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Kent Narrows, Maryland Boat Rentals

Page 1 of 124 listings

Pershing 65 Power Mega Yacht Rental in Stevensville, Maryland
Events in Stevensville · 6 guests

Pershing 65 Power Mega Yacht Rental in Stevensville, Maryland

New
$550hour
32' Center Console - up to 6 Guests from Stevensville, MD
Powerboats in Stevensville · 6 guests

32' Center Console - up to 6 Guests from Stevensville, MD

5.0
$375hour
34ft Sailing Yacht in Annapolis, Maryland
Sailing in Annapolis · 4 guests

34ft Sailing Yacht in Annapolis, Maryland

New
$300hour
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
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
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
Charter 41ft S/Y Selina II Sloop in St. Michaels, Maryland
Sailing in Saint Michaels · 6 guests

Charter 41ft S/Y Selina II Sloop in St. Michaels, Maryland

5.0
$250-$349hour
Sunset Champagne Cruise on the Chesapeake Bay
Sailing in Saint Michaels · 6 guests

Sunset Champagne Cruise on the Chesapeake Bay

New
$55person
Fully Crewed Annapolis Sailing Cruises
Sailing in Annapolis · 6 guests

Fully Crewed Annapolis Sailing Cruises

New
$175person
30ft Bowrider! Enjoy a day on the water around the Chesapeake Bay in Maryland!
Powerboats in Annapolis · 8 guests

30ft Bowrider! Enjoy a day on the water around the Chesapeake Bay in Maryland!

3.7
Snoozed - Active 02 Jan 2025
Pristine Hooligan Departs from a Private Pier with a Captain and Fuel INCLUDED
Powerboats in Annapolis · 5 guests

Pristine Hooligan Departs from a Private Pier with a Captain and Fuel INCLUDED

New
$200hour
Historical Annapolis Private Boat Cruise onboard a beautiful Swift Trawler!
Events in Annapolis · 6 guests

Historical Annapolis Private Boat Cruise onboard a beautiful Swift Trawler!

5.0
Snoozed - Active 02 Jun 2024
Sail the Sea on the Pintita
Sailing in Annapolis · 20 guests

Sail the Sea on the Pintita

New
$500-$750hour
Come take a cruise on the Annapolis Jet Boat
Powerboats in Annapolis · 11 guests

Come take a cruise on the Annapolis Jet Boat

New
$500hour
Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways
Events in Annapolis · 8 guests

Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways

5.0
$250hour
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-$150hour
41' Lagoon Catamaran in Maryland
Sailing in Annapolis · 12 guests

41' Lagoon Catamaran in Maryland

5.0
Superowner
Best of 2023
$390hour
50ft Catamaran Charter with Water Toys - Annapolis, MD
Sailing in Annapolis · 12 guests

50ft Catamaran Charter with Water Toys - Annapolis, MD

New
$425hour
Just Repowered Cuddy Cabin/Walk Around bareboat fishing charter in Annapolis
Powerboats in Annapolis · 6 guests

Just Repowered Cuddy Cabin/Walk Around bareboat fishing charter in Annapolis

4.8
$95-$150hour
Maxum 30ft Yacht! Escape for a day on the Chesapeake
Events in Selby-on-the-Bay · 6 guests

Maxum 30ft Yacht! Escape for a day on the Chesapeake

New
$365hour
43ft Cruiser Express Yacht for Daily Charter
Events in Selby-on-the-Bay · 8 guests

43ft Cruiser Express Yacht for Daily Charter

5.0
$400hour
31' Chaparral 307 SSX Luxury Bowrider Rental in Edgewater, MD
Powerboats in Selby-on-the-Bay · 12 guests

31' Chaparral 307 SSX Luxury Bowrider Rental in Edgewater, MD

5.0
$250hour
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

Kent Narrows 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!