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Chesapeake City, Maryland Boat Rentals

24 listings
Keywest 2000wa w/ brand new reliable motor
Maryland · 5 guests

Keywest 2000wa w/ brand new reliable motor

New
$400day
Moomba Craz Pro 23ft Exceptional Watersports and Cruising!!
Powerboats in Newark · 12 guests

Moomba Craz Pro 23ft Exceptional Watersports and Cruising!!

5.0
$150hour
Learn to Sail in Havre de Grace, MD (Minutes off of I95 in Historic Havre de Grace, MD)
Tours in Havre de Grace · 2 guests

Learn to Sail in Havre de Grace, MD (Minutes off of I95 in Historic Havre de Grace, MD)

New
$200person
Starratt & Jenks Morgan 45ft Sailing Charter in Havre de Grace, MD - USCG Licensed Captain
Sailing in Havre de Grace · 6 guests

Starratt & Jenks Morgan 45ft Sailing Charter in Havre de Grace, MD - USCG Licensed Captain

New
$200hour
PHILLY FIRST LUXURY PARTY PONTOON BOAT IS FINALLY HERE!!! VOTE BEST OF 2022
Powerboats in Philadelphia · 10 guests

PHILLY FIRST LUXURY PARTY PONTOON BOAT IS FINALLY HERE!!! VOTE BEST OF 2022

New
$275hour
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
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
Superowner
$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
Spacious 38' Luxury Cruiser with plenty of room for celebrating or relaxing!!!
Powerboats in Essex · 6 guests

Spacious 38' Luxury Cruiser with plenty of room for celebrating or relaxing!!!

New
$150hour
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
Timber Creek Tour with a USCG Licensed Captain
Powerboats in Philadelphia · 6 guests

Timber Creek Tour with a USCG Licensed Captain

New
$60person
Philly Schuylkill River Tour with a USCG Licensed Captain
Powerboats in Philadelphia · 6 guests

Philly Schuylkill River Tour with a USCG Licensed Captain

5.0
$180hour
Philly Delaware River Tour with a USCG Licensed Captain
Powerboats in Philadelphia · 6 guests

Philly Delaware River Tour with a USCG Licensed Captain

5.0
$180hour
You don't have to own a boat to enjoy one.
Powerboats in Annapolis · 7 guests

You don't have to own a boat to enjoy one.

New
Snoozed - Active 02 May 2024
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
Robbins Chesapeake 40' Fishing Charters in Maryland
Fishing in Annapolis · 6 guests

Robbins Chesapeake 40' Fishing Charters in Maryland

5.0
$125-$150hour
STARCRAFT LUXURY PARTY PONTOON IS FINALLY HERE!!BEST OF BALTIMORE WINNER 2022...
Powerboats in Baltimore · 10 guests

STARCRAFT LUXURY PARTY PONTOON IS FINALLY HERE!!BEST OF BALTIMORE WINNER 2022...

5.0
$275hour
42FT PARTY YACHT BEST OF BALTIMORE 2022&23 WINNER!!!
Events in Baltimore · 12 guests

42FT PARTY YACHT BEST OF BALTIMORE 2022&23 WINNER!!!

5.0
$385hour
Cruise the Inner Harbor and beyond on a Monterey 350 Sport Yacht
Powerboats in Baltimore · 6 guests

Cruise the Inner Harbor and beyond on a Monterey 350 Sport Yacht

New
$325hour
Stunning!!! Smooth 26ft Larson Party Cabin Cruiser for Baltimore, Maryland
Powerboats in Baltimore · 8 guests

Stunning!!! Smooth 26ft Larson Party Cabin Cruiser for Baltimore, Maryland

5.0
$150hour
2016 Regal 31' Cruise The Inner Harbor, Annapolis, Hart Miller Island
Powerboats in Annapolis · 8 guests

2016 Regal 31' Cruise The Inner Harbor, Annapolis, Hart Miller Island

4.9
Best of 2023
$225hour
Fishing Charter in Pasadena, Maryland
Fishing in Riviera Beach · 6 guests

Fishing Charter in Pasadena, Maryland

5.0
$840day
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
Sunset Sail - Philadelphia Waterfront with O'Day 322 Sailing Yacht
Sailing in Philadelphia · 6 guests

Sunset Sail - Philadelphia Waterfront with O'Day 322 Sailing Yacht

5.0
$350hour

Chesapeake City Reviews

  1. GF
    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!