Set sail from Chincoteague Island on a relaxing afternoon cruise that blends stunning coastal views with a scenic stop at a waterfront bar. Perfect for families and groups seeking a laid-back water adventure.
More ways to explore the area's outdoor wonders
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Difficulty
easy
Duration
2 hours
Fitness Level
Suitable for all fitness levels since the tour is seated and relaxed on the boat
Wildlife
History
Chincoteague Island is famous for its wild ponies and annual Pony Swim, a local tradition dating back to the 17th century.
Conservation
The preservation of Chincoteague’s marshlands and waterways is critical; operators promote low-impact boating to protect wildlife habitats.
Bottoms Up Tiki Tours
Set sail from Chincoteague Island on a relaxing afternoon cruise that blends stunning coastal views with a scenic stop at a waterfront bar. Perfect for families and groups seeking a laid-back water adventure.
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.
Bring your own drinks and snacks
Guests are encouraged to bring their favorite food and drinks to enjoy during the cruise, enhancing your personalized experience.
Book early to secure your spot
Trips require a minimum of six passengers to run, so reserving ahead ensures your cruise departs as scheduled.
Wear layered clothing
Coastal weather can change quickly; layers keep you comfortable throughout the afternoon cruise.
Arrive promptly
Arriving on time at the meeting point helps make the smoothest departure and maximizes your time on the water.
Sunglasses
Protect your eyes during sunny afternoon cruising.
summer
Light jacket or windbreaker
Keeps you warm against coastal breezes that pick up in the afternoon.
spring
Hat with brim
Shields your face from the sun during the open water portions of the cruise.
summer
Reusable water bottle
Stay hydrated while enjoying the relaxing 2-hour trip.