Set sail on License To Chill, a two-hour sunset cruise exploring the scenic waterways of Chincoteague and Crisfield. Enjoy fresh local seafood spots, peaceful bay views, and a relaxing afternoon on the water.
More ways to explore the area's outdoor wonders
Hang tight — photos are loading
This usually takes just a second.
Difficulty
easy
Duration
2 hours
Fitness Level
No special fitness level required; suitable for all ages and mobility levels.
Wildlife
History
Chincoteague has a rich maritime history tied to the oyster and crab fisheries dating back over a century, shaping local culture and economy.
Conservation
The local community actively participates in oyster restoration projects to maintain healthy bay ecosystems and support sustainable fisheries.
Bottoms Up Tiki Tours
Set sail on License To Chill, a two-hour sunset cruise exploring the scenic waterways of Chincoteague and Crisfield. Enjoy fresh local seafood spots, peaceful bay views, and a relaxing afternoon on the water.
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 Food and Drinks
This cruise allows you to bring your own snacks and beverages to enjoy during the trip—plan accordingly for your comfort and preferences.
Arrive Early for Check-In
Be sure to arrive at least 15 minutes prior to departure to ensure a smooth boarding process and get settled comfortably.
Dress for Coastal Weather
Wear layers and bring sun protection; coastal winds and sun exposure can be stronger than expected midday.
Watch for Wildlife
Keep an eye out for local birds and marine life along the shoreline—binoculars can enhance the experience.
Sunscreen
Protects your skin from strong sun exposure on the open water.
summer
Light Jacket or Windbreaker
Helps guard against coastal breezes and cooler temperatures.
spring
Binoculars
Enhances wildlife and shoreline viewing opportunities.
Reusable Water Bottle
Keep hydrated throughout the cruise with your own water supply.