At Sunny Sail Charters we offer private sailing cruises for couples or small groups to celebrate that special occasion in a unique way. Imagine a cruise where you have the whole boat to yourselves and a crew dedicated to making sure you all have a great time.  We sail on the majestic upper Hudson River during summer months and the warm clear waters of the Florida Keys in the winter.  Browse our website, select from our gourmet menu (we challenge you to narrow your choices to just one) then decide on either a half-day, full-day or overnight charter for your perfect get-away.  Bring a few select friends with you to liven up the party!  Our facilities are excellent for up to six guests per charter.

"We really couldn't have asked for a better day.
Thank you so much for providing that for us" - charter guest

This picture was taken from the boat during a Hudson cruise.  It is the Saugerties Lighthouse on the upper river (Catskill mountains in background)

Your crew, Captain Bill and First Mate Laura, will prepare gourmet meals, discuss the local lore and raise the sails on Second Wind, our 43 foot Endeavour ketch.  Our goal is to have guests experience the wonderful feeling of sailing in unique places while enjoying great foods, cool refreshing boat drinks and, of course, excellent company.

"The ship, the scenery, the atmosphere, the food, the service...everything was top notch and first class!!" - charter guest

The Majestic Upper Hudson River is a smooth-water, fantastic scenery sail in the warm summer months.  It is relaxing and lots of fun.  Let the Catskill Mountains be your background as you sail one of America’s historic rivers.  Smell the spring blossoms, enjoy the lush summer foliage or take in the awesome fall colors of the upper Hudson valley.  Just don’t go ashore and drink with the ghost of Henry Hudson then fall asleep for 20 years like Rip Van Winkle!  

The Warm Waters of The Florida Keys are a wonderful place to enjoy day-sails along beautiful beaches or snorkeling trips to close-by reefs.  Multi-day sailing trips following The Keys, in the protected Hawk channel, are a fun and exciting way to visit ports we’ve all heard about – Key West, Key Largo and Biscayne Bay, to name a few.  

Enjoying a beautiful day (or week!) on the water with us is a unique way to celebrate anniversaries, birthdays, reunions or other special occasions with family and friends.  Learn how to sail a classic cruising yacht, take the helm and help your experienced crew trim the sails, or just sit back and relax.  Whatever your choice we'll make sure you have a safe cruise and a great time.

Money-back, bad weather guarantee for day charters – We want all of our guests to fully enjoy their cruise.  If the weather does not cooperate on the day of your charter, we will call you the day before to discuss our options.  If we decide to cancel the charter and cannot agree on a date to rebook your cruise, we will gladly give you a full refund.

Please browse our website to learn about the places we love to visit, our great boat and us!  Then, fill out the information sheet or call to book your cruise!  It will be one of the best decisions you ever made.

If you are not quite ready to charter today, please join our mailing list.  We'll keep you posted on open dates and where we are chartering in the future by sending a short email every couple weeks.

We hope to see you soon!

Captain Bill and First Mate Laura   

                                 Gift Certificates Available!