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All listings near me

Find Sailing Charters Near You

4.9
(4,818 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
$185/hour
Sail on the Potomac in Washington, DC aboard the 28ft Hunter Sailboat
Sailing in Washington · 6 guests

Sail on the Potomac in Washington, DC aboard the 28ft Hunter Sailboat

New
$280/hour
Instant Book
Luxury Sailing Catamaran ⭐️⭐️⭐️⭐️⭐️
Events in Washington · 12 guests

Luxury Sailing Catamaran ⭐️⭐️⭐️⭐️⭐️

5.0
Superowner
Best of 2025
$650+/hour
SEARAY SLX400 | $750hr | 13 People
Events in Washington · 13 guests

SEARAY SLX400 | $750hr | 13 People

5.0
Superowner
Best of 2025
$800/hour
Instant Book
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

5.0
$240/hour
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
Charter 42' Lagoon Catamaran in Annapolis, MD
Sailing in Edgewater · 12 guests

Charter 42' Lagoon Catamaran in Annapolis, MD

5.0
$425/hour
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
$150/hour
VIKO 30 Premium Sailing Yacht In Deale, MD
Sailing in Deale · 5 guests

VIKO 30 Premium Sailing Yacht In Deale, MD

New
$925/day
Captain Bill invites you to find your Sailing Dream on Chesapeake Bay.
Sailing in Mayo · 6 guests

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

5.0
$175/hour
Experience the Serenity of Sailing SV Magic
Sailing in Mayo · 6 guests

Experience the Serenity of Sailing SV Magic

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

Charter 44' Orana Cruising Catamaran In Deale, Maryland

5.0
$450/hour
Instant Book
 VIKO S 35 Sailboat in Deale
Sailing in Deale · 6 guests

VIKO S 35 Sailboat in Deale

New
$298/hour
38-ft Hunter 376 Sailing Adventure in Annapolis
Sailing in Annapolis · 6 guests

38-ft Hunter 376 Sailing Adventure in Annapolis

5.0
Superowner
$138+/hour
Instant Book
New Yacht Charter Bali 5.4 Sailing Catamaran in Annapolis Maryland
Sailing in Annapolis · 13 guests

New Yacht Charter Bali 5.4 Sailing Catamaran in Annapolis Maryland

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

Sail the Sea on the Pintita

New
$500+/hour
50ft Catamaran Charter with Water Toys - Annapolis, MD
Sailing in Annapolis · 12 guests

50ft Catamaran Charter with Water Toys - Annapolis, MD

5.0
Snoozed - Active 03 Jun 2025
 Sail in Style Aboard the 2024 Seawind 1160 Lite – Your Perfect Charter Escape
Sailing in Annapolis · 13 guests

Sail in Style Aboard the 2024 Seawind 1160 Lite – Your Perfect Charter Escape

New
$350+/hour
STARZ -Lagoon 42 Catamaran in Chesapeake Bay
Sailing in Annapolis · 13 guests

STARZ -Lagoon 42 Catamaran in Chesapeake Bay

New
$400+/hour
JEHM of the SEA 2014 CATALINA 445 Sailboat for Amazing Day in Chesapeake Bay!
Sailing in Annapolis · 12 guests

JEHM of the SEA 2014 CATALINA 445 Sailboat for Amazing Day in Chesapeake Bay!

5.0
$250+/hour
SLOWDOWN - DUFOUR 430
Sailing in Annapolis · 12 guests

SLOWDOWN - DUFOUR 430

New
$250+/hour
 SWEET & SALTY FOUNTAINE PAJOT HELIA 44 CATAMARAN
Sailing in Annapolis · 12 guests

SWEET & SALTY FOUNTAINE PAJOT HELIA 44 CATAMARAN

5.0
$400+/hour
DOS MILAGROS Beneteau Oceanis 45 Sailing Yacht in Chesapeake Bay!
Sailing in Annapolis · 10 guests

DOS MILAGROS Beneteau Oceanis 45 Sailing Yacht in Chesapeake Bay!

New
$232+/hour
34ft Sailing Yacht in Annapolis, Maryland
Sailing in Annapolis · 4 guests

34ft Sailing Yacht in Annapolis, Maryland

New
$250/hour

Local Sailing Reviews

  1. CE

    Clifford

    SWEET & SALTY FOUNTAINE PAJOT HELIA 44 CATAMARAN

    Sarah was helpful in lining me up for a sail boat for Mothers Day and in recommending a captain and in adjusting time to meet our needs.

  2. ST

    Sherzod

    38-ft Hunter 376 Sailing Adventure in Annapolis

    Great experience, it was my first time boat sailing and Alberto and his wife were great. My fiance and I had a great time. Highly recommend!

  3. 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!

  4. NW

    Nicole

    Luxury Sailing Catamaran ⭐️⭐️⭐️⭐️⭐️

    I hosted my 50th birthday on this vessel!! Absolutely, positively an amazing experience! The vessel is absolutely beautiful and spacious. There was plenty of room on this vessel for my 12 guests! The Captain Shane provided excellent customer service throughout the entire trip. He very responsive to any questions that I had !!! If you want an stellar experience, this is the way to go!!!!!!

  5. Dennese

    Dennese

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

    Sailing with Captain James was a dream!! You will not regret this experience! Not only is he hospitable, he is full of life and passion which only made our trip better. We enjoyed every part of our trip the only sad part was that we didn’t book longer. 100/10 would book with Captain James again!!

  6. KM

    Kelley

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

    If you’re looking for a unique and fun way to celebrate a special occasion, or just want to take advantage of the beautiful weather and get out on the water, this is it! I booked a Sunday afternoon trip with friends to celebrate my 36th birthday and it absolutely exceeded my expectations. Captain James was communicative and professional leading up to the trip; he’s a skilled captain and a joy to be around. His catamaran is clean and safe, and equipped with everything you could need, including a sound system and bumpin’ playlist! I will absolutely be booking with him again.