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

    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
    $649/ 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
    $525/ boat

    Egmont Key Snorkeling Charter for Families

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

    5.0 200 reviews
    $649/ boat

    Winter Park Clear Kayak Chain of Lakes Tour

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

    4.9 946 reviews
    $64/ person

    Emerald Cut Kayak Adventure in Apopka

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

    4.7 4.9K reviews
    $49/ person

    Orlando Kayak Tour on Secluded Blackwater Creek

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

    5.0 563 reviews
    $80/ person

    Manatee Kayak Tour at Blue Spring State Park

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

    5.0 563 reviews
    $70/ 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
    $260/ 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
    $200/ person

    One Hour Airboat Eco Tour & Wildlife Encounter

    Glide across the St. Johns River on a guided airboat and meet resident wildlife afterward

    4.9 2.4K reviews
    $42/ person

    Sea Doo Jet Ski Rental

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

    $120/ jet ski

    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

    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
    $385/ boat

    Manatee Kayak Tour at Blue Springs Orlando

    Paddle Blue Springs State Park to observe manatees and diverse wildlife with a Florida Master Naturalist guide.

    4.9 1.5K reviews
    $80/ person

    Orlando Alligator Kayaking Experience

    Paddle an eight-mile wild river and spot massive alligators with expert guides

    4.9 1.5K reviews
    $100/ person

    Cruise Harris Chain Lakes in 10 Person Pontoon

    Cruise the Harris Chain in a spacious 10-passenger pontoon for a full or half-day lake adventure

    4.8 301 reviews

    Kissimmee Cypress Forest Kayak Tour with Guide

    Paddle through pristine Shingle Creek cypress forest with expert guidance and wildlife insights

    4.8 729 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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