Sailing Lessons Chesapeake

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. With its grand maritime theme, sailing embraces you to the core the minute you walk in the door!

Chesapeake sailing lessons and cruising courses

The Eastern Shore of Maryland is known for its beautiful harbors, stately homes with lush green lawns reaching down to water's edge, and delicious fresh seafood. Steeped in rich colonial history, prestigious Talbot County, where our Chesapeake sailing school is located, boasts the most shoreline in the continental United States and is considered one of the premier destinations in the Mid-Atlantic Region and the Chesapeake Bay is the best place for sailing.

Offshore Sailing School has its sailing school at The Inn at Perry Cabin in beautiful St. Michaels on the Eastern Shore of Maryland: April through mid-November.

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Fast Track to Cruising® Course

Our Fast Track to Cruising course is a unique experience at our Chesapeake Sailing School campus - taking you from want-to-cruise to ready-to-cruise in 8 days. During the first three 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.

The next five days you'll learn on a fabulous new Hunter 50 and go home with three sailing certifications: Day Sailing, Coastal Cruising and Bareboat Cruising.

Plan to arrive Thursday and depart the following Friday. An eight day package, double occupancy (staying ashore the entire time in a beautiful room at The Inn at Perry Cabin) plus your tuition and everything that goes with the instruction, starts at $4125 per person. 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 $4000.

Learn to Sail Course

This is the most comprehensive, best known course to get you thoroughly ready for sailing mid-sized sailboats (30 feet or more). Two schedules are available – three full days or five half-days.

In our Learn to Sail course, you learn on the award-winning Colgate 26 sport boat, designed by our founder Steve Colgate and famed yacht architect Jim Taylor. The per person rates below include your accommodations in a standard room at The Inn at Perry Cabin, tuition, textbooks, certification, log book and diploma.

Pick your start date and give us a call today 888-454-7015.

Three full days – Monday through Wednesday, starts at $1480
Three-full days – Friday through Sunday, starts at $1680
Five half days – Monday through Friday starts at $1995

Learn to Cruise

If you have taken our Learn to Sail course or have equivalent experience, now you can learn to sail and handle big boats on your own or a bareboat charter with ease. Our five-day Bareboat Cruising Preparation course is the perfect next step for a meaningful and relalxing vacation. You start with a morning classroom session, then learn in half-day sessions aboard a fabulous Hunter 50! 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 you'll return to your beautiful room ashore at The Inn at Perry Cabin, perhaps sip a cocktail or a cup of warm tea in an Adirondack chair on the lawn – just as the sun sets and the moon rises to cast bright shadows on the boats at anchor in the harbor. If you are traveling with friends and family who do not wish to learn to sail or cruise, this stay-ashore Bareboat Cruising Preparataion schedule is a wonderful way to each pursue your pleasures. Complete Bareboat Cruising Preparation Course packages start at $2645 per person double occupancy and include: your accommodations at The Inn at Perry Cabin in a standard room, course tuition, textbooks, two cruising certification levels, logbook and diploma.

The Live Aboard Cruising version of this course allows you to spend your entire time aboard the Hunter 50 learning, as you sail from anchroage to anchorage each day, If you and your spouse or family want to concentrate only on the learning and living aboard experience, with little down time for exploring ashore and enjoying other resort amenities, this is an excellent option. Complete Live Aboard Cruising course packages start at $2525 per person double occupancy and include: one night ashore at The Inn at Perry Cabin in a standard room, your course tuition, all breakfasts, lunches, snacks and three dinners aboard, textbooks, two cruising certification levels, diploma and logbook.

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 Hunter 50, relearning the skills you need for bareboat chartering. Packages per person double occupancy start at $960 and include one night at The Inn at Perry Cabin in a standard room and eight hours of instruction aboard the Hunter 50.

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 $880 double occupancy and includes your six hours of instruction and two nights at The Inn at Perry Cabin in a standard room.

Sailing Lessons

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.

Corporate Programs

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. If you're looking for a unique, meaningful activity and a fine location to meet with your managers or board, combine your gathering with one of our Corporate Sail-Race Challenges®. You'll be amazed at the outcome! Corporate programs are priced 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.

Where sailors love to sail

This location for sailing lessons Chesapeake Bay is outstanding. Here is where sea captains long ago retreated to protected coves and racing sailors today head out for friendly competition on our continent's largest estuary. With a watershed extending from New York to North Carolina, and Appalachia to the Atlantic, this is the cradle of life where salt and fresh water mix. Read Scott Nugent's story about the St. Michaels Learn to Sail gift his wife gave him here.

Upscale, elegant, old-world and fun

St. Michaels, Maryland on the Eastern Shore has a magical charm, with immaculately kept colonial, Inn at PErry Cabin, St. Michaels, Maryland federal and Victorian homes and handsome churches. Many of these homes are summer retreats for sailors. On St. Michaels main street you'll find small town charm with homes converted to delightful restaurants and shops. Lining the harbor are wonderful seafood eateries from very casual to candlelight dining, where you can enjoy breakfast, lunch and dinner in the open air and watch boats come and go.

"St. Michaels was a gorgeous facility for learning to sail. Our instructor was absolutely terrific. He was so knowledgeable and patient - he made sure you understood every aspect of sailing the Colgate 26. We highly recommend this course and location to anyone interested in learning to sail. Outstanding experience!
Diane V. Gensler – Holtland, PA

Glorious views in an artistic retreat

This is an upscale peaceful place bathed by glorious views. The renowned Maritime Museum is a short walk from our Chesapeake sailing school and the heart of town. All manner of artistic talent blooms among scenes of steamboats, century-old log canoes, and every other type of water craft you can imagine. A short drive from the Inn at Perry Cabin in St. Michaels are more towns with old-world charm and impressive vistas.

Sailing Lessons Chesapeake, Maryland Here's where you can take a two-hour Sailing Lesson, try a two-day introduction to sailing, get certified with our signature three-day Learn to Sail or Fast Track to Cruising course or hone your cruising skills with our Bareboat Cruising Preparation course.

You'll stay in elegance at The Inn at Perry Cabin on the Miles River, a 54 mile tidal waterway which flows into the Eastern Bay of the Chesapeake. The river itself produces an abundance of blue crab, oysters and succulent fish. The restaurant at Perry Cabin is renowned for its incredible fare and beautiful location overlooking the river.

As you can see, two or three days or a week with Steve and Doris Colgate's Offshore Sailing School at The Inn at Perry Cabin on the Eastern Shore of the Chesapeake is a very special experience.

All our course programs are packaged with accommodations at this fine resort.
Rates without accommodations will be quoted only for those with homes in the area.
All prices listed on this page are subject to change. Please verify costs when you call.

Chesapeake Sailing Lessons available at The Inn at Perry Cabin:

Fast Track to Cruising- an eight day Chesapeake Bay adventure that takes you from novice to big boat skipper with three sailing certifications
Learn to Sail - three action-packed days weekends or weekdays (with a discount for weekday schedule)
Bareboat Cruising Preparation - five super 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 give you cruising basics or refresh rusty skills
Two-hour Sailing Lessons - for those visiting the resort at The Inn at Perry Cabin
Two-Day Any-Day Learn to Sail - a 6-hour introduction to sailing the Chesapeake
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 team without any previous sailing experience
Private Courses - All regular courses may be taken as a private experience with a spouse or teen of the entire family (maximum 6)