Windjammer Barefoot Cruises
Welcome Aboard Kick off your shoes and get ready for an adventure you’ll never forget.
Informality rules! T-shirts and shorts are all you need. Stow your gear in your air conditioned cabin, complete with modern amenities. Who said anything about roughing it?
Start your day with complimentary Bloody Mary’s, fresh baked breads and pastries, followed by a bountiful breakfast. Lunch is served on board or picnic style on the beach.
Toast the sunset with Rum Swizzles and hors d’oeuvres, but save room for a hearty dinner, complete with wine… all on the house!
The night is still young! Put on your best toga or pirate gear and get ready to party!
And when we weigh anchor, let our crew do all the work or take your turn at the helm and learn the ropes.
Do as little or as much as you like. You’re off to explore the Caribbean.
It’s hard to believe that more than 60 years have passed since I sailed with my first group of shipmates to the Bahamas. Little did I know that so many people would come to love the Windjammers as much as I do. Almost 2 million people have sailed with us around the world and to the most remote parts of the Caribbean.
Lifestyles and trends have changed but, we’re still about barefoot fun, adventure and the romance of sailing a traditional tall ship. There’s plenty of food and grog, always friendly
service and the ship is yours to roam.
For those that have sailed with me in the past, I raise my rum swizzle to you, loyal shipmates.
For all the others that have only dreamed of sailing on a tall ship, I say stop dreaming and start living. I invite you to escape to an adventure that will satisfy the pirate in your soul.

Our Backyard!
Grenada
Barbados
St. Vincent
Trinidad
St. Lucia
Aruba
Curaçao Bonaire
Martinique
Dominica
Antigua
Guadeloupe
Nevis
Marie-Galante
St. Kitts
Sint Maarten
Tortola
S th A i
THE
VIRGIN ISLANDS
THE ABC ISLANDS
VENEZUELA
WINDWARD &
LEEWARD ISLANDS
THE
GRENADINES
Oranjestad
Indicates Homeport
Atlantic
Ocean
C a r i b b e a n
S e a
Playa
Herradura
Colon San Blas
Golfito
Quepos
PANAMA
COSTA RICA

We’ve been cruising “down island” for more than 50 years.
Like the pirates of yesteryear, we know all the right people in
all the right places. Windjammer’s tour planners spend grueling
hours researching and selecting onshore excursions that
are fun, authentic, and designed to put you face-to-face with
the local environment and local cultures. Each day, shipmates
may be offered a selection of 3-4 tours that range
from mellow snorkeling tours to active hiking to
adrenaline-pumped 4-wheel jungle adventures.
Families
Junior Jammers Club* & Teens
June through August
Kids and teens rule the waves on
two family friendly ships -
S/V Legacy and S/V Polynesia.
*Free for Children Ages 6-12
Single Sailors
Singles cruises are fun, laid-back and
trés hip. Our balanced booking policy
guarantees an even mix of fun-loving
singles. Call and ask about upcoming
Singles Only Cruises.
Weddings &
Honeymoons
What can be more romantic than
tying the knot on board a tall ship?
A Caribbean honeymoon under
white sails! Weddings or honeymoon,
Windjammer can fulfill your
every fantasy. Call and ask for a free
copy of our Tie the Knot at Sea
brochure. Our staff of barefoot
romantics can help you plan the ultimate
wedding or honeymoon.
Groups & Charters
It is less expensive and more fun to
travel with a group of friends, family
or colleagues. So why not charter a
tall ship for your next family reunion
or company event? Just imagine sailing
the Caribbean on your own private
yacht for a week. We will customize
the perfect itinerary, activities,
and menus tailored to your group’s
size, budget and interests. Our
Ship-to-Shore
Pre & Post Cruise Hotel Stays
What’s the rush? We invite you to
stay a while. From budget to luxury,
we’ll book your stay at the lowest
rate! There’s nothing like a little landlubbin’
before or after a cruise.
SeaChest
From beach towels to custom
nautical tees
Who Sails on Windjammer?
Windjammer shipmates are a motley crew of interesting folks from all over the U.S.
and abroad. You won’t know if the guy or gal sitting next to you is the CEO of a
Fortune 500 Company or an average “Joe.” And the best part is… no one cares. Once
your ship sets sail, it’s all about relaxing and getting into the down-island groove. Any
pretenses are quickly forgotten, and a familial sense of camaraderie soon develops
among passengers.
When the wind fills the sails of a
300 foot tall ship, you’ll know
just how thrilling it is
to soar like a bird…