Recommended by NYC’s Original City Guide!  Click here to read more. 

All aboard!! Witness the splendor of Manhattan—its twinkling soaring skyline, iconic waterside landmarks, and color drenched sunsets from aboard the deck of a schooner. This evening sail is enjoyed from the deck of the 80-foot Adirondack, which departs from Chelsea Piers. Other sails are also available at different times. Chelsea Piers, Pier 62 and West Side Highway (around 23rd St.), 212-627-1825, sail-nyc.com/browse-by-boat/schooner-adirondack

Classic Harbor Line launches scenic dining cruises to and from Dutchess County

August 21, September 11 and October 2, New York City and Poughkeepsie 

New York City and Poughkeepsie, NY… Classic Harbor Line launches a new series of cruises this summer and fall 2016 that explore the picturesque Hudson River Valley!  The dates for each one-way passage between Manhattan and Poughkeepsie have been hand-picked to feature Dutchess County events and activities and attractions for fun in Dutchess County, as well as, detailed information on return travel. Each passage will include a 4-course dining experience aboard the 1920s inspired yacht, Manhattan, as guests cruise on the majestic Hudson River!

The NYC to Poughkeepsie Hudson Valley Brunch Cruise will run on Sundays, August 21, September 11 and October 2, 8:30 AM – 12:30 PM, departing from Chelsea Piers, Pier 62 in Manhattan.

The Poughkeepsie to NYC Hudson Valley Dinner Cruise will run on Sundays, August 21, September 11 and October 2, 4:00-8:30 PM, departing from 1 Main Street in Poughkeepsie, Waryas Park (floating dock next to the Poughkeepsie Ice House)

Tickets for each leg are $144. Book here.

• Sunday, August 21: Jazz in the Valley at Waryas Park | NORTH BOUND LEG | Enjoy a relaxing 4-course brunch cruise up the Hudson River and a live jazz music event at the Poughkeepsie waterfront park; special discounted jazz tickets with reserved seating are available for purchase with cruise tickets.

• Sunday, August 21: SOUTH BOUND LEG | Take a train to Poughkeepsie to enjoy Jazz in the Valley (special discounted reserved seating tickets for purchase with dinner cruise) and waterfront attractions or arrive by10:44AM to meet the Roosevelt Ride for complimentary shuttle service to visit FDR Presidential Home, Library & Museum and Eleanor Roosevelt’s Val-Kill in Historic Hyde Park! Advance shuttle reservations required. Then board the Manhattan at 4:00PM in Waryas Park for a dinner cruise to NYC.

• Sunday, September 11: Hudson Valley Wine & Food Festival | Enjoy a special admission to this annual affair at the Dutchess County Fairgrounds in Rhinebeck, NY. Arrive by boat in Poughkeepsie then take Amtrak to Rhinecliff and a short cab ride to event.

• Sunday, September 11: SOUTH BOUND LEG | Take Amtrak to Rhinecliff and a short cab ride to enjoy a day at the Hudson Valley Wine & Food Fest or a take a train to Poughkeepsie for waterfront attraction; arrive by10:44AM to meet the Roosevelt Ride for complimentary shuttle service to visit FDR Presidential Home, Library & Museum and Eleanor Roosevelt’s Val-Kill in Historic Hyde Park! Advance shuttle reservations required. Then board the Manhattan at 4:00PM in Waryas Park for a dinner cruise to NYC. 

• Sunday, October 2: Sip & Sweet Farm & Wine Tour | NORTH BOUND LEG: A complimentary shuttle will meet you at the Poughkeepsie dock upon arrival and take you on a Dutchess County culinary adventure. 1:45PM to 6:30PM. The route includes a visit to Crown Maple at Madava Farms and Millbrook Vineyards & Winery (Additional fees apply for optional tour and tasting at each site).

• Sunday, October 2: SOUTH BOUND LEG: Take a train to Poughkeepsie and arrive by10:44AM to meet the Roosevelt Ride for complimentary shuttle service to visit FDR Presidential Home, Library & Museum and Eleanor Roosevelt’s Val-Kill in Historic Hyde Park! Advance shuttle reservations required.

Poughkeepsie waterfront attractions, walkable from the dock include:

Walkway Over the Hudson – Visit the world’s longest elevated pedestrian bridge at 212’ feet over water and 1.28 miles across. Take a five-minute stroll along the Hudson River to Upper Landing Park and ride the glass-enclosed elevator to unprecedented views of the Hudson Valley.

Bridge Music – Notable composer Joseph Bertolozzi rigged the historic Mid-Hudson Bridge with microphones to record sounds for his full compositions. Listening stations on the bridge invite visitors to hear his creations while standing above water and enjoying the nearby views of the Walkway.

Walkway Loop – The loop allows visitors to hike or bike across the Mid-Hudson Bridge to paths on the
river’s west bank, across the Walkway Over the Hudson, and back to Poughkeepsie waterfront; maps available.

Rent a Bike – Leisure Bike Rentals ($8 per hour or $35 per day plus $3 per person for insurance/ helmets included). Enjoy riding over 18 miles of uninterrupted trails on the Dutchess County Rail Trail which includes the Walkway Over the Hudson. Advance Reservations required. Your bike and helmet will be delivered dock side.

Hudson River dining: 

Poughkeepsie Ice House – Enjoy dining inside or al fresco dockside on the Hudson River. River Station – Enjoy dining inside or al fresco with views of the Hudson River. Amici’s – Enjoy Italian dining near the Hudson River.
Mahoney’s Irish Steakhouse & Pub – Enjoy American and Irish fare near the Hudson River.
Shadows on the Hudson – Enjoy dining inside or al fresco overlooking the Hudson; only .7 miles/15 min. walk from dock.

Book an overnight stay in Dutchess County! Email [email protected] to learn about special hotel rates.

Classic Harbor Line will be offering “Educational Sailing Cruises”  every afternoon at 3:30PM on sailing cruises on the Schooners through the end of September.  Speak up (Teens) and get the opportunity to raise the sails and take the helm of the steering wheel! Learn the basics of sailing as you are gliding by the Statue of Liberty. 

Use online promo code: SAIL10 and receive $10 off your tickets. 

Are you doing a staycation for Labor Day weekend?  Join us on a number of different cruises this weekend to enjoy your city from the water.  Brunch on a yacht, or sail on a 105 foot schooner.  Grab your out of town guests for an AIANY Around Manhattan Architecture Tour, or get away for a full day and cruise up the Hudson River to Bear Mountain.  Which ever cruise you choose you are sure to take it all in and relax on this Holiday weekend.  

Click here for a NYC Sailing

Click here for the Best NYC Brunch 

Click here for AIANY Architecture 

Click here for our Full Day to Bear Mountain

See what New Yorkers want to do before the end of the summer in NYC! 

Click here to read more about what Ric Addison the CEO from Addison Hospitality Management Group has to say.