Florence/ Tuscany/ Cinque Terre Itinerary

This looks overly ambitious, Heather.

You have one full day for Florence, birthplace of the Renaissance. Home to Michelangelo and his first teacher, Ghirlandaio, as well as Botticelli, Massaccio, Donatello, Fra Angelico, and many more - and sites of their art in a number of churches, the Medici home, the Pitti Palace, as well as three different museums, two of which will be crowded and will have long lines.

Then perhaps you have 24 hours, perhaps less for Lucca which is ok, but 24 hours or so for “Tuscany” makes no sense.

What does “Tuscany” mean to you?

A day and two nights for Cinque Terre worked for us in 2003. I am not sure how well it works with today’s crowds, though I suspect it’s doable. What’s changed is the need to get a reserved time slot for at least some trails which may or may not be “one way.”

Then off you go to Milan for perhaps 36 hours.

You merely have 7 full days (8 nights) in Italy plus two international travel days. Too little time for Florence plus Tuscany plus Cinque Terre plus Milan.

Consider instead

• 4 nights Florence
• 3 nights in Tuscany.
• 1 night Pisa or Florence. Fly home from Florence or Pisa through Milan (without seeing the city)

Or

• 3 nights Florence
• 1 or 2 nights Lucca or Pisa
• 2 or 3 nights CT
• Last night Pisa or Florence. Fly home from Florence or Pisa through Milan (without seeing the city.

FYI, the airport in Pisa is quite small and very near the city. We actually walked from our downtown Pisa hotel to the airport to catch an early morning flight to Milan and then a flight from Milan to Boston the same day, arriving at Logan in the afternoon.

Lucca is not a good base for Tuscany-too far north and west for the areas most want to visit in Tuscany

Consider Siena instead-take bus from Florence-quicker and better than train as it drops you up in town

4 locations with just 8 nights (=7 days) is not giving any location the time it deserves
Almost more time spent traveling than actually being somewhere

Italy is meant to be savored and enJOYed. You are doing too much. Florence needs a minimum of 3 FULL days and that is never enough. Florence is also in Tuscany, so what is it you want as far as Tuscany? Personally, I'd stay in Florence as long as you can and book some day trips into more of Tuscany - we have used WalkAboutFlorence - their BEST OF TUSCANY TOUR and their CHIANTI WINE & FOOD SAFARI TOUR - both great. RS also recommends Roberto for tours in his books.

CT is crazy crowded. And Milan is underwhelming to us compared to Florence and Venice. With the short amount of time you have, I'd focus on Florence w/day trips into Tuscany. If you want to add another location, I'd choose Venice, but it needs 2-3 Full days minimum. I'd take the train to Milan only to get home - go in ONE day before if you need. But Florence will be your highlight.

I suggest that you consider staying in Florence for all the time you would like to devote to Tuscany. There are so many organized tours that originate from there whether it be for a wine tour or to visit other Tuscan towns. There is also easy train and bus access for “do it yourself” day trips to Lucca, Sienna etc. it will save you a ton of time by not moving locations every day or two and I think you will find that Florence is fabulous on its own. There is so much to see, do and enjoy. I haven’t been in the Cinque Terre since 2013 and it was crowded then. I haven’t been back but I’m now going back to Florence for the fifth time!

An option to consider for this 8 night / 7 day trip is to stay in Florence, either in the thick of the Centro Storico or in the Oltrarno ('beyond the Arno') for 4 or 5 nights and pick any number of day trips: to Siena via morning 131R bus (~1.5 hrs ea way dependent on road traffic) and arrange for a private guide which while pricey is a terrific value for the experience; to Lucca by train (~1 hr 15 min) checking out this small city on your own and biking its wonderfully preserved ramparts (easily done in ~30 minutes, the flat path is only about 3 miles in length); to Pisa Centrale station by high speed train (just under an hr), strolling the less than a mile walk to the Campo dei Miracoli to get your Leaning Tower of Pisa pic and maybe even climb its 251 well worn marble steps; to elsewhere in Tuscany by taking either a joinable small group tour or a private tour by toursbyroberto.com, there are some really great choices on his site. Then high speed train it (just under 2 hrs) to Milan and spend your remaining 3 or 4 nights in the financial and fashion capital of Italy. If you feel up to braving the hordes both in town and on the trail for a short Cinque Terre stay you can train to Monterosso al Mare from Florence in 2.5 to 3 hrs with minimum 1 connection. Get your Italian Riviera fix at lightning speed during the absolute height of the season then train from Monterosso direct to Milan in 3 hours. I suggest discussing the pace you want to commit to, being prepared for hiccups that can wreak havoc on a tightly scheduled itinerary and go with an "I am in Italy and it's all golden" mindset to help you deal with the summer crowds you're gonna be sharing space with. I prefer fewer stops and a slower pace wherever I'm laying my head during anytime of the year but of course, this is your trip and you do you. I'd get on to looking for accommodations stat which may help make some decisions for you, depending on room availability and price. Have a great trip!

hey hey Heather C
have you been to italy before seeing you are a first time poster? who is "we" as how many people and are kids involved?
you are over planning way too much without much time to enjoy the towns/cities.
check-in times are 3-4pm and check-out times are 10-11am. spend more days in florence and take a train to lucca for the day, instead of constantly packing up, moving out, getting to train to travel again. florence is in tuscany, where were you hoping to go?
as ChinaLake67 mentions take a tour out of florence.
tuscan-wine-tours.com tuscanwinetour.com italyxp.com (day trips & excursions) bus to siena from florence
booking.com or incinqueterre.com
you pick the town that has hotels available with your dates, it's really evening first night full day 2nd day, then check out. there will be crowds, how many cruise ships in ports adds up to hundreds & hundreds, trains will be crowded, so many last minute getaways this summer, more to come plus you're right before USA labor day, lots of daytrippers, expect unexpected, train delays, crowded restaurants (many need reservations) with the crowds
check train schedules out of milan to airport (MXP) giving 3 hours for check in, immigration/passport.
have a great trip< enjoy, have a spritz and lots of gelato.
aloha