Things to do in Longwood

    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.

    Popular Activities in Longwood

    Private Boat Charter with Snorkeling & Water Toys

    Island-hop around Anna Maria with snorkeling gear and water toys on a private charter

    5.0 200 reviews
    $1,124

    Longwood Private Boat Tour: Island Hopping

    Customize a 4-hour private island-hopping adventure for families, up to 6 guests per boat

    5.0 200 reviews
    $733/ boat

    Anna Maria Island Private Dolphin & Snorkel Tour

    Spot dolphins and enjoy sandbar swims, snorkeling, and paddle boarding on a private 2-hour outing

    5.0 200 reviews
    $435/ boat

    Anna Maria Island Family Fishing Charter for Kids

    Enjoy a 3-hour catch-and-release outing with kid-friendly fun, sandbar stops, and included drinks and gear

    5.0 200 reviews
    $593/ boat

    Egmont Key Snorkeling Charter for Families

    Island-hop for 4 hours with snorkeling and water toys, tailored for families

    5.0 200 reviews
    $733/ boat

    Winter Park Clear Kayak Chain of Lakes Tour

    Paddle transparent tandem kayaks through scenic lakes and canals on a guided 2-hour adventure

    4.9 1K reviews
    $80/ person

    Private Winter Park Clear Kayak Tour

    Explore Winter Park's lakes and canals on a private 2-hour clear kayak tour with a guide

    4.9 1K reviews

    Silver Springs Clear Kayak with Manatees Orlando

    Paddle crystal-clear waters to spot manatees, monkeys, and more, guided by experts in Florida's largest spring.

    4.9 3.9K reviews

    2Hr Clear Kayak & Paddleboard Rental Orlando

    Explore Orlando’s calm lake system in transparent kayaks or stable paddleboards at your own pace

    4.9 3.9K reviews

    Clear Kayak Gator Tour at Silver Springs

    Paddle crystal-clear Silver Springs waters to observe alligators and abundant wildlife with expert guides

    4.9 3.9K reviews

    Bioluminescent Comb Jelly Clear Kayak Night Tour

    Paddle clear kayaks at night to witness glowing comb jellies and brilliant stars.

    4.9 3.9K reviews

    Clear Kayak Dolphin & Manatee Tour in Orlando

    Beginner-friendly paddle across a biodiverse lagoon to spot dolphins, manatees and stingrays

    4.9 3.9K reviews

    Date Night Glow Kayak & Champagne in Orlando

    Sip sparkling wine as LED-lit clear kayaks or boards glide across gator-free Lake Ivanhoe at sunset or under the stars.

    4.9 3.9K reviews
    $87/ vessel

    LED Night Glow Clear Kayak Tour on Lake Ivanhoe

    Glide across Lake Ivanhoe in a clear vessel illuminated by multi-color LEDs for a unique nighttime Orlando adventure.

    4.9 3.9K reviews

    Dog Paddleboard & Clear Kayak Tour in Orlando

    Learn paddleboarding or clear kayaking alongside your dog on a calm, gator-free Orlando lake.

    4.9 3.9K reviews

    Orlando Sunset Clear Kayak or Paddleboard Experience

    Paddle crystal-clear kayaks or stand-up boards at sunset on calm Orlando lakes

    4.9 3.9K reviews

    Clear Kayak Tour on Lake Ivanhoe, Orlando

    Glide over gator-free Lake Ivanhoe in transparent kayaks or stable paddleboards with expert guidance.

    4.9 3.9K reviews

    Rock Springs Clear Kayak Tour

    Paddle crystal-clear springs in a guided clear kayak and spot wildlife along the way

    4.9 3.1K reviews
    $80/ person

    Emerald Cut Kayak Adventure in Apopka

    Paddle crystal-clear Rock Springs Run and float back downstream on a guided, family-friendly outing.

    4.8 5.1K reviews
    $55/ person

    Emerald Cut Clear Kayak Tour

    Paddle the Emerald Cut of Rock Springs Run in clear kayaks on a guided 2-hour adventure

    4.8 5.1K reviews
    $100/ kayak

    Shuttle Run Self-Guided Paddle From King's Landing to Wekiva Island

    Paddle 8.5 miles downstream from King's Landing to Wekiva Island with return shuttle included

    4.8 5.1K reviews

    Self-Guided Day Paddle on Rock Springs Run

    Explore Rock Springs Run at your own pace on a 4-hour paddle

    4.8 5.1K reviews

    Orlando Kayak Tour on Secluded Blackwater Creek

    Paddle secluded Blackwater Creek with expert guides and small groups for an immersive nature escape

    5.0 717 reviews
    $90/ person

    Manatee Kayak Tour at Blue Spring State Park

    Paddle serene Blue Spring waters to encounter manatees and abundant wildlife up close

    5.0 717 reviews
    $79/ person

    Sunset Paddle Among Manatees

    Glide through Blue Spring at sunset to see manatees and abundant wildlife

    5.0 717 reviews
    $84/ person

    Paddleboard Rental Belle Isle with Flexible Times

    Explore Florida's scenic waterways at your own pace with flexible pick-up and drop-off times

    Rainbow Springs Paddle & Waterfall Hike Adventure

    Paddle crystal-clear springs, hike to waterfalls, and spot wildlife on a guided 4-hour escape

    $100/ person

    Guided Rainbow Springs Kayak Tour with Naturalist

    Paddle crystal-clear Rainbow River and Indian Creek with a knowledgeable guide.

    $66/ person

    Paddle Crystal Waters & Spot Wild Manatees

    Explore crystal-clear Silver Springs and spot manatees and wildlife on a beginner-friendly paddling tour.

    $66/ person

    Winter Park Lakes Guided Kayak & Paddle Tour

    Explore scenic canals and lakes near Orlando on a 2-hour guided paddleboard or kayak tour

    $55/ person

    Dolphin & Manatee Paddle Board Tour

    Guided 2-hour paddle to spot dolphins and manatees just 45 minutes from Orlando

    $66/ person

    Chocolate Kingdom Factory Adventure Tour

    Discover how cocoa becomes chocolate on a guided, interactive factory tour in 45 minutes

    4.7 3.2K reviews
    $20/ person

    Seaplane Tour Tavares: St. Johns River Wildlife

    Fly low above the St. Johns River for sweeping wildlife views on a thrilling 1-hour seaplane adventure

    5.0 259 reviews
    $299/ person

    Seaplane Tour Over Orlando Theme Parks & Gators

    Spot alligators and fly over Orlando theme parks on a thrilling 45-minute seaplane ride

    5.0 259 reviews
    $230/ person

    Can-Am ATV Rental at The Ranch

    Ride premium Can-Am ATVs on scenic forest trails for a thrilling 1-hour adventure

    5.0 2.8K reviews

    Sea Doo Jet Ski Rental

    Make waves on Orlando’s lakes during a 60-minute ride with fuel and safety gear

    $137/ jet ski

    Guided 1.5-Hour Horseback Trail Ride at Lake Louisa State Park

    Enjoy a scenic guided trail ride in Lake Louisa State Park, ideal for beginners ages 8+.

    4.7 3.5K reviews
    $136/ rider

    Segway Half-Day Grand Excursion

    Explore Lake Louisa State Park by off-road Segway with a guide, plus a picnic lunch

    4.7 3.5K reviews
    $158/ person

    Self-Captained 2-Hour Catamaran on 13 Lakes

    Captain a two-person catamaran across pristine Florida lakes for an unforgettable two-hour adventure

    5.0 678 reviews

    Clear Kayak Bioluminescence Tour in Orlando

    Experience glowing bioluminescence and stargazing on a beginner-friendly clear kayak or paddleboard adventure.

    4.9 3.9K reviews

    Explore the Charm of Longwood

    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.

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