Join us on Second Wind for a relaxing vacation sailing the historic Hudson River. We'll sail the river from Catskill to New York City with several stops along the way for sightseeing and enjoying the beautiful Hudson Valley. These charters are private and all-inclusive. Youare our only guests on the boat and he only money you'll spend after reaching the boat is if you go ashore for tours, sightseeing or mementos. All meals and drinks are pre-planned and prepared on-board according to your tastes. You fill out a "likes and dislikes" questionnaire ahead of time and we'll stock the boat with all your favorites.
Multi-day custom charters are limited to a single couple. Second Wind is a two cabin boat with one at each end of the vessel (forward and aft-cabin layout). The crew will be sleeping in the bow while our guests enjoy their own private aft-cabin with queen-sized bed, private head and private stand-up shower. (See our Pictures and Videos page for a full-size floor plan.)
Here is a sample itinerary. We'd love to customize a special trip for you!
Day 1 - Fly into Albany airport (ALB) or take the train to the Hudson Amtrak station. We'll help you arrange for your last easy leg to the boat then settle into your own private cabin with separate head and shower. Once you are comfortable, we'll depart Catskill and sail south along the river following the beautiful Catskill Mountains to Hyde Park, NY. We'll stay in Hyde Park for the day where you can go ashore for a great tour of the Vanderbilt Mansion.
Day 2 - We'll leave on the morning tide to continue our sail south. Possible sites to visit and stay overnight are historic Newburgh where Henry Hudson visited in 1609 and described as, "A very pleasant place to build a town..." Take a relaxing walk (or short cab ride) to the Washington's Headquarters State Historic Site where George Washington made some of his most important contributions to shaping the American republic.
Day 3 - Continuing our sail down the Hudson we'll pass the deepest waters near West Point and Bear Mountain. The river really opens up at Haverstraw Bay where we can roll out all of our sails before we end our day at the Tarrytown marina. From here it is a short taxi ride to Kykuit - home for 4 generations of the Rockefeller family. From the Historic Hudson Valley website, "For architecture, remarkable gardens, art, history, and spectacular scenery, a trip to Kykuit is simply amazing."
Day 4 - We'll sail under the Tappan Zee Bridge with the skyline of New York City spreading out ahead of us. Maybe we'll take a short sail into New York Harbor to view the Statue of Liberty before we tie up at the 79th Street Marina in Manhattan for a great ending to a beautiful trip. After (usually tearful) goodbyes, you'll take a short cab ride to Penn Station where you board Amtrak for a much quicker trip back to your car in Hudson. Easy transportation is also available to the New York airports.
** Free pick and drop-off from the Albany International Airport for Hudson River charters 4-days or longer
We would love to customize a multi-day charter for you and can provide some great options based on our extensive experience in these beautiful cruising areas. If you would like to take a hand in planning your cruise, here are some excellent resources to browse -
Discover more exciting and historic places to visit on your charter at Historic Hudson Valley (opens in a new window)
We've created a visual tour of our trip on Google Maps. Click HERE to open the map and view points of interest (opens in a new window)
Use our Hudson Mileage Chart to help plan our day on the river. By limiting our sails to 5-6 hours a day (25 - 30 miles), there will be plenty of time for sightseeing ashore.
These are all-inclusive, private charters - gourmet meals, snacks, boat drinks and all boat expenses are included. You have the whole boat to yourselves with a crew dedicated to making sure you have a great time.
Multi-Day Vacation Rates
Night
Rate
Trip Total
1
$800
$800
2
$800
$1600
3
$700
$2300
4
$700
$3000
5
$600
$3600
6
$600
$4200
Additional nights are the same rate as night #6
Discounts Available!
$100 per day discount for single guest
$50 per day discount for round-trip (guests arrive and depart at our normal berth)
Protection for your charter investment - We provide an industry standard Yacht Charter Agreement for all charters longer than one day. A sailing charter on a crewed yacht is a large investment of your money and valuable vacation time. This agreement provides you guarantees on our crew, boat and facilities along with details of any clothing or gear you might want to bring. Click HERE to download a blank Yacht Charter Agreement. Please call if you have any questions.
Ready to take the next step? Visit our Reserve Your Cruise pageand fill out our easy Quest Information form. Or, please call us at (518) 210-3309 if you have any questions.
Join us on Second Wind for a relaxing vacation sailing the historic Hudson River. We'll sail the river from Catskill to New York City with several stops along the way for sightseeing and enjoying the beautiful Hudson Valley. These charters are private and all-inclusive. You are our only guests on the boat and he only money you'll spend after reaching the boat is if you go ashore for tours, sightseeing or mementos. All meals and drinks are pre-planned and prepared on-board according to your tastes. You fill out a "likes and dislikes" questionnaire ahead of time and we'll stock the boat with all your favorites. 
Multi-day custom charters are limited to a single couple. Second Wind is a two cabin boat with one at each end of the vessel (forward and aft-cabin layout). The crew will be sleeping in the bow while our guests enjoy their own private aft-cabin with queen-sized bed, private head and private stand-up shower. (See our 
Day 1 - Fly into Albany airport (ALB) or take the train to the Hudson Amtrak station. We'll help you arrange for your last easy leg to the boat then settle into your own private cabin with separate head and shower. Once you are comfortable, we'll depart Catskill and sail south along the river following the beautiful Catskill Mountains to Hyde Park, NY. We'll stay in Hyde Park for the day where you can go ashore for a great tour of the Vanderbilt Mansion.
Day 4 - We'll sail under the Tappan Zee Bridge with the skyline of New York City spreading out ahead of us. Maybe we'll take a short sail into New York Harbor to view the Statue of Liberty before we tie up at the 79th Street Marina in Manhattan for a great ending to a beautiful trip. After (usually tearful) goodbyes, you'll take a short cab ride to Penn Station where you board Amtrak for a much quicker trip back to your car in Hudson. Easy transportation is also available to the New York airports.