Travel Advice: Italy Travel Itinerary

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I recently received an email from a reader named Charlie who is planning his first trip to Italy and looking for some itinerary advice.

Here is an excerpt:

Dear Vagabondress,

My wife and I are planning a trip to Italy the end of September and early October.  Our mission is 2 fold.  Attend a wedding of some dear friends of mine (Italian women, French man) on 9 Oct just outside of Milan and see some of the wonderful sights and history of Italy.   I can project about 10 days in Italy (2 other days to travel there and back) for a total of 12.

This is my 1st time to Italy and of course, I want to see it all, but due to time and $$$, I will not be able to see everything.  Should we just focus on a northern Italy adventure (Venice, Florence, Tuscany, …) or see as many cities as we can stand starting in Rome and making our way north to Milan?  The latter I’m not too crazy about, but I could do it if it were necessary.   We love to travel (long distance) but we would rather not pack up every day or night just so we can say we’ve been there.

We are considering flying into Milan from Wash Dc on arrive on 29th of Sept.   Travel to Florence (see below) same day to start our trip.

Day 1:  San Gimignano (stay here several nights as a base) and taking day trips in the region to….include Pisa, Lucca, Florence…?

Day 4 Venice:  2  days

Day 6 or 7 open at this time

We have to be in the Milan area by Friday, Oct 8th to meet up with the wedding party etc.

Since then, we’ve chatted a bit more, and he gave me some more details. Turns out he’s very open to Rome as well!

Here is my advice for you, Charlie:

1) Try not to leave out Rome! Rome is a fantastic city, and it would be a shame if your first trip to Italy didn’t include it.  Include at least two full days in Rome.  There are so many sites.

2) San Gimignano might not be the best base for you. It’s a beautiful Tuscan hill town, and the boar dishes are sublime, but it’s very far from other major destinations.  If you and your wife are renting a car, though, and don’t mind long distances, it could work.

Plot out the places in Tuscany that you’d like to visit.  (Hint: Pisa and Lucca can be done together. You don’t need much time in Pisa.)  Then find a town for your base that is in a relatively central location.

Personally, I would stay in Florence — the city center, natch — and take the train and bus to towns each day.  The trains are frequent and efficient — plus, you don’t want a car in central Florence!  I think this could work out nicely, since you could spend the morning at Florence museums like the Uffizi, then take off for an afternoon in a nearby Tuscan town.

3) Venice can be done in one day. I know I’ll get a lot of flak for this, and I do, but Venice is absolutely doable in one day, provided you leave early in the morning.  It’s a three-hour train journey from Florence.  Ideally, two days would be best.

Keep in mind that many final trains home from Venice leave in the late afternoon.

4) Don’t bother sightseeing in Milan. Get there in time for the wedding festivities, of course.  But compared to Rome, Florence, Venice and the hill towns of Tuscany, Milan doesn’t have many must-sees.  You’ve got precious little time; use it elsewhere.

Here’s my itinerary for you:

Weds 9/29: Fly to Rome in the evening.

Thurs 9/30: Arrive in Rome. Enjoy some light sightseeing.

Fri 10/1: Rome.

Sat 10/2: Split your day between Rome and the train to Florence.  Just make sure you arrive in time for a bistecca fiorentina!

Sun 10/3: Florence sightseeing.

Mon 10/4: Visit some Tuscan hill towns.  Return to Florence at night.

Tues 10/5: Visit more Tuscan hill towns.  Return to Florence at night.

Weds 10/6: Final day in Florence — use it however you’d like.

Thurs 10/7: Early train to Venice.  Sightseeing all day in Venice.

Fri 10/8: Train from Venice to Milan; arrive in time for the wedding festivities.

Sat 10/9: Wedding day in the village outside Milan.

Sun 10/10: Fly home.

Now, that’s with Florence as your Tuscan base.  You could alter this itinerary to have a base somewhere in Tuscany, but I’d recommend you spend the final night in Florence so that you can get an early train to Venice (likely via Bologna).

Just know this — this is a rushed itinerary.  You and your wife need to decide what would be best for the two of you — would you come back feeling like you needed a vacation to recover from your vacation?  Or would you feel terrible if you didn’t visit a certain destination?

If you feel like you’d rather cut a destination in favor of having a relaxing trip, read the guidebooks, do some research, and decide what’s best for you.  That’s because everyone, myself included, would give you a different opinion. But this is your vacation!

Good luck, Charlie!  Hope you enjoy your time in Italy.  May it be the first trip of many!

Have any advice? Where would you go if you had ten days in Italy? Please share!

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27 thoughts on “Travel Advice: Italy Travel Itinerary”

  1. I Have heard so much about Italy and all my friends visit there no a regular basis. A family member is getting married there next year and i can’t wait to go. I enjoyed the way you presented it.

  2. I love venice, I could spend weeks there. It’s true that you really need at least 2 or 3 days to get the most out of venice, but if you can only spare 1 day of your trip then it’s certainly still worthwhile.

  3. Kate, We’ll be staying in Florence for 15 days. We are flying into Peretola on Swiss and will take a taxi to the apartment we’ve rented which is about 1 1/2 miles from Ponte Vecchio. We are not renting a car. We are going to take a bus or the train everywhere. After reading your response to Charlie, we feel better about trying to visit Venice & Rome for just a day each (mainly because we’ve already paid for accommodations and don’t want to double up on that expense). Obviously, we don’t plan to see an awful lot in Venice & Rome, but we may never get back to Italy, so we at least want to say we saw those cities. We’re going to take the Walkabout Tour to Cinque Terre, and plan to do daytrips to Siena, Montepulciano, Fiesole (bus No. 7), San Gimignano, Greve in Chianti, Lucca and maybe, Cortona. We want to do a winery tour, but think those tours are really too expensive. We read info about a 15 Euro tour from Florence but that seems to be defunct. We plan to alternate day trip days with a day in Florence, but your idea about seeing a museum, etc in Florence in the morning and making a trip to a nearby town in the afternoon sounds like a good idea. Do you think our itinerary is too ambitious? Any suggestions? Thanks. -Barry

    1. Barry, I think basing yourself in Florence is a great idea, and much of your plan sounds good. Don’t try to visit ALL those Tuscan towns — might be a bit much. Cut out Cortona (too far/too touristy) and fit Lucca and Pisa into one day. Cinque Terre is quite a ways from Florence — there’s no way you can do it justice in a day. Two, minimum.

      1. Kate, Thanks for your response. I appreciate it. We’ll really be playing it by ear once we get there on Monday. Our plans are pretty fluid. We will try to spend a leisurely day in Lucca. Cortona isn’t a must see, either. Cinque Terre – well, we’re going on a tour (it’s paid for) for a long day. We’ll make the best of it. Counting down the days: 4. -Barry

  4. Hello,
    I need some help with an itinery in Italy. It will me my husband, my 23month old daughter, and I. However I will be leaving with my mom and daughter on the 8th feb and my husband will join on the 15th feb but then I leave on the 18th feb and they leave out on the 21st feb. We are going for pleasure with no time or entertainment constrain. This will be my husband, my daughter and my first time to Italy. My mom has been ther lots of times before. We are thinking about Florence, Rome, Naples, Venice and Pompee but not in that order. Can you help us create a plan on things to visit. My mom and daughter will be there for 12 days, my husband 6 days and myself 9days. PLEASE HELP IT WOULD BE GREATLY APPRECIATED… 😉

  5. While I agree with most of your good advice Kate, especially leaving out any sightseeing in Milan and the way you have arranged the trip – I’m going to be the one to give you grief about Venice 😉

    IMO, you can’t experience the magic of the city in only one day. I’d recommend slicing a day off of Florence and adding it to Venice or cutting it out altogether and returning when you can give it a proper visit 🙂

  6. Kate,

    My wife and I are going to Italy for first time the first 2 weeks of September. We have a wedding to attend just north of Milan on near the end of our trip..

    Looking for advice on how best to spend our time…..we want to enjoy the visit vs. trying to cram too much into the 14 days we plan on being there….we are not tourisy type folks….looking for unique food and lodging and romance.

    Appreciate your advice……M

    1. Hi, Mike — I no longer have the time to respond to requests like these for free; if you’d like an itinerary, email me (contact form at the top) and I can work out a rate. Either way, have fun in Italy!

    2. Hi mike my husband and I recently got married in northern Italy and spent 2 months on honeymoon.. I would love to help with your itinerary- I have so many great tips especially related to budget travel, and just started a blog dedicated to traveling. Check it out and feel free to email me with some details of your time and interests.. And hate my blogs please! Thanks 🙂 -jodi

  7. dear Kate,
    I have been invited for a family reunion at the Palazzo Mannocchi in Petritoli in July 2013.I will be travelling from Cyprus and I really need advice on the best way to get there, my husband doesn’t want to drive on the ‘wrong’ side of the road but if you think its the best solution i could try.We will probably land at Rome so what do you suggest?trains? buses ?driving?and where do we head for ,for the quickest and easiest route ?
    Hoping you can help.
    ps. we are in our 60’s

    1. Hi, Alison — without knowing much about you, I would suggest flying to Rome and renting a car. You’ll probably need to rent one at one point anyway to get to a village that small. Also, drive up to Umbria! You’ll love it! And you’re close!

      As for driving on the wrong side of the road, just talk him through it. Doing that with my boyfriend in Croatia next week!

  8. can’t believe you’re charging for travel tips?
    honestly people, go to thorn tree forum and you will find plenty of people who will help you for free.

    1. You bet I do. Considering the number of people emailing me asking for help every day — if I helped everyone who needed it, I wouldn’t have time for anything else.

  9. For the first time, I’m spending Christmas break away from family and friends since I started graduate schooling in Pavia a month ago. Please advice me of a good itinerary that will complement a stay in ROME from December 25 to Jan 1 (since a family adopted me for the holidays). I am on school break starting Dec 21st up to January 6.

    Thank you for your feedback.

  10. By the way, I hope by chance during your trip to Southeast Asia you spent some time in my beloved country — the Philippines!

    More power to you!

  11. Hi Kate

    Wish you every success and hope you continue with the good work. Be safe wherever you are.

    Really learnt a lot from you.

    I am doing a 3 city tour-Rome, Florence and Venice in March this year and I am gonna keep reading and researching places to visit, most of it in the Italian countryside.

    Kind regards


    1. Many thanks to Kate for the excellent advices.

      We even ate some of the things she suggested, folyatella(not the correct spelling) in Naples and ribolita in Pisa. Its a Tuscan dish.
      For Rome, we purchased a metro ticked just outside the main train station and you’ve got yourself a hop on hop off ride all around town taking you to most if not all the historical sites.
      For Florence, at the train station look for the day tours on the buses taking you to the Roman countryside like San Gimignano, Chianti and even to a guided tour in Sienna. I think that a part of Quantum of Solace was shot in the main square there.
      Venice is doable in a day or less. I hired a car and drove to Verona to hold Juliet just for good luck and then to Lake Garda (stunning) and then onto Milan (waste of time) but I wanted to see what the hype was about. # days in each city including a train to Orvietto (from Rome) and then another train to Naples and Sorrento.

      You don’t need to book in advance for anything. There’s plenty for everyone in Italy.
      For the Muslims out there, Europe’s largest mosque is in Rome and there’s plenty of halal food.

  12. Heya, Kate!
    So, I’m organising a group holiday (myself and six others) in Italy between August 8th and August 19th. We’re staying in Rome, and so far I’ve got a plan together that is the following:
    Saturday 8th – Travelling to Italy.
    Sunday 9th – Naples.
    Monday 10th – Pompeii.
    Tuesday 11th – chill out day in the villa we’re staying in (by a lake, soooo).
    Wednesday 12th – Rome (sightseeing).
    Thursday 13th – beach day, followed by dinner in Trastevere.
    Friday 14th – Vatican City.
    Saturday 15th – Rome (food tours).
    Sunday 16th – a day to fill with whatever we like, maybe going back to places we liked in previous wanders.
    Monday 17th and Tuesday 18th – Tuscany OR Pisa OR Florence.
    Wednesday 19th – Travelling home.

    Are there any changes you think I should make to the plan? And are there any places in each specific city/region you think we would we fools not to visit? Also, do you have any warnings/tips for travel specifically in Italy (we’ll be doing a lot of train journeys)?
    Whilst this is primarily a holiday, it is also something of a taster for me (I plan to travel Italy and Greece during my Gap Year next year).

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