Chincoteague’s Up The Bay Pony and Wildlife Tour by Boat is a charming, engaging way to explore the waterways surrounding Chincoteague and Assateague Islands. Priced at $75 per person and lasting approximately 2 hours, this tour offers a close-up look at the famous wild ponies, alongside a variety of native wildlife like eagles, pelicans, and dolphins. The experience is led by a captain with over 40 years of local knowledge, ensuring you get a genuine, authentic view of this unique ecosystem.
What we love most about this tour are two key aspects: first, the personalized approach where the guide asks about your interests and tailors the trip accordingly, and second, the small group size (max six people), which makes the experience intimate and flexible. Plus, the tour’s wheelchair and stroller accessibility means it’s inclusive for many travelers.
A possible consideration is the weather-dependent nature of boat trips. Since the tour requires clear skies and calm waters, poor weather might lead to cancellations or rescheduling, so it’s worth planning with a bit of flexibility.
This tour suits travelers who crave up-close wildlife sightings, enjoy local stories, and appreciate a more personal, relaxed outing. Families with children, wildlife enthusiasts, or anyone wanting a comfortable, informative ride will find it especially rewarding.
Key Points
- Personalized Experience: Guides tailor the tour based on your preferences and questions.
- Wildlife Viewing: Excellent opportunities to see ponies, dolphins, eagles, and more.
- Expert Guides: Captain Mike has over 40 years of local waterway knowledge.
- Accessibility: Suitable for wheelchair users and strollers.
- Small Group: Max six travelers for an intimate experience.
- Flexible Timing: Sunrise and sunset tours available.
Exploring the Waterways of Chincoteague and Assateague

This boat tour is a delightful way to see the islands from a different perspective. Instead of walking or driving, you’re floating along the waterways, which instantly immerses you into the natural rhythm of the area. The two-hour duration strikes a nice balance—long enough to explore multiple spots but not so lengthy as to feel tiring.
From the start at 2246 Curtis Merritt Harbor Drive, you’ll meet your captain—most likely Mike, a local with decades of sailing experience. His familiarity with the waters shines through from the first moments, guaranteeing you’re in expert hands.
The tour begins with a questionnaire about your interests, which allows the captain to focus on what excites you most—be it ponies, birdlife, or dolphins. This sets the tone for a customized experience that feels more like an outing with a knowledgeable friend than a scripted tour.
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The Assateague Island Adventure

One of the highlights is the passage through the southern and northern parts of Assateague Island. Here, you’ll witness the famous Chincoteague Ponies, roaming freely across the marshes and beaches. The boat’s small size and maneuverability allow you to get as close as possible without disturbing these gentle creatures.
A favorite moment among visitors is passing the Pony Swim and Assateague Lighthouse, both iconic sights that add a scenic and historic element to the trip. Several reviews mention how the guide’s knowledge enriches the experience: “Mike knows all the ponies and works very hard to provide optimal viewing opportunities,” says one traveler.
On some days, the boat ventures out into the open ocean in search of dolphins. Seeing these intelligent creatures leap and play is a real treat that many visitors cherish. As one reviewer notes, “We saw dolphins which was great,” emphasizing the unpredictability and excitement of wildlife encounters.
Wildlife Encounters and Bird Watching

Beyond the ponies, the waterways are teeming with birdlife like eagles, ospreys, herons, and pelicans. The captain is adept at pointing out these species, sharing stories and facts that deepen your appreciation for how these animals coexist in this delicate environment.
According to reviews, the eagle sightings are a common highlight, and many visitors get close enough to admire these regal birds perched in trees or soaring overhead. The marshes are also home to Riptide, a well-known pony, and the guide’s ability to identify and tell stories about individual ponies adds a personal touch that makes the experience memorable.
The Dolphin Sighting Potential
Dolphins are not guaranteed, but the chance to see them in their natural habitat is a bonus. The open ocean cruise portion offers an exciting opportunity for wildlife lovers, especially during the right season. One reviewer shared, “We saw dolphins which was great,” which underscores how spontaneous and exhilarating wildlife encounters can be here.
The Comfort and Practicalities

The boat itself is described as pristine and comfortable, with a cover top that provides shade during hot days—a feature that some reviewers suggested could be added or improved. Captain Mike responds promptly to such feedback, noting that during the warmer months, the tops are typically up for sun protection.
The small group size makes for a more relaxed and engaging atmosphere. You won’t be jostled or ignored in a crowd; instead, you’re encouraged to ask questions and participate actively.
The cost of $75 is quite reasonable for an experience packed with wildlife, scenery, and local stories. Compared to larger tours, this one offers more value for money because of its intimate nature and the level of personal attention.
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Who Will Love This Tour?

If you appreciate learning about local wildlife and want to see the famous ponies in a natural, undisturbed setting, this tour is ideal. It’s perfect for families, bird watchers, and wildlife enthusiasts. The accessible nature of the boat also makes it suitable for travelers with mobility challenges.
Those seeking a calmer, more personalized experience will find this tour a refreshing change from larger, less intimate boat rides. Meanwhile, visitors with flexible schedules might enjoy the sunrise or sunset options for a truly magical experience.
Final Thoughts

This boat tour around Chincoteague and Assateague Islands offers more than just a chance to see the ponies—it’s a full immersion into the area’s natural beauty and wildlife. The expert guidance and small group setting enable a more meaningful connection with the environment, making it a highlight of most trips to the area.
For wildlife lovers, families, or anyone wanting a relaxed, authentic experience, this tour provides an excellent combination of scenery, stories, and wildlife sightings. The value for money is clear, especially given the personalized attention and the opportunity to see dolphins, eagles, and many ponies up close.
In short, if you want to spend a memorable couple of hours on the water, learning about this unique ecosystem from a local who truly cares, this tour is a highly recommended choice.
FAQ

How long does the tour last?
The tour is approximately 2 hours, providing plenty of time to see wildlife and enjoy the scenery without feeling rushed.
What is the meeting point?
The tour begins at 2246 Curtis Merritt Harbor Drive in Chincoteague. The guide will be waiting there for your scheduled departure.
Is this tour suitable for all ages?
Yes, the tour is generally suitable for most travelers. It is wheelchair and stroller accessible, making it inclusive for many.
What wildlife might I see?
You can expect to see wild ponies, eagles, pelicans, herons, osprey, and possibly dolphins during the open ocean portion.
How many people are in each group?
The tour is limited to 6 travelers maximum, ensuring a comfortable, personalized experience.
Can I cancel if my plans change?
Yes. The tour offers free cancellation up to 24 hours in advance for a full refund.
What should I bring?
Comfortable clothing, sun protection, and cameras are recommended. The boat has a cover top during warmer months for sun protection.
Is the tour weather dependent?
Yes, the experience requires good weather. If canceled due to poor weather, you can reschedule or receive a full refund.
In all, Up the Bay Pony and Wildlife Tour by Boat offers an authentic, well-reviewed chance to explore one of Virginia’s most unique ecosystems. It’s a perfect choice for those who want a relaxed, informative, and wildlife-rich outing in Chincoteague.
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