STEP 1
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!
STEP 5
Advanced
Training
ASA 105/106
Advanced Courses,
Advanced Seminars
like Lee Chesneau’s
Weather course,
Take diesel repair
classes, Take Safety-
at-Sea Seminars
Go night sailing,
Crew on passage of
more than 100nm
The Five Step Plan to
Your Sailing Dream
Sailing Lessons Two Can Sail Logo
This Five Step Plan is a suggestion for charting
your route to your cruising sailing goals. Of course, this
route highlights where Two Can Sail can help you meet
the milestones (or waypoints as we nautically call them)
along the way. We believe that you will find the cruising
lifestyle highly rewarding and following this Five Step
Plan will allow you both to cruise anywhere in the world
with confidence and enjoyment.
Sunset in the Florida Keys sailing with Jeff & Jean
Sunset Dreams do come true with the Five Step Plan to Cruising
Living the Dream with Two Can Sail
The Five Step Plan to Your Sailing Dreams
STEP 3
Buying The Boat
Learn more about
design, systems,
construction,
and what
compromises to
make, Attend our
"Try Before You
Buy" workshop, Pick
the right boat for
you, Shop, Survey,
Insure, Purchase
STEP 2
Cruising
Experience

Bareboat Charter,
Join Flotillas,
Sail new places
like the BVIs and
Abacos,
Read Sailing
magazines and
Books, Join in local
club races,
Go to boat shows
STEP 4
Learn Your Boat
Learn what’s best for
how you plan to
cruise, Choose
additional equipment,
Learn systems ops
and maint., Short runs
to learn how she
handles, Sail
disconnected from
shore, Make your first
offshore passage
STEPS LEAD
UP TO:
Sunset cocktails
in the cockpit of
your new
cruising home in
some tropical
paradise!
Kate & Mike enjoying a sunset on the Five Step plan
Idyllic Beaches are a part of Cruising with Two Can Sail
ASA Flotilla Fleet at Useppa Island
Cruising with Two Can Sail
Two Can Sail Logo
"The 5 Step Plan to Buy
a Boat to Go Cruising"
Written By Captains
Jeff Grossman &
Jean Levine, AMS
Click Here to Purchase now!
Two Can Sail Logo
"The 5 Step Plan to Buy a Boat
to Go Cruising"