56 days in Winter Haven Itinerary

Created using Inspirock Winter Haven travel route planner
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Winter Haven
— 53 nights
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Winter Haven
— 2 nights
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Winter Haven — 53 nights

Chain of Lakes City

Winter Haven boasts over 50 lakes within its borders, most notably Florida's famed Chain of Lakes.
You've now added Indigo's Billiards, Bowling & Games to your itinerary. Solomon's Castle and Paquette's Historical Farmall Tractor Museum will appeal to museum buffs. Your cultural itinerary includes sights like Lakeridge Winery & Vineyards and Dinosaur World. Venture out of the city with trips to Lakeland (Munn Park, Big Cypress Golf Club, &more), Clermont (Waterfront Park, Kings Ridge Golf Club, &more) and Lake Catherine Blueberries (in Groveland). Plan for a day of cool, family-friendly fun on the 29th (Sat) at Legoland Florida Resort. The adventure continues: look for all kinds of wild species at Circle B Bar Reserve, play a few rounds at Riverwood Golf and Country Club, admire the majestic nature at Lake Kissimmee State Park, and hike along General James A. Van Fleet State Trail.

To find out how to plan a trip to Winter Haven, use our trip itinerary maker.

Orlando to Winter Haven is an approximately 1-hour car ride. You can also take a train. In October, plan for daily highs up to 86°F, and evening lows to 68°F. On the 15th (Thu), you'll travel to Winter Haven.
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Parks · Outdoors · Golf · Museums
Side Trips

Winter Haven — 2 nights

Chain of Lakes City

Escape the urban bustle at Willowbrook Golf Course and Florida National Scenic Trail. Venture out of the city with trips to Zipline (in Brooksville), Wild Horse Rescue Center (in Webster) and Skyview At Terra Vista (in Hernando). Enjoy Winter Haven some more: pick up a one of a kind souvenir at Sherman's Antiques.

To find where to stay, ratings, maps, and other tourist information, refer to the Winter Haven online visit planner.

Wrap up your sightseeing on the 17th (Sat) to allow time to drive back home.
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Outdoors · Parks · Golf · Wildlife
Side Trips