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All listings in Baltimore

Great sailboat rentals near Baltimore, Maryland.

Page 1 of 112 listings

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
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
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
Charter 42' Lagoon Catamaran in Annapolis, MD
Sailing in Arnold · 12 guests

Charter 42' Lagoon Catamaran in Annapolis, MD

5.0
$425/hour
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
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
2022 Catspace 38 Sailing Catamaran in Chesapeake Bay
Sailing in Annapolis · 12 guests

2022 Catspace 38 Sailing Catamaran in Chesapeake Bay

New
$334+/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
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
Luxury Lagoon 42 Catamaran for 12 in Annapolis
Sailing in Annapolis · 12 guests

Luxury Lagoon 42 Catamaran for 12 in Annapolis

New
$335+/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
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. 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. 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.

  3. TM

    Thomas

    New Yacht Charter Bali 5.4 Sailing Catamaran in Annapolis Maryland

    This is a great boat and we had an absolute blast. worth every penny!

  4. DD

    Danuta

    Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

    What an enjoyable experience! Captain Joe was always attuned to our wishes, making an extra effort to make this afternoon pleasant for all. His company is very agreeable. We wish we could relive yesterday's feeling of complete relaxation over and over!

  5. George

    George

    Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

    HIGHLY recommend Capt Joe for a fantastic sailing experience out of Rock Hall. Joe worked with us to get a last-minute booking when another booking fell through. He and his crew are experts and you will not be disappointed. He let us take the helm and participate as much or as little as we wanted to. Sol Searcher is a beautiful, well-equipped boat - plenty of comfort and speed (wind dependent of course.)

  6. LR

    Loretta

    Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

    What a gorgeous day on the water aboard Sol Searcher! Captain Joe was an awesome host for our day! Peaceful, serene and exactly what we were hoping for to bring the summer to a close. What a lovely world we have to enjoy when we step away from the hustle of life and take the opportunity to take in all that it has to offer. Thank you Capt’n Joe for a wonderful sailing experience. Until we meet again, Loretta and Greg