5 Best Places to Visit in Italy in October

1. Tuscany

Tuscany is on every list for harvest season and while typically I suggest you avoid popular places at popular times, there's a real obvious reason I kept this one here. Just know that Tuscany isn't one specific place but an entire region in Italy.

September and October is when the grapes are harvested from the vines. Please be aware that the exact date for harvest depends on that year's weather so there's no hard and fast deadline here.

It's the most "exciting" time to visit wineries and see the behind-the-scenes work that goes into producing your favorite wines. You can expect pleasant weather and be able to spend more time outdoors than you can here in the summer (if you don't know, the summers in Central Italy are brutally hot).

The Tuscan countryside is huge and encompasses a lot of small towns and even the city of Florence. Personally, I prefer the towns and the natural beauty of Tuscany more than it's capital city, Florence.

If you want a more local experience, I recommend you stay at an agriturismo instead of one of the big vineyards. This will show you a more farm-to-table experience rather than mass production. It's also a good way to find fewer crowds while still enjoying fall in Tuscany.

To really enjoy the region, I highly recommend you rent a car. The easiest option would be to rent from Florence or wherever you fly into the country. A general note for driving in Italy: if you plan to stay in cities or towns that have decent train stations, I'd skip the car. To see more nature and small towns, like what you can expect from Tuscany, a car is indispensable.

Where to Stay in Tuscany

We've only ever stayed in one agriturismo in Tuscany but it was a 10/10 experience for us. L’oasi di Cice is a small bed and breakfast in Rufina that offers a nice tranquil stay and some very delicious food.

Other areas to consider in Tuscany include:

• Siena
• Lucca
• Montefioralle

Side note, if you end up around Montefioralle, I highly recommend a meal at I'Desìo Ristorante. You'll definitely want to make a reservation. Know that it's a price per person and they serve what they make that day - no menu required!

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2. Collio

Collio is another wine region but one that's far less known than famous Tuscany. Collio stretches from northern Italy across the Slovenian border. It's about an hour drive north from Trieste, where Raf and I live.

Like Tuscany, Collio is easier to explore when you rent a car. The easiest place to rent a car in the area is from the Trieste Airport.

Although you can enjoy wine tastings throughout the year in this area, just like in Tuscany, you can experience the grape harvest and see picturesque vineyards at their prime in the fall.

Collio is full of small towns and rolling hills. It's really a quiet area and best for those that want a true getaway and to not see many other foreign tourists around. Even within Italy, Collio isn't super well known.

Where to Stay in Collio

I'd also recommend staying at an agriturismo or at one of the region's vineyards. If you prefer a bigger town with more to do and to just make a day trip or two to a winery, I'd suggest Gorizia. This, alongside Nova Gorica on the Slovenian side of the border, are the shared capitals of culture in Europe for 2025. Udine is another option but slightly farther from most of the vineyards.

Prefer to stay in Gorizia to be able to visit more wineries during your trip? I recommend:

• Budget Stay: TORTORELLA Apartments: These apartments are essentially right in the middle of both towns, ideal for those that want to walk the entire weekend.
• Mid-Tier Stay: Sottocastello 3: This is another option in a similar area as the budget option above.
• Luxury Stay: Residenza al Parco: This is a great choice for those that drove since you'll get free parking here. It's also a bigger space and has a small garden to start your day slowly.

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3. Reggio Emilia

Reggio Emilia is one of my favorite small towns in Italy that I've visited this year. If you've been following along with us, you know we've spent a lot of time in Emilia Romagna for one reason or another. During one of our trips we stayed in Modena for a week.

On a whim, I took a day trip to Reggio Emilia from Modena. And I'm so glad that I did. Personally, it gets my vote over far more famous and busier Parma. Compared to Modena, I'd say it's like the city's little sister.

The historic center of Reggio Emilia is full of charm, bustling alleyways, local shops, and delicious restaurants. And the best part? Most people focus their attention on Bologna, Modena, or Parma, and skip over Reggio Emilia.

I assumed this would mean the city is quiet but, at least when I visited, it was lively and had a fantastic atmosphere surrounding it. You can expect to see more Italians than foreign tourists and enjoy more of a day-to-day ambiance, rather than only seeing people on vacation.

Here's how I would plan the ideal day trip to Reggio Emilia.

Where to Stay in Reggio Emilia

Want more time here than just a day? I'll be honest, the historic center is far nicer than the outskirts so if budget allows, I would recommend you stay as central as possible.

I recommend a stay at:

• Budget Stay: Student's Hostel Della Ghiara: There's a really nice shared area and garden, perfect if you're traveling with kids that need some extra space to run and play.
• Mid-Tier Stay: Hotel Posta: This hotel is right in the center of town, just steps from Piazza Prampolini in a historic building. You can choose from a variety of room types.
• Luxury Stay: Loft of Love: Also located right in the center, this one-bedroom apartment is unlike any you've stayed in before. The ceiling is a work of art and really unique.

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4. Milan

I'm not a big city girlie but do love a weekend or so in one. Personally, I don't understand why people flock to cities in the summer months. The temperatures are hotter here than on the coast or in the mountains and more people are off work and out and about. Yes, there's a bit more vibrancy and things to do but, personally I find cities way more enjoyable any other time of the year.

So this is as good a time as any to pay a little visit to Milan.

Just know that Milan is really big and can be quite spread out. I know it can be tempting to just spend a few hours here, visiting the Duomo and little else, but really there's a lot more to Italy's most cosmopolitan corner than just that.

Wander the streets, pop into small shops, and enjoy the international food that's pretty hard to find in other areas. According to local friends, the best neighborhood to get a sense of daily life in Milan is Navigli. Head this way for an aperitivo to see a different side to the famous city.

As a bonus, from Milan you can get to almost anywhere in the country. Milano Centrale, the main train station, is huge and really well-connected. I'd suggest starting or ending your Italian trip here.

Where to Stay in Milan

Although it's a big city with a lot of unique areas, these recommendations will keep you relatively central to the things that brought you to the city:

• Budget Stay: Spiga 46 Suites: Enjoy having your own space at this small studio rental - just be sure to note that this one doesn't come with a kitchen.
• Mid-Tier Stay: Dream Suites Milano: For more space and nicer amenities, this one bedroom apartment can accommodate 4 guests.
• Luxury Stay: Grand Hotel et de Milan: Here you'll be in the heart of the shopping district and staying in a very chic hotel to fully round out your experience.

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5. Aeolian Islands

Last, but certainly not least, let's head down to the tip of southern Italy to the Aeolian Islands (Isole Eolie in Italian). For anyone that's still hoping to get in some beach time, this is the destination for you. While you can expect cooler temperatures than the summer heat brings, you'll likely still have good enough weather to enjoy the beaches.

Most say the weather is still warm enough for a dip in the sea but I think that'll depend on you and just how sunny the particular day is.

The Aeolian Islands are a cluster of 7 islands that sit off the coast of Calabria and Sicily. They're accessible by ferry from a few different ports but it'll really depend on which island you want to visit and where you're arriving from to decide on the best way to visit.

I'll be honest, we haven't yet been to the Aeolian Islands but they're high up on my wish list for 2026. The islands themselves are diverse, even if they're nearby one another, with black sand volcanic beaches next to verdant green landscapes. Regardless, the water is clear and refreshing.

Since the islands are harder to get to than Sicily or the not so far away Amalfi Coast, you can expect them to be less touristic. Some shops and restaurants might be closed for the season.

This article digs deep into the Aeolian Islands and how to best plan your trip there.

Where to Stay on the Aeolian Islands

From what I understand, it's a nice idea to either full island hop while here or pick one island and get to know it really well. I think that decision should come down to what type of traveler you are (for Raf and me, it'd be to pick 1 and explore thoroughly).

These recommendations stretch across 3 islands:

• Budget Stay: B&B Villa Maristella: Located on the southern tip of Lipari, this BnB is simple yet offers great views and a good bang for your buck.
• Mid-Tier Stay: Il Gabbiano Relais: I've heard a lot of good stuff about Stromboli, the island that this hotel is located on. The hotel itself offers private rooms, views, and an outdoor swimming pool.
• Luxury Stay: Therasia Resort Sea and Spa: Enjoy the luxury treatment on Vulcano at this impeccable resort. This is best for those that want to fully relax as you'll be tempted to spend most of your stay within the confines of the hotel.

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Weather in Italy in October

Italy is a big country when you think about how far it stretches from north to south. Given that, the weather can change quite a bit from the mountains of northern Italy to the beaches of southern Italy.

Regardless, the entire country gets 4 seasons, with the northern end receiving colder weather than the south. October is fall in Italy so you can expect cooler weather that's perfect to spend outdoors. Nighttime temperatures tend to dip quite a bit so you'll definitely want to pack a jacket or a sweater.

Note that many houses in Italy suffer from relatively poor insulation. This time of the year it's not uncommon for it to feel colder inside than it does outside. I'm currently fighting that in my own home in Trieste, where indoors is sweatshirt and sweatpants weather but I can still wear a t-shirt when I step outside. If the building you stay in has central heating, it most likely won't be turned on until November.

A rain jacket is never a bad idea but from my experience many hotels offer free umbrellas in case you want to leave the jacket at home.

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Where Will You Visit in Italy in October?

With stunning landscapes throughout the country, fewer tourists, and better weather (in my opinion), visiting Italy in October is a real treat. Although it might not be the ideal weather for a day spent swimming in the sea, it's a fantastic time to spend time outside and walk around the cities and towns you've been dreaming of.

My last piece of advice would be to do your best to not fill your trip with only the biggest and most famous sites in Italy. There are so many charming villages, small cities, and natural beauty spread in between that for a real Italian adventure you won't soon forget, you should get off the tourist trail, at least a bit!