Seas the Day

"The ocean stirs the heart, inspires the imagination, & brings eternal joy to the soul" - Wyland

Let us Customize Your Excursion  - Call us Today

Cracker Jack Life invites you to discover the beauty of Tahiti, Greece, East Carribean and the Virgin Islands

Leave the crowds behind and join us for a private, tailored experience sailing the seas. Choose your destination, boat size, trip length and island activities. Your options are endless: swim with the sea turtles, visit secluded beaches only accessible by boat, and enjoy time with your family and friends.

Consider us your captains, crew and concierge.

Captains for hire

Experienced Captains and Custom Experiences

Step on board as the crew warmly welcomes you to your new home for the trip of a lifetime. After settling in, you'll begin your adventure with a visit to one of many majestic islands. An island with a mystic, enchanting ambience that can also offer some exciting snorkeling and diving.

Whether you are of an adventurous nature or simply wanting a quiet and relaxing time, Cracker Jack Life can provide the best charter vacation to suit your preferences. We will tailor the perfect vacation to your wants and needs; whether it’s for a family getaway,  a "grab your friends" special birthday event or a wedding anniversary milestone, you can rest assured that we’ll make each and every occasion a memorable one. Snorkeling and diving are extremely popular sports enjoyed in many areas, with superb visibility offered by crystal clear waters. A holiday with water sports including windsurfing, kite surfing, water skiing, wake boarding and paddle boarding are also available to you when you charter with the Cracker Jack Life crew.

Private Cruising aboard your Luxury Catamaran

Embark on a carefree, Caribbean sailing vacation in the tropical beauty of the British Virgin Islands. Experience a dream getaway and idyllic destinations aboard the privacy of your fully, crewed yacht.

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Where do you want to sail?

The white sand beach of Petite St. Vincent

Eastern Carribean

Beautiful palm-fringed beaches, expanses of untouched rainforest await


British Virgin Islands

Beautiful Bays and Famous Caribbean Beach Bars

Bora Bora Yacht Club


The mythical destination with visions of an idyllic island paradise 



Ancient History and Gourmet Foods headline this excursion

Beautiful fishing villages to explor


Sail beautiful coves and towns that you wouldn’t otherwise see


"Twenty years from now you will be more disappointed by the things that you didn’t do than by the ones you did do, so throw off the bowlines, sail away from safe harbor, catch the trade winds in your sails. Explore, Dream, Discover.”

–Mark Twain