We did this past week actually. I didn’t get to spend a lot of time in each area but found that for our style the most sensible option is going to be East Greenwich (or directly surrounding areas).

The reason we came to this conclusion:

• E. Greenwich most resembles our current home in FFC. Lots of woods, charming town, schools (private and public), large lots, plenty of beautiful old homes
• ease of access to both the train and the airport are important for us and not driving 45 minutes is going to make our living easier.
• How we personally spend our daily lives is mostly homebodies, but when we want to strike out for our adventures 2-3 times per week we can given this is a very convenient home base to beaches, Jamestown, Newport etc.

Many of the other areas certainly had their charm but it felt like for us a lot of trade offs for our needs. Jamestown for instance is beautiful and has a lovely town, but smaller lots, less dense woods, not as convenient. Bristol / Barrington has lots to like but definitely less convenient for commuting to Boston/NYC and where our children will likely go to schools for instance.

So for us, despite everything having plenty to like, EG seems like the easiest pick that affords us the quaint life that we currently enjoy without going overboard as well as access to things to do given everything is so easy to drive to for a day trip. It was great to ponder the possibilities on a map but there really is no substitution for going there and that helped us choose pretty quickly.

To your point real estate in EG is pretty sparse, and I don’t want to minimize the expense, but we also are coming from an area that is SHOCKING even to us (lots of properties being relisted for double and triple pre Covid levels) so I at least take solace that we aren’t paying as crazy prices as we would otherwise have to here.

Best of both worlds!

Ooph penn station…that’s not so bad. It won’t be all the time I need to go to NY so definitely doable. And Boston is also easy from there for a drive so have best of both worlds. I can look this up but do you happen to know if that Kingston station is the Acela or is it the slower Amtrak service?

Thats great! Granted I have only been to newport once so I dont even know if this is a fair question, but how do you live your life around the busy, likely annoying tourist aspect? Is it the type of thing that when you are there you just know the local spots and so it doesnt impact you much or is it something you have to wrestle with over the summer and find obnoxious?

They all sound pretty awesome to be honest which is part of the challenge of narrowing things down when you have to pick. Any suggestions? Seems like I’m on the right track with EG and Bristol but if you were me and you had to cut it off at top 3-4 places to consider what would they be?

Well I don’t plan on skiing in Rhode Island but the rest would be great and seems achievable. Nice thing about Rhode Island is that it’s even closer to NH/VT than where we are currently so cuts down on the diriving Tim to some of the closest real mountains

What makes it better so hands down? I don’t have a view so genuine question. Appreciate the feedback. Seems like EG is the “easy, sure thing” for us based on some feedback

What are the logistics to train from there to NYC? How long does it take and how many transfers?

Middletown and Portsmouth both look very nice I was honestly just reluctant to sign up for challenging commutes (albeit infrequent) so that’s why I figured the islands would be harder

I like this. Our goal with money is to achieve durable personal freedom (which is what we consider to be true wealth). We don’t believe in materialism at all but we do like the option of sitting in a nice cafe or occasionally going out for a nice bite to eat. We aren’t drinkers rather readers, homebodies and like to take up new hobbies from time to time (I worked on a regenerative farm for a few months recently and shortly after learned how to sail in a small sailboat for example). Is there something about the daily lifestyle outside of the people you prefer in Bristol vs EG such as the town?

What about Bristol do you like more?

Yeah just based on Redfin looks like the options are normal homes and then a large leap to massive estates on the little peninsula there. Not seeing much in between. But will keep an eye out as inventory comes to market over the next couple of months.

Patience, years of plotting a course in this direction, lots of long hours and ultimately carving out a niche that has paid off substantially over the past few years. Sorry don’t want to be too specific but if I can do it anybody can. Just zoom out and work backwards. Where do you want to be in ten years, what does it take to get there, and pluck away.

We love Vermont just can’t live there right now. Would love to one day live somewhere along the lake though.

What’s the dividing line between west and east Greenwich? Yeah seems like it checks most boxes tbh. Hard to see what the downfalls are especially for me given I already live in higher tax area

Is that just a woodsier / slightly further away area? Interesting will look

Why is this getting downvoted? Seems like a reasonable opinion. What are pros and cons vs e Greenwich?

They are post 2015;)

That sounds pretty nice. If you are in the woods probably less trafficked as well and seems very convenient to train access. What specific towns in these areas would you suggest?

Interesting. The hang up with Newport is just getting ourselves right into another joneses situation, lack of directly accessible train routes and smaller lots. Sounds like a fun daily lifestyle though. When we were considering Portsmouth NH (before deciding it was just not convenient enough to NY) it had a similar vibe.

Thanks, have not looked there will check it out. It sounds like E Greenwich / Kingston is generally more accessible by train to the bigger cities which may sway us in that direction though we may give up some benefits of acreage and peacefulness. P.S. your name immediately evoked phantom garlic fart aroma when I read it. Well played.