One day while going for a jog along the banks of the Hudson River in Palisades Interstate Park I see this beautiful blue hulled sailboat anchored in front of Edgewater Colony. I didn't take any pictures or study it well but it had to be at lest 35'. Might have had 2 masts. Was there a few days and later I saw it sailing north. It reignited my dream of getting a sailboat.
For a couple of weeks now I've been giving it some thought and doing some research and hoping that next season I might start sailing in some fashion. But I have a lot of questions I was hoping people in the area might be able to answer. Also some general questions regarding boats too look into.
Cliff Notes Err... this got to be longer than I realized. Looking for advice on boats for the area and advice on destinations and time to get there for day, weekend, extended local trips. If you sail in the area please let me know what type of boat you have, and what are some of the benefits of it and limitations for these waterways

So far thinking about something in the 25-30' range with less than 4' draft.
I've had friends and family with power boats but they've always been outside the city. Either down the shore or on the Long Island Sound. Living in the NYC area makes any decent place to go for a swim a bit of a trek.
If you're on the Hudson River, please tell me some local sails you take, especially overnight/long weekend cruise destinations. Ones where you can go for a nice swim would be helpful. I can google beaches and marinas, what I'm looking for is some real world trips people have taken with details like the make/model of boat, marina they left from, where they sailed to, where docked, anchored, etc, how long it took, any tide/wind considerations they had to make for their trip. Don't need specifics like all the way points and exact times but something to give me an idea.
I'm familiar with some marinas and destinations in the area and have been using Google Earth to explore a few nights this past week but since I've never been on a long trip on a sailboat or
I plan on taking an ASA course or two and likely charter a few times before buying. Any sailing school recommendations would be good. The club in Croton really has me interested as they have 24' Rainbows and 26' Pearsons available for members.
I can't stop looking at boats and trying to learn more about them and trying to understand my needs.
My sailing experience is very limited to a bit of dinghy sailing on a lake many years ago. (Hence the ASA course plan). Though I've never owned a boat I've spent some time on power boats, helping to maintain sometimes, learning about boat safety, rules of the road, etc. Spent some overnights.
Boat Requirements:
Hopefully some people can give me some recommendations on models that might fit my needs in this location. I've been looking at a lot of different models online. Hoping to help narrow down what I'm looking for.
I've been trying to come up with requirements for what I would need for a boat. Would like to hear advice from anyone that sails in the area regularly as to what features, specs are important for sailing the around Manhattan, up the Hudson, Down the Shore and on the LI Sound. MAYBE even down the coast to Florida every couple of years or so. And how my requirements below will handle the conditions in the area. Or if I have any misinformed expectations.
I'd be looking for something fairly small and used. Don't mind doing a lot of cleaning, sanding, varnishing, painting, some electrical, upgrading cusions, etc, but hoping to find something that can sail and power. I'm pretty handy and have a few tools and like to learn how to fix things but want something I can sail right away and improve as I go. Seeing lots of boats well bellow $10k with this economy and time of year and hoping to find something in the $5k area if possible. Don't mind old.
I don't have room for a trailer at home so would need to rent a slip. Prefer the NJ side. Closest places to me in Englewood Cliffs and Edgewater don't permit sailboats so it looks like Weehawken, Hoboken, Jersey City or possibly Alpine if I can get a shallow draft boat. I was hoping to find something closer to the George Washington Bridge but that doesn't seem possible and may change my plans.
Size
Looking in around the 25-30' range. This seems to be about a minimum range to meet my requirements. Looked at some 22 footers that seemed nice but lack an enclosed head which I would really like to have.
I think I'd feel a little safer on something a little bigger. Was thinking about building a PocketShip at one point but it seems very small for this area and the cost of building one seems to buy a nice used boat.
What's the minimum size boat I should be looking for based on my needs?
Shallow Draft....
Even if I don't plan on renting a slip at Alpine I'd like to be able to rent a transient there from time to time to access the park. The marina is only about 4' deep so a boat with a swing keel would be nice. There are also some little shallow beaches/landings right off Shore Trail that look like nice spots to anchor near. I don't want to land on the beach but don't want to have to anchor all the way out either.
Would any of the boats the have a shallow draft pose a problem as far as sailing around Manhattan? (Hudson, East Rivers, Hell Gate, etc)
I've read a bit about shallow fin keels, centerboards, swing keels and there pros/cons. Would like to hear some real world advice about sailing around manhattan/shore/sound with these types of boats.
I also don't want a boat that heels excessively.
Speed
I don't need anything that will win a lot of races but is 5.5-6 knots reasonable for these sizes in this area? Can someone give me some real world sailing speeds cruising around here? The theoretical hull speeds of the boats I've looked at seem to be in this range.
Accomodations
I'm just over 6' tall and would like to have at least some spots where I can stand up straight in the cabin as well as being able to fit comfortable in one of the double berths.
Most of the time I'll be sailing alone or with just one person but want the ability to go out with another couple or a group of friends for a weekend trip. Even if it's a little tight. Not looking for hotel style amenities, more like a floating rustic cabin.
Don't plan to live aboard but would like to take overnight and week long trips and possible stay a night or two at the dock for a change of scenery.
Would like to be able to sleep at least 4 adults, 2 double berths would be ideal, but 1 double V Berth and 2 singles is fine.
I really like the configurations that have a double berth under the cockpit.
Would be nice if the V berth was enclosed or at least curtained off.
Ideally 4 people can relax and layout to sun. 2 in the cockpit, 2 on deck. Don't mind if the 2 on deck aren't perfectly flat (won't be in boat sizes I'm looking for) but just that it's somehow possible.
Enclosed Head. I prefer a marine toilet with a holding tank and not just a porta potty.
Shower. Would like to have the option of taking a shower in the cabin even though I won't do it frequently. Just a way to rinse/cool off from time to time. Is there any way to get just a holding tank plumbed in the floor of the enclosed head and use a solar shower? That would be fine for the few times I'd use it since many boats in this range don't seem to have hot water heaters or even pressurized water.
Galley Simple sink and 2 burner stove with ice box is fine. Adding a 12v fridge or cooler would be nice. Don't mind adding another battery and possibly solar panel to keep it cool in a future upgrade.
Dining Would like at least room for 4 in the cabin.
Engine. Prefer inboard diesel but outboard is fine too. Any thoughts on this? Getting an outboard would mean more room inside for a smaller boat and the ability to have the double berth under the cockpit that I like.
Steering. The smaller boats seem to mostly have tiller steering. I understand the benefits of it and have read many threads on the subject. If possible I would prefer to find one with a wheel steering to make it more comfortable for guests in the cockpit. Are wheels on older small boats unreliable/prone to failure?
Boats I've been researching
in the 22-26' range it seems I'd have to make some sacrifices but there are some nice older Catalinas, Hunters, O'Days, Pearson's available that meet most of my needs. Concerned about smaller sized boats as far as speed and safety though.
27' seems to be the sweet spot and I can get most of what I'm looking for. Again mostly the same brands.
30-33'. Maybe a little more size than I want but look like nice boats. Only concern is that boats this big in my price range would need a lot of work.
Catalinas seem to be popular and have decent reviews on here. The layout of the deck makes it seem like at least one or 2 people can lay out on the forward deck.
Hunters seem to have bad reviews but others really like them. Wheel steering is more common on them but the shape of the deck makes it seem like someone can't lay out on the forward deck but maybe on the cabin top? Any experience?
The others brands are fewer and not always available in a shoal draft version which is an important requirement unless someone can convince me it's not really safe for the sailing I want to do.
I've put a lot of thought into this, hoping some of you can fill in the theoretical with the practical.