I think June is the start of the peak season at Machu Picchu. The winter is the dry time there. However, it is cooler.

My parents live on the island of Skiathos, and we go every year. The easiest way to get to the Greek Islands is to fly to London and then book a package holiday through one of the holiday companies such as First Choice or XL, there are lots of them. Maybe that would be a cheaper option than using a US travel agent to book the trip. There are also companies in the UK that put together island hopping trips, since there is a network of ferries between the islands.
Good Luck with the trip planning.

Hi stonest
With your budget you have many, many choices if you are willing to travel budget. This is tourist hotels and not 4 or 5 stars accomodations. You can go to Greece. Check out Gate1. We have traveled with them and was impressed with our accomodations and their services. http://www.gate1travel.com/greece-tr...v08-mar09.aspx

Or, go to one or two of the Hawaiian islands. Rent from VRBO.com: http://www.vrbo.com/vacation-rentals/usa/hawaii
Click on the island of choice and view all your possibilities. Your tickets right now would cost between $800.00-900.00 each you could fly into Honolulu and then fly out of one of the other islands (open-jaw ticket) vrbo has many rentals to choose from. I would suggest a car rental however so that you can really tour the areas.

Thanks for the advice, everyone! As an update, we decided that we're going to do Greece--been working with a travel agent in Athens and he's really made it an affordable trip for us. Keeping our fingers crossed that the dollar continues to get stronger!

Thanks for all the advice though--I've researched several of your ideas and I think we'll be doing several of them within the next couple years!!

I was reading through all this getting ready to say "you can do Greece beautifully cheaper than Hawaii!" I'd probably not use a travel agent, but you 'gotta do what you gotta do'. There are wonderful rentals in Greece for cheap -- VRBO for one Homelidays for another, without having to pay travel agent fees for finding a place.

Thanks for the update! Maybe hubby and I will head there in 2010. That will be our next big trip after baby #3, who isn't conceived yet. But I like to plan ahead!