Free Concierge Service
    Text or call 1-877-GREET-WELL
    Ask AIAI
    Ask AIAI
    Why travelers choose Greetwell

    Curated by our team

    Every experience is hand selected and approved by Greetwell.

    Personal concierge

    Real humans available to help before, during, and after your booking.

    Intimate & authentic

    Including unique in-home experiences you won't find anywhere else.

    Easy booking & cancellation

    Reserve in minutes with free cancellation on most experiences.

    Greetwell

    Experiences that stay with you long after the trip

    Greetwell curates authentic local experiences and provides personal concierge support in over 500 destinations, helping you explore confidently wherever you go.

    About

    • Our Story
    • For Experience Providers
    • For Hospitality Partners
    • For Developers

    Resources

    • Travel Guides
    • Help Center
    [email protected]1-877-GREET-WELL

    Safe & Secure Payments

    © 2026 Greetwell, Inc. All rights reserved.
    Privacy PolicyTerms
    Free Concierge Service
    Text or call 1-877-GREET-WELL
    Ask AIAI
    Ask AIAI
    1. Local experiences
    2. /All experiences
    3. /Winter Park FL

    Best 204 things to do in Winter Park, FL

    Showing 49-72 of 204 results
    Guided Manatee Paddle Tour at Silver Springs
    Stand Up Paddle Boarding

    Guided Manatee Paddle Tour at Silver Springs

    Paddle Silver Springs’ clear waters with a guide and look for native wildlife

    Paddle Silver Springs’ clear waters with a guide and look for native wildlife
    5.0 • 561 reviews
    $84/ person
    2-Hour Winter Park Sunset Paddleboard & Kayak Tour
    Kayaking Tours

    2-Hour Winter Park Sunset Paddleboard & Kayak Tour

    Paddle or kayak Winter Park’s lakes and tropical canals with a guided 2-hour tour

    Paddle or kayak Winter Park’s lakes and tropical canals with a guided 2-hour tour
    5.0 • 561 reviews
    $84/ person
    2-Hour Bioluminescence Paddleboard Tour in Merritt Island
    Stand Up Paddle Boarding

    2-Hour Bioluminescence Paddleboard Tour in Merritt Island

    Paddle after sunset and watch the Banana River glow

    Paddle after sunset and watch the Banana River glow
    5.0 • 561 reviews
    $111/ person
    2-Hour Dolphin & Manatee Paddleboard Tour
    Stand Up Paddle Boarding

    2-Hour Dolphin & Manatee Paddleboard Tour

    Paddle Merritt Island mangroves with a guide and spot dolphins and manatees

    Paddle Merritt Island mangroves with a guide and spot dolphins and manatees
    5.0 • 561 reviews
    $84/ person
    Private Paddleboard Lesson On Lake Conway
    Paddleboarding

    Private Paddleboard Lesson On Lake Conway

    Learn to paddleboard with a private pro lesson on calm Lake Conway

    Learn to paddleboard with a private pro lesson on calm Lake Conway
    5.0 • 561 reviews
    $111& up
    Explore Anna Maria Island on a 6-Hour Island Hopping Cruise
    Boat Tours

    Explore Anna Maria Island on a 6-Hour Island Hopping Cruise

    Private 6-hour island-hopping charter for up to 6 guests

    Private 6-hour island-hopping charter for up to 6 guests
    4.9 • 243 reviews
    $1,124& up
    Explore Anna Maria Island on a 4-Hour Island-Hopping Cruise
    Boat Tours

    Explore Anna Maria Island on a 4-Hour Island-Hopping Cruise

    Private 4-hour island-hopping boat tour for up to 6 guests

    Private 4-hour island-hopping boat tour for up to 6 guests
    4.9 • 243 reviews
    $733& up
    Cruise Anna Maria Island on a 2-Hour Dolphin Tour
    Dolphin Watching

    Cruise Anna Maria Island on a 2-Hour Dolphin Tour

    Private 2-hour dolphin tour with sandbar stops for up to 6 guests

    Private 2-hour dolphin tour with sandbar stops for up to 6 guests
    4.9 • 243 reviews
    $435& up
    3-Hour Family Fishing Charter in Anna Maria Island
    Fishing Charters

    3-Hour Family Fishing Charter in Anna Maria Island

    Private family fishing trip with sandbar swim time for up to 6 guests

    Private family fishing trip with sandbar swim time for up to 6 guests
    4.9 • 243 reviews
    $593& up
    Private Egmont Key Snorkeling Charter in Cortez
    Snorkeling

    Private Egmont Key Snorkeling Charter in Cortez

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

    Island-hop for 4 hours with snorkeling and water toys, tailored for families
    4.9 • 243 reviews
    $733& up
    Island-Hopping Private Boat Charter From Anna Maria
    Boat Tours

    Island-Hopping Private Boat Charter From Anna Maria

    Private 3-hour island-hopping charter with snorkeling and paddle boarding for up to 6

    Private 3-hour island-hopping charter with snorkeling and paddle boarding for up to 6
    4.9 • 243 reviews
    $593& up
    Single Kayak Rental at Sebastian Inlet
    Kayaking Tours

    Single Kayak Rental at Sebastian Inlet

    Paddle the Indian River Lagoon at your own pace in a stable single kayak

    Paddle the Indian River Lagoon at your own pace in a stable single kayak
    $40/ kayak
    Tandem Kayak Rental at Sebastian Inlet
    Kayaking Tours

    Tandem Kayak Rental at Sebastian Inlet

    Paddle the Indian River Lagoon at your own pace

    Paddle the Indian River Lagoon at your own pace
    $57/ kayak
    1-4 Hour Stand-Up Paddleboard Rental at Sebastian Inlet
    Stand Up Paddle Boarding

    1-4 Hour Stand-Up Paddleboard Rental at Sebastian Inlet

    Paddle the Indian River Lagoon at your own pace

    Paddle the Indian River Lagoon at your own pace
    $40/ paddleboard
    Dolphin & Manatee Guided Kayak Tour at Sebastian Inlet
    Kayaking Tours

    Dolphin & Manatee Guided Kayak Tour at Sebastian Inlet

    Paddle calm lagoon waters while learning about Florida’s coastal wildlife

    Paddle calm lagoon waters while learning about Florida’s coastal wildlife
    $99& up
    Daily Cabana Rental in Longwood
    Outdoor Picnics

    Daily Cabana Rental in Longwood

    Gather in a renovated cabana with a summer kitchen and grill

    Gather in a renovated cabana with a summer kitchen and grill
    4.6 • 4.9K reviews
    $367
    VIP Cabana Rental in Longwood
    Outdoor Picnics

    VIP Cabana Rental in Longwood

    Private riverside cabana with grilling space and a sandy waterfront area

    Private riverside cabana with grilling space and a sandy waterfront area
    4.6 • 4.9K reviews
    $266
    Barefoot Cabana Rental in Longwood
    Outdoor Picnics

    Barefoot Cabana Rental in Longwood

    Relax in a renovated covered cabana with a sandy gathering area and gas grill

    Relax in a renovated covered cabana with a sandy gathering area and gas grill
    4.6 • 4.9K reviews
    $249
    Wekiva Island Cabana Rental in Longwood
    Cabin Rentals

    Wekiva Island Cabana Rental in Longwood

    Relax in a renovated waterfront cabana with direct water access

    Relax in a renovated waterfront cabana with direct water access
    4.6 • 4.9K reviews
    $198
    Daily Cabana Rental in Longwood
    Outdoor Picnics

    Daily Cabana Rental in Longwood

    Relax in a renovated private cabana with a grill and reserved parking

    Relax in a renovated private cabana with a grill and reserved parking
    4.6 • 4.9K reviews
    $254
    Beach Club Cabana Rental in Longwood
    Self Guided and Passes

    Beach Club Cabana Rental in Longwood

    Private waterside cabana with a grill, picnic table and direct water access

    Private waterside cabana with a grill, picnic table and direct water access
    4.6 • 4.9K reviews
    $379
    Guided 2-Hour Wekiva River Paddle Tour
    Kayaking Tours

    Guided 2-Hour Wekiva River Paddle Tour

    A beginner-friendly river outing with paddling tips and an optional swim break

    A beginner-friendly river outing with paddling tips and an optional swim break
    4.6 • 4.9K reviews
    $85& up
    30-Minute Lake Jesup Airboat Tour
    Boat Tours

    30-Minute Lake Jesup Airboat Tour

    Glide across Lake Jesup while looking for alligators and native birds

    Glide across Lake Jesup while looking for alligators and native birds
    4.7 • 1K reviews
    $46/ person
    Lake Jesup Lunch Airboat Ride
    Boat Tours

    Lake Jesup Lunch Airboat Ride

    Spot Florida wildlife, then enjoy a lakeside lunch and souvenir photo

    Spot Florida wildlife, then enjoy a lakeside lunch and souvenir photo
    4.7 • 1K reviews
    $58/ person
    12345…9