Along Virginia’s pristine coastline, two standout kayaking destinations deserve special attention: Assateague and Chincoteague Islands.
The well-organized tours by Assateague Explorer (4.3 stars) make these waters accessible to all skill levels, offering both single and tandem kayaks. Morning and afternoon slots let visitors choose their ideal paddling time.
I especially love the Chincoteague Pony Swim Kayak Tour, planned for 2025. This unique experience puts you right in the middle of the action during the famous annual pony crossing.
Unlike crowded shore viewing, the kayak tour (limited to 100 people) provides an intimate vantage point with shuttle support.
Let’s explore the best kayaking tours Virginia has to offer.
Key Points
- Assateague Explorer Wildlife Cruise & Kayak Tour offers a popular 4.3-star rated kayak experience along Assateague and Chincoteague Island.
- Chincoteague Pony Swim Kayak Tour by Assateague Adventures provides a unique opportunity to observe the annual pony swim event from the water.
- Kayak tours in Virginia’s natural habitats, such as scenic waterways and wildlife-rich areas, offer adventure and immersion in the region’s natural and cultural heritage.
- Kayak tours cater to both seasoned kayakers and beginners, with necessary equipment provided and guides offering information on local wildlife and natural landscapes.
- Advance booking is recommended for these limited-group kayak experiences due to their popularity and to ensure a memorable adventure.
Kayak Tour Along Assateague & Chincoteague Island, Virginia
One of the popular kayak tours in Virginia is the tour along Assateague and Chincoteague Island. Offered by Assateague Explorer Wildlife Cruise & Kayak Tour, this 4.3-rated tour allows visitors to experience the natural habitat of wild ponies.
The tour options include single or tandem kayaks, with morning or afternoon departures. The tour provides all necessary equipment, including the kayak, paddle, and personal flotation device.
The meeting point is at Veterans Memorial Park in Chincoteague, and the tour returns to the same location. The group size is limited to a maximum of 25 travelers.
While the tour isn’t wheelchair accessible, service animals are allowed. It’s important to note that the tour isn’t recommended for those with back problems, pregnant travelers, or individuals with heart conditions, as a moderate level of physical fitness is required.
Guides offer information on the local wildlife, including bald eagles and various bird species. Experiences may vary due to weather conditions, but many travelers have reported enjoying close encounters with the iconic wild ponies.
Read our full review: Kayak Tour Along Assateague & Chincoteague Island, Virginia Review
Book now: Check availability
Chincoteague Pony Swim Kayak Tour 2025 With Shuttle
As the sun rises over the tranquil waters of Chincoteague, adventure-seekers gather at the east side boat ramp for the Chincoteague Pony Swim Kayak Tour 2025.
Operated by Assateague Adventures, this thrilling excursion allows visitors to witness the annual pony swim from the unique vantage point of a kayak. For $300 per person, guests embark on a shuttle-supported tour that includes all necessary equipment, such as kayaks, life vests, and snacks.
With a maximum capacity of 100 travelers, this small-group experience ensures an intimate and personalized outing. The tour begins at 6:00 am and returns to the meeting point, providing ample time to observe the iconic pony swim and explore the scenic waterways.
Whether you’re a seasoned kayaker or a first-time adventurer, this tour offers an unforgettable opportunity to learn about the rich natural and cultural heritage of Chincoteague.
Read our full review: Chincoteague Pony Swim Kayak Tour 2025 With Shuttle Review
Book now: Check availability
Recap
Virginians and visitors alike can enjoy a wealth of exceptional canoe and kayak experiences across the state. From tranquil paddles along Assateague and Chincoteague Islands to the iconic Chincoteague Pony Swim, Virginia’s waterways offer unparalleled natural beauty and unique adventures. Whether you’re a seasoned paddler or a first-time enthusiast, these top-rated experiences promise unforgettable memories on the water.