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All listings in Chesapeake Bay

Incredible sailboat rentals in Chesapeake Bay, United States.

Page 1 of 235 listings

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
Experience the Serenity of Sailing SV Magic
Sailing in Mayo · 6 guests

Experience the Serenity of Sailing SV Magic

4.9
$165/hour
50ft Catamaran Charter with Water Toys - Annapolis, MD
Sailing in Annapolis · 12 guests

50ft Catamaran Charter with Water Toys - Annapolis, MD

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

Catamaran in Maryland

5.0
Superowner
Best of 2023
$390/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
$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
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
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
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
Chesapeake Bay Sailing Charter - 33' Cape Dory sailing from Kilmarnock, Virginia
Sailing in Kilmarnock · 6 guests

Chesapeake Bay Sailing Charter - 33' Cape Dory sailing from Kilmarnock, Virginia

5.0
$73+/hour
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
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
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
$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
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
Sail on the Potomac in Washington, DC
Sailing in Washington · 6 guests

Sail on the Potomac in Washington, DC

New
$280/hour
Charter 42' Lagoon Catamaran in Annapolis, MD
Sailing in Edgewater · 12 guests

Charter 42' Lagoon Catamaran in Annapolis, MD

5.0
$425/hour
Melges 24 - One Design Racing Experience
Sailing in Hampton · 8 guests

Melges 24 - One Design Racing Experience

5.0
Superowner
$100/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
50ft Catamaran Charter with Water Toys in St. Michaels, MD
Sailing in Saint Michaels · 12 guests

50ft Catamaran Charter with Water Toys in St. Michaels, MD

New
$525/hour
Relaxing historic sailing experience in St. Michaels, Maryland - Half Day Sail
Sailing in Saint Michaels · 6 guests

Relaxing historic sailing experience in St. Michaels, Maryland - Half Day Sail

5.0
$325/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
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

Sailing Reviews in Chesapeake Bay

  1. George

    George

    Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

    HIGHLY recommend Capt Joe for a fantastic sailing experience out of Rock Hall. Joe worked with us to get a last-minute booking when another booking fell through. He and his crew are experts and you will not be disappointed. He let us take the helm and participate as much or as little as we wanted to. Sol Searcher is a beautiful, well-equipped boat - plenty of comfort and speed (wind dependent of course.)

  2. BS

    Bill

    Charter 32' Modern Hunter Sailboat In Gloucester, Point Virginia

    I highly recommend a sail with Captain Bill. The entire experience was exciting and relaxing at the same time. Whether an experienced sailor or a novice with boats, just being on the open water will refresh and invigorate. 5 ⭐️⭐️⭐️⭐️⭐️

  3. TM

    Tom

    38' Hunter 376 Cruising Monohull in Annapolis, Maryland

    Captain Alberto and Grace were amazing, and helped with a very romantic sunset sail. The were ver gracious, accommodating, and knowledgeable. If we get the chance we will definitely come back and hire them again!

  4. 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.

  5. AE

    Ashanda

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

    James is a wonderful captain! Our crew had the most amazing time!! The views were so picturesque! It was a chilly, fall morning but absolutely perfect!

  6. 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!