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Find Sailing Charters Near You

4.9
(4,639 Reviews)

Page 1 of 10240 listings

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
$150hour
Sail on the Potomac in Washington, DC
Sailing in Washington · 6 guests

Sail on the Potomac in Washington, DC

New
$280hour
$275 HR | 8 people | Sea Ray 330 Sundancer Yacht
Events in Washington · 8 guests

$275 HR | 8 people | Sea Ray 330 Sundancer Yacht

5.0
Superowner
$275hour
$400 M-Th | $600 F-Su | 13 ppl | Luxury Yacht SLX 400
Events in Washington · 13 guests

$400 M-Th | $600 F-Su | 13 ppl | Luxury Yacht SLX 400

5.0
Superowner
$400hour
Sailing Catamaran, National Harbor Ready for Sunrise, Sunset or Any Time Cruise
Sailing in Oxon Hill · 6 guests

Sailing Catamaran, National Harbor Ready for Sunrise, Sunset or Any Time Cruise

New
$200hour
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-$190hour
Luxury Sailing Catamaran ⭐️⭐️⭐️⭐️⭐️
Events in Baltimore · 12 guests

Luxury Sailing Catamaran ⭐️⭐️⭐️⭐️⭐️

5.0
Superowner
Best of 2023
$399-$499hour
Charter 42' Lagoon Catamaran in Annapolis, MD
Sailing in Edgewater · 12 guests

Charter 42' Lagoon Catamaran in Annapolis, MD

5.0
$425hour
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
This Sailboat Captain invites you to find your Sailing Dream on Chesapeake Bay.
Sailing in Mayo · 6 guests

This Sailboat Captain invites you to find your Sailing Dream on Chesapeake Bay.

5.0
$150-$200hour
Instant Book
Experience the Serenity of Sailing SV Magic
Sailing in Mayo · 6 guests

Experience the Serenity of Sailing SV Magic

4.9
$165hour
Charter 44' Orana Cruising Catamaran In Deale, Maryland
Sailing in Deale · 10 guests

Charter 44' Orana Cruising Catamaran In Deale, Maryland

5.0
$2,600day
 VIKO S 35 Sailboat in Deale
Sailing in Deale · 6 guests

VIKO S 35 Sailboat in Deale

New
$298hour
50ft Catamaran Charter with Water Toys - Annapolis, MD
Sailing in Annapolis · 12 guests

50ft Catamaran Charter with Water Toys - Annapolis, MD

5.0
$450hour
Catamaran in Maryland
Sailing in Annapolis · 12 guests

Catamaran in Maryland

5.0
Superowner
Best of 2023
$390hour
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
New Yacht Charter 2022 Bali 5.4 Sailing Catamaran in Annapolis Maryland
Sailing in Annapolis · 13 guests

New Yacht Charter 2022 Bali 5.4 Sailing Catamaran in Annapolis Maryland

New
$1,100hour
Sail the Sea on the Pintita
Sailing in Annapolis · 20 guests

Sail the Sea on the Pintita

New
$500-$750hour
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
34ft Sailing Yacht in Annapolis, Maryland
Sailing in Annapolis · 4 guests

34ft Sailing Yacht in Annapolis, Maryland

New
$250hour
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
Catalina 425 Sailing Yacht in Rock Hall, Maryland
Sailing in Rock Hall · 6 guests

Catalina 425 Sailing Yacht in Rock Hall, Maryland

5.0
$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
$150hour
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

Local Sailing Reviews

  1. MO

    Mike

    38' Hunter 376 Cruising Monohull in Annapolis, Maryland

    Phenomenal experience!! Highly recommend. Best value if you're looking for a private charter in the Annapolis area. This was my first experience with Getmyboat and was a little weary but everything was professionally done as if this was a corporate tour. Alberto and Grace were so sweet and accommodating. Boat dock is 10 mins from downtown with ample parking which Alberto outlined prior to arrival. There were 6 large adult individuals in our party and I was a bit concerned that we would be cramped, since that was the advertised upper limit of the charter, but there was more than enough room for all of us. We discussed the itinerary upon arrival and Alberto was extremely accommodating and stopped right outside the harbor in a great spot for us to swim for an hour or so. We then sailed around for a couple hours and felt very safe the entire time. Boat was clean and well maintained. Not the glitziest boat relative to some of the amazing yachts around town but at the price they charge it was a phenomenal value. I will 1000% book again and would highly recommend.

  2. DZ

    Dunja

    Luxury Sailing Catamaran ⭐️⭐️⭐️⭐️⭐️

    Captain Shane and Captain Andy were extremely communicative and helpful throughout the entire process from booking all the way through the excursion. The catamaran was clean, beautiful, and the entire charter was a great experience! I would strongly recommend S&S and if I ever host another boating event, I know who to go to!

  3. AN

    Ashley

    Experience the Serenity of Sailing SV Magic

    We rented Josh’s boat to do our engagement pictures! He was helpful with timing to catch the best sunset and navigated the boat so our photographer could get the best shots. There was room below for outfit changes and speakers on board to enjoy our time!

  4. Jordan

    Jordan

    50ft Catamaran Charter with Water Toys - Annapolis, MD

    Captain Deren and the crew were amazing — they made my birthday so special. They were super accommodating the entire day for everyone! They were even kind enough to put up some birthday decorations for our group. I’m definitely going to be booking with Captain Deren again!

  5. RZ

    Rachel

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

    David was communicative and professional during the booking process. He was easy to reach and very responsive. Leading up to the trip, he communicated everything we needed to know. Our boat ride was smooth sailing and relaxing. It was a nice Father’s Day trip for the family. We hope to book again soon!

  6. EL

    Elford

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

    This is A Comfortable Pontoon, An easy going Captain, and a REALLY RELAXING way to Enjoy the Water! We had a Wonderful Day! Celebrating a 24 year anniversary. Make an inquiry, hit the “Book Now” button, have a good time!