JOIN THESE TRIPS/EVENTS OR LET US HELP YOU PLAN YOUR OWN ADVENTURE

Plan Your Own Adventure and Save!!
The Caribbean, Greece, Brazil and More

Charter a bare-boat with/without a captain/crew for less than you think!

Check out Anegada !

"By The Cabin" Crewed Charters in The  BVI
8 days/7 nights from $1,900 - $2,400 per person

Want to explore the Caribbean (BVI, Grenadines, or St Lucia) in fully-catered luxury? You’ll find exactly what you’re looking for when you book a by the cabin charter.

There are options galore on this unique cruise – hiking, safari tours, and plenty of snorkeling and diving

Past "By the Cabin" Pictures

British Virgin Islands Interline Regatta
"Party like Rock Starz"
October, 2024

JUST $2,300 Per PERSON


Cruise the  British Virgin Islands
The wildest sailing regatta anywhere!
Past Interline Pictures

ANTIGUA, GUADELOUPE AND DOMINICA

For just $79-$210/day
Depending on the Yacht and Season


Endless Possibilities Tour
St. Vincent and the Grenadines
 July - September 2024
 

Last year was amazing!

ST. John Carnival
U.S. Virgin Islands
July 1 - 8, 2024

Don't stop the Carnival!!

Foxy's "Years End" Celebration British Virgin Islands
December 26/27 - Jan 3/4

The best place to spend New Years Eve in the Caribbean

Book early for 2024!
2019 Was Listed as One of The Best New Years Eve Celebrations In The World.... and 2023 Was Crazy

Space Won't Last

​WERE SAILING TO CUBA
Cuba in 2024-2025


Flexible Dates

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 Picture
 

U.S. Virgin Islands Annual Chili Cook-Off
​August, 2024


Experience a Texas Chili Cook-Off Caribbean Style

Book Early and Save!

The Greek Cyclades and Ionian Isles
June - September
 LIMITED SPACE FOR 2024!

Our Last Year ...See the Ancient Ruins of Delos and the Sunsets of Santorini


​JOIN THE FUN - COME WITH US AND SAIL. RELAX. EXPLORE



If you don't see anything here for you, let us know if we can help you plan your own sailing adventure. We can discover the perfect yacht for your budget, a skipper, a float plan and much much more! 


Start Planning Today  Click Here


CaribeSail recommends protecting your investment by purchasing travel insurance, especially when traveling overseas. Whether you are on a cruise, hotel, or chartering a yacht for a sailing adventure.  Click on the link below for more information and the types of coverage provided through CaribeSail's partner Allianz

Trip Protection - Travel Insurance
Allianz Global Assistance Travel Insurance Protection Products
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