Ti Amo Italy! We avoided the scarring over-abundance of tourists in Rome/Venice and were generously rewarded by the quiet of the Tuscan countryside. Summers do get hot, but the dry fresh air make it bearable – nothing a glass of cold vino can’t fix. However it is not easy to rent an automatic drive vehicle, be sure to book well in advance (invest in a nice car, Italians drive fast). Life can’t get too hard when the biggest dilemma of the day is “how much more can I eat?” Enjoy the fresh produce and make those calories count!
Our route:
Rome -> Florence (via train) -> Montalcino -> Bolgheri -> Cinque Terre -> Modena
We did an aggressive 1000km of driving in 6 days, but if you had the luxury of a more leisurely schedule I would strongly suggest at least 2 days in each small town. This would give more buffer for day trips to other Tuscan icons Pisa, San Gimigiano, Sienna and Montepulciano. We technically wandered into Liguria (Cinque Terre) & Emilia-Romagna (Modena) in search of food and drink too… what a wonderful world of fresh produce! Would definitely return for a proper visit of Parma & Bologna.
<Florence>
The capital of Tuscany! Not a huge fan of tourist hubs but we had to make a stop for a proper Florentine steak. Do make an effort to buy tickets for all attractions online ahead of time as entrance to the Duomo and Uffizi is capped daily. Walking shoes are a must as the winding streets are still better navigated by foot (many car restrictions) and save your shopping for Rome airport (tax free) or a day trip to The Mall as the luxury brands were not very well stocked.
Food: Trattoria Mario is gaining popularity among tourists yet it retains a strong family run atmosphere. We ordered their signature Florentine Steak for 2 (1kg), requesting it to be done medium as their typical serve for locals is rather rare. Popular sides include the ribolita which is a Tuscan white bean bread stew (VERY filling), pork ragu pasta although I wish I had also ordered their simple grilled vegetables too. Two glasses of Chianti were the perfect pairing; the tannins were such a complement to the char on our steak! Do some shopping at the San Lorenzo Market, there are plenty of food souvenir stores you can stock up on herbs, vacuum packed porcini mushrooms, olive oils. Check out the 2/F large food court for a lunch on the go. Sadly failed to make reservations at Osteria delle Tre Panche (truffle), Osteria Vini Vecchi Sapori (pasta) as Italians are very particular about their summer holidays, we did a quiet meal at Savini Truffle Experience run by the best known truffle family in Tuscany. Best rendition was the tagliolini with delicate cream sauce – really lets the truffle shine. Diners also get a discount on their truffle products – I highly recommend their truffle raw peaches and truffle honey!
Hotels: Could not have picked a better place to stay. Relais Luce Florence is a small B&B in a historical apartment building with an old-school elevator. It was walking distance from the train station where we were coming from Rome, and served a wonderful breakfast on their terrace with a view of the Duomo. We chose a Superior Room for a bit more space.

Sights: The Duomo (although the Siena Duomo is more intricate inside), Santa Maria Novella, Ponte Vecchio. We also did a guided tour of the Uffuzi Gallery (the penultimate collection of Renaissance art) to skip the line and ensure we saw all the highlights (Primavera by Bottecelli is my absolute favourite).
Shopping: Stick with the Italian brands if shopping in the city. Gucci has a large store, but other European brands such as Chanel were poorly stocked. For souvenirs, drop by Dr Vranjes to shop for the intense diffusers – Rosso is their best selling scent. Make a trip to The Mall, it can be reached either by shuttle buses or car. We arrived at 11am and were still ahead of most crowds, although Gucci is constantly at least a 30-45min wait and would suggest to be strategic around that. 4-5h should be more than sufficient, Global Blue and Premier Tax Free both have offices there should you want to instantly process your refunds.
<Montalcino>
Home of the Brunello di Montalcino – what a cute town on a hill peppered with small enotecas and other food/wine experiences. Also a great base to explore nearby Montepulciano, or San Gimignano (medieval Manhattan) slightly further away. Tip: the inner town is pedestrian only, park at the meter parking opposite the fortezza or slightly further outside the city walls. Do ask if your hotel offers a parking rebate.
Hotels: There really is only one place you should stay in Montalcino, and that is at the rooms of Drogheria Franci. Franci own the best of everything in this town; the restaurant, glass store, organic foods stores. They also only have 3 rooms (1 used to be their Grandmother’s room) which have now been tastefully renovated and stocked with luxury amenities. It is a walk up (hope you don’t have too much luggage) but that is a small cost to stay right inside the old town when you are hoping to drink (and not drive). There are other agriturismo in the area for the winery experience if you are planning for a longer stay.
Food: Drogheria Franci also runs the best modern styled restaurant in town; def check out their wine cellar and order from their extensive wine list. Their breakfast spread was incredible with home baked tarts and pies served along with classic cold cuts. We had lunch at Re di Macchia which is an amazing hole in the wall with Nonna styled Tuscan classics. Known for their lasagne and ravioli but if we weren’t so full from breakfast we would definitely have also ordered their wild boar stew to pair with some Brunello. However I didn’t quite agree with raving online reviews about their tiramisu which felt too sweet. For a wine based meal and food on the side visit Enoteca Fortezza (more details in the separate Brunello vino journey).
Sights & Shopping: Stroll around town the small streets and find an al fresco trattoria or osteria for a spot of wine or espresso. I highly enjoyed shopping in the charming small stores, there is a perfumeria pharmacia stocked with boutique Italian brands. They sold the largest selection of Marvis toothpaste I have ever seen (and so much cheaper than in Asia), buy a couple of special edition flavours for a unique souvenir!
<Bolgheri>
Another wine lovers paradise~ We took the scenic route and drove up along the coast. Wind down your windows (or if you’re driving top down in a convertible) and immediately you feel a rush of humidity. The salty air begs for a visit to the beach! Would recommend 3 days here if you can afford the time to just kick back and relax with some vino.
Hotels: I didn’t want to leave! Relais Sant Elena would be the perfect backdrop for an intimate Tuscan wedding. Pictures alone cannot do this oasis justice. As tempting as it was to lie in bed, the scrumptious breakfast spread always drew me out. An array of freshly baked cakes, herbed eggs, cold cuts and bruschetta – it was hard keeping to less than 3 servings of anything… The pool is nothing short of incredible, with a view of the rolling hills and a sweet hot tub. While D took a soak, I preferred lying in the shade with a rich hot chocolate. They also make an excellent olive oil, if only I had room to bring it back in my luggage. It is technically located in Bibbona, a small seaside town 15 minutes from the wineries of Bolgheri. Sant Elena has a long private road placing you undisturbed within the golden fields, the perfect escape.

Food: You cannot go to Marina di Bibbona without a visit to La Pineta. Jokingly known as the Michelin starred beach shack, the carpark really does not build your expectations up for what a wonderful place it actually is. Run by a pair of twins, expect old school Italian glamour x beach resort. The wine BOOK was extensive and educational, with the good wine by the glass served by Coravin to ensure freshness. Totally blown away by the sage linguine with squid (al dente!), we also enjoyed the ricotta stuffed squash blossoms.
If you have arranged for a visit to Ornellaia, be sure to stop by Osteria Magona for lunch right after (just next door). Famous for its meats (although we preferred our Florentine steak at Mario’s), its a delightful setting with a huge wine store if you are keen to do some shopping before you leave.
Sights & Shopping: For the hot afternoons you aren’t taking a nap, visit the small town on Bolgheri for some gelato and its small souvenir stores. The enotecas were significantly marked up, but still worth a visit if you are keen on simple tastings. There is much more around Marina di Bibbona, would go there to soak in the laid back beach town atmosphere. Campgrounds available if that’s your thing!