Florida vacations, New York vacations, British Virgin Islands vacation from Offshore Sailing 

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We offer much more than Florida Vacations at Our Locations

Get away and learn!

Do something special on your next vacation. Take home a lifelong skill and endless opportunities to see the world under sail. Go from Beginner to cruise-ready in one week or learn the basics in just three days during one of our beautiful Florida Vacations. Call us to find out more about a glorious sailing vacation in dream island settings: 888-454-7015.

Where You Can Learn and Have Fun!

All of our campus locations are at exceptional learning vacation getaways... we offer much more than just Florida Vacations. Discover our New York Vacations or a British Virgin Islands Vacation. We have chosen each for its unparalleled sailing conditions, vacation appeal with great amenities, shore-side accommodations, proximity to airports, good interstate highways and commuter convenience. Click here to view Offshore Sailing Specials
 
 

 

 

New York and New Jersey

New York Vacations with Offshore Sailing SchoolOffshore Sailing's northern locations include two very convenient bases on the Hudson River, easily accessed by public transportation. Learn more about New York Vacations from Chelsea Piers, a fantastic recreational facility with just about every sport you can imagine including a golf driving range, is in New York City at 23rd Street on the Hudson River. Liberty Landing Marina, a full-service well-protected boating facility is in Liberty State Park near the ferry to the Statue of Liberty and thriving Jersey City. This is the home of our Offshore Sailing Club where (after you learn with Offshore) you can sail seven days a week and participate in regattas, full-moon sails and other social activities all season long. If you can't get away to one of our spectacular resort campuses, our city opportunities will truly take you away every minute you are on the water. Don't miss out on one of our wonderful New York Vacations.
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Chesapeake Bay

Chesapeake Bay vacations with Offshore Sailing SchoolOne of the most popular cruising grounds in the United States is the Chesapeake Bay, our continent's largest estuary. St. Michaels, Maryland is the center of a magical waterworld on Maryland's fabled Eastern Shore. This Victorian resort town is steeped in history with wonderful shopping, waterside restaurants, and great sailing. Our home here is the Inn at Perry Cabin, a luxurious manor house resort and spa, nestled on the Miles River next to the legendary Maritime Museum. Our boats are at the edge of the Inn's lush green lawn where tea and drinks are served in late afternoon. A pleasant drive from Washington, D.C. and less than two hours from Baltimore and Philadelphia, Perry Cabin offers deluxe accommodations and an unparalleled culinary experience with seamless attentive service. A great location for couples to learn to sail and cruise, the Inn's Linden Spa is unparalleled for pampering, wellness and rejuvenation.
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British Virgin Islands - a Caribbean paradise

British Virgin Islands vacation with Offshore Sailing SchoolIf you really want to get the feel of island sailing and enjoy a British Virgin Islands vacation – our long-time (since 1970) base in Road Town, Tortola in the British Virgin Islands is a the ultimate sailing and cruising destination. Tucked in The Moorings Village in Road Town, you learn and live among the crème de la crème of cruising yachts, and sail from one exotic island to another. The Mariner Inn has a huge pool, outdoor dining in two spots, and friendly taxis ready to whisk you away to beaches on the other side of the island. You'll sail in Sir Francis Drake Channel among the most incredible green islands you've ever seen. The water everywhere is deep blue and clear, with fantastic reefs for snorkeling and diving. This is truly a piece of paradise - don't miss out on your chance for a British Virgin Islands Vacation!
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Southwest Florida

Three absolutely delightful Florida vacation locations are each different in their own way. 

Florida Vacations with Offshore Sailing SchoolSouth Seas Island Resort on Captiva Island is “Florida’s Tahiti,” an incredible vacation destination the Colgates discovered in 1975 when they searched for a winter campus in the States. It offers truly unique Florida vacations. The moment they drove down the tree-lined road from the causeway connecting Sanibel and Captiva to the mainland, they were hooked. You will be too! The resort is captivating in every way with a variety of accommodations in hotel rooms, marina and beach villas; plus kayaking, golf, tennis, fishing, bicycling, shelling, jogging paths, fun restaurants and more. This is the perfect getaway for singles, families and couples. With miles of sandy, shell-strewn beaches, sailing in the Gulf and Sound, manatees surfacing in the harbor and dolphins playing as you sail — you just won't find a better place to relax, learn and refresh (unless you choose one of our other delightful locations below).

Pink Shell Resort Florida vacations with Offshore Sailing School

Pink Shell Beach Resort and Spa on Fort Myers Beach is on the northern tip of beautiful Estero Island, just 30 minutes from Regional Southwest Airport and your home base for many unique Florida Vacations. The moment you cross Mantanzas Bridge and look out to an endless Gulf of Mexico horizon, you know you're in for a special learning vacation treat. The island is romantic, fun and honky tonk — with a multitude of eateries from rousing open-air bars with island crooners to white-clothed shore-side dining. Pink Shell has lovely marine decor accommodations in two towers surrounding an incredible free form pool and a three-story building with its own big pool. Everything overlooks the Gulf with huge lanais. All units have kitchens or kitchenettes. And the resort has every water toy you can imagine, plus the lovely Aquagene full-service spa. This is a great spot for singles, couples and families.

St. Petersburg, Florida vacations with Offshore Sailing School

The Mansion House Bed and Breakfast in historical St. Petersburg on Florida’s Suncoast is the perfect place for singles or couples to spend their Florida Vacations. Accommodations are in two beautiful homes on a quiet residential street, with its own large pool and spa and on-site masseuse. Every morning you'll enjoy a wonderful breakfast (as part of your package of course) and when you return from sailing cookies and tea will be waiting. The B&B is walking distance to our boats in the municipal marina, the famous Pier in the Vinoy Basin, wonderful water-side restaurants and the heart of downtown St. Petersburg. Ever changing and more and more cosmpolitan, downtown has wonderful shopping and more restaurants than you can possibly visit in your short stay.  The famous St. Petersburg Yacht Club is near our boats, and when you wander the narrow streets you'll be amazed at the uniqueness of this city that looks more like a village with old restored homes throughout. If you crave the beach, it's just a 20 minute drive away. 

Click here to find out more about our Florida locations.

to book a learning vacation package at a great sailing destination.

Or call 888-454-7015 for more information.  


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