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.

Cambridge, Maryland Boat Rentals & Yacht Charters

Page 1 of 124 listings

Sailing Adventures on the Choptank River
Sailing in Cambridge · 6 guests

Sailing Adventures on the Choptank River

New
$100/hour
Catamaran |15 People |Choptank River
Sailing in Maryland · 15 guests

Catamaran |15 People |Choptank River

New
Superowner
$700/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
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
Hinckley| 13 PPL | St. Michaels & Annapolis | $3K 4hrs
Powerboats in Saint Michaels · 13 guests

Hinckley| 13 PPL | St. Michaels & Annapolis | $3K 4hrs

New
Superowner
$750/hour
Instant Book
41’ Bristol Sailboat Charter in Solomons Island, MD
Sailing in Solomons · 6 guests

41’ Bristol Sailboat Charter in Solomons Island, MD

New
$90/hour
Cruise in Comfort Aboard "Chill Time" – 31ft Cabin Cruiser in Solomons Island
Powerboats in Solomons · 6 guests

Cruise in Comfort Aboard "Chill Time" – 31ft Cabin Cruiser in Solomons Island

5.0
$200/hour
Unforgettable Boat Day | 11 ppl | $300hr
Events in North Beach · 11 guests

Unforgettable Boat Day | 11 ppl | $300hr

5.0
Superowner
$300/hour
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
 VIKO S 35 Sailboat in Deale
Sailing in Deale · 6 guests

VIKO S 35 Sailboat in Deale

New
$298/hour
Cruise the Chesapeake Bay!
Powerboats in Deale · 6 guests

Cruise the Chesapeake Bay!

5.0
$200/hour
Charter 44' Orana Cruising Catamaran In Deale, Maryland
Sailing in Deale · 10 guests

Charter 44' Orana Cruising Catamaran In Deale, Maryland

5.0
$250+/hour
VIKO 30 Premium Sailing Yacht In Deale, MD
Sailing in Deale · 5 guests

VIKO 30 Premium Sailing Yacht In Deale, MD

New
$925/day
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
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
Snoozed - Active 02 Jul 2026
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
31' Chaparral 307 SSX Luxury Bowrider Rental in Edgewater, MD
Powerboats in Selby-on-the-Bay · 10 guests

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

5.0
$275/hour
Private Yacht Charter: On 40ft Regal Commodore
Events in Selby-on-the-Bay · 10 guests

Private Yacht Charter: On 40ft Regal Commodore

5.0
$400/hour
Take your Sailing Dream on Chesapeake Bay.
Sailing in Mayo · 6 guests

Take your Sailing Dream on Chesapeake Bay.

New
$175+/hour
Hunter Passage 42' Sailboat - Take your Sailing Lessons on Chesapeake Bay
Sailing in Mayo · 6 guests

Hunter Passage 42' Sailboat - Take your Sailing Lessons on Chesapeake Bay

5.0
$150+/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
Durfour 430 Sailing Yacht to Discover the Chesapeake Bay
Sailing in Annapolis · 12 guests

Durfour 430 Sailing Yacht to Discover the Chesapeake Bay

New
$210+/hour
2022 Catspace 38 Sailing Catamaran in Chesapeake Bay
Sailing in Annapolis · 12 guests

2022 Catspace 38 Sailing Catamaran in Chesapeake Bay

New
$334+/hour

Cambridge Reviews

  1. AH

    Alexandra

    38-ft Hunter 376 Sailing Adventure in Annapolis

    Alberto and Grace were the perfect team. They are kind, knowledgeable, respectful, communicative, safe and I would recommend them to anyone. This was our first time sailing in Annapolis, and we could not have asked for a better experience. We hope to share future experiences with them. Everything was perfect.

  2. KG

    Katerina

    43ft Cruiser Express Yacht for Daily Charter

    We went on a boat ride with Captain Rob for my boyfriend's birthday and it was an amazing experience. We were able to bring our own drinks and Captain Rob had a cooler to store them in and keep them cold so we did not have to carry much. The initial boat that we booked was not available on the day of our ride so Captain Rob upgraded our boat to a much larger yacht without charging us anything additional. He was very kind and knowledgeable and answered all of our questions without making us feel inexperienced. Everything was on time and the experience was flawless and exactly as I had hoped it would be. We will absolutely be back this summer for longer trips and with more people. Highly recommend Captain Rob!

  3. BF

    Bruce

    38-ft Hunter 376 Sailing Adventure in Annapolis

    This was our 2nd sail with Capt Alberto. He is super friendly and easy to talk with. And he invites his guests to take an active role in sailing, or to just kick back and relax if they prefer. Great experiences for our family.

  4. JR

    Jeanean

    Cruise in Comfort Aboard "Chill Time" – 31ft Cabin Cruiser in Solomons Island

    We arrived and were greeted by the friendliest person Capt Tim. He was wonderful, very hospitable and attentive. He anticipated all of our needs for the evening. The waterfront scenery was surprisingly beautiful, seeing all the different styles of homes. An added bonus while coasting to the cove, we encountered a family of dolphins. It was a very exhilarating night. The view of the sun setting over the water was perfect from the float. The boat was quite spacious, enough for an impromptu dance party with the blue aura lights while finishing the evening. If you are looking for a fun filled evening full of laughter, and excitement. This is the thing to do

  5. NA

    Nardos

    Unforgettable Boat Day | 11 ppl | $300hr

    We had a fantastic trip! We had 8 family members from 4 years old to the grown folks. AJ coordinated everything, all went like clock work. The captain had great knowledge of ins n outs of the Patomac and was fun to chat with. We swapped some great and funny stories. Sunset by the Georgetown waterfront was spectacular. We were lucky to have a clear day and everything was dazzling. I highly recommend this trip for a family fun day out.

  6. Liz

    Liz

    Cruise the Chesapeake Bay!

    Captain Steve was incredible. He made our two hour boat outing experience unforgettable. We stopped around monuments to snap some scenic photos and even when we got caught in some rain, we all were fully covered in the inside of the boat. We will certainly book again soon!!