GUIDED PADDLEBOARD & KAYAK TOURS IN WINTER PARK, FL

Peaceful morning paddles and glowing sunset tours through the Winter Park Chain of Lakes. Beginner-friendly, paddleboard or kayak hybrid, photos included!

Couple enjoying a sunset kayak paddle tour in Winter Park, Florida — perfect for date night and romantic outdoor adventures
Scenic paddleboarding through the historic canals of Winter Park, Florida surrounded by tropical greenery

EXPERIENCE THE NATURAL BEAUTY of Winter Park by Paddle Board or Kayak Hybrid

Experience one of Florida’s most beautiful paddle spots with a guided paddleboard or kayak hybrid tour in Winter Park, just minutes from Orlando. This historic Chain of Lakes features elegant homes, lush greenery, and charming canal passages, perfect for a calm, scenic paddle adventure.

Whether you want to stand up and paddle, or prefer a relaxed, seated kayak hybrid experience, we’ve got you covered. Our experienced local guides provide all the gear, instruction, and even capture the moment with complementary digital photos, so you can relax, explore, and enjoy.

No experience needed. Just bring your sense of adventure.

WINTER PARK PADDLEBOARDING & KAYAK TOUR OPTIONS

Explore our two most popular guided tour experiences. Whether you’re a morning explorer or a sunset chaser, we have the perfect paddle waiting for you. All tours are beginner-family friendly and include your choice of stand-up paddleboard or kayak-style setup, plus all gear and digital photos.

Paddleboarders gliding through a lush, tropical canal on the Winter Park Chain of Lakes in Central Florida
Paddleboarders exploring Winter Park’s urban paradise with scenic canals and lush greenery in Orlando, FL

DAY PADDLE TOUR

Morning Paddle Tour on the Winter Park Chain of Lakes

Start your day with a peaceful paddle through the scenic Winter Park Chain of Lakes. With calm waters and quiet surroundings, this morning tour is perfect for spotting wildlife, enjoying the golden light, and soaking in the natural beauty of Central Florida.

  • Launch Times: 9AM or 11AM

  • Duration: 2 Hours

  • Includes: Paddleboard or kayak hybrid setup, paddle, life vest, lesson, and digital photos

  • Launch Point: Kraft Azalea Garden – Winter Park, FL

Couple paddleboarding and kayaking together on Winter Park Chain of Lakes, Orlando FL
Sunset paddleboarding tour on Winter Park Chain of Lakes in Orlando, Florida

SUNSET PADDLE TOUR

Sunset Paddle Tour on the Winter Park Chain of Lakes

Experience golden hour on the water with our sunset paddleboarding and kayak tour. As the sun reflects off the calm lakes and canals, this magical tour delivers unforgettable views and peaceful vibes. It’s one of the most beautiful ways to end your day in Florida.

  • Launch Time: 6:30PM

  • Duration: 2 Hours

  • Includes: Paddleboard or kayak hybrid setup, paddle, life vest, lesson, and digital photos

  • Launch Point: Kraft Azalea Garden – Winter Park, FL

REAL WORDS FROM HAPPY PADDLERS

★★★★★

“Our Otter Paddle tour in Winter Park totally exceeded expectations! The canals were absolutely peaceful and beautiful, and our guide was calm, professional, and made the experience both fun and safe. We can’t wait to come back!”

-Rachel F.

★★★★★

“I had an amazing time paddleboarding in Winter Park! Our guide was incredibly knowledgeable and kind, and the canals were stunning full of birds, lush vegetation, and peaceful water. The weather was perfect, and the whole experience felt so relaxing. I can’t wait to come back and try another paddleboarding adventure with Otter Paddle. Highly recommend!”

-Vera T.

★★★★★

“This was such a fun paddleboarding adventure! I love that it’s off the beaten path but still super accessible from Orlando, a perfect alternative to the theme parks. Winter Park is such a cool area to explore, and our guide was experienced, knowledgeable, and brought all the good vibes. Plus, she takes amazing photos!”

-Chrissy D.

★★★★★

“Beautiful paddle on the lakes and through the canals! Our guide a small business owner, is so knowledgeable about the local wildlife and the rich history of Winter Park. We had a great time and I definitely recommend Otter Paddle!”

-S.L.

FREQUENTLY ASKED QUESTIONS - WINTER PARK PADDLE TOURS

  • A: Not at all! Our Winter Park paddle tours are beginner-friendly, with calm water and clear, step-by-step instruction from your experienced guide. Whether it’s your first time or you’re just getting back on the board, we’ve got you covered, great vibes included.

  • A: Yes, for your safety, all guests must be comfortable in and around water and have basic swimming ability. While our paddle tours are beginner-friendly and include life vests, feeling confident in the water is essential.

  • A: Yes! We offer kayak hybrid paddleboards for guests who prefer a more relaxed, seated paddling experience. You’ll select your preferred setup during booking for each guest in your group.

    Our kayak hybrid option combines the agility of a paddleboard with the comfort of a kayak. It features a premium seat that attaches securely to the paddleboard and a lightweight carbon fiber kayak paddle for smooth, easy cruising. This is a great choice for anyone who wants to kick back, stay seated, and enjoy the scenic views without standing.

  • A: All of our Winter Park paddle tours launch from Kraft Azalea Garden, a peaceful lakefront park tucked in the heart of Winter Park, Florida. This shaded launch spot offers easy water access and beautiful views of Lake Maitland, the perfect setting to begin your paddle adventure.

  • A: Yes. All participants must be at least 4 years old to join our Winter Park paddle tours. Guests 17 and under must be accompanied by a parent or guardian for the entire experience.

    For safety:

    • Ages 4–12 ride on the same paddleboard as a parent

    • Ages 13–17 may paddle their own board

    • If a child age 12 or younger has paddleboarding experience and the parent feels confident they can safely keep up with the group, they may paddle solo

    Not sure which setup is best for your child or family? Just reach out, we’re happy to help make your adventure safe and fun for everyone!

  • A: Yes, our paddleboards are designed to comfortably accommodate one adult and one child (ages 4 to 12) on the same board. This is the recommended setup for most families with younger paddlers.

    If your child has previous paddleboarding experience and you’re confident in their ability to keep up safely with the group, they may paddle on their own board with your approval.

    We want every family to feel safe and supported, so if you’re unsure about what’s best for your child, just ask, we’re here to help you choose the right setup.

  • A: Yes! With our “Bring My Own Vessel” option, you’re welcome to join any of our guided tours using your own paddleboard or kayak. Just select this option during booking to receive an automatic $20 discount.

    Your tour still includes:

    • Our signature photo and video package

    • Full guide support and safety overview

    We ask that you arrive early to allow time for unloading and setup. Please bring all necessary gear, including a life vest with whistle, and be ready by your scheduled check-in time. This ensures a smooth and timely start to your adventure!

  • A: As much as we love animals, pets are not permitted on our paddle tours. We understand that your dog is part of the family, but for the safety and comfort of all guests, we have a no-pet policy during guided experiences.

    Thank you for understanding, we want to ensure everyone has a safe, enjoyable time on the water.

  • A: Yes, this is Florida, and alligators do live in our natural waterways, including the Winter Park Chain of Lakes. However, we want to reassure you that we have never seen an alligator on this waterway during our tours.

    We paddle in well-traveled, residential areas where alligator activity is minimal. Our guides are highly experienced and trained to keep all guests safe and comfortable. We’ve guided thousands of peaceful paddle tours with zero alligator-related incidents.

    If you have any concerns, feel free to reach out. We’re happy to answer your questions and help you feel at ease on the water.

  • A: Florida weather can be unpredictable! We do operate in light rain, which can make for a peaceful paddle. However, if there’s thunder, lightning, or unsafe weather conditions, your tour may be canceled for safety.

    If Otter Paddle Orlando cancels a tour, you’ll have the option to:

    • Reschedule

    • Or receive a gift card that never expires

    Please note: we do not offer refunds for weather-related cancellations. Our gift cards give you full flexibility to rebook whenever you’re ready.

    Safety is always our top priority, and we’ll stay in touch with updates if weather becomes a concern.

  • A: All of our paddle tours are guided group experiences, led by a friendly, knowledgeable local guide. We keep groups small and personal for a relaxed, connected vibe on the water.

    While solo guests are welcome to book, please note we require a minimum of two guests for a tour to operate. If you’re the only one booked, we’ll reach out to let you know. If no other guests join at least 24 hours in advance, you’ll have the option to reschedule or receive a full refund.

    Looking for a private paddle tour? Just reach out, we may be able to accommodate!

  • A: Yes! Otter Paddle gift cards never expire and can be used toward any of our guided paddleboard or kayak tours.

    They make a perfect gift for:

    • Nature lovers

    • Outdoor adventurers

    • Travelers visiting Florida

    • Locals looking for something new to experience

    • Birthdays, holidays, anniversaries, or just because

    Gift cards are available directly through our online booking system, easy to purchase and even easier to enjoy.

    Give the gift of relaxation, sunshine, and time on the water, Florida style.

IMPORTANT TOUR INFORMATION & POLICES

  • At Otter Paddle Orlando, we understand that plans may change, and we strive to accommodate our guests whenever possible. However, last-minute cancellations impact our operations and limit availability for others. To ensure fairness and efficient service, we have established the following policies.

    Cancellations Made in Advance: Cancellations made 72 hours or more before the scheduled booking date are eligible for a full refund. If a cancellation occurs within 72 hours of the booking date, guests may choose to reschedule or receive a gift card. Unfortunately, cancellations made on the day of the booking, as well as late arrivals and no-shows, are not eligible for a refund.

    Late Arrival Policy: We allow a 10-minute grace period for guests who may be delayed. After this grace period, we are unable to accommodate late arrivals, as it may disrupt the experience for other guests. Guests who cancel on the day of their tour, arrive after the 10-minute grace period, or do not show up but contact us on the day of their reservation may receive a gift card. However, a $75 rescheduling fee must be paid to obtain the gift card. Guests who contact us after the scheduled tour date will not be eligible for a refund, reschedule, or gift card.

    Weather Policy: For the safety of our guests, Otter Paddle Orlando reserves the right to cancel tours in the event of unsafe weather conditions, unforeseen circumstances, or any other reason that may compromise guest safety. While we do operate in light rain, if a tour is canceled by Otter Paddle Orlando due to weather or safety concerns, guests will have the option to reschedule their tour or receive a gift card for future use. Please note, that refunds will not be issued in these circumstances.

    Strictly Enforced: All policies are strictly enforced to ensure fairness and smooth operations. Gift cards issued by Otter Paddle Orlando do not expire, providing guests with the flexibility to reschedule at their convenience. This cancellation policy is subject to change. We will make every effort to communicate updates in advance, and we recommend reviewing our policy at the time of booking.

    By booking with Otter Paddle Orlando, guests acknowledge and agree to comply with the policies outlined above.

  • For the safety of our guests, Otter Paddle Orlando reserves the right to cancel tours in the event of unsafe weather conditions, unforeseen circumstances, or any other reason that may compromise guest safety.

    While we do operate in light rain, if a tour is canceled by Otter Paddle Orlando due to weather or safety concerns, guests will have the option to reschedule their tour or receive a gift card for future use.

    Please note, that refunds will not be issued in these circumstances.

    • A completed waiver is required for each participant prior to check-in. Once the reservation has been made, you will receive a booking confirmation email with online waiver instructions + more.

    • Each participant must be a confident swimmer, comfortable in and around the water, must be fully mobile and in good physical condition to join this tour. Paddle boarding is a physical activity.

    • Minors under 18 years of age must be accompanied by a parent/guardian.

    • Minors 4-12 years of age must be accompanied by a parent/guardian on the same paddle board.

    • Minors 13-17 years of age may paddle board on their own, with a parent/guardian next to the minor for the full duration of the tour.

    • Minors 3 years of age and under are not permitted.

    • Pets are not permitted.

  • Otter Paddle Orlando requires a minimum of two guests per tour.

    If you are the only guest booked for a tour we will notify you at least 24 hours in advance. If the tour minimum is not met, you will have the option to:

    • Reschedule to another available tour

    • Purchase a second spot to turn your experience into a private tour

    • Receive a full refund

    We’ll always do our best to accommodate solo guests, and this flexible option allows you to guarantee your adventure, even if you're the only one booked.

 

ABOUT THE WINTER PARK CHAIN OF LAKES

Your adventure takes place on the breathtaking Winter Park Chain of Lakes, featuring Lake Maitland, Lake Osceola, and the scenic Venetian-style canals that connect them. This peaceful waterway system is surrounded by lush landscapes, historic homes, and wildlife offering some of the most beautiful paddling in Central Florida.

We launch from Kraft Azalea Garden, 1365 Alabama Dr, Winter Park, FL 32789. This shaded, lakefront park is a true hidden gem, located just 20 minutes from downtown Orlando.

Whether you're a local looking for a peaceful nature escape or a visitor searching for a relaxing paddleboard or kayak tour near Orlando, we’ve got you covered.

LET’S GET YOU ON THE WATER

Whether you're standing tall on a paddleboard or relaxing in our seated kayak hybrid setup, this peaceful guided tour is your chance to unwind, connect with nature, and experience Winter Park from a whole new perspective.

  • All Skill Levels Welcome - No experience needed

  • Photos Included - Capture the moment with our premium photo + video package

  • Perfect for Families, Couples, and First-Time Paddlers

Spots fill up quickly, especially for sunset tours and weekends, so don’t wait, book your Winter Park Paddle Adventure today and paddle into something unforgettable. Reservations are required at least 12 hours in advance. Once your reservation is complete, you’ll receive a confirmation email with everything you need to know for your upcoming adventure.

  • Premium Paddle Board or Kayak Hybrid

  • USCG-Approved PFD (Life Vest) + Whistle

  • Dry Bag for Your Essentials

  • Friendly, Knowledgeable Tour Guide

  • Paddle & Water Safety Instruction

  • Professional Photo + Video Package

High-performance NIXY paddle board used by Otter Paddle Orlando, designed for stability and smooth paddling on Florida’s scenic rivers and springs.
All Tours Include:
  • Explore the water with our kayak setup, combining the agility of a paddle board with the comfort of a kayak.

  • Our premium paddle boards boast top-notch stability and performance, while our kayak option features a deluxe kayak seat and kayak paddle for an enhanced, leisurely adventure.

Nixy Kayak Paddle
Paddle Board Kayak:
Nixy Kayak Seat