Join us for a carefree, relaxing sail on the upper Hudson River where you will enjoy beautiful scenery in the comfort of a classic cruising sailboat. Smell the spring blossoms, enjoy the lush summer foliage or take in the awesome fall colors of the upper Hudson valley. Let the Catskill Mountains be your background as you sail one of America’s historic rivers while we serve you gourmet foods and cool, refreshing boat drinks. Learn a little of the History of the Hudson Valley and hear some of the local folklore of days gone by - just don’t go ashore and drink with the ghost of Henry Hudson then fall asleep for 20 years like Rip Van Winkle!
"You and your wife exceeded my expectations and provided us with a magical night that we will remember forever! Thanks again!!!" - J.C., White Plains, NY
Choose from our standard Hudson River charter packages or call for a customized trip. All of our charters depart from Catskill, NY and we sail the upper Hudson between Kingston and Albany. These are private charters - your party has the entire boat to themselves - and include a crew who's only desire is to share their love of sailing in beautiful waters. Our half-day and full-day charters include beverages with assorted hors d'oeuvres. We would love to serve up to six people on your cruise.
We are a 15 minute taxi ride from the Hudson Amtrak Train Station
Click on the link below for more information on our Hudson cruises -
Just-For-Fun Sail - Join us for calm water sail with a beautiful view of the Catskill Mountains. Lowest per-person price for a private charter!
Half-Day Lunch or Sunset Dinner Charter - These include appitizers and boat drinks for the entire cruise then a great meal with a fantastic view. Our Sunset Dinner Charter is the most popular cruise with our guests!
Full Day Cruise - Spend a full day with us on the water for great pictures of the Catskill Mountains and Hudson lighthouses. All-inclusive with a full day of beverages, appetizers and both a gourmet lunch and dinner.
Hudson River Vacations - Experience a truely unique vacation of a lifetime on Second Wind. We'll wine-n-dine you on a private sailing charter that is customized especially for you. Take advantage of our sailing and cruising experience in the beautiful Hudson Valley to visit famous towns and historic attractions. Help raise and trim the sails or just sit back and enjoy the ride - either way you'll leave us with memories to last a lifetime. These are all-inclusive, private sailing charters. You will be the only guests on our boat and we'll do everything possible to make sure it is the best vacation you've ever had.
Join us for a carefree, relaxing sail on the upper Hudson River where you will enjoy beautiful scenery in the comfort of a classic cruising sailboat. Smell the spring blossoms, enjoy the lush summer foliage or take in the awesome fall colors of the upper Hudson valley. Let the Catskill Mountains be your background as you sail one of America’s historic rivers while we serve you gourmet foods and cool, refreshing boat drinks. Learn a little of the History of the Hudson Valley and hear some of the local folklore of days gone by - just don’t go ashore and drink with the ghost of Henry Hudson then fall asleep for 20 years like Rip Van Winkle! 
Choose from our standard Hudson River charter packages or call for a customized trip. All of our charters depart from Catskill, NY and we sail the upper Hudson between Kingston and Albany. These are private charters - your party has the entire boat to themselves - and include a crew who's only desire is to share their love of sailing in beautiful waters. Our half-day and full-day charters include beverages with assorted hors d'oeuvres. We would love to serve up to six people on your cruise.