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All listings in Baltimore

Great sailboat rentals near Baltimore, Maryland.

Page 1 of 114 listings

38ft Seawind 1160 Luxury Sailing Catamaran in Essex, Maryland for 12 Guests
Sailing in Essex · 12 guests

38ft Seawind 1160 Luxury Sailing Catamaran in Essex, Maryland for 12 Guests

5.0
$799+/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
Limited Availability
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
Limited Availability
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
Welcome Aboard Optimystic! Create a beautiful memory on the water.
Sailing in Essex · 6 guests

Welcome Aboard Optimystic! Create a beautiful memory on the water.

5.0
$150/hour
New Yacht Charter Bali 5.4 Sailing Catamaran in Annapolis Maryland
Sailing in Annapolis · 12 guests

New Yacht Charter Bali 5.4 Sailing Catamaran in Annapolis Maryland

5.0
$1,100/hour
Charter 42' Lagoon Catamaran in Annapolis, MD
Sailing in Annapolis · 12 guests

Charter 42' Lagoon Catamaran in Annapolis, MD

5.0
$425/hour
42 foot Captained Catalina Sailing Yacht Located In Rock Hall, Maryland
Sailing in Rock Hall · 6 guests

42 foot Captained Catalina Sailing Yacht Located In Rock Hall, Maryland

5.0
$150+/hour
Luxury 2022 Excess 11 Catamaran for 12 in Annapolis
Sailing in Annapolis · 12 guests

Luxury 2022 Excess 11 Catamaran for 12 in Annapolis

New
$335+/hour
Private Annapolis Sailing Experience on a Classic 37' Nauticat Ketch
Sailing in Annapolis · 6 guests

Private Annapolis Sailing Experience on a Classic 37' Nauticat Ketch

New
$150+/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
Luxury Lagoon 42 Catamaran for 12 in Annapolis
Sailing in Annapolis · 12 guests

Luxury Lagoon 42 Catamaran for 12 in Annapolis

New
$335+/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
34ft Sailing Yacht in Annapolis, Maryland
Sailing in Annapolis · 4 guests

34ft Sailing Yacht in Annapolis, Maryland

New
$250/hour

Sailing Reviews in Baltimore

  1. 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!!

  2. 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.

  3. Geoffrey

    Geoffrey

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

    Icarus is a great boat and very well equipped. The sails and everything else on the vessel are in great shape and the fact it only draws 4' 6" is perfect for the Chesapeake. I spent a week on Icarus and everything worked well. The value of chartering Icarus is undeniable. I plan to charter Icarus again. Icarus has a lot of sail area, so if the winds are strong douse the headsail early.

  4. LM

    Liz

    Welcome Aboard Optimystic! Create a beautiful memory on the water.

    Charles was an outstanding guide. Before the outing (which was a birthday gift for my fiancé) he even offered to pick up a cake so that it could be a surprise. He and his wife made us feel at home right away as if we were out just sailing with friends. It was a gorgeous late afternoon / sunset sail with the option of swimming and cooking on the boat. We didn't rush back. Riding on the bow was so relaxing. He took time explaining sailing tips to my fiancé and let him drive the boat for awhile. Communication was clear. We'd love to book again with Charles and Renee!

  5. AV

    Ariel

    38-ft Hunter 376 Sailing Adventure in Annapolis

    We had a lovely experience out on the bay. Captain Alberto let my husband steer the boat & put the kiddos to work as well. We were able to play & relax as well while out on the water. Very family credibly experience and lovely to get to know the captain & his wife! Overall 5 stars for a sailing experience on the bay!

  6. Erika

    Erika

    38-ft Hunter 376 Sailing Adventure in Annapolis

    We had such a great time! The boat was perfect and Alberto and his wife were great hosts. It’s a good sized boat, kid-friendly (they had kids life jackets), and the cabin was spacious with plenty of room to eat.