Sailing Vacations & Courses

Over 50 Years of our family giving you more of what you go to sailing school for!SM


See video clips from actual trips.

NEXT TRIP: Virgin Islands (BVI), January 8-15, 2022!  Read on, or  Hit us up to see about joining.

MOST RECENT TRIP:  Italy! Bay of Naples, Pontines, Amalfi Coast.  See plenty of pics and some prose in our Blog Rant about this and prior trips, as well as our Instagram.

Panorama at the Baths of Virgin Gorda, dusk. Steve Card, photo.

Earn ASA Cruising or Coastal Nav Certification (103, 104 or 105), AND get a great sailing vacation as well!

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 40-47 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!

IN THAT PIC: typical young charter yacht we book from Sunsail or The Moorings – the world’s largest charter companies, and for good reason. This model is what we sailed on our Croatia trip out of Dubrovnik!

Trip pricing includes everything except flights, transfers, personal incidentals 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
  • surfing and SUP
  • windsurfing and kite boarding
  • fishing
  • beachcombing
  • light hiking
  • bike and moped rentals
  • exploring small towns and villages
  • local festivals
  • fun dining and imbibing spots
IN THAT PIC: the gang gets their beach on, during our September ’21 trip in Italy. This is a hideaway somewhere between Amalfi and Positano.

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



      • Dates: January 8-15, 2022
      • Yacht: Jeanneau Sun Odyssey 40 – 3 cabins/2 heads
      • Premiere Yacht from Sunsail: 1-3 years ‘young!’
      • Location: Tortola BVI
      • Fly to: Tortola (EIS) St. Thomas (STT)
      • Trip: instructional sailing vacation
      • Earn: ASA 103 or 104 certification
      • Price: $3750 per cabin, or $1875 pp, double occupancy.
      • NB: you must be fully vaccinated to join us!

For more info, or to score a spot (or more), hit us up!

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?  We can take you.  Just contact us to discuss.