August - going to Germany for 8 days, then to Venice, Cinque Terre, Tuscany (in a car), then to Rome - for a total of 21 days.
Any suggestions on flights, and accommodations while in italy?

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We stayed in a great airbnb in La Spezia when visiting Cinque Terre, it was super easy to get to the villages by train and the prices for accommodation were way better. Just look for places within walking distance from the train station!

AirBnB!! As for flights within Europe, look on Momondo.

You need to reserve in advance entry into cinque terre.

We stayed in Riomaggiore and walked along the remainder of the towns over the 4 days spending some time in each. This town is at the end of the cove by the fishing village and has a beautIful cafe over looking the village. Train station was about a 20 minute walk cobble streets and lots of stairs but its worth the view.

http://yvrdeals.com/seattle-to-paris-france-522-cad...

From Paris by train or flight go Germany

Ryan air. Alitalia. Lufthansa. Klm. Air france. Lots more. Europe is pretty cheap from city to city. Buses or trains are reasonable too. Depending on duration you could look into an interail ticket. Pricing will depend of time of year.
Accomodation: Italy is an old European country. Every where you stay will have character. Air bnb is a good option but you miss out on the culture that comes with hotels or hostels that might be more central.
Also. Booking from canadian .ca sites sometimes can be much cheaper than .it/.ie .uk or visa versa
So for example I could punch in same details on all sites: it will appear like this or opposite. Good to check various domains.
(.ca) 390 cad reduced to 159cad
(.ie)267 eur/ 417cad to 216 eur 340cad

Also. August in Italy. Some places often close for lenghtly times due to public holidays. A quick google you'll see reference to Italy's family holiday month as being August. It can be nice and quiet or extra busy as everyone is on vacation. Good to be aware of it though or it could be disappointing.

Check Airbnb in Italy. Stayed in one in Venice and one in Rome last year and both were amazing.

We stayed in a airbnb in Cinq, Rome, Venice and had a great experience.

I'm also going to europe in august for about the same time frame haha

Stayed in an Airbnb in Rome that was awesome. Stayed at Hotel al Piave in Venice and they were lovely.