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Ultimate luxury Tuscany itinerary | Planning the perfect 5 days in Tuscany

Ultimate luxury Tuscany itinerary | Planning the perfect 5 days in Tuscany

Last Updated on November 13, 2023 by Eve Dawes

How to see all of the top things to do in just 5 days | Get the most out of your luxury vacation in Tuscany

Tuscany in 5 days is possible and allows you to see all of the major sights. If you’re looking for luxury Travel in Tuscany and luxury Tuscany tours these are some of my personal favorites. Including my favorite Michelin restaurant in Florence that’s right on the river. This was our luxury Tuscany itinerary for 5 days in Tuscany. Although it’s easily tweaked if you’re spending less time there, I’ll let you know what I think you can skip. In this Tuscany travel guide you’ll find everything you need to see, the best Tuscany restaurants, wineries to visit, things to see and tours to do for an elegant gourmet vacation. Including some lesser known local spots like Montecatini Terme.

Tuscany 5 day itinerary | Luxury travel

When my husband first said we needed 5 days in Tuscany to see it properly I thought he was mad. I’m used to doing a few days in one place and then moving on but he was right. Shhh, don’t tell him I said that!

Tuscany offers so much to see and is such a big area to cover (23,000 KM / 8,900 Miles sq). It can be hard to put together a sightseeing itinerary to make sure you’re not missing anything. From can’t miss towns and wineries, to luxury accommodations, luxury Tuscany tours and experiences of a lifetime they’re all in this blog post. This is what I think you should know before you go.

This Tuscany 5 day itinerary post contains affiliate links.

5 perfect days Tuscany Antinori Chianti Classico lunch wine tasting rooftop restaurant Rinuccio 1180Antinori Chianti Classico late lunch and wine tasting at rooftop restaurant Rinuccio 1180

How to start planning your Tuscany trip

When you’re trying to see Tuscany in 5 days, you’re best to choose a few things you really want to see so you’re not rushing around too much. Especially as the speed limit is so slow. Honestly, a few towns and a few wineries is good, you don’t need to try to see them all! In this Tuscany travel guide I’ll explain how we did so much in 5 perfect days in Tuscany and our itinerary.

The towns, while beautiful, are quite similar. They’re mainly walled hill top towns with similar tourist stores and you’re going to find great restaurants wherever you go. So pick a few from the list below that appeal to you and map the route. That way you’ll still be able to relax and soak everything in at a more Italian pace. As well as luxuriate over aperitifs and meals, and enjoy your hotel and each other too.

Tuscany was the starting point of our Italy vacation so we flew straight into the capital of Tuscany, Florence/Firenze. The region of Tuscany is located in central Italy. 

How to get around Tuscany

To experience the most of Tuscany in your own time I highly recommend hiring a car if you’re comfortable driving abroad and aren’t planning on drinking like a fish. With that being said, the police are really hot on speeding and there are tons of speed cameras so stick to the speed limit unless you want to come home to a ticket.

The Italian drivers speed, ignore that, and play it safe! We used Waze for our navigation as it’s brilliant at showing where the speed cameras are. Also, look out for ZTL Zones, Limited Traffic Zones (called Zona Traffico Limitato or ZTL in Italian) found in most major cities such as Florence and Pisa. These are no entry zones!

If you’re not planning on driving, there isn’t Uber or Lyft (2019) but your hotel can book taxi’s or private drivers for you.

Tuscany Luxury Hotel Recommendation

We did a lot of research on finding our accommodation. I knew I wanted to stay in castle and somewhere scenic. Although the names a bit deceptive and it’s not really a castle, we weren’t disappointed in this 5 star hotel. They also offer quite a few luxury Tuscany tours which we booked, more on those below but do not miss the Truffle hunting!

Como Castello Del Nero Tuscany

Dining in Tuscany | The Best Places to Eat & What to Avoid

When it comes to eating in Tuscany and finding the best restaurants there’s everything from Michelin restaurants to local gems. Just be sure to avoid the main piazzas to avoid the main tourist traps. Instead explore down narrow side streets or where looks packed with locals. If you’re booking a Michelin restaurant be sure to book well in advance!

Best Tuscany Restaurants For An Authentic Taste of Tuscany

One of the best restaurants in Tuscany, not just in my opinion but on all review sites is actually at the hotel we stayed at and I recommend: Como Castello Del Nero. So definitely add this to your Tuscany luxury travel itinerary. The hotel has 2 restaurants and I recommend both for 2 different reasons.

The first and the one they’re most famous for is La Torre Gourmand Restaurant, a Michelin star restaurant which is one of the best fine dining restaurants in Tuscany. Try to make a reservation to dine on the terrace with its beautiful views and not inside so you can experience the views. It’ll definitely be a highlight of your luxury Tuscany itinerary.

Book La Torre Gourmand restaurant.

Their other restaurant is La Taverna. A more casual dining option which serves estate-to-table authentic Tuscan lunch & dinner for a real taste of Tuscany. It’s also a great spot for a night cap and overlooks the rolling hills. You’ll also need reservations for this restaurant as it’s very intimate with very few tables.

Views Tuscany hills pool side restaurant Castello Del Nero Hotel Italy

La Locanda di Pietracupa, Madonna di Pietracupa

We ate here on the first night as I found it on Trip Advisor and it was only a 10 minute drive from the hotel. What a great way to start the vacation. We sat on the terrace and had the most amazing Tuscan food and service.

Since we wanted to try a lot of their menu we planned on sharing each course. We didn’t even ask them, they just served everything beautifully split between us. Don’t miss out on their great wines.

Food highlights: Steak tartare, truffle pasta with zucchini flower, steak & roast potatoes. Can you tell we like steak?!

Antica Scuderia, Val Di Pisa

Where do I start with Antica Scuderia? Located in the quaint town of Val Di Pisa with only 24 residents and a monastery, a 12 minute drive from the hotel. This place is amazing!!! We actually dined here at lunch time as part of our truffle hunting experience (the highlight of our trip, more about that above). Give yourself enough time to visit the wine shop a couple of doors down! Oh, and for a food coma nap afterwards.

La Torre Gourmand Restaurant, Michelin restaurant at Castello Del Nero hotel.

Try and dine on the terrace overlooking the Tuscan vineyards rather than inside which doesn’t have viewsI

Tuscany Travel Guide | Top Travel Tips

These are some travel tips a lot of other Tuscany travel guides won’t cover but are really good to know before you go.

SPF & Mosquito Repellant: The Summers in Tuscany Italy are hot and chances are you’re going to be doing a lot of walking and be outside a lot. Make sure you have your SPF protection and wear plenty of mosquito repellant at all times, you’ve been warned! I went out one morning for 5 minutes without it and came back 10 mosquito bites the worse.

Tipping: There isn’t always a place on the check to add a tip, if that’s the case, leave cash. 10% is average. Many places add a cover charge on (bread, water, service, etc) it’s normal, so expect it on your bill. Hotels often have a city tax too which gets added onto your nightly rate.

Shoes: Take good walking shoes! It was fun tracking how much we walked on our iPhones. It made me feel less guilty about all of the carbs, wine, and missed workouts.

They’re little things but good to know in advance so you don’t get moody or flustered about it on vacation.

Helpful Maps: includes maps of each city

5 perfect days in Tuscany Italy | Book the hotel

Find all my looks & beauty favorites not just from this 5 days in Tuscany itinerary post but from all of my posts in 1 feed on the LTK app.

Once you’ve downloaded the app, you can also screenshot any of my LTK posts on Instagram to instantly get the product details for your look.

How to minimize jet lag

There’s nothing worse missing out on a day of vacation because of jetlag. Especially when you’re spending a lot on your vacation and have a jam packed Tuscany itinerary. To make sure you get the most our of your 5 days in Tuscany and don’t miss a moment, make sure to hydrate well on flights.

I always drink so much water to offset the champagne and recycled air. I tried the natural supplement No Jet Lag for the first time on this flight. I’m not sure if it works or not but it can’t do any harm to try!

Hydrate well on flights. Natural supplement  No Jet Lag . Not sure if it works but it can’t do any harm to try!

Let’s Connect: What’s your favorite place(s) in Tuscany?

If you’ve been working with a luxury travel planner, reading Tuscany travel guides or doing your own research for your luxury Tuscany itinerary and are feeling overwhelmed, feel free to reach out to me. Whether to double check anything about our 5 perfect days in Tuscany itinerary or to ask my opinion on something, I’m happy to give my opinion.

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