PS: In case it isn't clear about how to use booking.com to find hotels on short notice, I generally

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My fiance and I are traveling to Italy in July for our honeymoon. We are flying into Milan, driving to Venice and then down to Tuscany and onto Rome. I have been to Italy prior but in the month of June, I was always able to pull into most towns and get rooms without reservations. Is July going to be more challenging to find rooms available?
Based on my experience of flying into Milan and going to Venice. Imo I would take the convenient train from Milan to Venice. If you don't what are you going to do with the car when you are in Venice? cheap airlineticket You don't need one and can't use one there.
Then when leaving Venice take the convenient train to Tuscany. You could rent a car there and drive around to wherever you want to go. You can drive to Rome if you have time to stop along the way. I would do your car rental and road trips once you get to Tuscany. But, others cheap airlineticket my have opinions that differ from mine.
Small Gems in Tuscany, well remember it will be hot and most of the Gems will not have A/C. I like the little towns that failed to become Siena or Florence and there are loads. So maybe Buonconvento, San Querico, Ponte d'Arbia or Colle di Val d'Elsa (upper town).
How long ago was this? Since you can't drive in Venice (no cars) or Rome (ZTL) along with many other cities/towns (ZTL), this plan doesn't seem practical. For Venice, you would not only have the daily cost of the car rental, but also the parking to just let it sit (30-40 per day) the entire time you are there.
I agree with elizzie about taking the train and either picking up the car in Tuscany or as you leave Venice. cheap airlineticket I would drop it somewhere in Tuscany also (depends on where you plan to visit)and take the train to Rome.
You can find rooms, but it's really not a pleasant activity. I don't enjoy spending my limited vacation time driving around looking for a place that has availability. It's been about 4 years since I did that and won't be doing it again.
I would say that if you "wing it" in looking for accommodations, you could easily fall into having cheap airlineticket to take whatever is available, or spending a lot of otherwise more useful time looking for a room. And since it is a honeymoon trip, I personally would have everything booked beforehand. Part of the fun is looking for places to stay on-line, reading people's reviews and suggestions, seeing cheap airlineticket pictures, etc. And then knowing that you have a confirmed place to stay that you like and not worry about looking for something. This is my personal preference, everyone has their own. Good luck and congratulations.
elizzie400 is absolutely on-point with the train recommendation. Parking a car while you see Venice would be costly, to say the least. A more items about the trains: 1. they arrive and leave on time, 2. you arrive generally in the middle of town, and 3. you arrive relaxed not and not frazzled cheap airlineticket along with not worrying cheap airlineticket about costly parking.
As for making or not making hotel reservations, after traveling in Italy for 34 years we always have a reservation and a room waiting for us. It eliminates wasting time trying to find an accommodation, not to mention humping your luggage while you look. With so many websites available you would know what type of property you've booked even before you set foot into it. You could go directly to the hotel, check-in, cheap airlineticket and then either snooze or begin touring cheap airlineticket around on foot.
If you book with venere.com or booking.com and others, you can read reviews by people cheap airlineticket who have actually stayed there. cheap airlineticket We've used venere for years and have never had an unpleasant surprise. We've also use booking.com and hotel.com and have also been happy with those websites, as well.
I live in Italy and travel cheap airlineticket through Italy all the time, every month of the year, without reservations. If you are traveling with internet connectivity, you can use booking.com and don't need to drive around looking for places to stay.
I recommend taking a train to Venice rather than driving. If you like to drive, pick up the car in Venice and drive to Tuscany. In July, it can be nicer to have an air conditioned car all the way rather than be hauling luggage through train stations to car rental offices.
PS: In case it isn't clear about how to use booking.com to find hotels on short notice, I generally select and book my hotels for my next stop the night before, directly through the booking.com website. I look for hotels with air con, wifi, parking -- and I have never not been able to find a hotel in my target area with what I want at an affordable price. I have never experienced booking.com losing a reservation for me.
The days of schelepping luggage around or driving around cheap airlineticket looking for availabilty have been over for several years for people who travel with an internet connection. That said, even before I traveled with an internet connection, I traveled with the Michelin Red Guide and a cell phone, and always had a place booked within 15 minutes of looing.
cheap airlineticket I'm guessing that the USD being stronger against the euro than it has been in several cheap airlineticket years, together with a steadily improving U.S. economy, is causing more and earlier bookings at least in the usual destinations.
If you intended to head to small, less-visited towns and villages, you'd probably have no trouble with lodging. But if your itinerary cheap airlineticket includes the usual stops mentioned cheap airlineticket here and in every guidebook, and/or you have specific expectations or wants because this is your honeymoon, then I would have reservations before arriving anywhere.
Thank you for all of your information, I appreciate it so much and it has helped me in so many ways! We will defiantly take a train to Venice. If you have any suggestions for a place or area to stay in Venice that is reasonable let me know. Thank you!!