Taking the plunge

[CalebD]

Tempest - Good point about the sailing clubs that exist in NY Harbor or on the Hudson.
This one is probably the least expensive. They sail Solings out of Weehawken: SailNY - New York City's Community Sailing Association
This one is on the west side of Manhattan. They have J 24's: New York City Sailing, Manhattan Sailing, NYC Sailing Lessons
There are other options, including rentals farther afield in City Island, Stamford, Oyster Bay etc.

[BarryL]

Hey,

If you want to spend 2-3 nights on board, have something that sails reasonably well, and has some creature comforts (pressure hot and cold water, enough batteries to run lights for a few days, maybe a shower on board) I would look for a boat around 28'

Some good options are Catalina 27. Tartan 27, O'day 28. Newport 28, Pearson 30 (the P30 is a great sailing small 30), etc.

Good luck,
Barry

[AndreasNYC]

Thank you for all your kind advice.
I will look through all the suggestions and come up with more questions if I need to.

[bljones]

Some good advice so far. Here's my take as well.
Want a salty boat that chicks dig?
Folkboat
Stonehorse 23

Want a class racer?
J 24

Want a weekender?
Seaward 25

All are available below your budget.

[AndreasNYC]

OK so what is the oldest boat I should consider?
Does it matter? does fiber glass eventually go back.
How old is too old for the Hull?

A

[AndreasNYC]

Also should I look for something with a spinnaker or is that something that can be added later easily?
Are they too dangerous for a beginner?

[PaulinVictoria]

Spend $5k, have a laugh and then see where you end up in a couple of years. I can recommend the C&C24, fast, fun, plenty of space below
Gives you a bigger boat feel without the expense.

[AndreasNYC]

http://www.yachtworld.com/core/listi...g_id=1508&url=

what do people think of this boat?

[TQA]

Originally Posted by AndreasNYC

http://www.yachtworld.com/core/listi...g_id=1508&url=

what do people think of this boat?

Not a bad looking boat on the surface. It is at the top end of your range length wise and the maintenance costs willl be significantly higher as you will need to find a yard to haul and store it for you.

It is likely that you could have just as much fun on a 22 footer like a Caatalina 22 take it home on a trailor and store it in your yard during winter.

The smaller boat/sails/anchor/ would be easier to muscle around when things go wrong. But on the bigger boat things will happen slightly more slowly and the platform will be steadier esp when you are on the foredeck.

The learning curve will be about the same on both boats.

[AndreasNYC]

I don't have a back yard I am afraid so it will have to be stored one way or another
I guess I could suspend it from the side of my Manhattan building and claim it was a giant window box