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10/05/2024  ± 1 day
All listings near me

Find Sailing Charters Near You

4.9
(4,656 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
$200/hour
Sail on the Potomac in Washington, DC
Sailing in Washington · 6 guests

Sail on the Potomac in Washington, DC

New
$280/hour
$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
$275/hour
$500 M-Th | $600 F-Su | 13 ppl | Luxury Yacht SLX 400
Events in Washington · 13 guests

$500 M-Th | $600 F-Su | 13 ppl | Luxury Yacht SLX 400

5.0
Superowner
$500/hour
Limited Availability
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
$215/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
Luxury Sailing Catamaran ⭐️⭐️⭐️⭐️⭐️
Events in Baltimore · 12 guests

Luxury Sailing Catamaran ⭐️⭐️⭐️⭐️⭐️

5.0
Superowner
Best of 2023
$499+/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
$2,600/day
 VIKO S 35 Sailboat in Deale
Sailing in Deale · 6 guests

VIKO S 35 Sailboat in Deale

New
$298/hour
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+/hour
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
$1,100/hour
Sail the Sea on the Pintita
Sailing in Annapolis · 20 guests

Sail the Sea on the Pintita

New
$500+/hour
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
$150/hour
34ft Sailing Yacht in Annapolis, Maryland
Sailing in Annapolis · 4 guests

34ft Sailing Yacht in Annapolis, Maryland

New
$250/hour
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
$175/hour
Catalina 425 Sailing Yacht in Rock Hall, Maryland
Sailing in Rock Hall · 6 guests

Catalina 425 Sailing Yacht in Rock Hall, Maryland

5.0
$150/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
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
$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
Experience the Charm of St. Michaels Aboard the 41ft S/Y Selina II Sl - 2 Hours
Sailing in Saint Michaels · 6 guests

Experience the Charm of St. Michaels Aboard the 41ft S/Y Selina II Sl - 2 Hours

New
$350/hour

Local Sailing Reviews

  1. 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.

  2. CC

    Catie

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

    Our experience with James was nothing short of incredible! We booked a short rental for our engagement pictures session, and James’ boat was beautiful, immaculate, and incredibly picturesque. James was quick and incredibly safe as well as a very skilled captain who accommodated multiple pick ups/drop offs for our shoot and did everything in his power to get the pictures we wanted. We would recommend him for photography or a nice sailing day - we will definitely be back!

  3. SP

    Sydney

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

    We truly could not have asked for a more perfect sailing experience with Captain James!! Our time on the water was so fun thanks to his warmth, hospitality, knowledge, and love for sailing. Our group (including a toddler) loved experiencing the DC area all the way to Mount Vernon. We surprised our friend for her birthday and it was the most fun. I highly recommend this for any and every group looking for a different experience around DC!

  4. SW

    Stacie

    38' Hunter 376 Cruising Monohull in Annapolis, Maryland

    Our sailing trip exceeded our expectations! Captain Alberto is a complete treasure: he shared his sailing knowledge and involved us in the sail as much as we wanted - The boat was clean and comfortable with space to enjoy the trip both above and below deck. We only had 2 in our party, but 6 people would absolutely be comfortable given the space. We hope to book a trip with Capt. Alberto again!

  5. Cliff

    Cliff

    38' Hunter 376 Cruising Monohull in Annapolis, Maryland

    I found Captain Alberto and his first mate lovely wife were the ultimate hosts and storytellers. What I didn't expect, was to get impromptu sailing lessons. It was a beautiful day on the Chesapeake and I would highly recommend this to anyone who wants to truly appreciate the beauty and magnificence and physics of sailing

  6. AL

    April

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

    I could not have asked for a better experience. Our captain was very informative and made sure we understood all safety procedures. I am definitely looking forward to book again.