Available: Winter Season

Sail a cruising yacht in the Florida Keys for one week this winter. Located in Key West with easy and affordable access to Miami and Ft. Lauderdale Airports by rental car.
The yacht has 3 separate cabins and comfortable accommodations for up to 7 people. Boats are easy to sail with roller furling jib and reefing mainsail.
Sail the beautiful turquoise waters with steady winds behind the Florida Keys protected from the Atlantic swells to Marathon Keys and back or Dry Tortuga. The ultimate tropical climate is awaiting you as winter is setting into force across the country.

USCG licensed Captain on board so you can relax and not worry about where to go safely.
Sailing instructions are also available if you wish to incorporate class certifications into the trip.
This is a great way to get valuable hands on experience and enjoy cruising on a sailing yacht all in one.

Yachts:
Beneteau Oceanis 390
Columbia 45 ketch

Cost:
$1000 per person plus expenses and travel
$1500 per cabin 2 persons plus expenses and travel
Passport Sailing Club Members $500 per person plus expenses and travel
Passport Sailing Club Members $750 per cabin 2 persons plus expenses and travel

Course Options: When added to a Sailing Vacation.
Please call 914-235-6052

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Marathon Key/Key West Vacation

Here is a typical sail plan for our five days in paradise:

Day 0: Meet at Boot Key Harbor, Marathon Key and settle in onboard our new home, Cuki, a Colombia 45 foot ketch. Marathon Key is located half way down the Florida Keys, 90 miles south of Miami. It can be reached by private or rental car, or by flying into Miami (MIA) or Fort Lauderdale (FLL) airports and taking a reasonably priced shuttle to Marathon Key.

Day I: In the morning we leave our mooring at Boot Key Harbor, Marathon Key and head west through the mooring field, request an opening of the Boot Key Drawbridge and sail southward into the clear blue waters of the Keys. We will likely encounter the most pleasant of sailing conditions: temp. 73 degrees F, and about 10 knots of favorable wind with one-foot seas. We sail parallel to the keys and easily reach our planned destination, New Found Harbor, well before sunset. We cautiously ease our way up the narrow channel and successfully set the anchor, leaving us plenty of time for a sailing review, our d’oeuvres and a dinner on board.

Day II: There is no rush. We enjoy morning coffee, plan the day and get underway about 10 am. We thread our way down the narrow channel, and set sails in Hawk Channel. We see several other sailboats ahead, and once we assess that they are on the same course, following them simplifies our navigation and steering. We alternately sail and motor to enjoy the peace of a motorless world but also to insure our arrival in Key West before sunset. We drop the hook off Wisteria Island, with the town of Key West immediately across the channel. After a little coaxing the anchor holds, and we turn our attention to a toast a glass of wine and our first Key West sunset. After sunset we take “Magic Penny” water taxi to town and enjoy dining and absorbing the Key West nightlife.

Day III: From our first moments of consciousness we know it’s going to be another day in paradise. We have the whole day to visit Key West. Following our morning ritual of fresh coffee and a swim, the Magic Penny water taxi arrives to take us to shore. Our choices for this day are many more than we can fit in. We may begin at the local Internet café, or walk along Duval Street and the myriad of side streets gawking or photographing the sights that uniquely color this town. We can rent a moped or electric vehicle, or visit the southernmost point in the U.S. or go to the beach. We can go parasailing or SCUBA diving, take a tour of Hemingway’s home, or enjoy the many tiki bars and fine dining. Key West is truly a playland with something for everyone.

Day IV: We shake off the previous evening, sip our morning coffee, and then weigh anchor for our return trip. Often at this time of year winds are from the north and we can have a moderately rough ride returning to Marathon. However sometimes the wind gods smile upon us and the they blow from the west. We round Key West point and turn to a course of 70 degrees magnetic -- which we pretty much kept to all day. That afternoon we select New Found harbor or another safe harbor along our route, and again enjoy the evening with nature’s show and a “home-cooked” dinner while gently swinging from the hook (and perhaps a movie on DVD).

Day V: The rhythms of our sailing life come easily as we continue our sailing journey to Marathon. We motor or sail, depending upon the conditions, and reach Boot Key Harbor in the early afternoon, replenish the 100 gallons of water we’ve depleted, pass through Boot Key Draw bridge and hook onto our home mooring. We enjoy cocktail hour and the sunset. Then we take the dinghy to town for dinner and the evening’s entertainment at the local tikibar. It’s our final night together, and we sense we have both lived “Margaritaville” and returned an accomplished sailor.

What you may expect from this vacation:
This kind of trip is not for everyone. Those who think that the perfect vacation equates with being a pampered lounge potato might look elsewhere. Those who are desirous of a vigorous adventure beyond words and expectations this is an excellent choice.

Sailing knowledge and skill development: You will have an experienced U.S. Coast Guard licensed captain on board to help you hone theoretical knowledge and practical sailing skills. Whether your next area of interest is the art of boat handling, seamanship, navigation, sail trim specifics or docking and anchoring our accelerated instruction starts by meeting you exactly where you are at and raising your skills to the next level. During the five day/night voyage you will have the flexibility to learn and practice as much or little as you desire.

ASA Certification (option): NYSS encourages each member to increase their knowledge and skills by attaining the ASA certifications. If your next sailing goal is to become certified in the ASA Basic Coastal Cruising (103), or Bareboat Chartering – intermediate coastal cruising (104) this is a way to combine a great vacation and return home prepared to take the written exam for certification.

Note: This option includes the Key West sailing/instruction vacation, and all necessary class-room preparation and practice on shipboard. To complete the certification process students are required to attend a subsequent one-day review and written exam at NYSS in New Rochelle.

Much more than just sailing: This trip offers so much more than sailing skill-building. Yes, it promises to advance your sailing competence and confidence but beyond that, it delivers exciting new experiences and lasting vivid memories of an enriched life. For us at NYSS, sailing is a powerful metaphor for life! On this vacation you may find yourself regaining a balance of activity and reflection. You may come away with a new appreciation for life at 6 knots or for the real meaning of “safe harbor”. You will also have plenty of opportunities to know the flavor of Key West – be it at Hemmingway’s home or at Sloppy Joes bar. You may stare in silent awe at sunsets you have not noticed before, and be reminded that living close to nature is also living close to your soul.

Text by Capt. Howard Edson