Table for Two in Tuscany: Romantic Itinerary for Places to Eat, Stay, Drink & Explore
Last Updated on August 30, 2023.
Tuscany is not in a hurry.
Arguably the most famous region in Italy – and yes, we say arguably because Italians have very, very strong opinions – Tuscany is steeped in history, culture, and beauty. From the art and jewelry left by the Etruscans to gems of the Renaissance to works by present-day artisans, Tuscany lets us know that it’s time to slow down and take it all in.
And that is why it’s the perfect place for a romantic getaway.
- Hotels, Dining and Shopping Experiences in Florence
- On To Siena: Exquisite Hotels, Restaurants & More
- Moving on to Monteriggioni
- Final Stop: San Gimignano
- Book The Trip
Let’s be honest: if we’re away with our significant other, do we want to be racing around on frenzied tours that cram as many sites as possible in a day or two? Of course not. We want time to linger, to take in the sweeping vistas, to savor a glass of wine with a magnificent meal, and to wander ancient alleyways until we’re lost. In other words, we want to be in Tuscany.
To start our getaway, let’s begin in Florence. Florence is remarkable in so many ways but one thing that stands out immediately is how small and intimate it feels despite being a perpetually hot tourist destination. It’s very easy to get out of the crowds simply by turning down a side street, but it’s difficult to get too lost because Il Duomo stands as a reference point.
We could list all the incredible sites in Florence – really, David is even more impressive in person – but we’re going to focus on food, wine, and delightful little shops.
Depending on your mood or your budget, we’ve got you covered from all angles. Enjoy an opulent dinner at the Four Seasons, or relax and have a casual aperitivo at some of our favorite wine bars. You can visit all of the stops below in a self-guided fashion, or if you’d prefer a locally guided experience, book a sunset food tour with Eating Europe or taste the flavors of Florence With Locals.
Le Volpi d L’Uva
Piazza dei Rossi, 1
Nestled in a small side street, Le Volpi e L’Uva is a wine lovers haven. Explore what is currently being poured or take time to comb the racks for impressive finds. Perpetually humming with activity, grab a seat at the bar and order some bites – everything is delicious, even the crostini.
Four Seasons Florence
Borgo Pinit, 99
Is there really a need to send people to the Four Seasons? It kind of sells itself, right? While that may be true, The Four Seasons in Florence is elegant and lush with exquisite attention to detail. It’s a must for an afternoon aperitivo before secreting away back to the hotel for a “nap.”
Casa del Vino
Via dell’Ariento, 16r
Casa Del Vino is the sort of the anti-Four Seasons: it’s bustling with workers on lunch break who seem to be in no rush to get back to work. Grab a glass of wine and a crostini – which are so simple and so delicious – and wedge in somewhere. The people-watching is fantastic.
Via dell’Oche, 11R
For a more serious wine-centric dinner, it’s hard to go wrong at Coquinarius. The down-to-earth décor is balanced by a fabulous wine list with some esoteric gems nestled in. (Blanc de Morgex, anyone?) Even a simple meal of just a dish or two – though it’s absolutely worth exploring every course – will have you here for hours on end.
Via dei Conti, 8r
That said, if you’d like to plan one stellar, lowkey meal while you’re in Florence, Konnubio is it. The décor abounds with greenery and lowlighting, providing a soothing, elegant feel. The perfect table for two allows just enough privacy but still provides peeking views of the restaurant.
The menu is Italian with a twist: interesting ingredients provide delightful flavor combinations. The attentive staff will ask the right questions to provide exacting wine pairings as well. From front to finish, Konnubio is a memorable experience.
Borgo Santa Croce, 6
Since you’re in Florence, you may as well dip into some decadence, and AquaFlor is the place to do it. Located just steps from Piazza Santa Croce, AquaFlor is an artisanal perfumery settled along an ancient street once known for such perfume houses. The well-versed staff will ask a few questions about your fragrance preferences and will recommend a few to try. Each scent is unique to AquaFlor and are quite different from each other. This is the place to find a new signature scent.
Volterrani & Raddi
Piazza del Pesce, 7r
Volterrani & Raddi is steps from Ponte Vecchio and its many jewelers jockeying for the attention of ambling tourists. And just being steps away is a good thing because it’s a much more serene environment. Established in 1870, Volterrani & Raddi is still family owned and operated. The jewelry here is more understated than most along Ponte Vecchio and you’ll want to secure a little Florentine gem of your own.
Il Tamarino Stampe d’Arte
Via del Moro 46r
Il Tamarino Stampe d’Arte is a throwback to another era when Florence was the creative hub of Europe. The workshop produces a range of etchings using a technique from the 1500s. If you’re an art lover, this is the perfect place to find prints of Florence itself, or of something a little more fanciful, like botanicals.
Via Maggio and Via del Giglio
Via Maggio and Via del Giglio are both worth exploring. Antique shops and vintage clothing stores are clustered along each and hold some delightful treasures. And since Italy holds some of the top couture houses, expect to find a few vintage gems.
Piazza di Santa Trinita, 5r
Salvatore Ferragamo might not be the first museum that springs to mind when in Florence but since we’re indulging the senses, let’s take a dive into silk and fashion. There is a museum housed in the basement that explores the history of the fashion mogul. Exhibits change frequently and can range from an exhaustive collection of silk scarves to homages to previous industry icons.
Boboli Gardens, like David and the Uffizi Gallery, certainly isn’t unknown but it’s a must for a romantic rendezvous. It’s the perfect mix of nature-made floral beauty and man-made architecture wonder. It’s easy to lose a few hours there soaking it all in.
But we don’t want to just stay in a major city, do we? Let’s make the most of Tuscany by peeling off and venturing out into the countryside to smaller cities and towns that are impossibly breathtaking. Siena is about an hour south of Florence by car, but the ride seems to go much more quickly because the views are so beautiful. Rent a car ahead of time here.
Siena really transports us back to ancient times, with narrow stone streets and alleyways that wind around the many churches and cathedrals. Keep an eye out for artists painting the sweeping vistas en plein air.
Villa del Sole
Via del Sole, 6A
Siena can be a day trip from Florence but to really slow down and steep the senses, stay at least a night or two. Villa del Sole B&B is a gorgeous way to decompress and relax into vacation mode. And why bother getting up and out early when you can have breakfast on the stunning terrace? As with most places in Tuscany, it’s hard to get a bad meal here so deciding on where to eat really comes down to what kind of mood you’re in.
At Villa del Sole, the on-site restaurant Tar-tufo is exquisite and offers extensive wine choices. (Don’t worry – despite the name, there are plenty of non-truffle dishes available as well).
Gran Hotel Continental
Via Banchi di Spora, 85
Gran Hotel Continental is almost too beautiful for words. Staying here will immediately transport you to the days of opulent royalty. Channel your inner duke or duchess as you lounge in the lobby under gilded ceilings and chandeliers. Thankfully, this isn’t all fluff: the service and services are outstanding. Feel free to stay here for your entire stay in Siena and you won’t be disappointed.
La Taverna di San Giuseppe
Via Giovanni Duprè, 132
La Taverna di San Giuseppe is an experience. Located in an older cellar carved out of the ground, La Taverna di San Giuseppe is everything you would want as a quintessential Tuscan meal: classic dishes with the best ingredients, and the perfect local wine list to match – though if you really want to off-road and drink non-Italian wines, they have those too.
La Bottega dei Sapori Antichi
Via delle Terme, 39
If you’d rather just grab an armful of goodies for a picnic or an in-room nibble, La Bottega dei Sapori Antichi has everything you’d want and then some. Try some pecorinos of different ages along with a variety of olives, bread, and cured meats. The wine selection is also impressive and makes this a must-stop.
Panificio Il Magnifico Siena
Via dei Pellegrini, 27
Finally, you can’t be in Tuscany without trying some local goodies – it’s just not allowed. Panificio Il Magnifico Siena has an array of biscuits and pastries, including their delicious take on panpepato, a spiced confection that’s not overly sweet at all. Be sure to buy a wedge to take with you.
After we’ve gotten our fill of wandering around Siena – if that’s even possible – let’s head to Monteriggioni. Make sure to be good and hungry because we can linger over an epic lunch here for hours. A tiny little outcrop pretty high up, the views are just as impeccable as the food.
Osteria Antico Travaglio
Piazza Roma, 6a
Osteria Antico Travaglio never fails to delight, from start to finish. Everything is absolutely delicious but our favorites are the freshly fried artichokes (when in season, of course!), parpadelle with wild boar ragu, ravioli with truffles, and osso buco with chicory. Try a glass of Vernacchi de San Gimignano to sip as you slow down and taste your way through culinary heaven. Don’t skip a digestive: amaro del cappo.
Via Primo Maggio, 4
Monteriggioni is small and quiet, so there’s not a whole ton to do here. It is, however, the perfect place to linger poolside and doze in the sun. Hotel Monteriggioni is where you should do just that, with a pool and a hot tub side-by-side on the beautiful grounds. Spend the night and wake up late to have breakfast either in the dining room or in your own room before heading out to explore more of Tuscany.
San Gimignano is our last stop, and we could wax on about what a beautiful ancient city this is but that can be said about almost everywhere in Tuscany. So instead, we’ll focus on the towers: make sure to climb up whatever you can to be able to take in the views. They’re stunning.
Vegan Agrivilla I Pini
Località Santa Margherita, 37
Since San Gimignano is the last stop on our idle exploration of Tuscany, let Vegan Agrivilla I Pini be our last hotel. Don’t let the Vegan title scare you off – this place is the exact bed and breakfast nestled in among grapevines that you’ve been wanting. Adamantly farm-to-table, the restaurant here is as spectacular as the rooms and the environs. And since it’s only about a mile from town, it’s entirely possible to stay here and just amble into town as needed.
Via San Matteo, 87
However, if you’d prefer to stay right in town and skip the ambling, L’Antico Pozzo is it. Elegant, comfortable rooms offer peace and grace right off the street. Dining options are just as elegant with ample breakfast options and an exquisite bar in the wine cellar.
Piazza della Cisterna, 4
San Gimignano is home to Gelateria Dondoli, one of the most renowned gelaterias in all of Italy. If there’s a line out the door, we assure you it’s worth the wait. And while you can play it safe with flavors like lemon or pistachio, go for one of their signatures: crema di santa fina, which is a saffron and pine nut gelato that is utterly divine.
Profumeria Divina Toscana
Via S. Giovanni, 31
Like most Tuscan towns, San Gimignano is lined with shops for all sorts of trinkets. For fellow perfume lovers, check out Profumeria Divina Toscana for Italian-made scents you might not be able to find back home. And doesn’t everyone want the scent that transports them back to Tuscany?
La Vecchia Nicchia
Via San Marino, 12
For food, consider La Vecchia Nicchia for a taste of local flavor. It’s decidedly unfussy but the simple and tasty options make the perfect lunch. If you’re not quite that hungry, grab some wine and cheese to experience local flavors at the finest. That’s why you’re here, after all.
Via Capassi, 16
And finally, we come to Ristorante Perucà located in a cellar in San Gimignano. With a small, focused menu, Perucà brings the best of Tuscany on its plates. And of course, the wine list is fantastic but do yourself a favor and ask your server to pair your wines to you dishes. You’ll be oh-so-happy you did.
Book The Trip
We’ve clearly only scratched the surface of all that there is in Tuscany. It’s one of the many Italian regions that have captured our imaginations, and for good reason. However, if we’re looking to really unplug and spend time with our beloved surrounded by incredible food, art, and vistas, there’s nowhere better to be.
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