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$100-$300
All listings in Virginia

Incredible sailboat rentals in Virginia, United States.

Page 1 of 117 listings

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
$175hour
38' Hunter 376 Cruising Monohull in Annapolis, Maryland
Sailing in Annapolis · 6 guests

38' Hunter 376 Cruising Monohull in Annapolis, Maryland

5.0
Superowner
Best of 2023
$138-$150hour
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
Superowner
$150hour
Experience the Serenity of Sailing SV Magic
Sailing in Mayo · 6 guests

Experience the Serenity of Sailing SV Magic

4.8
$165hour
30 ft sailboat with highly experienced Captain in Baltimore Inner Harbor
Sailing in Baltimore · 5 guests

30 ft sailboat with highly experienced Captain in Baltimore Inner Harbor

5.0
$150hour
Sail out of Middle River onboard Hunter 41 AC Sailboat!!
Sailing in Essex · 6 guests

Sail out of Middle River onboard Hunter 41 AC Sailboat!!

5.0
$175hour
The Licensed Captain of this 42ft Sailboat, provides charters on Chesapeake Bay.
Sailing in Mayo · 6 guests

The Licensed Captain of this 42ft Sailboat, provides charters on Chesapeake Bay.

5.0
$175hour
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-$125hour
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
$125hour
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

4.5
$275-$375night
Sailing Adventure in Chesapeake Bay with 28ft Tartan Sailing Yacht!
Sailing in Annapolis · 4 guests

Sailing Adventure in Chesapeake Bay with 28ft Tartan Sailing Yacht!

5.0
$150hour
Melges 24 - One Design Racing Experience Or Charter
Sailing in Hampton · 8 guests

Melges 24 - One Design Racing Experience Or Charter

5.0
Superowner
$200hour
Fully Crewed Annapolis Sailing Cruises
Sailing in Annapolis · 6 guests

Fully Crewed Annapolis Sailing Cruises

New
$175person
Charter 41ft S/Y Selina II Sloop in St. Michaels, Maryland
Sailing in Saint Michaels · 6 guests

Charter 41ft S/Y Selina II Sloop in St. Michaels, Maryland

5.0
$250-$349hour
Fully Crewed Sailing Cruises Aboard 41' Sailboat in Rock Hall, MD
Sailing in Rock Hall · 4 guests

Fully Crewed Sailing Cruises Aboard 41' Sailboat in Rock Hall, MD

5.0
$150hour
 VIKO S 35 Sailboat in Deale
Sailing in Deale · 6 guests

VIKO S 35 Sailboat in Deale

New
$298hour
34ft Sailing Yacht in Annapolis, Maryland
Sailing in Annapolis · 4 guests

34ft Sailing Yacht in Annapolis, Maryland

New
$250hour

Sailing Reviews in Virginia

  1. JD

    Josiah

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

    Didn't believe we still have such wonderful people. Captain Dash and his co-captain are amongst the very best. Good service, friendly, timely, and most importantly, people Centered. My wife, kids, and I enjoyed riding with this team and we will always wish to ride with them.

  2. JR

    Josh

    38' Hunter 376 Cruising Monohull in Annapolis, Maryland

    Highly highly recommended! The boat is as advertised, but the real treat is spending time with Captain Alberto, and his wife Grace, who are such warm, loving, and knowledgeable people. They clearly know their boat inside and out, so you will never feel uncomfortable. But they also encourage guests to help running the boat and they have the knowledge to help everyone understand what is happening. Most importantly, they are simply fun to be around and a joy to talk to. I can't wait to sail with them again!

  3. BC

    Brian

    38' Hunter 376 Cruising Monohull in Annapolis, Maryland

    Across the board, a wonderful charter that exceeded expectations. It'd been some years since my wife and I had been on the water and what we expected was a day out refamiliarizing ourselves and just enjoying the Bay -- But Capt Alberto skillfully combined pleasurable sailing with private sailing lessons, a naval architecture primer, and boat buying 101. We can't wait to get back out on the water again with Alberto!

  4. Michael

    Michael

    38' Hunter 376 Cruising Monohull in Annapolis, Maryland

    We had an amazing experience today with Alberto and his lovely wife. The boat was beautiful. I’m interested in learning to sail and as soon as Alberto found that out he spent most of the day teaching me about sailing. He has deep knowledge and was very good at explaining things. They also both made us feel like good friends rather than customers. We will definitely sail again with them soon!

  5. JW

    Joe

    38' Hunter 376 Cruising Monohull in Annapolis, Maryland

    Captain Alberto and his wife, Grace, are such great hosts. They worked with us to reschedule because of a lightning storm. Communication was great. The boat is very nice and comfortable. We had a great time and learned a lot too. We will book with them again!

  6. MT

    Molly

    38' Hunter 376 Cruising Monohull in Annapolis, Maryland

    Fantastic experience! Alberto taught us how to sail and let us do as little or as much as we wanted to. We celebrated a friend’s birthday and this was the perfect mix of relaxing and doing something new. If you’re looking for an easy afternoon on the water with a few friends, this is the captain to book it with. 10/10 would recommend!