Sailing Vacation Courses

50th Anniversary of our family giving you more of what you go to sailing school for!SM

See video clips from actual trips.

NEXT TRIP  Italy! Sicily/Aeolian Islands.  September 28 – October 5, 2019.  Two spots taken with a third pending, so hurry up and hit us up.

Last 2 trips: Virgin Islands (BVI), January 19-26, 2019, preceded by Dubrovnik, Croatia on our Game of Thrones tour in September of 2018!

Dusk at the famous Baths of Virgin Gorda, BVI. Steve Card, photo.

Earn ASA Cruising or Coastal Nav Certification (103, 104 or 105), AND get a great sailing vacation as well!  We have room for three more on the first boat, so stay tuned for more trip details or just contact us for Q&A or to just get on board.


In Croatia we sailed THIS

And saw sights like THIS…

-typical stunning scenery in historic Croatia. Arieh Hammer, photo.

And THIS…

And, THIS…

Another great capture in Croatia by Arieh Hammer.

Want to sail in Italy with us this fall?  Or, come to BVI with us during the ‘off’ season in winter 19/20?  Read on, or contact us!


Join us in the Caribbean or the Mediterranean for an exotic sailing vacation! Learn how to sail a charter yacht and also have plenty of time to play, explore, or just relax.  Next time you’ll be ready to bareboat your own cruise.

You’ll be aboard a large, late model cruising auxiliary – typically 40-45 feet – with spacious private cabins, and fully appointed for a surprisingly comfortable week aboard.  Don’t worry – we go ashore whenever we want with our stable, inflatable dinghy with a rigid floor that’s almost more fun to drive than the sailboat!

Trip prices average out to be around $1850 per person, usually double occupancy.  That includes everything except flights, transfers, and some dinners ashore in the Virgin Islands.  (In Europe, we almost always dine ashore.)  There’s plenty to do besides the big-boat skills from the cruising courses.  Non-sailor friends and spouses enjoy these trips immensely.  Here are some ways you can play:

  • swimming and snorkeling
  • SCUBA
  • surfing and SUP
  • windsurfing and kite boarding
  • fishing
  • beachcombing
  • light hiking
  • exploring small towns
  • local festivals
  • fun dining and imbibing spots

When you’re not playing or chillaxin, you can be earning ASA 103, 104 or 105 certification (Basic Cruising,  Bareboat, or Coastal Navigation, respectively).  Certification is included in the trip price.

asa cert circle medium


We were on the cover – and in the pages – of ASA’s American Sailing Magazine, featuring one of our sailing vacation/course trips…

am sail greece shotThe couple shown working out something on the chart were pursuing their Bareboat 104 certification.  They had started with learn-to-sail/101 locally at our City Island base, and worked their way up to this trip.  The day after it ended, they switched to another yacht – which they’d chartered in advance – and set off on their own 1-week bareboat cruise in Greece’s famous Cyclades Islands!

Have a trip in mind for your own group or family?  We can take you.  Just contact us to discuss.