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All listings in Virginia

Incredible sailboat rentals in Virginia, United States.

Page 1 of 233 listings

38ft Seawind 1160 Luxury Sailing Catamaran in Essex, Maryland for 12 Guests
Sailing in Essex · 12 guests

38ft Seawind 1160 Luxury Sailing Catamaran in Essex, Maryland for 12 Guests

5.0
$799+/hour
Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland
Sailing in Rock Hall · 6 guests

Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

5.0
$150/hour
SEARAY SLX400 | $550hr | 13 People
Events in Washington · 13 guests

SEARAY SLX400 | $550hr | 13 People

5.0
Superowner
$550/hour
Instant Book
Charter 32' Modern Hunter Sailboat In Gloucester, Point Virginia
Sailing in Gloucester Point · 6 guests

Charter 32' Modern Hunter Sailboat In Gloucester, Point Virginia

5.0
Superowner
$125/hour
Hunter 42' Sailboat - Take a Charter or your Sailing Lessons on Chesapeake Bay
Sailing in Mayo · 6 guests

Hunter 42' Sailboat - Take a Charter or your Sailing Lessons on Chesapeake Bay

5.0
$150+/hour
34' Hunter Cruising Monohull In Rock Hall, Maryland United States
Sailing in Rock Hall · 4 guests

34' Hunter Cruising Monohull In Rock Hall, Maryland United States

4.6
$275+/night
2022 Chaparral 23' SSI  - Get up to 6 captained up and down the Potomac River
Powerboats in Fort Washington · 6 guests

2022 Chaparral 23' SSI - Get up to 6 captained up and down the Potomac River

5.0
$150+/hour
Let's Go Sail in Gloucester Point, Virginia
Sailing in Gloucester Point · 6 guests

Let's Go Sail in Gloucester Point, Virginia

5.0
Superowner
$117+/hour
Chesapeake Bay Sailing (w/ Captain) - 33' Cape Dory - Kilmarnock, Virginia
Sailing in Kilmarnock · 4 guests

Chesapeake Bay Sailing (w/ Captain) - 33' Cape Dory - Kilmarnock, Virginia

5.0
$15+/hour
Limited Availability
38-ft Hunter 376 Sailing Adventure in Annapolis
Sailing in Annapolis · 6 guests

38-ft Hunter 376 Sailing Adventure in Annapolis

5.0
Superowner
$100+/hour
New Yacht Charter Bali 5.4 Sailing Catamaran in Annapolis Maryland
Sailing in Annapolis · 12 guests

New Yacht Charter Bali 5.4 Sailing Catamaran in Annapolis Maryland

5.0
$1,100/hour
Come Experience the ambient waters of the Potomac on the Sylvan MIRAGE Pontoon!
Powerboats in Washington · 6 guests

Come Experience the ambient waters of the Potomac on the Sylvan MIRAGE Pontoon!

5.0
$185/hour
Welcome Aboard Optimystic! Create a beautiful memory on the water.
Sailing in Essex · 6 guests

Welcome Aboard Optimystic! Create a beautiful memory on the water.

5.0
$150/hour
Charter 44' Orana Cruising Catamaran In Deale, Maryland
Sailing in Deale · 10 guests

Charter 44' Orana Cruising Catamaran In Deale, Maryland

5.0
$250+/hour
Charter 42' Lagoon Catamaran in Annapolis, MD
Sailing in Annapolis · 12 guests

Charter 42' Lagoon Catamaran in Annapolis, MD

5.0
$425/hour
Private Sail on 44ft Leopard Catamaran | 6 People | Gratuity & Tax Included
Sailing in Saint Michaels · 6 guests

Private Sail on 44ft Leopard Catamaran | 6 People | Gratuity & Tax Included

New
$585/hour
Catamaran |15 People |Choptank River
Sailing in Maryland · 15 guests

Catamaran |15 People |Choptank River

New
Superowner
$700/hour
43 foot Captained Catalina Sailing Yacht Located In Rock Hall, Maryland
Sailing in Rock Hall · 6 guests

43 foot Captained Catalina Sailing Yacht Located In Rock Hall, Maryland

5.0
$136+/hour
$4400 | 2hrs | 49 Guests | Sailing Catamaran
Sailing in Washington · 49 guests

$4400 | 2hrs | 49 Guests | Sailing Catamaran

New
Superowner
$2,200/hour
Private Sail Up to 13 Guests | 44ft Leopard Catamaran
Sailing in Saint Michaels · 13 guests

Private Sail Up to 13 Guests | 44ft Leopard Catamaran

New
$580/hour
Luxury 2022 Excess 11 Catamaran for 12 in Annapolis
Sailing in Annapolis · 12 guests

Luxury 2022 Excess 11 Catamaran for 12 in Annapolis

New
$335+/hour
Luxury Lagoon 42 Catamaran for 12 in Annapolis
Sailing in Annapolis · 12 guests

Luxury Lagoon 42 Catamaran for 12 in Annapolis

New
$335+/hour
2022 Catspace 38 Sailing Catamaran in Chesapeake Bay
Sailing in Annapolis · 12 guests

2022 Catspace 38 Sailing Catamaran in Chesapeake Bay

New
$334+/hour
Durfour 430 Sailing Yacht to Discover the Chesapeake Bay
Sailing in Annapolis · 12 guests

Durfour 430 Sailing Yacht to Discover the Chesapeake Bay

New
$210+/hour

Sailing Reviews in Virginia

  1. Geoffrey

    Geoffrey

    34' Hunter Cruising Monohull In Rock Hall, Maryland United States

    Icarus is a great boat and very well equipped. The sails and everything else on the vessel are in great shape and the fact it only draws 4' 6" is perfect for the Chesapeake. I spent a week on Icarus and everything worked well. The value of chartering Icarus is undeniable. I plan to charter Icarus again. Icarus has a lot of sail area, so if the winds are strong douse the headsail early.

  2. JC

    Janna

    Hunter 42' Sailboat - Take a Charter or your Sailing Lessons on Chesapeake Bay

    We had a wonderful time on Captain Bill's boat! We booked a 2-hour charter and it was the perfect quick escape for our family of 6. The crew was friendly and welcoming. The boat had plenty of space to relax. It was a smooth, stress-free experience ideal for families or friends needing a taste of the water.

  3. DC

    David

    Charter 44' Orana Cruising Catamaran In Deale, Maryland

    Our group of seven spent a fabulous half day with Captain Rob and Mate Dianna. Couldn't have been happier with the whole experience. Communication was quick and easy. On board, they were super friendly and engaging. The vessel itself was spotless and super comfortable as we hung out on the front "trampoline" area, sailing around the Bay. Thanks for such a fun adventure. We are already talking about a future engagement!

  4. LM

    Liz

    Welcome Aboard Optimystic! Create a beautiful memory on the water.

    Charles was an outstanding guide. Before the outing (which was a birthday gift for my fiancé) he even offered to pick up a cake so that it could be a surprise. He and his wife made us feel at home right away as if we were out just sailing with friends. It was a gorgeous late afternoon / sunset sail with the option of swimming and cooking on the boat. We didn't rush back. Riding on the bow was so relaxing. He took time explaining sailing tips to my fiancé and let him drive the boat for awhile. Communication was clear. We'd love to book again with Charles and Renee!

  5. AV

    Ariel

    38-ft Hunter 376 Sailing Adventure in Annapolis

    We had a lovely experience out on the bay. Captain Alberto let my husband steer the boat & put the kiddos to work as well. We were able to play & relax as well while out on the water. Very family credibly experience and lovely to get to know the captain & his wife! Overall 5 stars for a sailing experience on the bay!

  6. Erika

    Erika

    38-ft Hunter 376 Sailing Adventure in Annapolis

    We had such a great time! The boat was perfect and Alberto and his wife were great hosts. It’s a good sized boat, kid-friendly (they had kids life jackets), and the cabin was spacious with plenty of room to eat.