Italy in 17 Days

It is ambitious. I done know if I could do it, but that is me. Do not let anyone tell you what to do. I would do fewer stops, but since I have been to all the locations I cannot tell you what to leave out.

The only caution I would give is you lose a lot of time on travel days.

It is your vacation. Do what you want

Italy in 17 Days
Posted by garrettedmunds on 08/11/26 07:08 PM
I am a first time poster on this site. Planning a 18 day vacation for early September in 2027

First, how many nights will you be there?

Second- Have you looked at the RS 17 day best of Italy tour ? ( https://www.ricksteves.com/tours/italy/best-italy-tour)

You look to be trying to cover at least as much territory, but without the convenience of a dedicated bus to take you door-to-door. and without a never lost guide who knows the most efficient way to get from Point A to point B.

It looks like a lot of time en-route, with not so much time 'being there'.

If you do stay in Bellano and fly out of Milan, it would be wise to spend the night before the flight IN Milan ( or near the airport, depending on flight time), not Bellano.
My $0.02

Thank you. Your comments will be definitely considered, especially Bellano. I am going to rent a car for the Tuscany portion and maybe a guide in Rome and some private tours.

hey hey garrettedmunds

it's your vacation you do you. does the 18 days count your arrive day and departure day which is 20, if not 16.
too many places in a short time is my opinion. check in time 3-4pm check out time 10-11am give 1/2 evening and full day then check out, not much time to see much. plus you will be spending lots of travel time on the road, waiting in train stations and not enjoy "being there"
where ever you stay make sure you have parking, mandatory IDP (aaa.com/IDP) in italy. read rules/laws/ZTL zones/winding & curvy roads which can be narrow. check times & days rental car places are open, many close early, half days, or not open on sundays.
book your places early since september is still considered high season, harvest time for wine and olive oil,
be in milan day before flight home. check your arrival and departure times for flight. good luck and have a fabulous trip
aloha

Welcome to the forum!

I believe you can contact the webmaster and ask them to move this post to the correct Italy thread. You might get more responses there. Sorry, can’t help with your itinerary but I know it will be a memorable 25th anniversary trip! Congratulations!

Here is the link to webmaster. Send a private message. https://community.ricksteves.com/users/1000

Whoa, maybe take a calendar page to write it all down, putting in travel days and times so you can visually see what you are proposing to do and if it makes sense to you.

This is ambitious, IMHO. What are the interests of you and your spouse? Cuisine, culture, outdoors activities, wine, history, etc? For example, I love art and artists, as well as ancient Rome. So for me, an 17 days / 18 nights (or whatever) first trip to Italy would include the major and minor museums of Rome and Florence, but that's not necessarily what other people want. Consider what has made you initially select all of the cities and towns in your initial itinerary.

Keep in mind that three nights means only 2 or 2+ days. And two nights means only 1+ days, which is not much time at all for cities like Florence and Venice. But that depends on what you want to see or do there. If you prefer the countryside, then consider skipping some of the cities.

Personally, Pienza is a little small and quiet for me. I prefer staying in Siena, and doing day trips from there. I love sitting on Siena's Campo with an Aperol spritz or a coffee drink, and people-watching!

Pencil out (literally or electronically) the destinations you have in mind, then pencil in the sites and sights that are must-sees for you. And also pencil in general travel times. Then you'll be better able to calculate how much time you'll have for the things that mean the most to you.

Garrett,
The first thing I would do is see how long travel time would be between places. That means time to check out of a lodging, get to the train station, time en route, locating your new lodgings on arrival in new place, getting there and checking in. If driving, don't assume a 60 mile drive will be an hour or hour and a half, as perhaps in the states. Assume, unless on the autostrada, that you will be driving more slowly on smaller roads, with unfamiliarity with signage, etc. Pay heed to the above comments. Each change of towns or cities you will lose half to most of a day (at least in my experience). Count your nights in a place. Yes, 2 nights = 1 full day. Also, part of the arrival or departure day can be used for sightseeing etc., if you arrive early enough or depart late enough.

Your plan is doable, but does seem, to me at least, overly ambitious. Do some research about train times and driving times. And list your must sees in each location to make sure you have enough time there. Best of luck!

Welcome!

It looks like you have 18 nights and I count 7 location changes. That means you will spend almost every other day in transit. Each location change will eat up at least a half a day.
A 2 night stay means just 1 full day in that location.
You don’t say what you are interested in seeing/doing so it’s hard to say if this works for you but IMO it is far too fast paced and way too many location changes/time spent in transit.

The only place you will need a car is in Tuscany/Pienza.

Arrive Rome
Rome 3 nights
Get car where?
Pienza 3 nights- Siena really deserves a full day and is about 1.5 hour drive from Pienza so not the best day trip from Pienza.
Drop car
Florence- 2 nights
Venice 2 nights
Bologna 3 nights
Cinque Terre- which town? Just 2 nights (1 full day) here is almost not worth the travel time
Lake Como/Bellano? 3 nights will take most of the day to get here 5-6 hour train ride
Depart Milan

You will need to be in Milan or at MXP night before your departure flight.

I would drop either the Venice/Bologna detour or drop CT or drop Lake Como. Give another night each to Florence and Rome and/or Pienza.

Spend some time on Google maps and the Trenitalia site to see exactly how much time these transits will consume.
Be brutally honest. How much time to pack up and check out, get to train station or pick up car, how much actual travel time, how much time to find parking or get from train station to hotel. How much time to check in, get settled and oriented.

All of your locations are lovely and worthwhile - maybe save something for next trip to Italy?

This is a lot.
Personally, I try to make my logistics as smooth as I can and try not to backtrack. You are starting in Rome and leaving from Milan. I'm going to hope you haven't bought tickets yet.

This may be controversial, but, looking at your itinerary, you should drop Rome. It's a significant outlyer as far as the places you're saying you want to see. You don't mention anything you particularly want to see in Rome. Just because it's there doesn't mean you have to go there. That will make it much easier to see the rest of the places you want to see.

Fly into Venice and out of Milan. Do another trip to Southern Italy.

Give yourself a chance to enjoy your anniversary trip.