16 nights.. where would you go?

I'm confused when you mention the expense of flights between Italy and other destinations. Is spending part of the time in Italy a requirement? Sixteen nights would be great if you just focus on Croatia and Slovenia. That would give you very few large cities and lots of time for relaxing (spending a few days on one or two of the islands off the Dalmatian coast).

How about something like this:

Fly into Zagreb, rent car, drive to Ljubljana
Ljubljana 2 nights
Bled 2 nights
Rovinj 3 nights
Plitvice 1 night
Trogir 1 night
Drop car at Split, then take ferry
Hvar 2 nights
Korcula 2 nights
Dubrovnik 3 nights

Flying into Zagreb makes the rental car affordable because you'll be picking it up and dropping it off in the same country. It's only about a 2 hour drive from Zagreb airport to Ljubljana.

What about Poland. We are planning a 15 night vacation there next August and I feel already it is not enough time. Maybe focusing on one country wouldn't be as hectic and Poland would fit into your budget. There are many smaller cities to visit and a friend told us not to miss Zakopane. Also, we went to St. Petersburg and Tallin in Estonia and enjoyed it and had plenty to see and do, great food too.

Poland is indeed a very nice country. I went there last year for some sentimental family reasons, and this year again with the beloved one. Lots of history (too much, if you read about it). Varied (after all, it does have Germany and Russia as - not always friendly - neighbours). Nice landscape (not dramatic for the most part, but pleasant after all). Good hotels (no need to take those anonymous international chains). Reliable rail connections (not always fast, but even on that lost platform somewhere outside a small village the train comes on the dot). The younger generation, especially in hotels and restaurants, speaks good English. And, outside Krakow and Gdansk, not many tourists, which gives you the feeling of discovering something.

Italy isn't a requirement, but we'd like to include it if we're near there and it would make sense with either Croatia or Greece. We are considering several itineraries but I thought I'd see if anyone had an idea I hadn't considered yet.

We're very active travellers and like to move around a lot (our last trip we walked over 117 miles) and prefer to see a few different countries on each trip if it makes sense. We enjoy getting around by train and car, however after our experience on the overnight train from Amsterdam to Munich, I think we'll avoid those for a while.

Other than being very active travelers and not wanting to visit all cities, what do you like to do? And what time of year would you go? Both of those would be huge factors in terms of deciding where you want to visit next.

I second the Croatia/Slovenia itinerary that Lane recommended

Hello Jennifer. I would go to Greece. Travelling to islands of Greece takes time, and you will have time for that. I recommend : fly to Athens, and the day you arrive at the Athens airport fly to the island Naxos. Your itinerary could go like this :
Fly to Athens and Naxos. Naxos = 6 nights.
Ferry boat to Mykonos. Mykonos = 3 nights.
Ferry boat to Samos. Samos = 2 nights.
Ferry boat to Kusadasi at Turkey. Bus to the ancient city Ephesus.
Ferry boat to Samos. One night at Samos. (a total of three nights at Samos).
Fly from Samos to Athens airport (a 45 minute flight).
Athens = 4 nights. (or 3 nights at Athens would be sufficient time there). I could recommend a hotel at Naxos town (Hora). If interested, send a Private Message to me.

A version of Lane's Croatia/Slovenia suggestion above, but starting in Budapest.

Fly into Budapest 3 nights
Train to Zagreb 1 night, then rent a car
Lake Bled 1 night
Ljubljana 2 nights
Plitvice 1 night
Trogir 1 night
Drop car at Split, then take ferry
Hvar 2 nights
Korcula 2 nights
Dubrovnik 3 nights

Land in Sofia,
2 nights in Sofia then you can hire a guide with a nice car and explore Bulgaria from west to east for about $300 a day including everything but food. Spend 7 nights working your way east to Istanbul. Istanbul for 3 nights then a flight to Budapest on Turkish Air. Finally 4 nights on Budapest. I did this a few years ago and i think it can be done in your budget. The trip explores a lot of extremes culturally and rural to city.

Lexma,

We're looking at end of Aug/beginning of Sept. We love exploring small towns and finding cute places to eat, shop, and relax. We are huge into art museums that focus on sculpture (Ny Carlsberg Glyptoteket is one of the best museums we've ever visited). We enjoyed visiting the Anne Frank Huis, Dutch Resistance Museum, and Dachau on this trip as I'm a WWII junkie (we also loved the White Bus exhibit at the National Museum of Denmark). My husband is also a huge beer lover and we found several good places to stop.

I didn't see Hungary or Austria on your list of where you've been. Budapest was a wonderful revelation to us a few years back, well worth several days, and at the drop of a hat James will give you as detailed a Hungary itinerary as you might want, including countryside. Vienna is another great city with one of the world's great art museums, the Kunsthistorisches Museum, a couple of palaces, an opera house rivaling Budapest's (or is it the other way round?), side trips on the Danube, and more. Between them is Bratislava, well worth a day. Your timeframe would let you explore this area to your hearts' content. Or branch out north to Poland or south to Slovenia, or east to Bulgaria. Your money will go farther in all these places except Vienna.

Greece would be a good candidate too, but it will probably be very hot that time of year. Might be a better bet for spring or fall.