Mike enjoys Key West with Jeff & Jean
Waypoint 1
A yachting vacation, experience the lifestyle.
Take a learning vacation on a yacht crewed by experienced sailors
and educators. Sail with us on our private yacht. This would be
analogous to what in the movies a Director would call an
“Establishing Shot”. It gives you a taste of what life is like for two on
a 50’+ class cruising boat while setting the stage and framework for
your five year plan.

Waypoint 2
ASA training & certifications (101 to 104 (bareboat charter))
These courses are available from many ASA schools. We suggest
either: selecting a school close to home, or selecting one that is near
the area you are most likely to do your first charters. We teach for
many of the schools in Florida including: Island Dreamer (Miami and
the Florida Keys), Sailing Florida Charters (Tampa Bay Area) and Gulf
Coast Sailing School (Pine Island Sound, near Ft. Myers).  Several of
these schools offer a fleet of charter boats on some of the finest
cruising grounds in the US. You may wish to spend a week with Two
Can Sail on an OI41 to earn your ASA 103 / 104 certifications while
sailing in the Caribbean like islands of the Florida Keys.

Waypoint 3
Daysailing, Daysailing, Daysailing including some racing
There is nothing that can replace time on the water actively sailing to
learn to feel and sense the environment of wind and wave and how a
sailboat responds to them. We recommend joining a local sailing
club (e.g. Windpath or Sailtime) and sailing every chance that you
can. Join your local Yacht club for their “beer can regattas”
(translation: not so serious fun races) where pick up crew are always
welcome. The crucible of racing provides lessons that are invaluable
in cruising, and yet are hard to learn from just cruising. Some even
choose to purchase a small daysailor to have personal access to
sailing as well as a first small step to learning boat ownership and
maintenance.
STEP 1
The Five Step Plan to your Sailing Dream
Couples Cruising Classes
Jean teaching women on a Catamaran in Antigua
Jeff and Jean Five Step Plan to you cruising Dreams
STEP 1
Learning about
the lifestyle,
Attend Seminars,
Learn to sail with
ASA training, ASA
101 Basic
Keelboat, Sail on
friends boats,
Take ASA 103
Coastal Cruising
and ASA 104
Bareboat
Chartering, Go
Day sailing!
Step One:
Learning the lifestyle and learning to sail
Jean teaching basics
on a Catamaran in
Antigua at ASA
Members Week
Kate & Mike learning from Jeff while sailing in Key West
Kate enjoys Key West with Jeff & Jean
Kate & Mike: On Step 1, Tasting the
cruising lifestyle while learning basics
from Jeff and Jean on a cruise to Key West
Beautiful waterfalls in Guadeloupe with Two Can Sail
Deborah plays water nymph in a secluded pool
with mountain side waterfalls in the rain forests of
Guadeloupe while cruising with Jeff & Jean
Jeff teaching a Women's Racing Tactics Class
Jean teaching a Women's Basic sailing class
Basic Sail Training
Jean teaching a Women's ASA 101 Class
Basic Sail Training
Jeff teaching an Intro to Racing Class
Can we do this? Couple doing basic ASA training with Jean
Yes we can!!  Couple doing basic ASA training with Jean
Basic Sail Training
101/103 Students "getting it"!
Two Can Sail logo
Sailing with Two Can Sail
Booking Options for Jeff & Jean