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Italy hotels/hostels

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My boyfriend and I (mid 20's) are getting ready to book an open jaw flight arriving in Venice on 5/16/13 and flying out of Naples on 5/26/13. We would like to spend no more than $100 per night for our room and stay within a good vicinity to the main attractions. Any suggestions on hotels or hostels? Also, do you have any suggestions on places we must go in each city(restaurants, shops, nightlife)? Excluding the price of our flights we'd like to only spend $2,000 while in Italy, does this seem doable?

5/16 - Arrive in Venice at 2:00PM
5/17 - Venice
5/18 - Train to Florence
5/19 - Florence (day trip to Siena)
5/20 - Florence (day trip to Pisa)
5/21 - Train to Rome
5/22 - Rome (Tour of Vatican City)
5/23 - From Rome to Sorrento
5/24 - Sorrento (Trip to Capri)
5/25 - Naples
5/26 - Fly out of Naples at 6:30 AM

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