Ideas for Caribbean / USA cruising base location?

[Midday Gun]

So I'm sure similar questions have been asked before, so I apologise if I'm treading over already covered ground, but these things change year to year, so I'm making my own thread.

I'm a UK resident, but currently I have a contract working in the north of the USA (Massachusetts) on a 3 week on / 3 week off rotation.
I currently fly back to the UK every 3 weeks. However my company will fly me most places, within reason, and I'm looking into potentially purchasing a boat somewhere in the Caribbean to spend my 3 week off period, I've always wanted to do some warm water cruising, and this seems like a great opportunity.

Ideally I'm looking for ideas for where I can keep a boat on a semi permanent basis, as I'll be a away for 3 weeks at a time, it needs to be relatively secure, and have reasonable transport links so I can get to work and back every 3 weeks.
This would be for around 9 months to a year, with the plan to transition to some longer term cruising after the job finishes.

I'm working, so not on a shoe string budget and I appreciate that finding somewhere secure enough to leave the boat for 3 weeks will cost more, but on the other hand I don't want to pay more than I need to, no need for a marina berth, I'm happy on a swinging mooring etc.

In my head, I'm thinking the Windward islands may be my best bet? Or maybe I'm way off the mark & would be better further North.

I've spent hours reading blogs & articles & feel like I'm going in circles at this point!

[Tin Tin]

See if you can get a mooring in St Francis https://www.saintfrancisresort.com/mooring-info.html


Fly in from Miami to Exumas direct.

[hpeer]

We have settled in Antigua, Jolly Harbor in particular.

My only concern is they are going through a large renovation which aychage the character of the place.

It is British enclave. Decent air connections. Well situated to visit nearby islands in a 3 week period. The harbor is well protected. You could leave you boat on a hefty anchorage system. Moorings and dockage are available. Check with the office about their annual rate with slip and yard included.

[SailingHarmonie]

What kind and what size boat?

Don't try to find the ONE PERFECT place.

That will just lead to analysis paralysis. There are literally hundreds of perfectly acceptable places to do what you want. You can always change your location as you get more experience if your first choice doesn't offer everything you need.

Just some tidbits. Flight connections from the USA to the French islands (Guadalupe, Martinique) are not good. If that is important for you, take them off your list.

In your situation, I would consider the Dutch side of Saint Martin. There are not a lot of marina slips available, but you only need one.

Don't discount Puerto Rico. Lots of quality marina space in Fajardo.

If I needed to have ONE place to keep a boat in the Caribbean year round, I would want a place with a significantly lower hurricane risk. Grenada is a good choice in that case.

[Midday Gun]

Some good suggestions from all, thanks.

I'm essentially at the ideas stage right now, but getting personal experience from people is always better than out of date articles.

Originally Posted by SailingHarmonie

What kind and what size boat?

Don't try to find the ONE PERFECT place.

That will just lead to analysis paralysis. There are literally hundreds of perfectly acceptable places to do what you want. You can always change your location as you get more experience if your first choice doesn't offer everything you need.

Just some tidbits. Flight connections from the USA to the French islands (Guadalupe, Martinique) are not good. If that is important for you, take them off your list.

In your situation, I would consider the Dutch side of Saint Martin. There are not a lot of marina slips available, but you only need one.

Don't discount Puerto Rico. Lots of quality marina space in Fajardo.

If I needed to have ONE place to keep a boat in the Caribbean year round, I would want a place with a significantly lower hurricane risk. Grenada is a good choice in that case.

Thanks, useful stuff.
Not decided exactly yet, but probably around 40 foot. Give or take.

I'm not determined to stay in one location all year around, but I have to move in my time off work & while 3 weeks sounds like a lot, it goes by very quickly when there's stuff to do!