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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
$3000 HR  |15 Guests|Catamaran - Choptank River
Sailing in Maryland · 15 guests

$3000 HR |15 Guests|Catamaran - 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
$3K 4hrs | 13 Guests | St. Michaels & Annapolis | Hinckley
Powerboats in Saint Michaels · 13 guests

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

New
Superowner
$750/hour
Instant Book
Pro-Line 240 Center Console - Sunset Cruises & Bay Fun
Powerboats in Chesapeake Beach · 6 guests

Pro-Line 240 Center Console - Sunset Cruises & Bay Fun

New
$160/hour
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
$300hr | 10 Guests | Chesapeake Beach
Events in North Beach · 11 guests

$300hr | 10 Guests | Chesapeake Beach

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 beautiful Bay!!!
Powerboats in Deale · 6 guests

Cruise the beautiful 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
$280/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
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
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
Hunter 42' Sailboat - Take a Charter or your Sailing Lessons on Chesapeake Bay
Sailing in Mayo · 6 guests

Hunter 42' Sailboat - Take a Charter or 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
$216+/hour
Luxury Lagoon 42 Catamaran for 12 in Annapolis
Sailing in Annapolis · 12 guests

Luxury Lagoon 42 Catamaran for 12 in Annapolis

New
$344+/hour

Cambridge Reviews

  1. SF

    Sierra

    38-ft Hunter 376 Sailing Adventure in Annapolis

    Captain Alberto and Grace were incredibly welcoming and accommodating during our time on their boat. Captain Alberto taught us all about sailing and we really enjoyed being involved with helping sail the boat. My friend group had such a great time; would recommend! We will definitely be back!

  2. R

    Rebecca

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

    We had the greatest time with Captain Tim and Chill Time cruises! From day one, Capt. Tim has been very responsive, communicative, and friendly! On the day of our charter, everything was amazing! From the onboard mimosas to the beautiful charcuterie plate, and the greatest inflatable float ever! We have zero complaints and we look forward to coming back again! Thank you for everything!!

  3. RM

    Richard

    38-ft Hunter 376 Sailing Adventure in Annapolis

    Capt. Alberto and his wife were awesome hosts! They were totally flexible about our schedule and it was great to hear about his prior sailing experiences. It was great to be with such an experienced host! We will definitely book with them in the future!!

  4. MK

    Michael

    38-ft Hunter 376 Sailing Adventure in Annapolis

    Capt Alberto is great. Very knowledgeable and very pleasant. He lets you participate in manning the boat as much as you want and is especially good and introducing new sailors to the glorious activity. Highly recommend!

  5. MB

    Maya

    38-ft Hunter 376 Sailing Adventure in Annapolis

    Capt Alberto and his wife were SO AMAZING!! They taught us how to sail and we sailed across the Chesapeake. Their boat is beautiful and their company is great. I highly recommend everyone book if they are looking to sail in the Annapolis area for a few hours, learn about sailing, and have a relaxing time.

  6. Cindy

    Cindy

    38-ft Hunter 376 Sailing Adventure in Annapolis

    We had a wonderful time on the water with Captain Alberto and Grace! Their wealth of sailing knowledge of the bay and beyond was quite entertaining and impressive. Thanks for sharing your lovely boat with us.