With young kids? Aaargh -- too much stuff to tote along. With older elementary/tweens/teens or just parents? Go for it.

It would be fun. Cayman is relaxing, so you won't be tired.

Did it once, in 2008....We did 6 days at the beach....came home, did laundry, repacked, and went to Hawaii for 2 weeks. At the time, I was working on projects where I was the PI and there were no other performers. Now, it would be hard to take three weeks off.

I do it fairly frequently. It is the same as traveling in general. For example, if I go to South East Asia, I will likely staying in several types of locations in more then one city. If I drive somewhere far, I will likely do a mini trip to somewhere on the side. We have two annual trips (a music festival and horseback riding camp) that we always string together because the timing works better and if saves us a few driving hours. You just need to make sure you are packed correctly for each destination and that you will be in the right mindset upon arrival. For the camping/horseback riding trip, we always add a day in the middle at a comfortable hotel with laundry and a pool to clean up for the next leg. But there is no reason not to do what you are considering.

I think it would be fine. Especially if you have a car--you can just leave your NYC clothes and coats locked in the car, and you don't have to lug them with you to the Caribbean.

I would just think of that as one vacation that has 2 destinations. Kind of like when I combined a trip to Barcelona with one to Paris-I got to see 2 cities I wanted to see and I saved money by not having 2 sets of international flights.

I've done it, to save money. A week visiting my family in California, then a week in Hawaii. Or a week in the Caribbean, then a few days in Atlanta for a friend's wedding.

It's not that big a deal, though if I had unlimited funds/vacation time I'd prefer to spread it out.

PP here. It sounds as if you are leaving the car in NYC - assuming you have a safe place to leave it??!! It will be pricey. I suppose you could leave another suitcase in the trunk and switch when you get back to NYC? Are different wardrobes/climates involved?

I like to spread out any vacations, given the choice.

The one and only time I did it I was in high school and even then found it too stressful. Depends on the personality and temperament of the people traveling...

My life is a series of back-to-back vacations. Sometimes has has to pick different clothes.

suckstobeme.com

I advise against. You need time to rest from first trip and you don't want to rush through things if you don't have to. I stress if you don't have to as going to NYC is cool and you don't want to miss it but I would advise waiting a little to build up the excitement again.

Anonymous wrote:We have done international (about 8 hour flight), then domestic (about 1 hour flight from home). We flew straight from one to the other, which meant packing entirely different clothes. Is it inevitable, OP?

No we don't have to do it.

I try to plan my trips back-to-back. Dog stays in the kennel. Flight arrangements often cheaper. Once you're gone anyway it's easier than setting on the details in motion again. Usually I'm fulfilling a family obligation.

We have done international (about 8 hour flight), then domestic (about 1 hour flight from home). We flew straight from one to the other, which meant packing entirely different clothes. Is it inevitable, OP?

Would it be a bad idea to do one week in grand cayman followed by four days in NYC?
We would drive to NYC fly to cayman then stay in NYC for four days then drive home.