Mike enjoys Key West with Jeff & Jean
A yachting vacation, experience the lifestyle.
Take a learning vacation on a yacht crewed by experienced sailors
and educators. Sail with us to
sample the cruising life style. 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 40' -  50’+ class cruising boat while setting the stage and
framework for your five year plan.

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:
Sailing Florida
Charters (Tampa Bay Area) and Island Dreamer (Miami and the
Florida Keys).  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  to earn your ASA 103 /
104 certifications while sailing in the warm protected water of the
Florida Bays.

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
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
101/103 Students "getting it"!
Two Can Sail logo
Sailing with Two Can Sail
The Lifestyle
First: Buy our Book!
Then: Attend Seminars,
Take a Sample-the-Life
Style Sail,
Learn to Sail
with Formal Classes
like Basic Keelboat,
Sail on Friends
Boats,
Take more classes
like Bareboat
Chartering,
Go Day sailing!
The Life Style & Learn to Sail