This is a wonderful chance to bond with your father and spend precious time together. If you both stay safe this could be an adventure you both cherish the rest of your lives. No doubt you will have setbacks -- cruising has been referred to as "fixing
boats in exotic places" and sailing has been described as "throwing
money into the sea while being splashed by cold water".
Others have all given good
advice about being good crew, but the following info will help you have a more pleasant experience. Maybe you will want to direct your dad to this thread too, so he can comment on any advice you receive:
Do not dress like you would on land in similar
forecast temperatures: It's much colder on the
water. In April you will need warm
winter clothes in
New England especially at night (temps will likely be in the 40-60 range) and you really should have a
cabin heater. Since that boat probably doesn't, and you'll probably only need it for the trip I would suggest an inexpensive catalytic
propane camp
heater such as a Coleman Black Cat. Bring winter clothes such as insulated ski pants and waterproof gloves, and ski goggles because a constant damp
wind even with temps in the 40's will penetrate your clothes and make your eyes pool with
water, and goggles will help vision immensely. The water temps will be cold (40's and low 50's) so it will be life threatening if anyone goes
overboard, and you'll lose your strength quickly -- any ability for self-help will be
lost in minutes. I strongly recommend you rig jack-lines and harnesses and both use them even in calm
weather especially if leaving the
cockpit underway or at night.
Putting aside the
weather (which might be warm if you luck out), the boat your father bought is great for coastal bays and fairly calm water, but is not designed for heavy
offshore conditions. I would recommend you watch the forecasts carefully (there are lots of great weather sites if you have a smart phone) and don't chance getting caught out in storm conditions. On the Atlantic coast you have many sheltered routes to take but there are times when you must go outside (such as the NJ shore) so avoid conditions with easterly winds. Winds from the NE and SE will typically only last a few days at a time but you should wait them out when you need to be on the Atlantic because they produce rough conditions and make harbor entrances dangerous, in many cases. You should find things to do and wait it out if necessary. DON'T LET YOUR SCHEDULE FORCE A DECISION TO GO OUT IN RISKY CONDITIONS.
Since it will be a new boat for both of you, your dad should go over all the mechanicals and
rigging with a
surveyor and make any needed
repairs (if he hasn't already), and a sea trial is a must. If you stay in
Long Island Sound the first leg of your trip to
NYC will likely provide adequate shake-down to find where the gremlins are and there are plenty of full-service
marinas along the way if you need
repairs or upgrades. The trip through New York's Hell Gate should be started at slack water, at the start of the ebb tide, and you can ride a fair
current all the way down through the East River (it's breathtaking to motor-sail right next to the
NYC skyline and it goes too fast) past the Statue of Liberty and out into the Atlantic. If the
wind is from the S or E you should put-in and wait behind Liberty Island or Staten Island to avoid the wind-against-current conditions -- otherwise your next stop is Atlantic Highlands, NJ where you will wait if need be for good weather to go down the NJ coast (1-2 days). You will want to time your trip up Delaware Bay so that you don't have wind-against-current conditions. Then into the Chesapeake down to the
ICW.
I would recommend you or your dad pick up copies of the Map-Tech cruising Guide to
Long Island Sound, and another to cover NJ to the Chesapeake. There are other guides for the
ICW and you should also reference
http://www.activecaptain.com