Savor curated wines and gourmet charcuterie aboard a scenic 2-hour cruise around Chincoteague Island. Perfect for a relaxed 21+ escape with friends or a unique date idea.
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 as the cruise is relaxing and seated the entire time.
Wildlife
History
Chincoteague Island has a rich maritime history, famous for its annual pony swim and local fishing traditions.
Conservation
Efforts in Chincoteague focus on protecting the delicate coastal ecosystem and maintaining the wild pony population with sustainable tourism practices.
Bottoms Up Tiki Tours
Savor curated wines and gourmet charcuterie aboard a scenic 2-hour cruise around Chincoteague Island. Perfect for a relaxed 21+ escape with friends or a unique date idea.
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.
Arrive Early for Parking
Plan to arrive at least 15 minutes early to find parking and check in smoothly.
Dress for the Weather
Bring layers or a light jacket, as breezes on the water can be cool even in summer.
Limit Mobile Phone Use
Enjoy the moment and the views by minimizing phone distractions during the cruise.
Follow Responsible Drinking Guidelines
This experience is 21+, so please enjoy wine responsibly for everyone’s safety.
Light Jacket or Sweater
Keeps you warm against cool breezes on the water.
spring
Sun Hat
Protects your face from strong sun during daytime cruises.
summer
Bug Spray
Helps prevent mosquito bites during warmer months near the water.
summer
Sunglasses
Reduces glare reflecting off the water for clearer views.