sightseecrets October 3, 2019

Tribeca Sailing Package

Sight Seecrets Exclusive: Private Island Escape

Couple’s Two-Hour Private Oh!asis Sail

(New York City)

Let’s get Nauti-cal—

Big lights. Big city. Big romance. How can extraordinary 360-degree Manhattan Island views not inspire Big Bear Hugs? Leave the Big crowd behind, as you and your honey sail away inside the privacy of your own boat while enjoying sun-and-salty sea kisses and your very own gourmet bite of the Big Apple.

Hot summers or cool seasons, Sight Seecrets Exclusive: Private Island Escape

—Couple’s Private Oh!asis Sail heats up any relationship. Experience the ultimate romantic adventure with Tribeca Sailing. Surprise wedding proposal, anniversary gift, mini-moon or just-because-I-love-you-to-the-max occasion, pen the next chapters of your love story aboard Tara, a U.S.A. built 1964 Hinckley Custom Pilot 35 sailboat designed by the famous Sparkman and Stephens design team.

Out of the 117 Pilot 35’s built, you sail on the 25th that rolled out of the Hinckley Company Maine facility. Sailing Tara is not only distinct and stylish, but super comfortable since she glides through New York Harbor like an Olympian. Sudden inclement weather? No worries, nestle together inside her lovely varnished wood interior.

Plus, whether you tour with Captain David, Captain Sam, Captain John or Captain John D., you are ensured of a safe, relaxing journey the minute you leave the North Cove Marina. True New Yorkers, they share city secrets that even take locals by surprise.

The city dresses to impress, especially when observed from the water, and there is no ending to her mystic, history, charm or personality. Secrets shared and spectacular sites include the Freedom Tower, Battery Park, Governors Island, historic Jersey Central Railroad, Ellis Island. Float into a New York state of mind with up-close and personal views of the Statue of Liberty, not to mention a stardust-inspiring view of Lower Manhattan and the Brooklyn Bridge.

As if you aren’t awestruck enough, a gourmet picnic meal crafted by one of the finest caterers in the city tops off a Big Day in the Big City meant to create Big Times and Big Memories that sail into a couple’s future forever.

Sight Seecrets Exclusive: Private Island Escape

Couple’s Two-Hour Private Oh!asis Sail

101 (For a complete list of common questions and additional information,

  1. Psych yourself up for a fab boat ride. Whether this is your first time on a boat or umpteenth time, this is a unique experience that is meant to bring a special kind of closeness to your partner that is unattainable in routine daily life. Novel experiences, in general, uncover intimate, secret saucy sides to your partner–and to yourself–allow and enjoy it!
  2. What should I wear and pack? Sailing during the spring and fall, it is best to dress in layers. It can be cooler at sea than on land so it is advised to bring a jacket or sweatshirt. In the summer months this is not necessary. At a minimum you should bring a hat, sunglasses and sunscreen. Spray jackets are provided, if the weather turns or you need an extra layer.

Soft soled shoes such as boat shoes or sneakers are preferred footwear. Flip flops, open toes, hard soles and high heels are not recommended. If you wear hard soled shoes or high heals you will be asked to go barefoot for safety reasons. 

  • What do I do with my personal items? Any bags, backpacks or personal items can be stowed inside the cabin. Computers and delicate electronics should not be brought on board. Tribeca Sailing or affiliates cannot assume responsibility for personal items stowed inside the cabin or anywhere on the vessel. You bring personal items onto the vessel at your own risk. Tribeca Sailing or affiliates are also not responsible for items that fall overboard.
  • Who is Captain David Caporale? He is the operator/owner of Tribeca Sailing, and a licensed USCG captain with a spotless safety record. He is responsible for all aspects of providing the excellent service to his customers and partners. He is the single contact for Tribeca Sailing.
  • Can I steer or help sail the boat? Can you teach me how to sail? ABSOLUTELY!  If the weather conditions permit you may take the wheel, help with sail controls as much as you like.  The captain prides himself on helping people understand how a sailboat works and can offer any level of training you desire.
  • Can I play my own music on board? Tara has a Bluetooth speaker for you to connect to your phone so you can play any music of your choice during your private sail.
  • Are there bathroom facilities? There is a public restroom inside Brookfield Place.  Tara has a bathroom for limited use.
  • Do you offer 2-hour Sunset/City Lights cruises? You bet. The demand is high; advance reservations are mandatory.
  • Can you help me stage a picture-perfect marriage proposal? Of course! Drop us a line, and we will assist to make it an extraordinary day trip to remember for a lifetime.

Sight Seecrets Exclusive: Private Island Escape

Couple’s Two-Hour Private Oh!asis Sail


  1. Sailing Season is April through November, seven days a week.
  2. Departure: North Cove Marina, 225 Liberty Street, Brookfield Place, New York, NY 10281

  3. North Cove Marina is located in Battery Park City on the corner of Liberty Street and South End Avenue. 
  • Cruise Duration: 2 hours
  • What about inclement weather conditions? What happens if there is a threat of rain? Our goal is to keep passengers safe. Mother Nature can be tricky and weather conditions are variable. Unless extremely adverse weather conditions prevent us from leaving the dock for safety reasons, we will sail in the rain, heat, cold, humidity, etc. Every effort will be made to contact you two hours prior to your sail as we have updated information regarding any extremely adverse weather conditions. However, this is not always possible and may result in a last minute cancellation of your sail, even after you have arrived at the dock. On the day of your sail, if you have any questions regarding the weather, please do not hesitate to call. Please note that long-term forecasts are incorrect 99% of the time. Only the captain of the vessel will be able to cancel a sail.
  • What are your Cancellation Policies? 15 days prior to sail booked: You may cancel and receive a refund minus a 15% service fee.

Within 5 to 15 days of sail booked: You can reschedule your sail up to October 31st of the next years sailing season and no refund will be made available.

Within 5 days of sail booked: No re-booking and no refund.

Please arrive 15 minutes early as we will set sail five minutes past your scheduled sailing time. If you do not arrive by five minutes past your scheduled departure (even by one minute) no refund will be made available. This policy is designed to make sure everyone gets their proper sailing time as with a tight schedule we cannot delay our departure.

If you cannot make your sail for any reason, for example, illness, lost luggage, traffic, delayed subway’s, etc. you will be able to join any public non-private sail that has seats available within two hours of that sail as long as there is already a booking.  For example, if the 6pm sail already has two people booked you may request to join that sail after 4pm. This offer is valid for the same year of your originally booked sail and will expire on October 31st of that same year.

Please refer to Terms, Conditions, Weather and Cancellation Policy below for more details.

  • Terms, Conditions, Weather and Cancellation Policy
  • Tribeca Sailing NYC reserves the right to cancel any sail due to adverse weather conditions. Adverse conditions include but are not limited to  excessive winds, thunder and lightning storms and other extreme conditions. We will make every attempt to notify you two hours prior to your sail if there will be a cancellation. There may be times when we are not able to contact you with two hours notice. Only the captain of the vessel can cancel a sail due to weather conditions.
  • If Tribeca Sailing NYC cancels your sail due to adverse weather conditions you will receive an email voucher valid until October 31st of the following sailing season. If your entire party has arrived in New York by airline and cannot book another sail during your stay we will make exceptions to our cancellation policy and offer you a full refund minus a 15% service fee.
  • Please note that sailing will occur during the following conditions: Light rain, cloudy skies, cold or hot temperatures and humid conditions..
  • Re-booked sails are not able to be changed or canceled. Re-booked sails are for equal or lesser value sails booked. You may upgrade with an additional charge to any sail of more value. Re-booked sail of lesser value will not receive a refund but you will receive a credit for another sail valid until the end of the following sailing season.
  • Tribeca Sailing NYC or You S.A. LLC cannot be responsible for last-minute mechanical failures. If you sail is cancelled for mechanical reason you will receive a full refund.
  • Length of time for each sail is flexible in nature due to tides, winds and other weather conditions. Sailing NYC or You S.A. LLC cannot be held responsible for sails that end earlier or later than scheduled. There are no full or partial refunds for sails ending prior to the scheduled arrival time.
  • Safety is our priority. Tribeca Sailing NYC and You S.A. LLC strongly recommend that each passenger wear a USCG approved Life Jacket. (New York State law requires persons under the age of 13 must wear a Life Jacket. Parents or guardians are responsible for determining if a minor ages 13-17 must wear a Life Jacket.) Adults 18 years old and up have the sole responsibility to decide if they wish or wish not to wear a Life Jacket.If you wish to wear a Life Jacket, one will be made available. The person booking the sail is required to inform everyone in their party about our life vest policy prior to boarding.
  • Sight Seecrets Exclusive Packages are designed for adults 21 and over
  • All passengers, parents or guardians are required to sign a release form. No passenger will be allowed go sailing without signing the release form. Refusal to sign a release form will not result in a refund.
  • Tribeca Sailing NYC will not sail with just one person signed up for a specific time slot without obtaining approval prior to making a reservation.
  • Gift Certificates are non-refundable.
  • Gift Certificates are valid until the end of the following sailing season regardless of the time stamp on certificate. For example if purchased May of 2018, the certificate is valid until the October 31st of the 2019 sailing season. All gift certificates have a face value and may require additional payment if set prices are increased.
  • Privacy Policy and Personal Information: During registration on this website, we may collect personal contact and/or transaction related information for Tribeca Sailing NYC and/or You S.A. LLC use only. We may also collect certain website usage data. We will not sell, share, or otherwise distribute this information to any third party without your consent and knowledge.
  • What if I am running late will the boat wait for me?

Please arrive 15 minutes early as we will set sail five minutes past your scheduled sailing time. If you do not arrive by five minutes past your scheduled departure (even by one minute) no refund will be made available. This policy is designed to make sure everyone gets their proper sailing time as with a tight schedule we cannot delay our departure. If you are running late for a private sail, no worries as we can leave when you arrive. We will have to conclude our sail at the normal finishing time.

If you are running late, please call 917-593-2281 ASAP.

  • May we tip our guide? Tipping is optional and graciously accepted but never expected.
Text Box: Over 155 proposals aboard Tara--AND COUNTING!!!
Hint! Hint! Hint!

Sight Seecrets Exclusive: Private Island Escape

Couple’s Two-Hour Private Oh!asis Sail

The Secret Life of Captain David Caporale

What would you say is one of the most romantic sights during the duration of the New York Harbor cruise?

There is nothing like being directly underneath the Statue of Liberty especially at sunset. The view back of lower Manhattan is truly one of the most beautiful sights in the world.

Okay, Captain, we’re dying to ask this, if you don’t mind! You spend a lot of time on the water. What do you like to do on land?

Eat good food at great restaurants!

Tara is a popular sailboat for couples. Can you give us one or more examples of some of your most memorable excursions sailing with couples?

With over 155 proposals aboard Tara, I like to ask how couples meet. One couple met on a bus in London but never had the guts to go out for a coffee. Two years later they met in NYC by accident when she showed up at his office looking for a job. They were celebrating their 11 year anniversary aboard Tara!

Are there any particular kinds of couples that you like to spend time with on the water?

Happy ones!

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