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Greece-Italy Trip for first time

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I'm planning for a trip next September with my husband to Greece and Italy. It's our first time to both places, but our third trip to Europe. We will be flying from Cairo. Please check my itinerary and please feel free to criticize it. Also I would be very grateful if you can help me with some hotel recommendations.

1- Greece: 2 nights in Hydra and 3 nights in Athens. Do you have hotel recommendations for Hydra and Athens? a Central hotel in Athens would be great. app EUR 100/night as a budget.

2- Italy: 2 or 3 nights in Venice. Do you have hotel recommendations? app EUR 100/night as a budget.

3- Train from Venice to Pisa. Leave our luggage in the train station, visit Pisa Tower.

4- Collect our luggage and rent a car from Pisa and drive to Tuscany.

5- 2 nights in Greve: Do you have hotel recommendations? app EUR 100/night as a budget.

6- 3 nights in Montepulciano: Do you have hotel recommendations? app EUR 100/night as a budget.

7- Drive to Rome. Do you recommend leaving the car outside Rome or drive to the hotel, leave the luggage then return the car to the rental company?

8- 5 nights Rome: Do you have hotel recommendation for Rome in a central area? App EUR 100/night as a budget.

thanks
wella

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