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 sailing the Chesapeake Bay. 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!

New Chesapeake sailing lessons available

Our Accelerated Fast Track to Cruising course is now available at out Chesapeake Sailing School location. The first two days are on our lively Colgate 26 sailboats as you learn the basics and all the whys of sailing theory and techniques. The next five days you'll sail a fabulous 43' Beneteau.You'll go home with three certifications: Day Sailing, Coastal Cruising and Bareboat Cruising.

This is the perfect course if you have little or no sailing experience or haven't sailed in awhile and feel rusty. You'll go from want-to-cruise to ready-to-charter in just 7 days, all while vacationing at The Inn at Perry Cabin, a premier waterside resort.If you just want the basics, take our three or five-day Learn to Sail course.  If you know how to sail but need charter experience, go for Bareboat Cruising Preparation. And if you only have a weekend, try our Big Boat Refresher/Learn to Cruise Adventure. It's all right here on out Chesapeake Sailing School!

Where sailors love to sail

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 best place for sailing the Chesapeake.

The 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 Appalacia 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, 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 candelight dining, where you can enjoy breakfast, lunch and dinner in the open air and watch boats come and go.

"St. Michaels was a gorgeous faciliy for learning to sail. Our instructor, Dave Manheimer, 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 artisitc 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. 

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. 

Chesapeake Sailing Lessons available at The Inn at Perry Cabin:

Fast Track to Cruising- a seven day Chesapeake Bay adventure that takes you from novice to ready to charter big boats all over the globe
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
Weekend Big Boat Learn to Cruise/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 - an 8-hour introduction to sailing the Chesapeake
 

 to learn more about your Chesapeake Bay sailing vacation
or call 888-454-7015 to talk to a friendly sailing advisor.

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