Money and time no object? I would do a tour of the Pacific islands on a 110 Wally sailboat complete with crew so I get to do the fun stuff like helming and none of the boring stuff I don’t feel like doing that day. Would hit at a minimum Galapagos, Tahiti, Fiji, New Caledonia and on down to the Sundays in Australia. Would take about 6 months although I could spend a lifetime there.

If I was time limited to two weeks? Sailing in the Bahamas in a Outreamer cat, these are as large as I can safely handle with my partner and its a lot lot shallower than the Wally so I get to explore far more of the Bahamas. Shorter holidays I want less flight time, so direct like this is perfect.

Malta I have been wanting to see the hypogeum for a while.

New Zeeland. But not by plane - by ship! I hate flying, but half around the globe on a small luxury cruise ship or yacht would be nice.

Cape Breton, Nova Scotia.

The Moon.

Failing that, Low Earth Orbit.

I handle this, as do most poor people, by not asking ourselves this question, not even fantasizing about it, for why torture yourself with something you never can do?

I would go to Freemoneyland and get free money

Japan. Several European countries.

The fuckin moon, and it’s not even close. Get me off this rock

The sun.

I’d just rent a cabin in a nearby mountain.

I don’t see the appeal in going far away from vacation.

Probably any other country where I could get a doctor to take a look at my heart condition without having to take out a loan against my house to pay for it.

I’d like to see Japan deeply. I’d go all the way across the country and make sure to stay at rural spots along the way to enjoy the stillness between cities.

My son asked me this yesterday. Japan.

A tour through the Nordic countries.

I’ve only ever seen Sweden from the highway from Malmö to Stockholm to get to a boat to Estonia in time, and only saw bits of the harbor in Helsinki during that trip. I’d love to take more time to explore Denmark, Norway, Sweden and Finland.