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.

Congratulations on your upcoming 25th anniversary! My husband & I did our first Rick Steves tour for our 25th anniversary. : ) Three years later we did the Rick Steves 17-day Best of Italy tour. Looking at your plans, I would encourage you to strongly consider doing that Italy tour, instead. Don’t worry; there’s lots of free time during the tour. But, it will maximize your experiences, and it’s a wonderful way to leave the stress of renting a car, and all of the little things and just concentrate on your time together in an excellent variety of “wow” locations. You didn’t mention the Dolomites. During that trip, it was a bonus for us that we really enjoyed!

After that trip, we did several independent itineraries back in Italy and also other countries. But we learned so much from those first two RS tours that I continue to apply to many independent trips now.

We covered much - not all of that (we missed Genoa and Bologna) - in TWO 18 day trips.

The second trip was to see what we had missed the first time we were in Rome, Florence and Venice - and we spent 4 nights in Rome, 4 nights in Florence and 2 nights in Venice on that first trip and pretty much duplicated that time on the second, but with a third night in Venice. We spent time in Cinque Terre (2 nights) and Tuscany (6 nights) on trip #1 and in Padua (day), Verona (1 night), Bellagio (3 nights) on Lake Como and Milan (3 nights) on Trip #2.

Whatever you do, have a great trip. Travel at the pace that is comfortable for you.

For many, slowing down makes sense. It means more cafes while you linger over a cappuccino, enjoying a park or a piazza, more lingering in churches to take in Caravaggio or Michelangelo or Bernini, and fewer days spent in train stations and on 3 or 4 hour train rides. Less time moving-in and packing-up. Sometimes less is more.

For others, there are so many places that one needs to go.

Happy Anniversary. Buon Viagge.

In my opinion (which is worth what you paid for it), you are planning way, way too much for the time available. I'm exhausted just reading about it.

The amount of time "lost" getting from one place to another will be a big part of the trip. The short stays in many locations will not give you nearly as much time to explore the area as you think.

You want to return with good memories of good food, good wine, people, and places you've seen and experienced. I'm afraid you will return with memories of train stations and landscapes whizzing by the window. And if you are driving, you'll not even remember the landscapes.

An anniversary trip is definitely one where perhaps less is more.

Sorry to be so harsh. I really don't mean to rain on your parade, just offering food for thought. Apologies if I've stepped on your feelings, just trying to be honest.

I really want to thank everyone for the comments. I am putting together spreadsheet on travel times which I need to put the worst case s for time. We keep hearing from people that you got to see Rome, Florence and Venice. Truthfully, I’ve always wanted to go to Lake Como. That’s why it’s on my list. So yeah I think we’re gonna cut something back here. It’s just a matter of what we want cut. As people that aren’t that interested in churches and seeing old buildings and more interested in smaller towns and good food and meeting locals, let me pose this question. The chopping block. Lake Como? Venice? Bologna? Cinque Terra,? Florence? Rome? Tuscany? I think Tuscany is a must. Interested in your comments and I’m also gonna look at the RS 17 day bus tour as suggested. Thanks again. DA

Garrett,
Lake Como is important to you, so keep that in. Cinque Terra is an outlier, IMO and very crowded and the opposite of relaxing. Venice is a city for lovers, so keep that since it is an anniversary trip. Tuscany has several towns to relax, explore and enjoy. "Choose your own adventure" there. Personally I could spend three months in Rome, but that is me. So how about this....? Fly into Venice, sleep four nights (3 full days). Then to Tuscany for 6 nights (5 full days..pick your towns), maybe end in Florence. Train to Milan, for change to Lake Como and spend next 4 nights (3 full days) at Lake Como, then back to Milan for 2 nights (1 full day), and fly home from Milan. That is 16 nights with 3 change of location days (Venice to Tuscany, Tuscany to Lake Como, Lake Como to Milan. You will have an extra day to add to a location.
Remember, day 1 is arrival day and day 18 is departure day, minus 3 relocation days, that leaves 13 full days of fun and relaxation. Your relocation days may take only a half day to move, so there is extra time on those days. And of course you may wish to swap out one location for another one that I didn't mention. Use your own priorities. Try to make your plans calculating relocation time and see if that helps with your planning. Best of luck!

Sounds like a wonderful trip. Just remember this is your first trip. You will be back again when you fall in love with Italy. Everyone's travel style is different----some want to click off every town possible and others want to savor the true experience of the Italian culture. We have been to Italy 3 times and we still have not made it to Venice! Yes, it's on our bucket list but it was more important to us to actually enjoy the people, ambiance and culture of where we were. You have gotten some great advise-----just try and slow down the pace of the trip and you will be great!

Thank you, Judy and New, Nona and everyone else for your comments. It definitely has us talking and thinking.

There are so many places in Italy I want to return to and go for the first time. We have been 5 times I think. I have never been to Lake Como, but it seems to be high on your interest, so go. We didn't go to Rome until our 3rd trip and have never been to Venice. We have stayed,. in Pienza twice. Yes it is small, but very friendly and easy to go around to other towns in Val d' Orcia. The only thing we did in Cinque Terre was hike between two towns and that was worth it. he first town we stayed in in Italy was Lucca. I highly recommend Lucca. So with that said I would keep your 3 nights in Rome, 3 nights in Pienza. We took the fast train from Florence to Milan on our first trip though just to get to the airport. You could go to Lake Como from there. You also might look into Lake Garda. It isn't as internationally known as Como, but really beautiful. I would stay 3 nights minimum in all your stops. I didn't mention Florence and Venice, but you could stay there 3 nights each. As I suggested you could stay in Lucca for three as it is an easy train to La Spezia and Cinque Terre as well as Pisa. Happy anniversary. We are going back with family for my 80th and our 50th wedding anniversary. we will be hiking between towns in Cinque Terre again.

Sometimes I think the true hardest part of planning a trip somewhere (particularly the first trip) is learning how to balance all the recommendations and advice with what you actually really want to see and plan the trip for who you are.

I'm not sure this will help, but keep in mind that it is literally not possible to see everything anyhow. Any of these places will have things you can't squeeze in, and that's OK. (I think this is why Rick Steves says always assume you will be back- I think it's to help deal with the FOMO and trying to do too much.)

Considering how many very, very, old things there are in Italy, I think it's fairly safe to assume that they'll still be there later on when you want to come back. 😄

You've already said Lake Como is a must for you. What's the must for your wife? Start there, pick the two places that really matter to both of you and flesh it out from there. This is your anniversary trip, it's all about you.

If it's Rome and Lake Como, maybe you don't need to go to Cinque Terre- both are crowded areas with beautiful hilly towns and a body of water. (Very loose comparison, granted) If it's Tuscany for her and Lake Como for you, maybe skip the biggest city, which is Rome. Maybe you want to spend some time in a bigger city like Rome and then relax in an agriturisimo or a deluxe lakeside hotel (or both) and just eat food and drink great wine, maybe do a day trip to see Florence or Bologna, that works too.

I love all the replies and the advice. At the end of the day, I know it’s our decision, but that’s why we started early to take all this in from people who are knowledgeable travelelers. I really enjoyed today’s post from the lady who is going back to hike Cinque Terra to hike at 80 yrs. old and in her 50th and the other advice of each picking one place and “fleshing it out from there” We do feel some pressure from friends and family aboutthe big 3. Rome, Florence and Venice. I get that but “our Italy” is outside of the cities and really centers around the stove, the people, the wine and the land. That’s why we decided to skip a cruise, too many people coming into a place at the same time. Thanks again always look forward to more comment.

We do feel some pressure from friends and family aboutthe big 3. Rome,
Florence and Venice.

I'm just curious... is the pressure for the big 3 from people who have traveled to Italy or people who have not traveled to Italy?

A female friend and I did this 3-week trip about a decade ago: Arrive Rome and immediate train to Orvieto for one night --> outside Siena in an agriturismo 4 nights --> Florence 3 nights --> Lake Garda 3 nights --> Venice 3 nights --> Amalfi Coast 4 nights --> Rome 3 nights. (Venice to Amalfi Coast was purposefully planned so Dave the aviation geek could fly on easyjet [Venice to Naples] for the first time 🙂).

We alternated small locale and big city (Amalfi Coast lodging was in the village of Nocelle that had a population of something like 168). The cities were cool, but we both liked the more chill smaller locales the best.

One more thought... I think the reason the chill smaller locales were better liked was exemplified by this story...

We arrived in Orvieto. We stayed in a "religious house of hospitality" (former nunnery or something like that that still had a religious purpose). I entered my room in a building built in 1580. The window was open. A gentle breeze was blowing in the window. I could hear the sounds of kids speaking Italian and laughing while playing soccer and other games beneath my window. It was a moment of total relaxation as the thought of, "Ahhhhhh... I'm in Italy" ran through my head. Those moments came much more commonly in smaller locales than in the busy big cities.

I have the sense those are the kinds of moments you are looking for...

Follow your heart!

Thanks for your thoughts. Most of the pressure of the big three comes from my father-in-law who spend Italy and some friends who’ve been there. There’s also always the echo chamber of people who haven’t been there. But I’m sort of with you, what you describe us really what we are looking for this trip. We used to travel quite a bit up until 2016 and then I got cancer, dialysis for four years, a kidney transplant so things sort of stopped. I’m doing great now and looking forward to getting back to traveling and just feeling like a” normal person again”. So yes, small towns is more our thing. But from everything I’m learning from this group we are going to do everything we can like from airports or train terminals to our hotels by taking private transportation, which will should alleviate some of the stress in those areas. And then really only do a few big things in the big cities if we do go. Such as Rome Colosseum and Forum, Vatican, Sistine Chapel. Just celebrating not only our 25th but a celebration of being alive still. So very excited to go and leave some stress behind for a little bit. Thanks again for your input. I really appreciate it.

Glad you are a survivor. Glad you and your spouse get to do this trip. Even more reason to follow your heart.

It does seem like a lot and that can be stressful. We flew into Milan, rented a car and drove to Lake Como, then dropped the car in Venice. (Really could do this with public transport and not rent a car!). Then we took a train to Rome, train to Cinque Terra, train to Florence, rented car and stayed in Tuscany a few nights. We drove the car back to Milan airport and flew home from there. A highlight for us was that we stopped in Verona for our last night and had tickets for the opera there---it's a great venue! It was an easy drive back to Milan the next day.

Thank you. I hear Verona is beautiful and also Lake Gardo.

I love your story and I love that you are planning this trip. I hope you have a wonderful time. You certainly deserve it with all you’ve been through.

Based on what you’ve said, I think you should skip Rome. You aren’t into old buildings and churches and it’s bit of an outlier. It’s big and crowded and hectic. There is no reason to go. I would also skip Cinque Terre since it’s kind of a pain to get to and also crowded. Florence? I think you can skip that too, but you’ll be in Tuscany, so you could give it a little time. I did it as a day trip from Siena and that was plenty for me.

I actually think Judy had the perfect itinerary that best matches your situation and interests.

Please don’t listen to your father-in-law unless you have the same interests as he does, which it sounds like you do not. What was a great trip for him may not be a great trip for you. After all you’ve been through, I think a slower pace and smaller towns would be ideal. Wishing you continued good health and happy travels.

Thanks. Good advice. Luckily we have time to marinate on all these ideas and input. Seeking peace not hectic.