BAREBOAT CHARTERS & DAY RENTALS | ASA SAIL SCHOOL

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Chesapeake Bay’s Finest Bareboat Charters, Day Rentals, & Highest Quality Instruction

At Sail Solomons, we are dedicated to providing you with an exceptional sailing experience. We offer top-quality sailing instruction at our ASA Award-Winning sailing school, and luxury yacht charters on the Chesapeake Bay, Caribbean, and Mediterranean.

Our experienced Captains are available for instruction, charters, deliveries and marine consulting.

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DEDICATED TO PROVIDING YOU AN EXCEPTIONAL SAILING EXPERIENCE

Services

Bareboat Charters & Rentals

Sail Solomons offers yacht charter services with diverse options ranging from luxury vessels to bareboat rentals, ideal for exploring scenic coastlines and tranquil waters.

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Sailing Instruction

Our ASA Award-Winning sailing school in Chesapeake Bay, MD, provides comprehensive courses for all skill levels, emphasizing practical experience and navigation in diverse maritime conditions.

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Sailing Club

Our Sailing Club in Chesapeake Bay, MD, offers members exclusive access to a fleet of well-maintained yachts, regular regattas, and a vibrant community of sailing enthusiasts.

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Flotilla January 2025 – MARTINIQUE

*3 Cabins Left* Join Sail Solomons for a fantastic flotilla week in Martinique this winter!

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Latest News & Media

Riding the Winds: Uniting Passion and Precision on the Waves

Our Chesapeake Bay Sailing Instructors

Our team at Sail Solomons consists of highly experienced and certified sailing instructors and captains, each bringing a unique set of skills and backgrounds. From seasoned racers to former military officers, our leaders not only share a deep love for sailing but also a commitment to teaching. They are dedicated to providing comprehensive and engaging sailing education and charter experiences in the Chesapeake Bay and beyond, ensuring that every participant gains confidence and competence on the water.

Meet The Whole Team
Jeff Carlsen Owner, Instructor, Captain

Jeff Carlsen

Owner, Instructor, Captain

Jeff is a seasoned sailor and US Coast Guard licensed 100 Ton Captain with extensive experience from dinghies to ocean cruisers. He has spent two years cruising with his family across 12,000 miles from Newfoundland to the Virgin Islands, integrating sailing with home-schooling. A retired US Navy Commander and experienced racer, Jeff is passionate about teaching sailing with a focus on family-friendly and relaxed learning environments.

Chris Staley Instructor, Captain

Chris Staley

Instructor Captain

Chris is a lifelong sailor skilled in handling everything from dinghies to cruising catamarans. He’s a licensed Coast Guard Captain with a 100 Ton Master credential, and an ASA instructor since 2007, capable of teaching advanced sailing courses. Chris also has over a decade of experience as a charter fishing captain and operates commercial marine assistance vessels. His passion for teaching sailing is evident, and when not instructing, he enjoys sailing his Oday 34 around Solomons and fishing on the Bay.

Tom and Beth Ackerman

Instructor, Captain(s)


Tom and Beth, ASA-certified sailing instructors with a USCG Masters license, live aboard their Irwin 43, Ancora Qui, in Solomons Island. A lifelong sailor, Tom introduced Beth to sailing, and after his career as a physical therapist, they embraced the cruising lifestyle in 2022. Their plan is to summer on the Chesapeake and winter in warmer climates, sharing their passion for sailing with others

Sailing Stories: Why Sail Solomons?

“Lisa, I am really glad I was able to attend your Marine Weather class.  Your depth of knowledge and years of experience make you an excellent instructor for this topic.  While I am not planning any offshore sailing, I am convinced the course will enable much better day sailing and cruising on the bay.  My weather preparation for sailing has been comprised of the very brief NWS Coastal Waters Forecast for my zone and a reading of the observations from two data buoys.  Now I can use the Surface Analysis and Forecast maps for a deeper view and make an assessment of what is really likely to happen.  A better understanding of the land effects on wind will also be very useful.“

– Wayne G, ASA 119

“We just wanted to say thank you, Lisa & Andy, for the splendid 4 days 5 nights that we sailed the Chesapeake on the yacht Windhover. The attention to detail with bookings, planning, briefing, and advice was most appreciated. The yacht was in great shape. The many sailing lessons provided by Sail Solomons meant that we were incident free, well prepared, and able to relax and enjoy the whole time we were out there. Thank you once again, we loved every minute of it, and plan to do it again in a few months.“

– Vandy & David

“We (two couples) recently chartered with Sail Solomons for a week and had a wonderful experience. The boat was the cleanest, best maintained and best-equipped we have ever chartered. Andy and Lisa were great to work with, from the initial inquiry to the check in of the boat at the end. It was an absolute pleasure doing business with them. The orientation was thorough with no waiting, so we could start our vacation as soon as was feasible. They also provided great advice with our float plan and were available by phone to answer any questions as we went. We look forward to working with them again.“

– Karen & Doug, Bareboat Charter Guests

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Sailing Club

Our ever-popular Sailing Club gives members access to the daysailer or cruising fleet for low cost and stress-free sailing. Members enjoy social events, crew networking, discounts on courses, Caribbean flotillas and much more!

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