Chesapeake Bay Sailing Lessons
*Offered at Our Eastern Maryland Location
Discover the Thrill of Sailing at the Chesapeake Bay, MD, Sailing School
Why the Eastern Shore of Chesapeake Bay
In addition to immersing yourself in this wonderful sailing area, you'll want to explore historic St. Michaels, Maryland, the heart and soul of Chesapeake Bay sailing. Our fleet resides at The Inn at Perry Cabin, a luxurious seaside resort steeped in rich colonial history. All our course programs are packaged with accommodations at this fine resort. To get "up front and personal" with our team and what's like to learn in this historic Chesapeake location, read our Director of Operations latest report here.
What You Can Receive at The Inn at Perry Cabin
All prices listed on this page are subject to change. Please verify costs when you call.
- Fast Track to Cruising- a 7-day Chesapeake Bay Sailing adventure that takes you from novice to big boat skipper with three sailing certifications
- Learn to Sail - three action-packed Chesapeake Sailing days, weekends or weekdays (with a discount for weekday schedule)
- Bareboat Cruising Preparation - five super Chesapeake Bay Sailing days learning to cruise with time to relax and enjoy this beautiful area
- Live Aboard Cruising - five days of training while sailing and sleeping aboard as you move from anchorage to anchorage
- Bareboat Refresher - designed to refresh bareboat cruising skills
- Two-hour Sailing Lessons - for those visiting the area or staying at The Inn at Perry Cabin
- Two-Day Any-Day Learn to Sail - a 6-hour introduction to Chesapeake Bay Sailing
- Corporate Programs - Half and full-day programs for small groups (up to 10); build leadership skills and learn what it takes to work together as a team; no previous sailing experience required
- Private Courses - All regular courses may be taken as a private experience for two or the entire family (maximum 6)
Chose a Detailed Course Description
Fast Track to Cruising® Course
During the first two days you are immersed in our comprehensive Learn to Sail course, which takes you through intermediate sailing knowledge and skills on lively Colgate 26 sailboats. A seven day package starts at $4065 per person double occupancy. Maximum four taught per instructor per boat. You may also choose to do your cruising lessons while living aboard. The per person package double occupancy for the Fast Track to Live Aboard Cruising course starts at $3885. These rates include:
- A standard room at The Inn at Perry Cabin for 7 nights or 2 (if taking the Live Aboard course)
- Three certifications
- Diploma and logbook
The next five days you'll learn on a fabulous Jeanneau 439 and go home with three sailing certifications:
- Day Sailing
- Coastal Cruising
- Bareboat Cruising
Learn to Sail Course
Learn on the award-winning Colgate 26 sport boat, designed by our founder Steve Colgate and famed yacht architect Jim Taylor. This is the most comprehensive, best known course to get you thoroughly ready for sailing mid-sized sailboats. Three full days or five half-day schedules are available.
The per person rates below include:
- A standard room at The Inn at Perry Cabin
- Log book
Pick your start date:
- Three full days – Monday through Wednesday, starts at $1505 per person double occupancy
- Three-full days – Friday through Sunday, starts at $1707 per person double occupancy
- Five half days – Monday through Friday starts at $2040 per person double occupancy
Learn to Cruise
Our five-day Bareboat Cruising Preparation course is the perfect next step if you have taken our Learn to Sail course or have equivalent experience. You start with a morning classroom session, and then learn in half-day sessions. Your on-water schedule normally alternates mornings and afternoons throughout the week with a rewarding test sail without the instructor aboard on your last day. Each evening after your Chesapeake Bay Sailing adventures you'll return to your beautiful room ashore at The Inn at Perry Cabin.
Complete Bareboat Cruising Preparation Course packages start at $2685 per person double occupancy and the Live aboard Cruising version of this course starts at $2530 per person double occupancy. Both include:
- A standard room at The Inn at Perry Cabin
- Your course tuition
- Two cruising certification levels
- For Live Aboard only - all breakfasts, lunches, snacks and three dinners aboard
Weekend Bareboat Refresher Course
This weekend course allows you to refresh your big boat skills while staying at this beautiful resort. You get lots of experience handling our Jeanneau 439, relearning the skills you need for bareboat chartering. Packages per person double occupancy start at $965 and include one night at The Inn at Perry Cabin in a standard room and eight hours of instruction on the Chesapeake Bay aboard the Jeanneau 439.
Two-Day Any-Day Learn to Sail Getaway
This two-day mini-vacation is a great introduction to sailing. You'll learn in two three hour sessions - six hours total over two days, allowing free time to explore St. Michaels and relax at the spa or by the pool. The total package per person starts at $1135 double occupancy and includes your six hours of Chesapeake Bay Sailing instruction and two nights at The Inn at Perry Cabin in a standard room.
If you're planning to stay at The Inn at Perry Cabin but just want to get a taste of sailing, try our two-hour sailing lesson on a fun Colgate 26. A two-hour lesson is $150 per person, minimum two people (or $300 if private instruction desired). Each additional hour is $75 per person. Sailing lessons are available here mid-April through October.
This exclusive program is available at Perry Cabin for select small groups. If you are planning a meeting at the resort, consider adding a half-day or full-day program to bring everyone together in refreshing leadership and team building exercises.
Pricing starts at $275 per person for the half-day session; $395 full day - minimum four per boat on two Colgate 26 sailboats with expert coach/instructors.
Get Started Now
An Offshore Sailing School sailing vacation in Chesapeake Bay is for anybody that loves the outdoors, enjoys being on the water and wants to learn a new skill. You’ll sail away with not just a love of the water but with sailing skills that last a lifetime!
Or call 888-454-7015 to talk to a friendly sailing advisor