Best Day Trips from Windermere, FL

Toni Marie Cafferty November 6, 2026

A woman in a blue swimsuit sits in a kayak on a shaded, tree-lined river.

By Toni Marie Cafferty

Weekend plans feel easier when great getaways sit close to home. Windermere’s place among the Butler Chain of Lakes in West Orange County puts springs, trails, historic towns, and beaches within a reasonable drive. I enjoy sharing favorite escapes with clients who want a home base that makes adventure easy.

The sections below highlight outings with details drawn from official park, tourism, and college pages.

Key Takeaways

  • Nearby town: Visit Winter Garden about 25 minutes west of downtown Orlando.
  • Spring swim: Florida State Parks says Wekiwa Springs stays at 72 degrees year-round.
  • Historic stop: Florida Southern College in Lakeland has thirteen Frank Lloyd Wright-designed structures.
  • Gulf coast: VISIT FLORIDA says Clearwater is usually around two hours from Orlando via I-4 West.

Plant Street Market and the West Orange Trail

Visit Orlando describes Winter Garden as approximately 25 minutes west of downtown Orlando and about 20 minutes north of Walt Disney World. Its Plant Street Market is a community hub with 20 vendors offering organic eats and handmade products.

Winter Garden Highlights

  • Plant Street Market: Visit Orlando names Crooked Can Brewing as the anchor tenant.
  • West Orange Trail: Orange County’s trail brochure lists the multipurpose trail at 22.32 miles long.
  • Trailhead: Winter Garden Station sits at 455 E. Plant St.
Different tourism pages round the trail’s length differently, so the county brochure is the most reliable reference. Bring a bike or comfortable shoes and leave time for lunch downtown, since the market and the trail make an easy pairing.

Spring Swims at Wekiwa Springs and Kelly Park

Florida State Parks describes Wekiwa Springs as emerald springs feeding the Wekiva River, with water at 72 degrees year-round. The park at 1800 Wekiwa Circle in Apopka is open from 8 a.m. to sunset, 365 days a year.

Spring Details to Know

  • Day-use reservations: The park’s page lists a reservation requirement effective September 2, 2025.
  • Kelly Park: Orange County describes a year-round 68-degree running spring on some 355 acres at 400 E. Kelly Park Road.
  • Crowds: A July 2025 county article notes Kelly Park often reaches capacity, with guests lining up before 5 a.m.
Rules and capacity can change, so check each park’s page before you leave home and bring what you need for a full day outdoors. An early start improves your odds on busy days.

Mount Dora and the Dora Canal

VISIT FLORIDA describes Mount Dora as approximately 30 miles northwest of Orlando, about a 45-minute drive depending on traffic. The town is home to the Mount Dora Lighthouse, one of the few inland lighthouses in Florida.

Mount Dora Highlights

  • Lighthouse: The Mount Dora Lighthouse is described as one of the few inland lighthouses in Florida.
  • Dora Canal: VISIT FLORIDA calls the canal scenic and 1.2 miles long.
  • Travel time: The same page gives both 35-minute and 45-minute figures from Orlando.
Plan extra time on weekends, since traffic changes the drive and the town draws visitors. A stroll through town and a canal view make a relaxed outing.

Frank Lloyd Wright at Florida Southern College

Florida Southern College in Lakeland says thirteen Wright-designed structures rise across its hillside campus. The college calls it the largest single-site collection of Frank Lloyd Wright architecture anywhere.

Tour Options

  • Basic Walking Tour: The college lists it at 90 minutes.
  • In-Depth Walking Tour: The college lists it at about 2.5 hours.
  • Usonian House Tour: The college lists it at 20 to 30 minutes.
The National Park Service named the campus a National Historic Landmark in 2012, which adds to its appeal for architecture fans. The college’s pages list two different Visitor Center addresses, so confirm the address before navigating.

Clearwater and the Gulf Coast

VISIT FLORIDA says Clearwater is about 106 miles southwest of Orlando, usually around two hours via I-4 West. The city is also about 25 miles west of Tampa.

Gulf Coast Notes

  • Distance: The page lists about 106 miles from Orlando.
  • Water temperature: VISIT FLORIDA lists an average beach water temperature of 76 degrees.
  • East coast option: Visit Orlando places beaches about 90 minutes from Winter Garden.
Distances are measured to the city of Clearwater rather than a specific beach, and Windermere’s position will shave or add time. Check live traffic on I-4 before you leave.

FAQs

Which day trips from Windermere FL are best for a first-time visitor?

Winter Garden’s Plant Street Market and the West Orange Trail make an easy first outing, and Wekiwa Springs is a popular warm-weather choice. Mount Dora and the Gulf Coast suit a longer day. I can share timing tips based on your interests and preferred pace.

Do I need a reservation for Wekiwa Springs?

Florida State Parks lists a day-use reservation requirement effective September 2, 2025. Check the park’s page for current rules before you go.

How far is the beach from Windermere?

Visit Orlando says beaches are about 90 minutes from Winter Garden, and VISIT FLORIDA lists Clearwater as about two hours from Orlando. Traffic can change those times, so test the drive for your own schedule.

Reach Out to Toni Marie Cafferty

Reach out to Toni Marie Cafferty to find a Windermere home that makes weekend adventures easy.



Toni Marie Cafferty

Toni Marie Cafferty

About the Author

A true native, Toni Marie Cafferty calls Florida home. Originally from Jacksonville, she moved to Central Florida while attending the private university of Stetson where she graduated with a degree in Marketing and International Business. With time spent in Austria, Germany, Italy, Switzerland, and the Netherlands, she loves to explore other cultures. In her real estate career, she’s had the pleasure to work with buyers from around the world.

As a Realtors® daughter, Toni Marie was raised in the real estate industry and contributes her high level of client care to that of her mother. Toni Marie caters to the luxury market with a white glove-style all her own. Just as the Golden Rule states, “Do unto others as you would have them do unto you,” Toni Marie takes this to the next level offering superb client care. When asked, she says “it’s all about the details and being present with those you are working with whether it be in-person or over the phone. Be ahead of your client’s questions and help provide clarity and honest feedback.”

Toni Marie Cafferty’s Gold Standard (#tmcgoldstandard) has garnered respect from her colleagues and clients alike as she grows her real estate profession. In the past 9 years, she has managed over $106 million in sales and she’s not slowing down; rather she is expanding her reach with Compass to help more buyers find their place and continue to shatter records for her sellers. Most recently, Toni Marie has been the highest priced estate under contract in Windermere, Florida since 2019 and set a new price per square foot high in the exclusive community of Isleworth Golf & Country Club.

Toni Marie rounds out her career with a balance of time spent with her friends and family. Her husband, Brett, and their two dogs are looking forward to growing their family over the next few years as they continue to call Central Florida their home.

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Toni Marie Cafferty

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(904) 449-2184



 

851 W Morse Boulevard

Winter Park, FL 32789

Compass Florida