Tiki‑boat vibes, curated drinks, exclusive Pony Swim viewing, and private charters around Chincoteague Island.
Sunset sails, brunch boats, fishing day trips, Pony Swim vantage, tiki luaus, and private charters.
water-activities · Chincoteague
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.
“Every outing is organized with local river knowledge, basic safety instruction, and equipment checks before departure.”
Public sails and specialty cruises available
Curated wine and tiki bar options
Custom events: birthdays, proposals, groups
Exclusive boat vantage for Pony Swim
Open the individual experience guide to confirm current availability, pricing, policies, conditions, and inclusions before booking.
The operator provides clear meeting points, departure times, and destination coordinates for all outings.
Personal flotation devices, emergency protocols, equipment checks, and paddling orientations are provided before departure.
Recommended layering, water shoes, sunscreen, and dry bags are detailed in each experience guide.
Guides share rich knowledge of regional flora, fauna, scenic landmarks, and river navigation.
A glimpse into the experiences, natural landscapes, and adventures waiting on your next trip.
Images supplied on the current Bottoms Up Tiki Tours listing.
Bottoms Up Tiki Tours offers a variety of guided outdoor excursions, scenic routes, rentals, and custom itineraries tailored for families, couples, and adventure enthusiasts.
Yes. Most trips feature comprehensive safety orientations, equipment fittings, and calm routes suited for first-time adventurers. Check the details on individual experience guides for specific age and skill requirements.
Standard safety equipment (such as certified life vests and essential gear) is supplied for each booking. Detailed checklists regarding weather-appropriate attire and personal items are provided prior to departure.
Secure a spot on a public cruise or request a private charter for a tailored celebration.
wildlife-nature · Chincoteague
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.
boat-charters · Chincoteague
Experience Chincoteague, VA, from the water with "Brunch on the Bay," a two-hour floating brunch cruise featuring bottomless mimosas, local hors d’oeuvres, and stunning waterfront views. Discover why this open-air brunch is a perfect weekend upgrade on the Eastern Shore.
fishing · Chincoteague
Discover the ultimate Chesapeake Bay fishing adventure leaving from Chincoteague, VA. Spend a full day on the water with expert Captain David Barone Sr., enjoy local Eastern Shore cuisine, and fish prime spots around Tangier Sound on the No Excuse charter.
boat-charters · Chincoteague
Turn your celebration into an unforgettable adventure with Bottoms Up Private Charter in Chincoteague, Virginia. Customize your private cruise to enjoy stunning waterways, local wildlife, and a unique coastal experience.
boat-charters · Chincoteague
Experience the tranquil beauty of Chincoteague Island’s waters during the magical sunset hours. This two-hour cruise offers breathtaking views, wildlife sightings, and peaceful vibes perfect for families and adventurers alike.
boat-charters · Chincoteague
Set sail on Chincoteague Bay for a two-hour Tiki Luau Sunset Cruise that combines Polynesian-inspired dining, tropical beats, and stunning golden hour views. Discover why this floating island party is a must-do for visitors 21 and over.
boat-charters · Chincoteague
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.
water-activities · Chincoteague
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.
Click into any experience card above to view current dates, live availability, transparent pricing, cancellation policies, and booking details.