Sailing Adventures & Charters

In addition to our regular lessons, New Jersey Sailing School also offers opportunities to practice what you were taught. While our rental boats are a good way to practice the basics or just enjoy a day on the water, our Charter adventures are a great way to challenge your sailing. NJSS will be offering regular day sails and flotilla opportunities. We have one day ocean sails, weekend get aways, advanced classes, and one way ocean deliveries.


Click on Adventure for more details

Sunset Sails

Day Sails

Overnight Trips

Flotillas and BVI Trip


Our sailing adventures are limited in the number of passangers due to Coast Guard regulations and boat size. Due to the nature of the adventures, weather and conditions can have a significant effect on the program. Tides and currents are a major factor on our ocean trips and why go for a sunset sail in the rain. Rescheduling is available and our refund policy is more relaxed.


Our Charter Boats


In Brick:

302 Oday

In Highlands:

Beneteau 43.3


Sunset / Pleasure Sails

The boat is yours with one of our polite and experienced Captains. Enjoy the calm waters of the Metedeconk River and our picturesque shoreline or the open waters of Sandy Hook Bay. We sail in the evening and you are welcome to bring your favorite beverage and snack while you either relax with friends or take part in the running of the boat. Book it online and put your dates in the comments section. This is approximately a 3 hour sail. If we get weathered out we can reschedule. 


Day Sails

Set sail for the day or just a few hours (4 Hr Min). Out of our Brick location, we can make our way out to the ocean on a full day charter or just casual sailing on the Metedeconk for half-day sails. Out of our Highlands location, we can explore the open waters of Sandy Hook Bay or make our way up into NY Harbor. The Highlands location is more open water and a real sailing experience.


Overnight Trips

Our overnight adventures can take you up the Sandy Hook Bay or out into the Ocean. Limites are your time! Overnight charters price according to the trip and time. Contact our office to discuss details.


Up Coming Flotilla

Block Island (Labor Day Weekend) out of the Highlands on our 43 foot 3 cabin/head charter boat

Cost and Registration

We will set sail Friday afternoon from the Highlands, cruise off shore through the night to Block Island, arriving Saturday. After spending Saturday and Sunday morning on the Island, we set sail home on Sunday afternoon for Monday arrival home.

When: Friday September 1, 2017 Return Monday Sept 4

(Includes Night sail meals and snacks aboard.)


BVI Flotilla

In April 2018, we will be hosting our annual British Virgin Island ("BVI") Flotilla

Our team of Captains will be flying out of Newark Airport on TBD and returning on TBD. We will be sailing out of Tortola, BVI for an eight-day sailing adventure. The $1,700 cost is per person for a shared berth. This cost covers the vessel’s cruising taxes, captains, vessel insurance, and some pleasant surprises. You will be expected to share in the boat provisioning (est. $150/pp) and day-to-day chores along with the rest of the crew. Airfare is not included in this rate. You must register as soon as possible.  A $700 deposit per person is required to reserve you berth and start the process. DEPOSIT


In addition to the School Boats, individual boats are available for charter if you have the ASA 103 Coastal Cruising certification. The flotilla concept allows you to sail as a skipper in coordination with the lead boat, which will be captained by one of our ASA Instructor/Captains. This is a great way for a novice bare-boater to gain the experience with benefit of our captain's local knowledge. We are with you without being “with you.” The charter company requires a 30% deposit to reserve the boats. Ask for your own boat when booking this option. We will then work with you to select the right boat for the price that works for you. (All Boats MUST be booked through us to join the Flotilla).  


The charter company requires a 30% deposit to reserve the boats. This payment must be in as soon as possible so that we can reserve the desired boats. I was told that the boats were limited due to high volume. Final payment is due in full in February

American Sailing Certifications are also available for Basic Coastal Cruising and Bareboat Chartering for an additional cost of $150 per student. All necessary study material will be supplied. Challenge exams will be available for Basic Sailing and Basic Coastal Cruising for those of you not yet ASA certified. Lecture and course schedules will be blended into your vacation not to interfere with your full enjoyment of the islands and the sailing.

Time is of the essence so do not delay.

Flotilla 2018

Skipper Your Own Boat


For those qualified to bareboat their own vessel, we have the following quotes. (quotes are subject to change as per charter company. 

Mono-Hulls         Catamaran
Boat 38/2/1 Prem 41/3 47/3/3 51/4/4 404 Prem 4
Cabin/Head 2/1 3/3 3/3 4/4 4+2/4
Passengers 4 6 6 8 8
Boat Cost $4,898 $4,893 $6,288 $7,975 $8,825
Damage Waiver 432 472 472 472 472
VISAR Contribution 8 12 12 16 16
Fuel Charge 105 140 140 140 210
Parks Permit 50 70 70 90 90
Cruising Tax 64 96 96 128 128
Flotilla Fee 300 300 400 500 550
Total $5,857 $5,983 $7,478 $9,321 $10,291
Per Passenger $1,464 $997 $1,246 $1,165 $1,286


Boat Floorplans

38 Foot 2 Cabin 1 Head

41 Foot 3 Cabin 2 Head

47 Foot 3 Cabin 3 Head

51 Foot 4 Cabin 4 Head

404 Prem 4 Cabin 2 Head


For more information on New Jersey Sailing School & Charter, please contact us through our website by clicking here, or you can email us at or call us at (732) 295-3450.