Join Bottoms Up Tiki Tours for an exclusive boat ride witnessing wild ponies swim back to Chincoteague Island. Experience a rare view of this iconic tradition surrounded by nature and comfort.
More ways to explore the area's outdoor wonders
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Difficulty
easy
Duration
2–3 hours
Fitness Level
Minimal physical effort required; suitable for all fitness levels including families and seniors.
Wildlife
History
The Pony Swim tradition began over 90 years ago as a means for local ranchers to move ponies between Assateague and Chincoteague Islands for annual sale.
Conservation
Efforts by local organizations maintain the delicate balance between pony populations and the island’s natural environment, promoting sustainable tourism.
Bottoms Up Tiki Tours
Join Bottoms Up Tiki Tours for an exclusive boat ride witnessing wild ponies swim back to Chincoteague Island. Experience a rare view of this iconic tradition surrounded by nature and comfort.
Bottoms Up Tiki Tours is a Chincoteague-based tiki boat company specializing in narrated and themed cruises on the waters around Chincoteague Island and the Chesapeake Bay. The company offers a range of public and private experiences including Tides & Vine on the Water, Pony Swim vantage trips, Brunch on the Bay, Castaway Day Trippin’ Adventure, sunset and evening cruises, a Tiki Luau Cruise, Five O’Clock Somewhere cruises, and fully customizable private charters. Many experiences are 21+ with curated wine or tiki bar options; family-friendly choices are available for select daytime trips.
Each cruise features curated food and drink options, local stops like Don’s Seafood and Chinco Tiki, and an emphasis on island vibes, wildlife viewing, and waterfront scenery. Professional captains and crew operate licensed vessels and prioritize safety, local navigation knowledge, and guest comfort. Bottoms Up Tiki Tours serves both visitors and locals seeking memorable celebrations, date nights, group outings, or event-specific experiences such as the historic Chincoteague Pony Swim. The Pony Swim viewing option offers an exclusive boat perspective on the iconic island tradition.
Reservations can be made for scheduled public cruises or for private charters tailored to birthdays, proposals, corporate outings, or special occasions. The company highlights stress-free, all-inclusive day trips for anglers and food lovers, including the new Castaway Day Trippin’ Adventure for 2025. With a focus on hospitality, local partnerships, and unique floating experiences, Bottoms Up Tiki Tours provides accessible, authentic water-based recreation around Chincoteague and the Eastern Shore.
Booking is simple through an online system.
Tours Offered
10+
Public sails and specialty cruises available
Adult Cruises
Select 21+ trips
Curated wine and tiki bar options
Private Charters
Available
Custom events: birthdays, proposals, groups
Signature Event
Pony Swim Access
Exclusive boat vantage for Pony Swim
Secure a spot on a public cruise or request a private charter for a tailored celebration.
Book Early to Secure Your Spot
This popular event has limited private boat availability, so reserve your tour well in advance.
Bring Binoculars for Better Viewing
Enhance your pony watching experience by bringing binoculars to spot details from a distance.
Dress in Layers
Even on warm days, the breeze on the water can get chilly, so wear layers you can adjust easily.
Protect Your Gear from Water Spray
Bring a waterproof bag or cover for your camera and belongings as you’ll be on the water.
Layered Clothing
Adjust to varying temperatures and breezes on the boat by layering your clothing.
Waterproof Camera Case
Protect your camera or phone from water spray while capturing memorable photos.
Binoculars
Enhance your viewing experience by spotting ponies and wildlife in detail from the boat.
Sunscreen
Shield your skin from strong sun exposure while out on the water.
summer