts travel inland, heat up, rise and build into thunderstorms, usually along a rough line. Lying in the center of the state, the line of storms (the "seabreezes") often collide and become severe, with tornadoes (small EF0-1s...not like powerful Plains ones), 50+mph winds, and hail possible. Strong storms are usually preceded by cooler winds caused by the rain-cooled air (cold air sinks) rapidly flowing away from the storm. The temperature after a strong thunderstorm passes can drop from 95 to 75 and since the storms can be fairly small, you can drive 5 miles and the temperature will drop from 95 to 75.
Winter Haven Municipal Airport is located on the far northwest corner of town (near Auburndale) and only handles general aviation.
The nearest major airport is Orlando International Airport, which is approximately 45 minutes away. Orlando has hundreds of daily domestic and international flights. Tampa International Airport is further away (about 1 hour 15 minutes), but has a simple layout and is very convenient airport to get in/out of quickly.
Brown's Seaplane Base off US 92 (, 863-956-2243).
Winter Haven is a stop along the daily AMTRAK Silver Star and Silver Meteor routes. If you plan to arrive by train, you should have friends/family at the station to pick you up or have the phone number for a taxi to call when you arrive. The station is a poorly-maintained covered platform with a small office and is in a fairly unpleasant area beside a warehouse. Fortunately the trains arrive during daylight, but it's not a very great place to wait for hours. An alternative may be to use the Lakeland station, 20 miles to the west. Station is located at 1800 7th Street SW. Office phone is 863-683-6368.
Winter Haven is easily accessible from US 27, US 92, & US 17.
From Orlando: Take Interstate 4 west to US 27. Take US 27 south for 20 miles and turn right onto Cypress Gardens Blv. From US 27, it is roughly 5 miles to Cypress Gardens, and 8 miles to the center of Winter Haven.
From Tampa: Take Interstate 4 east to the Polk Parkway. Exit onto State Road 540 ("Winter Lake Road") and follow the exit straight (east). After about 10 miles, make a left onto US 17. It is about 3-4 miles from here to the center of Winter Haven.
Most of Winter Haven proper uses a grid system consisting of lettered "avenues" running north-south & numbered streets running east-west. The center of this system is the intersection of Central Avenue and 1ST Street on the east side of the small downtown area. With respect to this intersection, the city's streets are named Northeast ("NE"), Northwest ("NW"), Southeast ("SE"), & Southwest ("SW"). The direction is very important for addresses! There can be 4 different locations with the address "100 Ave. A". With higher numbered streets/addresses, the distance between these locations can be several miles. The system is simple, but can be very confusing.
Winter Haven is served by two bus services. Winter Haven Area Transit (WHAT, ) has many routes throughout the town. Citrus connection, , serves Lakeland and several intercity routes between major towns in Polk County. Routes and information about both can be found at: 
Legoland Florida, 1 Legoland Way (Located off Cypress Gardens Blv. just east of Winter Haven), . Hours vary throughout year.. The second Legoland park in the US in addition to Legoland in California. The park primarily caters to children and families and features rides, sculptures/scenes, and shows based on the popular Lego building blocks. The site was home to Florida's first theme park—Cypress Gardens—until 2008 and several elements of the former park remain, including the botanical gardens and it's canals, the water ski show which made Cypress Gardens famous, and the Island in the Sky platform which rises 150ft to give you a 360-degree view of the park and Central Florida. From Orlando take I-4 east to US 27 (exit 55), head south for about 20 miles, turn right (west) on Cypress Gardens Blv. (SR 540) and Legoland will be on the left at the 5th traffic light. If you're staying in Orlando, Legoland operates a shuttle from the Orlando Premium Outlets parking lot($10/rt) leaving at 9am and returning at the time the park closes. $75 (Ages 13-59), $65 (Ages 3-12, 60+). edit
Street Audubon Center/Lake Region Audubon Society, (From Cypress Gardens ROAD, turn onto Lameraux Road and drive through the neighborhood and the entrance is on the left.), ☎ 863-324-7304, . Great birding location along with nature walk trails. Periodic events held for families.edit
Watersports and Winter Haven just go together. Within the city limits lie a couple dozen lakes with public access. Sixteen of these are connected by canals to form the Chain of Lakes. The Chain of Lakes is known for excellent fishing and regularly hosts local and national fishing tournaments. Water skiing, water tubing, and zipping around on jet skis (sea doos) are popular pastimes and parking at boat ramps is scarce on sunny weekends. Fishing permits are required to fish in any lake, river, or stream. They can be purchased at local WalMarts, marinas, bait and tackle shops, or through the Florida Fish & Wildlife Conservation Commission (, 888-FISH-FLO). The county publishes a guide to all the county's lakes (including public access sites)available at the Polk Outpost 27. Boat Ramps—concrete ramps and adjacent parking—in Winter Haven are at: Lake Blue North (off Lake Blue Dr.), Lake Cannon (off Lake Cannon Dr.), Lake Hartridge Park (20th St. off State Road 544), Lake Jessie (off Lake Jessie Dr.), Lake Roy (off S. Lake Roy Dr.), Lake Sears (100 Lake Sears Dr.), Lake Ship-W.G. Roe Park (2403 7th Street SW), and at Lake Summitt (off Lake Summitt Dr.).
Barefoot Etc., ☎ 863-299-3613, . Water skiing lessons.edit
Briscoe's Ride Center, ☎ 863-521-1076, . Water skiing lessons.edit
Ron Scarpa Watersports, ☎ 863-299-7094, . Water skiing lessons.edit
World Barfoot Center, ☎ 863-877-0039, . Water skiing lessons.edit
Golfing is popular throughout the state and Winter Haven is no exception.
Cypresswood Golf & Country Club, 1099 Clubhouse Road, ☎ 863-324-6174. Semi-private 18-hole course. Lessons available, but no rentals.edit
Lake Bess Country Club, 218 Golf Aire Blvd., ☎ 863-326-9171. Public 9-hole course. Rentals and lessons available.edit
Willowbrook Golf Course, 4200 State Road 544 E, ☎ 863-291-5899. Public 18-hole course. Rentals & lessons available.edit
Take to the skies in a scenic WWII-era biplane ride over the areas lakes, complete with helmet, goggles, leather jacket, & scarf. Preston Aviation (, 863-956-2526) at the Winter Haven Airport.
Theatre Winter Haven (, 863-299-2672) is among the most acclaimed little theaters in the state. Various productions are held throughout the year and the Ridge Art Association, , hosts a free art gallery prior to Theatre Winter Haven performances. The theater is on the corner of Cypress Gardens Blvd. & US 17 (3rd Street W).
Action Paintball, 1751 7th Street SW, ☎ 863-224-6915, . Paintball complex with equipment rentals available.edit
For more information and a complete list of public events, see the city's website or call 863-291-5656.
Pickin in the Park is a music concert for local musicians held the first Friday of each month, except June-August, in Central Park from 6:30-8pm.
Car Cruisin' is the monthly car show featuring everything from antiques to hot rods held the first Saturday of every month, except December, in Central Park from 4-9pm.
Bike Night is a motorcycle festival/showcase held the 3rd Saturday of each month in downtown from 4-9pm.
St.Sophia's Greek Festival Greek festival held annually on a Friday-Sunday weekend in February by St.Sophia's Greek Orthodox Church (863-299-4532) off Winter Lake Road (State Road 540). Includes food, live music, dancing, & shopping.
Smoke on the Water Annual barbeque cook-off held in late February. Call 863-287-3075 for latest dates/details.
Central Park Art Festival Annual art festival in Central Park with judged entries, local entertainment, vendors, children's' activities.
Winter Haven Chain of Lakes Festival Cardboard boat races and activities to celebrate the Chain of Lakes. Held in April.
Carols in the Park Arts and crafts festival held in early December.
Holiday Lighted Boat Parade Boats decked out in all their shining glory taken on a parade route through the Chain of Lakes. Mid-December.
Book Traders, Inc., 41 3rd Street NW, ☎ (863) 299-4904, . Mon-Sat 9-6. Located downtown. Typical used bookstore with a large selection and reasonable prices. There's only one larger bookstore in the county, but about half their titles are serial romance/sci fi and a very small selection of non-fiction.edit
Friends of the Library, 325 Ave. A NW, ☎ (863) 292-0540. Mon-Sat 9-4. Located in the same building as the public library. Charity bookstore to support the library with donated books and volunteer staff. About 2/3rds of the books are non-fiction and there are 2-3 sections half off rotated weekly! Almost every book is under $5 with lots of $2-3 books! Moderate selection but with such great prices, it's definitely worth a look when in town.edit
Haven Books & Collectibles, 3085 Cypress Gardens Road, ☎ (863) 326-9491, . Friday 10-5 & Saturday 10-3 ONLY. Don't be fooled by the exterior. Inside, the building is packed with used & old/collectible books on wood shelves 8-10 feet high! If you're a book lover, this is one of those stores you can spend hours browsing. About half of the books are older (ie. before 1960) or collectible. Prices are modest, not too cheap but certainly not overpriced either. They have a small selection of collectibles in bins in the back center of the store (magazines, maps, postcards, etc.) and in the display cases around the front register. Unfortunately, they're only open a few hours Fri & Sat. edit
The weekly Farmer's Market is held every Thursday 8am-5pm on the corner of 3rd Street NW and Ave. G NW. All varieties of fruits and vegetables, especially one in season.
Sunshine Flea Market, 24200 Highway 27, ☎ (863) 679-1015, . Located on the west side of US 27 about a mile south of the Cypress Gardens Blvd. intersection and just a short distance out of town. Typical flea market with a fresh produce section, although some of the vendors purchase from wholesalers and aren't selling the local-grown stuff you'll find at the Farmer's Market.edit
Andrea's Family Restaurant, 1498 Havendale Blvd., ☎ 863-299-4564. Casual Greek and American fare. Daily specials.edit
El Nortenos, 1925 6th Street NW (US 17), ☎ 863-298-0993. Delicious Mexican cuisine. Lunch specials are a good value at $5-6.edit
My Natures Delight Cafe, 3015 Cypress Gardens Blvd., ☎ 863-318-8778. Organic raw vegan cafe.edit
Ray and Fran's Restaurant, 842 6th Street NW (US 17), ☎ 863-297-5923. Breakfast & lunch daily, Dinner Thursday & Friday. Amish-style cuisine.edit
Richard's Fine Coffee, 330 Ave. A NW, ☎ 863-291-3082. Coffeehouse in same building as library. Typical coffee offerings, cookies, biscotti, muffins, and some light salads and wraps. Free wi-fi, comfy couches, and outdoor tables/chairs. Library allows drinks with lids so you can grab a cappuccino and take it in the library. Open after library closes.edit
Dockside Bar & Grill, 1006 S. Lake Howard Dr.. edit
Fred's Southern Kitchen. Southern buffet. The dinner prices are a bit high ~$13. Lunch & breakfast are good values, though. Only open for lunch on Sundays.$13 dinner, $9 lunch, $6 breakfast. edit
Harry's Old Place, 3751 Cypress Gardens Road, ☎ 863-324-0301. Lunch Tue-Fri, Dinner Tue-Sat, closed between meals. Fresh seafood served in a rustic restaurant overlooking Lake Ned. Parking is tight, the lot is usually full, and you may have to park precariously on the side of a busy road, but the food is worth it. Seniors often line up before dinner opening for Early Bird Specials.$10-15. edit
Iamsterdam Panini Cafe, 5937 Cypress gardens Blvd., ☎ 863-269-8400. Located in front of Legoland. (Possibly closed at this time, please confirm)edit
Tsunami Sushi, 317 W Central Ave., ☎ 863-293-2395. edit
Holiday Inn Winter Haven, 200 Cypress Gardens Blvd., ☎ 863-292-2100, . Pool. Free Wi-Fi.edit
Howard Johnson Inn Winter Haven, 1300 3rd Street SW, ☎ 863-294-7321, . Pool. Pets allowed. Free wi-fi.edit
Lake Ida Beach Resort, 2524 6th Street NW (US 17), ☎ 863-293-0942, . Kitchen/efficiencies. Pool. Pets allowed. Free wi-fi.edit
Lake Roy Beach Inn & Suites, 1823 Cypress Gardens Blvd., ☎ 863-324-6320, . Kitchen/efficiencies. Pool. Pets allowed. Free wi-fi. Includes a small, sandy beach on Lake Roy, but right against Cypress Gardens Blvd.edit
Historic Lake Wales is just 15 miles away (about 10 from Legoland). Florida's Natural juice company has a "Grove House" across from their plant on US 27 with information about the citrus industry and free samples. Spook Hill is an optical illusion where you appear to roll uphill relative to the surrounding terrain, although its actually a slight downhill slope. Both make for fun, quick stops before or after a day spent at Legoland, while Bok Tower Gardens atop the highest point on the Florida Peninsula is a great half-day destination (especially for a picnic). For the adventurous, the city is the Skydiving Capital of Florida and east of town lies Lake Kissimmee where you can take a scenic airboat tours without driving south to the Everglades.
Lakeland is 30-45 minutes east (and along the route from Tampa) and boasts 12 Frank Lloyd Wright designed buildings which you can tour on the campus of Florida Southern College. Also in Lakeland are the Florida Air Museum and the 1920s-era Polk Theater renovated to its original vaudeville/movie theater glory.
Elsewhere in the county are the Fantasy of Flight museum, the Water Ski Hall of Fame, and the 29mi. Van Fleet State Trail for biking or walking off I-4 in Polk City or, from Winter Haven, take US 17 to Lake Alfred and take State Road 557/557A to Polk City.
Most visitors are likely spending a part of their trip in Orlando, which is 45 min to 1.5 hours away depending on where in the city you're heading to. While Kissimmee and Disney World are just 30 minutes away! En route, you can stop by Davidson of Dundee and Webb's Candy Factory, both along US 27, to watch citrus candies, chocolates, goat milk fudge, and other sweets being made and purchase some for the road or to take home.