Crazy Limitations on Vacation Destinations

Disneyland or World...  Or San Diego (Sea World, Zoo, Wild Animal Park, Legoland).  Just got back from Disneyland, and they treat you right.  In 3 days you can have a whirlwind of fun and excitement and it keeps you moving.

Or...

Maybe South Dakota (mount rushmore).  Philadelphia has museums, zoos, historical sites.  NY has broadway.

O.k. that's all I've got.

A long weekend in NY (fly to NYC or drive to Niagra) or San Francisco. 

Where do you think you'll end up working?

Since you are in Fon du Lac (neighbor of mine), may I suggest:

1). Mall of America in MN.
2). Door County
3). Chicago Mile
4). The Milwaukee County Zoo, then Boerner Botanical Gardens.

2 thoughts come to mind:

1) everything you're saying kind of points to an all inclusive beach resort vacation (anywhere but mexico).  I wouldn't do mexico with the state of affairs down there right now, but if you're brave enough, then it's an option.  Bahamas would be my first recommendation, then one of the British virgin islands, then maybe the Dominican Republic. they are cheap, easy, and have a lot of options for entertainment generally speaking.

2) Catalina Island is my second suggestion.

3) this on is a little bit of a head scratcher, but it's close to you and I HEARD (never done it) that it is fun.  Chicago.  A friend of mine that likes to travel, has told me that if you want to do a CITY for a vacation that #1 is probably Washington D.C., #2 is probably New york and # 3 is Chicago.  they have all the arts, all the sports, a ton of restaurants and is on the great lakes with various activities (kayaking through the middle of downtown was one that caught my attention).

So which is it?

I was just there last weekend and there is just too much traffic for that size of town! I was really surprised. The downtown area was definitely fun though.

I would do a California vacation of some sort - there would be beach time, wine tastings, and opportunities for runs/hikes for those who wanted to. 

Go to the DELLS!!!

I say this half in jest because I know you are in WI however:

- You have tons of outdoors stuff in the Dells. Zip-lining, Skiing, Canoeing, boating, hiking & top notch golf. There are some great roads to ride as well.

- Some excellent restaurants that are as good as most in any big city.

- You didn't mention if the families have younger kids but there are tons of waterparks (indoor & out, mini-golf, rollercoaster, etc etc.

- There is a nice casino close - if someone has the urge

- Last but not least - you can scout out the Rev3 half-iron course in advance for COJ!

What about something like a resort on the North Shore or some such? Or renting a cabin/house in an area like Bayfield or Grand Marais or Lutsen or someplace similar? Many of those kinds of places are close enough for hiking, MTB, that sort of stuff...but also conveneinet for folks who want to hang out at a pool or spa or go shopping or whatever.

ETA: We typically rent a house/cabin every year on a lake somewhere within about 2-6 hours from here. Whole family goes--my in-laws and their four kids, and all teh spouses and children. Everyone likes different stuff (although we all like drinking...), so people sort of mix and match interests.

Yeah, I am struggling with this one.

I am sure you're joking about the Mall of America!   That's funny.

If your family members don't like outdoorsy stuff, can you elaborate on what they do like?

Also, are you okay with a vacation that requires some work (sightseeing)?   Or looking for relaxing?  I know you want fun, but I still think this question applies.

Another thought might be the Miami area...there's a beach, golf, tennis, day trip to disney (<1hr), cape canaveral, deep sea fishin if you're so inclined at islamorada, outdoorsy stuff (a friend of mine rented a sea kayak and paddled around biscane bay, and was hanging with the dolphins), plus south beach nightlife which requires absolutely no effort to go nuts.

The weather is great in April (above, say Jacksonville, you're at risk in april for beach weather), it's a 2:15 flight from Chicago direct.  EZ Peasy.  

x2 on New Orleans or Miami

If you want to stay closer to home, you can get pretty wild in Chicago too...bars are open until 4am, lots to do during the day. 

I've always had a blast in Toronto too... 

I think you meant >1 for the Disney trip - unless you have a REALLY fast car!