Every now and then, I allow myself a delicious fantasy: I win the lottery and immediately go traveling in style, preferably bringing along a million of my friends!

Let’s say that I won 50 million dollars tomorrow.  Where would I go first?

Well, I’d want a destination with great weather in September.  That’s most important.  Next, I’d love to go luxury in an amazing hotel, something I rarely do.  And third, there has to be great nightlife!

So, where would I go?

Hvar image by Lena_Ni

It’s the tail end of the high season in Europe, so I’d visit a popular Mediterranean beach area: Santorini, Greece; Hvar, Croatia; or Ibiza, Spain.  The weather will still be glorious; the nightlife will still be hopping; the crowds will be GONE.  And that’s how I like it.

Vegas image by Evangeline

In Vegas – ALWAYS Vegas! – the pools are still open.  If I had the chance, I’d stay for at least a week – at the Wynn or the Encore.  God, I love those resorts.  Every day would be a new cabana at a new pool club: Tao Beach at the Venetian, Bare at the Mirage, Wet Republic at the MGM Grand, Moorea Beach Club at Mandalay Bay!

Maui image by David Winnie

Hawaii has always been a pipe dream of mine – being an East Coaster, Hawaii is just somewhere we don’t go.  I think this is a trip best split into two parts – half the time relaxing on the beach in Maui or Lanai, and the other half in Waikiki, partying with military men!

Any of these trips need to be planned well, so I’d probably arrange my reservations through a travel agency online like Liberty Travel. Having a trip that runs smoothly would be important in planning my dream trip!

So, if you were planning a dream trip this month, where would you go?

This post was sponsored by a third party.