Cookies & Agreements

By continuing to use this website, you have read and agree to the Terms of Use and agree to the collection and use of your information by cookies and similar technologies, as set forth in our Privacy Policy.

Kent Narrows, Maryland Boat Rentals

Page 1 of 124 listings

Come take a cruise on the Annapolis Jet Boat
Powerboats in Kent Narrows · 11 guests

Come take a cruise on the Annapolis Jet Boat

New
$360/hour
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
$375/hour
34ft Sailing Yacht in Annapolis, Maryland
Sailing in Annapolis · 4 guests

34ft Sailing Yacht in Annapolis, Maryland

New
$250/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
43 foot Captained Catalina Sailing Yacht Located In Rock Hall, Maryland
Sailing in Rock Hall · 6 guests

43 foot Captained Catalina Sailing Yacht Located 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
Rent a 31ft Sailing Yacht In Rock Hall, MD
Sailing in Rock Hall · 4 guests

Rent a 31ft Sailing Yacht In Rock Hall, MD

New
$250/day
Private Sail Up to 13 Guests | 44ft Leopard Catamaran
Sailing in Saint Michaels · 13 guests

Private Sail Up to 13 Guests | 44ft Leopard Catamaran

New
$580/hour
Private Historic 1935 Ketch Sail | 13 People | Gratuity & Tax Included
Sailing in Saint Michaels · 13 guests

Private Historic 1935 Ketch Sail | 13 People | Gratuity & Tax Included

New
$645/hour
Private Sail on 44ft Leopard Catamaran | 6 People | Gratuity & Tax Included
Sailing in Saint Michaels · 6 guests

Private Sail on 44ft Leopard Catamaran | 6 People | Gratuity & Tax Included

New
$585/hour
Lagoon 42 Catamaran in Chesapeake Bay
Sailing in Annapolis · 13 guests

Lagoon 42 Catamaran in Chesapeake Bay

5.0
$400+/hour
30' Catamaran Tour Boat in Annapolis - BYOB Private Cruise - 6 Guests Capacity
Powerboats in Annapolis · 6 guests

30' Catamaran Tour Boat in Annapolis - BYOB Private Cruise - 6 Guests Capacity

New
Snoozed - Active 25 Aug 2026
Sea Ray SLX 350 for 12 ppl in Annapolis/ Kent Island
Events in Annapolis · 12 guests

Sea Ray SLX 350 for 12 ppl in Annapolis/ Kent Island

New
Superowner
$350/hour
38-ft Hunter 376 Sailing Adventure in Annapolis
Sailing in Annapolis · 6 guests

38-ft Hunter 376 Sailing Adventure in Annapolis

5.0
Superowner
$100+/hour
Enjoy the best views of Annapolis, MD aboard this beautiful Lydia dinner yacht
Events in Annapolis · 128 guests

Enjoy the best views of Annapolis, MD aboard this beautiful Lydia dinner yacht

5.0
$480+/hour
45' Catamaran Tour Boat in Annapolis - BYOB Private Cruise - 32 Guests Capacity
Powerboats in Annapolis · 32 guests

45' Catamaran Tour Boat in Annapolis - BYOB Private Cruise - 32 Guests Capacity

New
Snoozed - Active 25 Aug 2026
New Yacht Charter Bali 5.4 Sailing Catamaran in Annapolis Maryland
Sailing in Annapolis · 13 guests

New Yacht Charter Bali 5.4 Sailing Catamaran in Annapolis Maryland

5.0
$1,100/hour
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
$350/hour
Annapolis | 50 Prestige Yacht for 13 People
Events in Annapolis · 13 guests

Annapolis | 50 Prestige Yacht for 13 People

New
Superowner
$650/hour
Yamaha SX210 Bowider w/Swim Platform 6 Passengers w/Captain
Powerboats in Annapolis · 6 guests

Yamaha SX210 Bowider w/Swim Platform 6 Passengers w/Captain

5.0
$115/hour
Relaxing Excitement of the Chesapeake Bay and tributaries on our Yacht
Events in Annapolis · 6 guests

Relaxing Excitement of the Chesapeake Bay and tributaries on our Yacht

New
$300/hour
Cuddy Cabin/Walk Around bareboat fishing charter in Annapolis
Powerboats in Annapolis · 6 guests

Cuddy Cabin/Walk Around bareboat fishing charter in Annapolis

4.8
$95+/hour
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
$280/hour
43ft Cruiser Express Yacht for Daily Charter
Events in Selby-on-the-Bay · 8 guests

43ft Cruiser Express Yacht for Daily Charter

5.0
$425/hour

Kent Narrows Reviews

  1. FC

    Francesco

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

    We simply loved our three days sailing excursion of the Chesapeake bay. The boat Icarus is very comfortable to maneuver and to live in for a family of four. The bay has numerous nice coves and spots were to stay for the night. Mr James help has been crucial for maximizing our time and energies on these limited days. Thank you Jiim!

  2. MI

    Maria

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

    One of the best sailing weekends we have ever experienced! The boat is manageable and in great shape! James is a great host, he explained everything when we got there, suggested an amazing route and was there when we got back to make sure everything went well. 100% recommended, we’ll definitely rent it again!

  3. 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!!

  4. 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.

  5. 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!

  6. 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.