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Skip to main content
Adventure Collective Logo
Adventure ExperiencesLocal ExpertsLocationsAbout
Menu

The Adventure Collective

The Adventure Collective Discover, plan, and share your outdoor adventures with our global community of explorers.

Add as a preferred

source on Google

Explore Adventures

  • All Adventures
  • Boat Charters
  • Water Activities
  • Fishing
  • Land Adventures
  • Motorized Land
  • Winter Sports

Explore Adventures

  • Aerial Adventures
  • Wildlife & Nature
  • Camping & Overnight
  • Climbing & Mountaineering

Find Local Experts

  • Browse Local Experts
  • Become a Featured Expert

Company

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  • Editorial Policy
  • Advertising
  • Add Your Business
  • Contact Us
  • The Adventure Network

Legal & Privacy

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  • General Terms and Conditions
  • Cookies and Marketing Preferences
  • Legal Notice
  • Information according to the Digital Services Act
  • Do not Sell or Share my Personal Information
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Adventure Town Guides

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© 2026 The Adventure Collective. All rights reserved.

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Chincoteague Cruises for Celebration, Relaxation, and Local Flavor

Tiki‑boat vibes, curated drinks, exclusive Pony Swim viewing, and private charters around Chincoteague Island.

  1. Adventure Tour Operators
  2. Bottoms Up Tiki Tours

Featured Cruises & Experiences

Sunset sails, brunch boats, fishing day trips, Pony Swim vantage, tiki luaus, and private charters.

Tides & Vine on the Water: Wine Cruise in Chincoteague, VA
Chincoteague

Tides & Vine on the Water: Wine Cruise in Chincoteague, VA

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.

Tides & Vine on the Water: Wine Cruise in Chincoteague, VA

Tides & Vine on the Water: Wine Cruise in Chincoteague, VA

water activities
Chincoteague, Virginia
100th Pony Swim Back: Chincoteague's Iconic Boat Tour
Chincoteague

100th Pony Swim Back: Chincoteague's Iconic Boat Tour

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.

100th Pony Swim Back: Chincoteague's Iconic Boat Tour

100th Pony Swim Back: Chincoteague's Iconic Boat Tour

Brunch on the Bay in Chincoteague, VA: Scenic Floating Feast with Bottomless Mimosas
Chincoteague

Brunch on the Bay in Chincoteague, VA: Scenic Floating Feast with Bottomless Mimosas

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.

Brunch on the Bay in Chincoteague, VA: Scenic Floating Feast with Bottomless Mimosas
Castaway Day Trippin’: Ultimate Full-Day Chesapeake Bay Fishing Experience from Chincoteague, VA
Chincoteague

Castaway Day Trippin’: Ultimate Full-Day Chesapeake Bay Fishing Experience from Chincoteague, VA

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.

Castaway Day Trippin’: Ultimate Full-Day Chesapeake Bay Fishing Experience from Chincoteague, VA
Celebrate on the Water with Bottoms Up Private Charter in Chincoteague, VA
Chincoteague

Celebrate on the Water with Bottoms Up Private Charter in Chincoteague, VA

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.

Celebrate on the Water with Bottoms Up Private Charter in Chincoteague, VA

Celebrate on the Water with Bottoms Up Private Charter in Chincoteague, VA

Sunset Cruise on Chincoteague Island: Experience Magical Evenings on the Water
Chincoteague

Sunset Cruise on Chincoteague Island: Experience Magical Evenings on the Water

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.

Sunset Cruise on Chincoteague Island: Experience Magical Evenings on the Water
Experience the Ultimate Tiki Luau Sunset Cruise on Chincoteague Bay
Chincoteague

Experience the Ultimate Tiki Luau Sunset Cruise on Chincoteague Bay

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.

Experience the Ultimate Tiki Luau Sunset Cruise on Chincoteague Bay

Experience the Ultimate Tiki Luau Sunset Cruise on Chincoteague Bay

Licensed to Chill: Relaxing Two-Hour Scenic Cruise Through Chincoteague and Crisfield Waterways
Chincoteague

Licensed to Chill: Relaxing Two-Hour Scenic Cruise Through Chincoteague and Crisfield Waterways

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.

Licensed to Chill: Relaxing Two-Hour Scenic Cruise Through Chincoteague and Crisfield Waterways
It's 5 O'Clock Somewhere! Unwind on a Scenic Afternoon Cruise in Chincoteague, VA
Chincoteague

It's 5 O'Clock Somewhere! Unwind on a Scenic Afternoon Cruise in Chincoteague, VA

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.

It's 5 O'Clock Somewhere! Unwind on a Scenic Afternoon Cruise in Chincoteague, VA

It's 5 O'Clock Somewhere! Unwind on a Scenic Afternoon Cruise in Chincoteague, VA

About Bottoms Up Tiki Tours

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.

Bottoms Up Tiki Tours fleet
Bottoms Up Tiki Tours team

Bottoms Up Tiki Tours — Chincoteague Island Cruises, Charters, and Specialty Events

Bottoms Up Tiki Tours operates vibrant tiki-boat cruises and private charters around Chincoteague Island and the Eastern Shore. Travelers searching for Chincoteague boat tours, Pony Swim viewing, sunset cruises, brunch cruises, or private charters find curated, themed experiences that combine local flavor, scenic waterways, and reliable service.

Signature Cruises and What to Expect

  • Tides & Vine on the Water — a 2-hour, 21+ curated wine and charcuterie cruise showcasing Chincoteague waterways. Ideal for wine lovers and small groups.
  • Pony Swim Vantage Trips — exclusive boat access for the iconic Chincoteague Pony Swim event. Offers unique wildlife viewing and cultural connection.
  • Brunch on the Bay — a 2-hour floating brunch with bottomless mimosas and catered hors d’oeuvres.
  • Castaway Day Trippin’ Adventure — an all-inclusive day trip for anglers combining breakfast, a full-day fishing charter, and dinner.
  • Tiki Luau Cruise — Polynesian-inspired sunset sailing with food, dancing, and tiki bar stops (21+ on select sails).
  • Five O’Clock Somewhere & License To Chill — relaxed 2-hour cruises stopping at local waterfront bars and seafood spots.
  • Private Charters — fully customizable cruises for birthdays, proposals, corporate events, and group outings.

Why book a Bottoms Up cruise?

  • Local knowledge: captains and crew navigate Chincoteague and Chesapeake Bay waters safely.
  • Variety: public sails, adult-only events, family-friendly trips, day-long fishing charters, and private boat rentals.
  • Partnerships with local vendors like Don’s Seafood provide authentic regional flavors.
  • Special event access such as Pony Swim viewing provides rare perspectives for visitors.

Planning and Practical Details

  • Most cruises allow guests to bring their own food and drinks on select sails; others include curated menus or bar service.
  • Several experiences are designed as 21+ events (wine cruises, tiki luau), while daytime trips welcome families.
  • Private charter options enable tailored itineraries, set menus, and special-request stops.

Ideal audiences and search keywords

Bottoms Up Tiki Tours appeals to:

  • Couples seeking romantic sunset cruises or wine tastings on the water.
  • Groups celebrating birthdays, reunions, or proposals via private charters.
  • Anglers and food lovers booking all-inclusive day trips on the Chesapeake Bay.
  • Visitors scheduling Pony Swim viewing from a boat for an authentic island tradition.

Search keywords to find these offerings: "Chincoteague boat tours," "Pony Swim boat viewing," "Chincoteague sunset cruise," "tiki boat cruise Chincoteague," "Chincoteague brunch cruise," "private boat charter Chincoteague," and "Chesapeake fishing day trip."

Book with confidence

Bottoms Up Tiki Tours emphasizes licensed vessels, professional crews, and clear reservation options for both scheduled public sails and private charters. For visitors prioritizing memorable, local, and social experiences on Chincoteague waters, these cruises deliver scenic views, curated food and drink choices, and specialized event access.

Plan ahead for peak-season dates and specialty events like the Pony Swim to secure preferred boats and times.

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Book a Cruise Before Seats Sail Away

Secure a spot on a public cruise or request a private charter for a tailored celebration.

wildlife nature
boat charters
Chincoteague, Virginia

Brunch on the Bay in Chincoteague, VA: Scenic Floating Feast with Bottomless Mimosas

boat charters
water activities
Chincoteague, Virginia

Castaway Day Trippin’: Ultimate Full-Day Chesapeake Bay Fishing Experience from Chincoteague, VA

fishing
water activities
Chincoteague, Virginia
boat charters
water activities
Chincoteague, Virginia

Sunset Cruise on Chincoteague Island: Experience Magical Evenings on the Water

boat charters
water activities
Chincoteague, Virginia
boat charters
water activities
Chincoteague, Virginia

Licensed to Chill: Relaxing Two-Hour Scenic Cruise Through Chincoteague and Crisfield Waterways

boat charters
water activities
Chincoteague, Virginia
water activities
boat charters
Chincoteague, Virginia

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