Milan-Santa Margherita-Tuscany and back.... Are we crazy?


New member
Hello! This is my first time posting here- my husband and I are in the early stages of planning an early October trip to Italy- we only have one week (not including flight time) and were hoping to hit both the Ligurian coast as well as Tuscany- just not sure if that is do-able without losing our minds ;)

It is easiest time-wise/least connections and most affordable for us to fly into Milan, not Florence- we were considering renting a car from Milan, driving the Santa Margherita/anywhere else in CInque Terre or Liguria or close by, spend two days there, and then drive to Tuscany and rent a farmhouse for the remaining four days- fly back through Milan- is this totally insane?

We are am active couple in our 30s, no kids, and want to do some great hiking, wine tasting and eating- we usually prefer off-the-beaten-path areas (I know, CT is not necessarily off the beaten path, but our friends tell us we "have" to go) - we want to steam away from " mainstream areas" and don't care for museums, art, etc- just want to explore through hiking an authentic Italian experience of food, wine and culture

Any input is very much appreciated- we have ultimate flexibility and haven't really started planning anything

Elena - Florence Guide

Well-known member
Ciao Lisa!

Buongiorno from the Tuscan seaside! :) I was reading your post and thought....mmm a what young fit couple! :) Your plan looks intense but not insane. Being mum with kids and enjoying the slow traveling I may have some doubts about the schedule but considering that you are motivated and without can do it!!

I might just suggest you to tour the Cinque Terre by train which is much are probably used to drive on very large roads, not the typical ligurian narrow steep streets which may give you a hard time in touring or parking. TRAIN + HIKING is definitely the best way to enjoy the coast. October is still great also by boat, if the weather allows ferries to sail.

You may find interesting info & maps on the following sites:
(public transportation to be downloaded)
Useful web site in English about suggestions, how to tour around all year round

If you decide to spend one or two nights in Santa Margherita you may relax, get rid of the jet-leg and then start touring Tuscany by car. Once you leave Liguria to Tuscany I would suggest you to go and visit TELLARO, which is a tiny village not as known as the CINQUE TERRE villages. Tellaro is as colorful, as lovely as the famous Cinque Terre but more enchanted, located on the cliff.

Once in Tuscany, if you wish to avoid very tourist areas, you may stop in PIETRASANTA and in LUCCA. Lucca is wonderful, relaxing, full of art, great local flavours and quaint squares. I Would suggest to spend a night in the green surroundings of Lucca, full of peaceful olive tree fields and vines. Great spot to enjoy the Tuscan countryside and the noble Villas (like VILLA TORRIGIANI) spread in Lucca surroundings.

If you enjoy authentic food experiences then I suggest you a stop in Monsummano at one of the best chocolate makers (SLITTI) and maybe a stop for natural spas in Montecatini.

According to what you are chasing "off the beating tracks" I would suggest you a farmhouse in Lucca or an historic house like Villa il Paradisino out of Florence (I find it absolutely stunning and the host is a terrific cook). For any specific accommodation you may refer to:

Keep us posted on the preparation of your trip! You'll have a wonderful time in Tuscany,
all the best


The Tuscan Expert ;-)
Staff member
Ciao Lisa,

I don't think it's totally crazy - if you're flying into Milan, you'll be driving down the coast already toward Tuscany so you can definitely stop to do hiking in Cinque Terre.

We've hiked both the entire trail 5T along the coast from Monterosso to Riomaggiore in a day. So you could park the car in Monterosso, the flattest of the towns and easiest to drive to, hike down, stay the night in Riomaggiore, eating lunch and dinner along the way... we had lunch in Vernazza, dinner in Riomaggiore.
And the day after, if you're not completely wiped out, do the trail high up in the range above the 5T, at the crest... the coast one is the "busiest" with people, as you'd expect... then there is a middle one, which can be tough as there is more variation in elevation, and then the one at the very top of the ridge which is great, hardly anyone ever makes it up there. Of course, the toughest part is the first climb but then you're pretty much on the crest the entire time so elevation change is minimal. Plan for a picnic on that day - buy sandwiches and any other treats at a bakery and take them along, you'll have great views and a great day out! Plan to sleep in Monterosso that night and enjoy it the next in the morning before jumping back in the car and heading on further south.

If at any time you feel like skipping part of the trail, you can jump on the train like Elena suggested - the 5 towns are connected and trains take minutes ;-)
The toughest part of the trail along the coast is between Monterosso and Vernazza since you do have to go up a cliff and back down, big elevation change.... but the rest after Corniglia is pretty flat.

If you've never been to Florence before, I think you HAVE to make your way there even if it isn't really off any beaten path ;) October is a great month to visit, there are less crowds than the summer and the weather is pretty good. But if you don't want to stay in the city, how about just outside? That way you can head into Florence to see the city but still have the experience of the countryside - for example, Poderino is an apartment in the southern outskirts of Florence, near the road you take into Greve in Chianti... so it would be very easy to head down into Chianti for a day trip into this beautiful wine region.

If you'd prefer staying in Chianti and not as close to Florence (you could still do a day trip into the city), I'd also recommend Le Sante Marie residence in Impruneta or this apartment near San Gimignano. If you're interested in a very charming, romantic B&B experience, I'd suggest either
Villa il Poggiale or Palazzo Malaspina.

Ok hope these suggestions help your planning, let us know if you need more ideas or suggestions! ;-)