Picking the brain of seasoned sailors

[GavinGonsalves]

Good day all,
I seeking some advice from some seasoned sailors, but first some background on myself. I am a union carpenter (relevancy: work that may have to be done to a boat), I am based in Ottawa Canada and I would like to sail from Canada to Trinidad & Tobago late this fall early winter, I would like to add this will be my first solo journey. My plan is to follow the coast of the US then cross over to the Bahamas and island hop to Trinidad. I anticipate the trip will take around 2 months +, in the process starting a youtube channel to document the journey. Now on to the picking of seasoned sailors brains.
I am currently looking for boats under 30 feet, and I am wondering the following;
1. Any advice on a boat I should be looking at?
2. Is $6000-$7000 too small of a budget for an under 30 foot boat?
3. Is comfort ratio, etc relevant?
4. Any advice regarding a cost I should be skeptical of, although I know I may have to install certain things like AIS, auto pilot etc?
5. Any advice of places to visit along the way as I have never made this journey?
6. Any advice for a first time solo sailor?

I apologize in advance if this thread or questions seem mundane. I welcome any feedback and thank you all for your time.

Gavin

[carstenb]

Originally Posted by GavinGonsalves

Good day all,
I seeking some advice from some seasoned sailors, but first some background on myself. I am a union carpenter (relevancy: work that may have to be done to a boat), I am based in Ottawa Canada and I would like to sail from Canada to Trinidad & Tobago late this fall early winter, I would like to add this will be my first solo journey. My plan is to follow the coast of the US then cross over to the Bahamas and island hop to Trinidad. I anticipate the trip will take around 2 months +, in the process starting a youtube channel to document the journey. Now on to the picking of seasoned sailors brains.
I am currently looking for boats under 30 feet, and I am wondering the following;
1. Any advice on a boat I should be looking at?Under 30 feet is a very small boat. It will be cramped, but the trip is doable

2. Is $6000-$7000 too small of a budget for an under 30 foot boat?I suspect you will end up having to pay more for a well-founded boat. But sometimes bargins do exist

3. Is comfort ratio, etc relevant?yes

4. Any advice regarding a cost I should be skeptical of, although I know I may have to install certain things like AIS, auto pilot etc?any boat you buy in that cost range will need a number of upgrades, sails, engine, electronics. Could be very costly, make sure you survey the boat/engine completely before buying
5. Any advice of places to visit along the way as I have never made this journey?Late fall early winter is a horrible time for the journey. If you try to go outside, then you will be battling the Gulf Stream the entire way. Not a good idea. Instead, jump into the ICW and run that all the way to florida then cross to the Bahamas. South of the Bahamas you will run into the Christmas winds, which will mean running close hauled against 25-30 knot winds and 2-3 meter high swells for something like 7-10 days.
That is tough work and since you intend to be solo, you have to consider if you are competent to do this. This is not an easy trip. I've done it in a 40 footer, double-handed and while we made it, we were not happy campers. From the Turks and Caicos, you will basically be off-shore - no bail-out.
When we did it we ran into really heavy weather, 40+knots, 4meter (14 feet) swells with a short period. you will also.
6. Any advice for a first time solo sailor?Look to see if you can find a boat for sale in the Caribbean instead of making the trip from Canada

I apologize in advance if this thread or questions seem mundane. I welcome any feedback and thank you all for your time.

Gavin

Gavin - if I sound negative it is because you need to investigate a lot of things before you attempt this. You don't tell how much sailing experience you have, just that this is your first solo. Do you truly understand the weather patterns you will be sailing into? While going outside coming down the east coast of the US is doable, there are many issues involved (not the least of which is Cape Hatteras).

But if you decide to try - good luck

[Hudson Force]

I believe you can have a wonderful and successful adventure if you dismiss the requirement of having any expectation of a cost, time schedule or destination.