The Agenda: What to Do and How to Pack for a Vacation in Tuscany

From shoes that are vineyard-appropriate to a bathing suit that can go from the pool to cocktails, here's what to pack in your carry-on for a trip to Tuscany.

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(Image credit: Getty Images / Sally Holmes / Morgan McMullen)

Welcome to The Agenda. Each month a Marie Claire editor opens up their Outlook cal to share an event they're looking forward to in the next few weeks—and that chic, globe-trotting women like yourself may want to add to your own calendars. Here, exactly where to go, what to do, and how to pack for your next trip.

The official last day of summer isn’t until September 23, but August marks the end of the summeriest summer days (I haven’t been “back to school” for years, but seeing the sales advertised still gives me dread-stomach). That means this month is your last chance to take a real summer vacation. Before work ramps back up in September (hi, fashion week!), I want to fully embrace the laziness of the last lazy days of the season. For me, this translates to taking the ultimate treat-yourself-vacation: a trip to Tuscany.

There are a zillion fantastic destinations to visit in Italy, but Tuscany is a primo place to unplug in a beautiful setting. I'm planning to fill the hours I usually spend on Slack with wine, books, pasta, more pasta, and gorgeous landscapes. These are three can't-skip activities for travelers heading to the Tuscan countryside, plus what to wear during each.

1. Wine Tasting at a Vineyard

Tuscany - Places To Visit

(Image credit: Jim Dyson)

Wine is one of my absolute favorite things and really, what screams "vacation" more than a whole afternoon centered around vino? Tuscany is vineyard central, so wine-tasting is a must while you're staying in the region. Olive oil is also Tuscany's thing, so bonus points if you can find a spot that offers both.

Let's be serious, wine-tasting on a straight-from-a-postcard vineyard also, obviously, sets the stage for the ultimate Instagram moment, so dress accordingly. I'm planning to pack cute-but-practical shoes and a fun, printed dress that will stand out in a gorgeous field full of grapes. I'm going to avoid anything too form-fitting for any adventure that involves being outside (it's going to be sweaty!!) or any kind of pasta consumption, because comfort (and factoring in a little extra breathing room) is key.

What to Pack for Wine-Tasting in Tuscany

2. Dinner at COMO Castello Del Nero's La Torre

The real move is to stay a night (or three) at COMO Castello Del Nero, which houses La Torre, a Michelin-star restaurant helmed by Executive Chef Giovanni Luca Di Pirro. The hotel, which is situated on the top of a quintessentially picturesque Tuscan hill (I mean, there are cyprus trees lining the driveway), has a gorgeous outdoor pool and patio which really sets the scene for a late-afternoon swim followed by a poolside aperol spritz before dinner. I'm planning to park myself under an umbrella and alternate between catching up on my book club reading and dozing off in front of the view before ending the evening at La Torre. The restaurant prides itself on using local ingredients (some grown right on the property) to create inventive and flavor-packed Italian fare.

Italy is the chic capital of the world (that's a thing, right?), so I love the idea of really going for it from the get-go with a bold pool lewk that can double as a top for evening (economic packing!). I'm planning to up the ante with my dinner-dressing this trip and embrace a slightly sexier vibe than I do at home where I'm usually sporting a more casual, jeans-and-a-T-shirt outfit. When in Rome Tuscany, right?

What to Pack for Dinner at La Torre

3. Road-Tripping to Montepulciano


(Image credit: Bildagentur-online)

Sure, the idea of driving in a foreign country is a bit daunting, but renting a car and braving Tuscany's winding roads is really the best way to see the countryside. My favorite thing to do is pick a destination (usually a destination that involves food), and then make small detours along the way. I'm planning to put some killer Montepulciano restaurants into the GPS (Osteria del Conte is top on my list) and make strategic gelato scenic stops at spots like the walled city of Montalcino and the hot springs of Bagno Vignoni to take in the sites. A warning: You can't actually drive through most of Tuscany's historic cities (including Montepulciano), so you'll have to park the car and explore inside the city walls on foot.

Sneakers will be your best friend on this leg of the trip since there'll be hills and cobblestones aplenty. Another thing to consider is that many churches and cathedrals you might want to stop in to see require visitors to be dressed appropriately—meaning your shoulders and knees must be covered. Since it's guaranteed to be next-level hot in August, I'm planning to wear breezy, midi-length skirts and dresses, plus carry a light cardigan or shawl in my bag to throw on for more modest moments.

What to Pack for a Road Trip in Tuscany

Sally Holmes

Sally is the Editor in Chief of Marie Claire where she oversees coverage of all the things the Marie Claire reader wants to know about, including politics, beauty, fashion, and celebs. Holmes has been with Marie Claire for five years, overseeing all content for the brand’s website and social platforms. She joined Marie Claire from, where she worked for four years, first as Senior Editor running all news content and finally as Executive Editor. Before that, Sally was at's the Cut and graduated with an English major from Boston College.