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First time travel to Greece, need help!

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My husband and I will be traveling to Greece for our 5-year anniversary in mid/late June 2012. We will be gone for 2 weeks. This is our first time to Greece and our first time traveling internationally together. I love travel, adventure, new places, history, and beautiful scenery. He is not sure how he is going to like international travel (he has only traveled for business and humanitarian trips in the past, never just for fun!) He values a good deal and a simple itinerary. Our combined goals are romance, low-key travel, but enough adventure/excursions so we don't get bored. We love culture (ie: don't feel the need to go to the touristy spots, or the places that cater to Americans) and we love exercise (hikes, etc). We are planning to pack as little as possible-a backpack each. To try and mesh our 2 styles the plan so far is to fly into Athens and then hop on a plane for Santorini. Spend a couple of days each on a couple islands (recommendations so far are: Santorini, Crete, and Paros or Hydra) and then go back to Athens to explore and do some day trips (possibly Peloponnese or Delphi). We are on somewhat of a budget, so we realize that the majority of our money will be spent on airfare and then we will have to save on lodging, food, etc. Our original budget was $3000 but we were told this is impossible.
1. Any general tips for first-timers?
2. Any tips on saving money, especially when it comes to airfare?
3. We have heard it is possible, on the islands, to just show up and find a last minute room, is this feasible in late-June?
4. Any must-see places on the islands or mainland (knowing that my husband doesn't want to be overwhelmed with high-paced tourist travel, he is more happy in a low key environment, taking a hike, exploring some ruins, checking out a little beach town, etc.
Thanks!!

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