Charter Sailboat Resources

By: Charter, Destinations

You might be daydreaming about a sailing vacation so we have put together a resource to help you plan your next great sailing adventure. 

Whether you have just begun to sail and have recently earned your ASA 101 certification or if you have already mastered ASA 114 and are a veteran of bareboat charters this resource should help you. There is something for everyone here with information on flotillas, sailing education courses, and bareboat charters.

S/V Tina, 53 Jeanneau: Capt. Alan W. and Iraida from Florida Josh V. from Illinois Eric F. from his assignment in Algeria Don S. and Yvonne P.


Flotilla sailing charter vacations bring together a fleet of sailboats, each operating independently with its own crew, along with a lead boat and flotilla leader who knows the local area well. By joining a flotilla, you can enjoy the freedom of skippering your own boat but have comfort in knowing that support and advice are on hand to help with navigation and local weather.

Learn to Sail Vacations

Combine your vacation with some sailing instruction. Nautilus Sailing will send an instructor to you at any of the 60+ destinations where Dream Yacht Charter offers charters. ASA schools around the world offer learn to sail charter vacations from The Grenadines to Baja California to Greece to Florida. If you want a sailing vacation with top-notch instruction, ASA has a school for you. Find a School

Luxury Sail Charter Aboard Arabella

Do you want to get out on the water and feel the wind in your sails but be free of all the responsibility of being in charge? Get pampered and experience the sailing trip of a lifetime on the Sailing Yacht Arabella. This is no ordinary sailing vacation as you tour the waters of New England or the British Virgin Islands with a professional crew on a mega yacht. You can choose to help with the sailing or you can sit on the deck as all 8 sails propel you to your next anchorage. 


Bareboat Charters 

The culmination of a quality sailing education is being able to sail confidently and safely in varying conditions. Your reward for getting to that point is a bareboat charter. You are in charge. Your itinerary. Your plan. Your memories. From start to finish your ASA education prepares you to do it all yourself on a sailing excursion.  

Take a Look at Some of Our Charter Vacation Resources:

Charter Resources

  • Your First Charter Sailing Vacation Today bareboat chartering is the culmination of your sailing education. When you walk across the deck and get your sailing diploma you step on to the metaphorical boat of your future and you can sail it anywhere you want!
  • Charter Sailboat Resources Whether you have just begun to sail and have recently earned your ASA 101 certification or if you have already mastered ASA 114 and are a veteran of bareboat charters this resource should help you.
  • Bareboat Charter in the BVI Getting aboard your bareboat charter is the goal when you get your ASA sailing certifications. Where do you begin? For many, it is a sailing vacation in the British Virgin Islands.
  • Choosing a Charter Boat Company It’s time for you to set off on your own and explore endless shorelines and secluded coves. You have mapped out your plan and you have reserved your vacation time now all you need is a boat. How do you choose a charter company to rent a boat for a week?
  • Choosing The Right Boat for Your Sailing Charter When you decide to take a sailing vacation aboard a sailing vessel that you will call home for a week or two you’ll be surprised by just how much you think you need.
  • What Is Your Role on a Boat? Chartering overseas is on the bucket list of many a sailor, but making it happen comes with a stipulation or two. A sizable number of countries require an International Proficiency Certificate that lets them know the charterer is trained, qualified and prepared to take one of their boats out to sea.