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Browse Chesapeake Bay Boat Rentals.

4.9(Average of 1,747 reviews in this area)
Page 3 of 8 (176 listings)
Chaparral 350 Signature Motor Yacht Rental in Washington, District of Columbia
Events in Washington · 9 guests

Chaparral 350 Signature Motor Yacht Rental in Washington, District of Columbia

5.0
$350hour
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
$450HR | +13 People | Double Deckers Boat
Events in Washington · 13 guests

$450HR | +13 People | Double Deckers Boat

5.0
Superowner
$450hour
18' Center Console Pocket Rocket fishing boat.
Fishing in Deltaville · 4 guests

18' Center Console Pocket Rocket fishing boat.

New
$325day
$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
41' Meridian Yacht for Charter in Washington, D.C.
Events in Washington · 13 guests

41' Meridian Yacht for Charter in Washington, D.C.

5.0
$325hour
2021 24' Sylvan L3 DLZ Pontoon Boat
Powerboats in Riviera Beach · 12 guests

2021 24' Sylvan L3 DLZ Pontoon Boat

5.0
$149hour
$300hr|10 people| Luxury Yacht
Events in Washington · 10 guests

$300hr|10 people| Luxury Yacht

5.0
Superowner
$350hour
Bluewater Coastal Cruiser 50ft for Entertaining in Washington, DC
Events in Washington · 13 guests

Bluewater Coastal Cruiser 50ft for Entertaining in Washington, DC

4.9
$350-$390hour
Maxum 2400 SE (26 feet) with captain in Washington DC ready to serve you!
Powerboats in Washington · 6 guests

Maxum 2400 SE (26 feet) with captain in Washington DC ready to serve you!

5.0
$200hour
EXCELSIOR - WASHINGTON, DC! CRUISE THE POTOMAC IN 5 STAR EXCELLENCE!!
Events in Washington · 12 guests

EXCELSIOR - WASHINGTON, DC! CRUISE THE POTOMAC IN 5 STAR EXCELLENCE!!

New
$400hour
Instant Book
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
Charter the 34ft Sundancer Motor Yacht in Washington,  DC
Events in Washington · 8 guests

Charter the 34ft Sundancer Motor Yacht in Washington, DC

5.0
$250hour
2022 Avalon Tritoon!!!!!!
Powerboats in Virginia Beach · 10 guests

2022 Avalon Tritoon!!!!!!

5.0
$199hour
38' Mini-Yacht!! - Large "Ultra Luxury" Adventure Boat in Hampton, Virginia!
Events in Hampton · 13 guests

38' Mini-Yacht!! - Large "Ultra Luxury" Adventure Boat in Hampton, Virginia!

5.0
Superowner
$199-$299hour
38' Dawson Sportfish Motor Yacht Charter in Norfolk, Virginia
Fishing in Norfolk · 6 guests

38' Dawson Sportfish Motor Yacht Charter in Norfolk, Virginia

5.0
$450day
Enjoy a Cruise Aboard this 29ft Cabin Cruiser!!
Events in Washington · 6 guests

Enjoy a Cruise Aboard this 29ft Cabin Cruiser!!

5.0
$225hour
Bayliner Cruising Boat for 6 People in Washington, DC
Events in Arlington · 6 guests

Bayliner Cruising Boat for 6 People in Washington, DC

5.0
$200hour
$300 per hour | 8 PPl | Water Activity + Grill BBQ | Monterey 322 Cruiser
Events in Washington · 8 guests

$300 per hour | 8 PPl | Water Activity + Grill BBQ | Monterey 322 Cruiser

5.0
Superowner
$300hour
Perfect Party Boat Rental In Potomac River, Washington
Events in Washington · 8 guests

Perfect Party Boat Rental In Potomac River, Washington

5.0
$275hour
The Innamorata... Most Elegant, Historic Yacht on the Potomac!
Events in Washington · 12 guests

The Innamorata... Most Elegant, Historic Yacht on the Potomac!

5.0
$290-$390hour
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
23ft Odyssey Pontoon Rental in Washington, District of Columbia
Powerboats in Washington · 12 guests

23ft Odyssey Pontoon Rental in Washington, District of Columbia

5.0
$250-$1,000day
Relax in the Sun in Edgewater and Annapolis
Powerboats in Edgewater · 10 guests

Relax in the Sun in Edgewater and Annapolis

New
$200hour

Chesapeake Bay Reviews

  1. George

    George

    34' Hunter Cruising Monohull In Rock Hall, Maryland United States

    Great value! Excellent sailing gear!! If you are an experienced sailor with at least one other person, you won't find a better value for day or overnight sailing near Annapolis. I will definitely be renting this boat again either with my family for the day or some buddies overnight. Took Icarus on a two night late-October trip from Rock Hall, overnight in Annapolis then St. Michaels with a couple buddies. James made the process VERY easy - very communicative and willing to go the extra mile for our convenience. This Hunter 34 sails really well (especially upwind.) It is set up that one experienced sailor and one other person can easily manage it. Comfort-wise it is probably better dockside on shore power in order to be able to utilize the cabin climate control system and power outlets for charging your phones (bring portable chargers if you won't be on shore power.) Returning the boat into the slip was a little tricky and James offered to be there to "coach us" in but we managed it on our own. The diesel was very reliable and fuel efficient - recommend you listen very carefully to James when he explains how to start it because can be a little tricky (as of Oct 2023.) Recommend you bring a handheld (or phone) GPS because as of Oct 23 the GPS is in the cabin. Bottom line - this is a great value - don't hesitate to book!!

  2. Janessa

    Janessa

    34' Hunter Cruising Monohull In Rock Hall, Maryland United States

    We had a wonderful experience chartering Jim’s sailboat over Labor Day weekend. Jim was very accommodating, walking through the boat with us and making sure everything was in great shape before we began our charter. We sailed from Rock Hall to Annapolis and back, spending two nights aboard Icarus. His upgrades to the boat really helped make it easier to sail and more comfortable to relax in, and Jim was always readily available if we had any questions. Could not recommend this more highly, and we don’t think there’s a better charter out there for the price in the Chesapeake.

  3. JM

    John

    34' Hunter Cruising Monohull In Rock Hall, Maryland United States

    Jim’s boat is an amazing sailing set up for those looking for a great way to explore the Bay. The boat is equipped with everything you’ll need for a day sail or an overnight as my wife and I did. It was a great boat to explore the Bay with and Jim gave us great recommendations on where to anchor out!

  4. BH

    Brack

    34' Hunter Cruising Monohull In Rock Hall, Maryland United States

    The boat is older but everything works. It has been well maintained and sails very well, with one owner only. Controls and lines are simple and straightforward. The owner was very responsive and helpful, including suggestions on destinations. The location is great, 10 feet from our car to the boat.

  5. Mark

    Mark

    34' Hunter Cruising Monohull In Rock Hall, Maryland United States

    Icarus is an older boat that shows it age a bit, but the rig was easy to sail and all of the equipment worked well. It was our first overnight charter and I was not disappointed at all. We had perfect weather and enjoyed our sail from/to Annapolis taking about 4 hours each way. Jim gave great advice and his communication was excellent prior to and during our charter. Absolutely no complaints.

  6. Travis

    Travis

    34' Hunter Cruising Monohull In Rock Hall, Maryland United States

    This 34' Hunter is comfortable, clean, fun to sail, and has excellent sleeping accommodations. We had a great sail across the Chesapeake bay in 3-4' waves and felt safe and secure the entire time. You will not be disappointed with this charter. James (the boat owner) is a class act and will always go the extra mile to make your charter experience unforgettable. If you're considering a charter on the Chesapeake, this is the boat for you! I hope to see you next year, James!