Sip curated wines and listen to smooth jazz aboard an elegant Virginia Beach charter. The Wine Down Wednesday cruise offers a midweek sunset escape on the Chesapeake Bay that's perfect for relaxing solo or with friends.
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Difficulty
easy
Duration
1.5 hours
Fitness Level
No special fitness required; suitable for all adults able to board the boat safely.
Wildlife
History
Virginia Beach has a rich maritime heritage, serving as an important naval and recreational area since the early 20th century.
Conservation
The operators support local waterway conservation efforts by minimizing waste and encouraging sustainable boating practices.
Legacy Boat Charters
Sip curated wines and listen to smooth jazz aboard an elegant Virginia Beach charter. The Wine Down Wednesday cruise offers a midweek sunset escape on the Chesapeake Bay that's perfect for relaxing solo or with friends.
Legacy Boat Charters is a Virginia Beach-based charter company offering a curated mix of ticketed events and private boat experiences on the Chesapeake Bay and Atlantic waterways.
Founded to deliver memorable outings for locals and visitors, Legacy Boat Charters provides themed evening cruises, private fishing and sightseeing charters, and unique vehicle-boat experiences from a 31-foot Luhrs and a five-seat JetCar.
The company operates ticketed weekly events including Tipsy Tuesday's, Wine Down Wednesday, and Friday Night Vibes: R&B Edition, each featuring curated music, handcrafted drinks, and sunset cruising routes. For private groups, Legacy Boat Charters offers the 31 ft Luhrs private charter accommodating up to ten guests, pontoon Broad Bay charters for relaxed group outings, and customizable date-night or special occasion cruises.
Legacy Boat Charters emphasizes safety and guest comfort with experienced captains familiar with Virginia Beach waters, clear pre-trip communication, and well-maintained vessels equipped with essential amenities such as air conditioning and onboard microwaves. Guests are encouraged to bring food, beverages, coolers, and games for private charters, while ticketed events include curated drink and music experiences.
Operating from Virginia Beach, Legacy Boat Charters serves day and evening charters focused on sightseeing, dolphin watching, sunset cruises, and casual fishing. The company’s combination of themed events, private options, and distinctive offerings makes it a versatile choice for romantic evenings, group celebrations, and adventure-seeking visitors.
Bookings offer flexible duration options, transparent pricing, and online ticketing for events. Legacy Boat Charters maintains required insurance and follows local safety regulations to ensure dependable outings and inspections.
Home Port
Virginia Beach
Operates from Virginia Beach waters
Max Guests
Up to 10
31 ft Luhrs accommodates ten guests
Trips Offered
Ticketed & Private
Weekly events and private charters
Vessel Types
Luhrs, Pontoon, JetCar
Multiple vessel options available
Reserve tickets for a themed evening or schedule a private 31 ft Luhrs or pontoon charter — spots fill quickly for weekends and sunset runs.
Book Early for Midweek Seats
Wine Down Wednesday fills up quickly—reserve your ticket in advance to secure your spot on this popular midweek cruise.
Dress for Evening Breeze
Evenings on the water can get cool, so bring a light jacket or layers for comfort during sunset.
Arrive 15 Minutes Early
Plan to arrive at least 15 minutes before departure to ensure a smooth boarding experience and get settled comfortably.
Stay Hydrated
Along with wine, enjoy provided non-alcoholic beverages to stay refreshed throughout the cruise.
Light Jacket
For cool spring evenings on the water to stay comfortable during the sunset cruise.
spring
Sunglasses
Protect your eyes from the low sun glare while enjoying the waterfront views.
summer
Camera or Smartphone
Capture stunning sunset moments over Chesapeake Bay during this visually rich cruise.
fall
Comfortable Shoes
Wear non-slip shoes suitable for boarding and moving safely on the boat deck.
winter