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30-Day Solo Europe Trip

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Hey all, I'm a 26 year-old female planning a 30 day trip to Europe from mid-August to mid-September. I have a $5000 budget. I can fly into/out of anywhere in Europe, with an origin of Chicago. I found a flight that allows me to fly from Chicago to Zurich, and then Madrid back to Chicago for $920. If there's something cheaper out there (or places that have cheap flights to/from Chicago), I'd love to hear about it.

I've already been to London, Paris, and Rome, so I don't need to return to those cities on this trip. I wouldn't mind more time in Paris, however.

Here's my working itinerary, and I'm not set on any of these destinations. I'm open to suggestions on better cities.

City/Days:
Zurich, 1
Lucerne, 1
Interlaken, 3 (with a day trip to Bern)
Prague, 2
Vienna, 2
Salzburg, 1
Venice, 2
Florence, 1
Tuscany, 2 (what city would be a good base?)
Cinque Terre, 2
Nice, 2
St. Tropez, 2
Aix-en-Provence, 2
Barcelona, 3
Madrid, 2

I could add a few days to the trip (up to 45), and could definitely edit this itinerary. I'm also looking for tips on whether to purchase a EuRail Global pass.

I want to get the most for my money ($5000), so I'll stay as long as I can afford. I would love to fit Athens, Santorini, and Mykonos in my trip, but not sure if it's realistic financially/time-wise.

Thanks!

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