I’m thinking about finally buying a vacation home. Looking for something that we can use for holidays and in a few years grown kids and use with their friends, eventually we can host multigenerational stuff with grandkids etc. kids are high school / middle school now. Fun town is critical. Something say up to 2-3 hours from an airport would be fine. Any suggestions? Open to mountain / beach / lake. Critical though is fun town and grown kids would want to spend time there.

Tuscany !

I don't see the attraction of a vacation home. Why be tied down to one place for vacations? I want the freedom to go anywhere, rent whatever I need, and then leave without thinking about maintenance and upkeep.

Are you planning to rent it as an ABnB or only use yourself? If this is only for your family use, I would want to keep it within a 3-4 hour drive from where you live. Otherwise, you will only use it a few times a year. From Chicago, I would be looking at Wisconsin lake houses. If you don’t know where everyone will live and want a central location, I would rent an aBnB for special events.

Florida. Cannot do wrong there.

I’m in Chicago also. Have a place by Sheboygan on Lake Michigan. 2.5 hour drive from Chicago. You can fly into ORD or Milwaukee, so very easy to get to. Summers are great with all the lake stuff you’d expect and Sheboygan is a nice little place and is continuing to grow. Solid golf courses too if you’re into that. Winters are pretty good too, and you can always drive up a bit up north for “more winter.”

Lake Placid, NY. Winter skiing and Summer boating, hiking, golf, etc. Year round good times. 2.5-3 hours north of Albany airport.

Ah now you’re onto something. Any recommendations for a spot in Cabo? Like a community? Looking for something with a pool, clubhouse, etc that you can rent out.

Great topic, following!

In-laws have a place on a lake near Hayward, WI. Once youngest child’s college is clear, we will buy a cabin there. 6 hour drive from Chicago. 2 hours from MSP airport. Fun central town with golfing, restaurants (not haute cuisine by any stretch), activities for kids.

If it wasn’t there we’d have tried a spot on coastal islands near Charleston SC

We bought a second home in Bluffton, SC near Hilton Head. It’s a golf course community so lot of that plus tennis, pickleball, boating, etc. Near the beach and not far from Savannah. The town is great with lots or bars and restaurants. We’re out of the DC area for easy 1.5 hr flight or 9 hr drive.

Wilmington NC

What about a ski town like Breckenridge?

We have a second home in CO. You go for the winter, stay for the summer. 45 min drive from the tiny airport.

Where do you live? That drives a lot of the decision.

Chicago. That’s what’s tricky. I want something sort of central because kids might go to school anywhere. I want something with a good draw to pull us together too. Something fun, something big enough. I don’t mind flying to get there but I don’t want to fly then drive for more than 2 hrs or so.

Charleston, Wilmington, Amelia Island,

Anchor for family. Place for kids to come back to. Establish traditions.

Yeah I felt the same way as retired partner for many years, but I wish I had bought something earlier. As the kids get older, I want them to keep coming back.

What about Jackson Wy or Park City Ut. Both under an hour from an airport and lots to do. Have you thought of doing fractional ownership? You could get 6 weeks a year for 1/8 the price.

As a fellow Chicagoan, I recommend Cabo. Great place to escape the cold, and a direct flight.

Wherever, building memories is a great plan. Still love the area we visited in eastern Ontario when I was a kid.

I had a vacation / 2nd home. Each trip there was spent doing work on it — minor repairs, things break, plumbing leaks, yard, etc. got to the point where it was more time doing work than I wanted to spend. And as kids get older and build their lives, how they spend their time off doesn’t always match yours.