Discover amazing Longwood activities and premium in-home experiences.
Longwood is a charming slice of old-world elegance married to modern living, where tree-lined streets and historic homes stand side by side with vibrant local shops and eateries. Known for its lush parks and engaging community events, this welcoming city invites visitors to explore the harmony between rich history and contemporary culture. Whether you're discovering hidden gems or enjoying outdoor adventures, Longwood offers an inviting escape that's both nostalgic and fresh.
Island-hop around Anna Maria with snorkeling gear and water toys on a private charter
Customize a 4-hour private island-hopping adventure for families, up to 6 guests per boat
Spot dolphins and enjoy sandbar swims, snorkeling, and paddle boarding on a private 2-hour outing
Enjoy a 3-hour catch-and-release outing with kid-friendly fun, sandbar stops, and included drinks and gear
Island-hop for 4 hours with snorkeling and water toys, tailored for families
Paddle transparent tandem kayaks through scenic lakes and canals on a guided 2-hour adventure
Explore Winter Park's lakes and canals on a private 2-hour clear kayak tour with a guide
Paddle crystal-clear waters to spot manatees, monkeys, and more, guided by experts in Florida's largest spring.
Explore Orlando’s calm lake system in transparent kayaks or stable paddleboards at your own pace
Paddle crystal-clear Silver Springs waters to observe alligators and abundant wildlife with expert guides
Paddle clear kayaks at night to witness glowing comb jellies and brilliant stars.
Beginner-friendly paddle across a biodiverse lagoon to spot dolphins, manatees and stingrays
Sip sparkling wine as LED-lit clear kayaks or boards glide across gator-free Lake Ivanhoe at sunset or under the stars.
Glide across Lake Ivanhoe in a clear vessel illuminated by multi-color LEDs for a unique nighttime Orlando adventure.
Learn paddleboarding or clear kayaking alongside your dog on a calm, gator-free Orlando lake.
Paddle crystal-clear kayaks or stand-up boards at sunset on calm Orlando lakes
Glide over gator-free Lake Ivanhoe in transparent kayaks or stable paddleboards with expert guidance.
Paddle crystal-clear springs in a guided clear kayak and spot wildlife along the way
Paddle crystal-clear Rock Springs Run and float back downstream on a guided, family-friendly outing.
Paddle the Emerald Cut of Rock Springs Run in clear kayaks on a guided 2-hour adventure
Paddle 8.5 miles downstream from King's Landing to Wekiva Island with return shuttle included
Explore Rock Springs Run at your own pace on a 4-hour paddle
Paddle secluded Blackwater Creek with expert guides and small groups for an immersive nature escape
Paddle serene Blue Spring waters to encounter manatees and abundant wildlife up close
Glide through Blue Spring at sunset to see manatees and abundant wildlife
Explore Florida's scenic waterways at your own pace with flexible pick-up and drop-off times
Paddle crystal-clear springs, hike to waterfalls, and spot wildlife on a guided 4-hour escape
Paddle crystal-clear Rainbow River and Indian Creek with a knowledgeable guide.
Explore crystal-clear Silver Springs and spot manatees and wildlife on a beginner-friendly paddling tour.
Explore scenic canals and lakes near Orlando on a 2-hour guided paddleboard or kayak tour
Guided 2-hour paddle to spot dolphins and manatees just 45 minutes from Orlando
Discover how cocoa becomes chocolate on a guided, interactive factory tour in 45 minutes
Fly low above the St. Johns River for sweeping wildlife views on a thrilling 1-hour seaplane adventure
Spot alligators and fly over Orlando theme parks on a thrilling 45-minute seaplane ride
Ride premium Can-Am ATVs on scenic forest trails for a thrilling 1-hour adventure
Make waves on Orlando’s lakes during a 60-minute ride with fuel and safety gear
Enjoy a scenic guided trail ride in Lake Louisa State Park, ideal for beginners ages 8+.
Explore Lake Louisa State Park by off-road Segway with a guide, plus a picnic lunch
Captain a two-person catamaran across pristine Florida lakes for an unforgettable two-hour adventure
Experience glowing bioluminescence and stargazing on a beginner-friendly clear kayak or paddleboard adventure.
Longwood is a delightful blend of history, nature, and community spirit. Known for its rich heritage and small-town feel, this city offers visitors a chance to step back in time while enjoying modern amenities. Begin your journey at the Historic District where Victorian-era architecture stands proudly amidst tree-lined streets. The Bradlee-McIntyre House Museum is a must-see for those interested in 19th-century design and local lore.
For outdoor enthusiasts, Wekiva Springs State Park provides an escape into Florida's natural beauty just minutes from downtown Longwood. Here you can kayak along crystal-clear waters or hike through lush trails teeming with wildlife. If you're visiting during spring or fall, take advantage of the mild weather to explore these serene landscapes without the summer crowds.
Food lovers will appreciate Longwood’s burgeoning culinary scene featuring everything from cozy cafes to eclectic eateries offering global flavors. Don’t miss out on trying some locally sourced dishes that highlight regional ingredients—perfect after a day spent exploring nearby attractions like Lake Jesup Conservation Area or Rock Springs Run Reserve. Whether you're here for relaxation or adventure, Longwood promises memorable experiences around every corner.