A trip of a lifetime?

Not open for further replies.
Next September I would like to surprise my husband with a trip to Tuscany for his 40th birthday, a dream I've lived with for a few years now.
I remember visiting Tuscany with my parents as a teenager; the beautiful, undulating landscape, magical Volterra and an orange light (...maybe my dream has developed a patina over time).

I would love some suggestions for a romantic 10 day escape from our busy, hectic life with the children. I don't mind driving, although it would be nice not to have to drive for too long. I'd love to go to Florence too. Essentially we're culture vulture's and I cannot wait to share the experience of Tuscany; history, art, wine, food and relaxation.
10 days are perfect for a slow, romantic, relaxing vacation in Tuscany

Ciao Hopeless Romantic,

The trip you have been in mind sounds like it would be very romantic and the perfect way to celebrate your husband's birthday together. If he has yet to visit Florence and Tuscany, you can make this the perfect occasion to experience the region together.

My first piece of advice is to not try to do and see "everything" in those 10 days - take it slowly! You're planning a vacation so it should be relaxing :). You don't want to need a vacation from your vacation! :D
The most important thing about planning your trip is to get tickets to get here and decide where to stay during those 10 days. All the other details can be planned loosely - and I really recommend remaining flexible about what you do on any given day. If you look at past threads, there are many questions on the forum asking about seeing Tuscany in xx days which might be a good starting point for suggestions of must-see places.

Ten days are about the perfect amount of time to spend in Tuscany and experience it in the best of ways. 10 days can be perfectly divided into two parts, where I'd recommend spending 4-5 days in Florence as your base and the rest somewhere in Tuscany. In Florence, you don't need to worry about a car at all. Aside from the fact that driving in the area is restricted, the city center is actually very small and you can walk everywhere.

You can spend at least 3 days getting to see Florence - if you love history, art, wine and food then you won't have a problem in finding things to do here or in Tuscany. You might use one of your days based in Florence to take the train to Pisa and see the Leaning Tower - I also recommend visiting the baptistery, cathedral and cemetery there. Another day you might consider visiting Lucca as well, a charming town with Renaissance-era walls still standing and on which you can walk or bike ride on.

The other 5 days I'd recommend looking for a b&b or farmhouse to stay in the Tuscan countryside. Here I do recommend renting a car so that you are free to move around without problems. If you stay in the triangle area between San Gimignano - Florence - Siena you'll be really centrally located to be able to get to the main villages and towns in Chianti and Tuscany with at most an hour's drive. Definitely return to Volterra, it is one of our favorite places in Tuscany. Consider that most Tuscan roads are two lanes and 50km/h your max speed limit so driving can actually be a pleasure as you go through the gentle undulating hills and landscapes.

As you continue to read and plan your visit, let us know whether we can provide further suggestions or help. In the meantime, enjoy planning your trip - it sounds like it will be very special for the both of you :).
A romantic holiday in Tuscany

Dear Hopeless Romantic,

what a nice nickname :)! I think your husband will love his birthday's gift, who wouldn't.

In 10 days in Tuscany you can visit many things to "savor" it completely. Because of this I suggest you divide your holiday in small parts to have the time to visit the places where you are going to stay. I suggest the following suggestions for your romantic holiday:

Florence: 2 nights in the cradle of the Renaissance give you the opportunity to visit most of the famous places in the city. You can read more about Florence here. Quick tip: try to be at Piazzale Michelangelo at sunset...the panorama is breathtaking for a romantic kiss ;) and then walk down hand in hand to the Ponte Vecchio.

Chianti: 3 nights for experiencing Tuscan country life and wine tasting. You can read this article to find out some suggestions on wine tasting in Chianti. Quick tip: I suggest you stay in a farmhouse which offers both a comfortable atmosphere as well as the chance to be immersed in the quiet Tuscan countryside.

Siena: 1 night - Visit the beautiful Piazza del Campo and the Cathedral and taste the local specialty, Panforte. While you are driving to Siena you can also stop at San Gimignano a beautiful medieval town and at Monteriggioni a really unique walled castle.

Volterra: 1 night - Visit this beautiful city and admire its beautiful panorama.

Even though the Cinque Terre are not in Tuscany, you may consider visiting this particularly romantic destination but you need to plan at least a night spent there. It is easily accessible by train from Florence and you don't need a car to visit the 5 coastal towns - read more about the Cinque Terre and these past threads to learn more:
Otherwise, I recommend spending a few days in Maremma which I personally love.

I hope these suggestions help you. Don't hesitate to ask for additional recommendations. I hope you'll share with us how your holiday in Tuscany turns out :)
Last edited:
I'll give you one day:

Rent a car and drive to Grève in Chianti.
There, two winery I recommend.

During the day, visit Montefioralle and book a wine tasting at Azienda Montefioralle. A small family production that bottles an amazing Chianti Classico.

If you have time, you can visit Grève and it's oddly shaped Piazza and taste some wines at Le Cantine.

At night, book dinner at Castello Verrazano. They have a tour and dinner named It's Magic. you visit the castle and the cellars, have dinner and taste their wines.
It's expensive (52E/person) but it's excellent value.

This will allow you to visit both a small and a large Tuscan winery.

Thank you Lourdes, Valentina and Mathieu for your helpful suggestions.

I have reserved a room at a B&B in Castiglion Fiorentino, a weeks package. The place looks absolutely beautiful and it has fabulous reviews. If I could afford it I would hire an Alfa Romeo :cool:
I expect we will fly into Florence, either I will visit from the B&B or if we're lucky we'll stay there a night a two. The B&B has kindly arranged to organise advance museum tickets for us if we'd like.
I am also wary of trying cram in too much. I would very much like to go to Volterra and I believe Montepulciano is quite close by.

I do have another question. I have booked a room, however there is the option of an apartment. I am very aware that Brits are finding Italy very, very expensive at the moment so I am trying to keep that in mind. Would an apartment be a better option? I believe there is about 400 Euro's difference in the room and the apartment cost. Therefore if we self-catered for lunches and some evening meals would it be worthwhile? E.g if we took packed lunches out for day-trips instead of eating out in cafes/restaurants.

I am really hoping that with good planning I can make the most of our trip.

You're help is greatly appreciated. Thank you
I saved a lot of money booking an Agriturismo for a week.
However, you do need a car and you do spend more time travelling.
It really depends on what you want to see.
B&Bs are also much cheaper then hotels.
an apartment might be better but consider the difference in costs

If you've booked a room that only includes breakfast, then you will have to eat out lunch and dinner. A whole 10 days eating out adds up.
Generally per night a b&b or a farmhouse b&b costs less than a hotel... an apartment might cost a bit more but allow you to save on some meals so overall might turn up to be less.

If the apartment makes sense in the whole scheme of things (is it 400 euros for the whole week?), you can go to the local supermarket and get your own breakfast items and stuff for making packed lunches or a few simple dinners.

The truth is that while Italian and Tuscan food is delicious, you might find it tiring to eat out all the time. The apartment would give you at least the option of deciding to return back and rest and not head back out for dinner. Let's say for the day you head out and will be out all day. You can eat lunch out but return back to the b&b, rest and stay in for dinner. On another day you can instead pack a lunch and weather permiting - September usually is pretty good - find a park and enjoy a quiet picnic and then head out for dinner that night.

Castiglion Fiorentino is in southern Tuscany - you'll definitely need to rent a car. While you can get there from Florence by train (are you in the town or in the countryside?), to move around and go to Volterra and Montepulciano you'll need a car so factor that in as well.
Thank you very much.

Lourdes you have written exactly what I was thinking. Eating out all the time will be too much for a week, I'm hoping an apartment will be flexible and that eating economically will outweigh the more expensive apartment.
I am expecting to have to hire a car.
I'm now thinking that we could fly into Florence and stay a couple of days before our week in Castiglion Fiorentino. That way we it would save us the trip back into Florence and probably the cost of a train when we will already have a car, if that makes sense.
I'm guessing we could book museum tickets ahead to save on queuing?

Maybe I don't need to book a room in Florence yet but when would be too late?

Thanks for your nice information. These suggestions are very helpful. I agree with you. Tuscany is a romantic destination for Honeymooners. I am glad to know that your information of Tuscany is really wonderful. There are many cafes & restaurants for tourists. You can spent lifetime in Tuscany. It's an attractive place. I enjoy reading about your travels and the people that you meet. ;)
Not open for further replies.