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Planning Help

I've posted several times about my upcoming honeymoon, so I'm back for more. I'm traveling in late June-Early July for two weeks in Italy. The flights are booked and the plan calls for arrival into Milan and departure from Rome.
I should mention that my fiance has asked me to keep the honeymoon a surprise so I can't get much input from her. I've been to Italy and she has not, so she'd defer to me anyway.
Originally, I was going to do CT for 4 full days, travel to Florence via quick stop in Pisa, Florence for two nights, travel to Siena, Siena for two nights, then travel to Rome via quick stop in Orvietto. The last 3 full days would be in Rome.
Now I'm thinking of only booking the first part in CT which we'll need to unwind from the wedding and then letting what happens happen. I think this approach will allow us to call an audibles and be much more of an adventure.

My questions are generally what do people think of the more open ended option? Relative to reservations, am I leaving too much to chance? Lastly, when I was in Italy I visited Florence and Siena and did both as day trips from the countryside. Would I be better off just staying in one or the other (and which one should I pick) as we'll be train people for this trip. We're both young, very fit, and able to go with the flow, so no matter what happens we'll have the time of our lives.
Thanks!

Posted by
1201 posts

It is hard to answer this question. You are traveling in a busy time frame to popular destinations. Could you wing it and come out ok, maybe.

The advantage of planning with advance reservations is that you can stay at the places you want to be, rather than what might be available the day you arrive. You won't have to spend part of your time finding accomodations.

Posted by
430 posts

My wife and I have traveled with and without reservations. I, personally, prefer having only a basic structure and getting last-minute hotels.

I like the idea of booking your stay in the CT and going with the flow from there, but you should certainly have some pre-researched options. You should also, absolutely, go ahead and reserve your last nights in Rome -- if you know for sure you'll do 2 nights there, book those now. (Rome can be tricky for last-minute stays unless you drop down to 2-star accomodations, in which case I find last-minute is your least expensive route.).

We spent our 5th wedding anniversary in the CT... now 10 years ago... and did it in the midst of a 17-day Italy/Switzerland trip for which we had exactly 2 nights pre-reserved -- Naples on night 1, Rome on night 17.

My vote: call an audibles after your 2nd day in the CT.

Only other comment -- regarding Florence -- I like to stay in Florence, but I also find something magical about it in the early morning hours. I've only day-tripped Siena, so can't help with whether it's a must-stay.

Posted by
801 posts

On the Florence / Siena, one or the other or both, it depends on what you want to do. If you're really into Renaissance art, then maybe skip Siena for this trip (you will return) and focus on Florence. If you're looking forward to enjoying some nightlife, there will be more of that in Florence, as well.

On booking ahead or not, we almost always book ahead these days. While we don't stay in expensive places, I am pretty picky about a convenient location, cleanliness and ambiance. You can't always do that on the fly. BTW, we stayed in a great B&B on our last trip to Florence, Casa dei Tintori. Alberto and Valeria were wonderful, and pretty much spoiled us. Also, I wouldn't want to have to spend time each day thinking about where I was going to stay that night.

And for Rome, at that time of year, things are likely to be booked up, making the hotel search a little more difficult. Actually, that's probably true about Florence, as well.

You'll still have some flexibility, even if you book ahead. You can take an early train or a late train from one place to another, or skip Pisa or Orvieto if you decide you want more time in the Cinque Terre, Siena or Rome.

Posted by
3262 posts

Your trip sounds great! For Florence/Siena, I would pick one and stay 3-4 nights--then day trip to the other. Siena would be my preference but many would disagree!

Congratulations on you upcoming marriage!