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March 31, 2024
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Chesapeake Bay Sailing Charters are the Perfect Way To Create New Memories
Enjoy a luxury sailing experience overseen by an expert captain and crew! Under the guidance of a USCG-qualified captain, your group will set sail to enjoy amazing views and unforgettable experiences in pure comfort and bliss! Perfect for groups, families, or couples, our sailing charters bring you to the Eastern Shore, Solomons Island, Middle Bay, and beyond to discover diverse Mid-Atlantic estuaries and ecosystems.
What can you expect when you experience one of the sailing charters Chesapeake Bay locals love? After leaving the marina, you'll be tended to by an experienced crew. Our passengers enjoy the experience of being "carried by the wind" to beautiful coves and inlets showcasing breathtaking views. As a hotbed for wildlife, Chesapeake Bay is a great spot for sighting ospreys, otters, swans, and herons. Passengers especially love watching glistening sunsets over the water from our yachts!
Our gorgeous, well-maintained catamarans and monohulls offer unparalleled comfort. Sail Virginia Yacht Charters also proudly prioritize eco-friendly practices to ensure that the beautiful Chesapeake Bay environment remains protected for many generations to come!
Book Your Sailing Adventure
Aventura 37 Catamaran | Bareboat Rental
The Aventura 37 Catamaran offers a unique sailing experience with its elegant and dynamic design. This catamaran is perfect for those seeking comfort and performance, featuring a raised helm station and a spacious cockpit that can accommodate up to 6 guests. Enjoy the luxury of cruising with ample storage space and a well-thought-out interior layout.
Fountaine Pajot Helia 44' Catamaran | Bareboat Rental
The Fountaine Pajot Helia 44' Catamaran, known as the Freckled Parrot, is a luxurious sailing yacht perfect for those seeking an exceptional cruising experience. Designed as an owner's catamaran, it offers a spacious starboard side owner's suite, two portside guest cabins, and a bright, open salon. Each cabin features private en-suites and large deck hatches for cooling sea breezes. The cockpit provides a large dining area and a cushioned daybed under the shade of the hard top coach roof.
Jeanneau Sun Odyessy 389 | Bareboat Rental
The Jeanneau Sun Odyessy 389 is a 2018 model designed by Marc Lombard, offering an exceptional sailing experience for smaller crews. This cruiser combines speed, stability, and good seakeeping with a spacious and comfortable design. The yacht features a wide, open cockpit for entertaining and outstanding accommodations below deck, making it perfect for a memorable sailing adventure.
22′ Capri Bareboat | Full day Rental
Experience the thrill of sailing with our 22′ Capri Bareboat full-day rental. Perfect for those who love the open water, this rental offers a day of adventure and relaxation on the Chesapeake Bay. Whether you're an experienced sailor or a novice looking to learn, the Capri 22′ provides a smooth and enjoyable ride.
Colgate 26' | Full Day Rental
Experience the thrill of sailing on the Chesapeake Bay with our Colgate 26' full day rental. This spacious and comfortable yacht is perfect for a day of adventure on the water. Whether you're a seasoned sailor or a first-time explorer, the Colgate 26' offers a smooth and enjoyable ride, allowing you to soak in the stunning views and fresh sea breeze.
Why choose us?
Set Sail With Us - Unforgettable Chesapeake Bay Adventures Await!
At Sail Virginia Yacht Charters, we believe everyone should have the chance to enjoy the beauty of sailing on the Chesapeake Bay. Our friendly team is here to help you create unforgettable memories, whether you're planning a special event, a romantic getaway, or a fun family day out.
Our tours let you experience the best of Chesapeake Bay, including chances to see dolphins and enjoy the peaceful waterfront. No matter if you're a seasoned sailor or trying it for the first time, we make it easy for you to have a fantastic adventure.
Bareboat
Ready to plan a custom trip where you supply your own captain and crew? Our beautiful vessels are at your disposal! Choose among our fleet to select a boat that fits all of your guests. Our spot on...
Ready to plan a custom trip where you supply your own captain and crew? Our beautiful vessels are at your disposal! Choose among our fleet to select a boat that fits all of your guests. Our spot on the harbor makes it easy to set sail to explore so many unique spots in Chesapeake Bay. We offer a wide range of cruise charter packages to ensure you get exactly what you need.
Captained
We proudly provide sailing charters offering complete service! Let us handle every detail while you relax and have fun with your group. Our experienced captains can build a custom tour itinerary th...
We proudly provide sailing charters offering complete service! Let us handle every detail while you relax and have fun with your group. Our experienced captains can build a custom tour itinerary that showcases the most beautiful waterfront and bay views imaginable! We even offer a brunch charter that lets you spend a dreamy, leisurely day on the water with your group without lifting a finger. Ready to plan your pampered experience on Chesapeake Bay with us?
Family-Friendly
Select a boat charter or cruise for all ages with Sail Virginia Yacht Charters! We happily cater to families planning bonding experiences or celebrating big occasions. Rest assured that we prioriti...
Select a boat charter or cruise for all ages with Sail Virginia Yacht Charters! We happily cater to families planning bonding experiences or celebrating big occasions. Rest assured that we prioritize safety and fun for our guests on every trip. Whether you're staying at a vacation home in Rock Hall or a hotel in downtown Norfolk, we make it easy to board a boat with the whole family.
Experience The Beauty Of Chesapeake Bay And Norfolk, VA
Norfolk is a charming Mid-Atlantic maritime city that's teeming with history and natural beauty. There's no doubt you'll be inspired to board a boat of your own after touring the famed USS Wisconsin that's docked at Nauticus. Norfolk is also home to many attractions, including the Norfolk Botanical Garden, Chrysler Museum of Art, Virginia Zoo, Hermitage Museum and Gardens, and MacArthur Memorial.
With so many things to see and do, visitors love exploring the city's waterfront area to enjoy views, exceptional restaurants, great shops, and historic attractions. And of course, no visit is complete without sitting down for a plate of famed Chesapeake Bay blue crab.
Explore the wonders of Chesapeake Bay when you visit Norfolk. Sail Virginia Yacht Charters provides the most elegant way to cruise the bay, letting you enjoy the beautiful scenery and marine life. We can't wait to show you amazing places just off the coast of the city, from hidden coves to lovely islands. Whether it’s a special occasion, a romantic getaway, or a fun day with family and friends, we have the perfect sailing experience for you!
Frequently asked questions
Approximately 3 hours, passengers need to be onsite 15 mins before departure, if running late please contact us. Your 3-hour charter booking is inclusive of time leaving and returning to the dock.
You can pay for your charter by using our online “BOOK NOW” button.
We are located at Willoughby Marina
1525 Bayville St
Norfolk, VA 23503
Parking is avalible at Willoughby Marina.
Willoughby Spit, Elizabeth River, Southern Chesapeake Bay
Maximum of 6 people per US Coast Guard Regulations
Yes, you can bring your favorite beverages and food along for the charter. Any dark-colored beverages, such as red wine, should be consumed in a cup that has a leakproof lid as they can stain the decks. Please ask us if you are unsure.
No. You are welcome and encouraged to bring your snacks and beverages to enjoy during the charter. We provide 2 bags of ice, bottled water, and paper products.
Spring and Fall: Layered clothing and a light jacket. Summertime: Light clothes, shorts, sunglasses, or a hat for the sun. We will ask you to leave your shoes at the dock. Please, no spray sunscreen.
Yes, we have life jackets for all ages/sizes. A life jacket is not a requirement to wear for ages 5 years and older. Children 5 years and younger are required to wear a life jacket.
The most common reason a sail is canceled is due to poor weather conditions that would make sailing uncomfortable and/or dangerous. We never enjoy canceling a sail, but if we must, we will call to inform our guests. We also encourage guests to call ahead the day of their sail to confirm their reservation and verify conditions. If this were to happen, we would reschedule your cruise.
Sailors often get wet when they sail. We have a covered area onboard but also encourage you to bring a poncho or rain jacket if it is forecasted to rain. If there is lightening we will cancel the sail or head back.
Absolutely, please let us know of any special occasion in advance.
Yes, all our boats over 30 feet have bathrooms onboard.
Tips are always appreciated if you feel that your crew has gone above and beyond to make your trip amazing.
Yes, please notify Captain in advance.
That’s okay! Our yachts have covered seating providing protection from the elements.