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.

All listings in Baltimore

Great sailboat rentals near Baltimore, Maryland.

Page 1 of 112 listings

AnnapolisBoatExperiences presents an Exclusive Sail on its Classic 37' Ketch
Sailing in Annapolis · 6 guests

AnnapolisBoatExperiences presents an Exclusive Sail on its Classic 37' Ketch

5.0
$200+/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
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
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
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
$344+/hour
Dufour 430 Sailing Yacht to Discover the Chesapeake Bay
Sailing in Annapolis · 12 guests

Dufour 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

Sailing Reviews in Baltimore

  1. SL

    Saskia

    38-ft Hunter 376 Sailing Adventure in Annapolis

    Captain Alberto and his wife provided a lovely sailing experience for myself and my elderly parents, and were so kind to help both of my parents on and off the boat with great care-- even assisting them to get back to our car. We really enjoyed our time out on the bay

  2. AB

    Alex

    AnnapolisBoatExperiences presents an Exclusive Sail on its Classic 37' Ketch

    Steve was an amazing host. His itinerary was punctual and we could tell he spent the time researching just how to make our experience just what we were looking for. Steve was a great captain and the boat is perfect for a few hours out on the bay. Can’t wait to ride with Steve the next time we come to Annapolis

  3. LH

    Laura

    38-ft Hunter 376 Sailing Adventure in Annapolis

    Alberto and his wife were absolutely wonderful hosts. They were welcoming, attentive, and made sure every detail of our sailing trip felt effortless. We had the most perfect day on the water, beautiful views, great company, and an experience we’ll remember for a long time. Highly recommend their boat and hospitality.

  4. PS

    Patricia

    38-ft Hunter 376 Sailing Adventure in Annapolis

    Alberto was great about communicating and flexible when we had to reschedule due to bad weather the first time. He and his wife hosted us, balancing chatting and talking with them and having our own time as friends. Definitely recommend and would book again

  5. AR

    Alison

    38-ft Hunter 376 Sailing Adventure in Annapolis

    We had such a fun experience with Captain Alberto and Grace. They were delightful company and the sailing was beautiful! Getting to steer and learn the ropes was an extra perk.

  6. JM

    Jerry

    AnnapolisBoatExperiences presents an Exclusive Sail on its Classic 37' Ketch

    Stephen was great from the jump and the boat was as advertised. Great communication, super flexible with the itinerary. Made it super easy for our group to show up and be on our way.