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Tuscany Travel Guide | Best of Tuscany in 1-5 Perfect Days Luxury Itinerary

Tuscany Travel Guide | Best of Tuscany in 1-5 Perfect Days Luxury Itinerary

Tuscany Italy
How to see all of the top things to do in 5 days.
Get The Most Out Of Your Luxury Vacation in Tuscany

Tuscany travel guide, your luxury Tuscany itinerary to 5 perfect days in Tuscany. Although it’s easily tweaked if you’re spending less time there and I’ll let you know what I think you can skip. Tuscany offers so much to see and is such a big area to cover (23,000 KM / 8,900 Miles sq.), especially when you’re trying to cram it all into 5 days! It can be hard to put together a luxury travel and sightseeing itinerary and make sure you’re not missing anything. In this Tuscany travel guide you’ll find everything you need to see and how to get a true taste of authentic Tuscany. As well as the best Tuscany restaurants to eat at, the best Tuscany wineries to visit, things to see and tours to do for an elegant and gourmet vacation in Tuscany villages and towns. Including some lesser known local spots like Montecatini Terme.

From can’t miss towns and wineries, to luxury accommodations and experiences of a lifetime they’re all in this blog post. What you need to 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

Tuscany travel guide & luxury Tuscany 5 day itinerary

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

Como Castello Del Nero Tuscany

Luxury Tuscany Itinerary Sightseeing Experiences | A Taste of Authentic Tuscany

Another reason we chose COMO hotel is that offers various experiences that offer different tastes of authentic Tuscany, whatever you’re looking for. From wine tasting to cooking classes, hiking to truffle hunting. Where better in the world to do a Truffle Hunting Experience than in Tuscany which was the highlight of our time there.

Tuscany 5 Day Itinerary | Tuscany Travel Guide

Here’s our full itinerary for 5 perfect days in Tuscany. Because we hired a car and did everything in our own time besides a tour, you can easily tweak this Tuscany travel guide and 5 day itinerary to work for you and your interests.

DAY 1 Tuscany – Arrival Day & Good Tuscan Food

After you land, give yourself that first day just to explore your hotel and relax. After picking up the hire car, we stopped by a really modern winery we had on our list to visit: Antinori Chianti Classico. We ate a late lunch at their rooftop restaurant ‘Rinuccio 1180’ on our way to the hotel.

Don’t judge, we were hungry and tired coming straight off the plane so opted for their burgers (no regrets, it was fantastic) and wine tastings. Reds for Mr. Dawes and whites for me. I loved all of mine but Lewis didn’t like any of his Chianti’s.

We then spent the afternoon relaxing by the pool before enjoying sunset drinks and heading out to dinner. The sunset our first night here was like something out of a gallery painting.

Tuscany Beautiful sunset views village Italy

Dinner is normally around 9 pm so you have plenty of time to enjoy the days fully and take your time getting ready for dinner before sunset drinks. Aperitivo hour(s) are part of the Italian culture you don’t want to miss!

The best apertivo we had was in Florence, more about that in the next post. I got quite into Aperol Spritz during this trip. We ate on the terrace of La Locanda di Pietracupa in a quaint Tuscany village which I highly recommend. Full details in the dining section below.

DAY 2 Tuscany Wineries- Chianti Winery Tour & Tastings, Monteriggioni & San Gimignano

If you’re looking for 5 perfect days in Tuscany, you have to include some wine tasting. No best of Tuscany travel guide or luxury Tuscany itinerary would be complete without a list of the best Tuscany wineries to visit. Tuscany is famous for its wines more specifically for its Chianti, Montepulciano, and Brunello Di Montalcino.

The Tuscany wineries are located in different parts of Tuscany and getting around is slow due to speed limits so we separated them into 2 days. Which also helped to prevent drink driving! I’m not a big fan of reds but I still love trying everything to get a taste of Tuscany wines and also just exploring these scenic places. We didn’t do any Tuscany winery tours (just tastings) as we’ve done so many between Napa, Sonoma, Amador, Oregon, Reims, and Epernay.

Our day started in Monteriggioni which is a tiny Tuscany village (30 mins S. of hotel) that stands out from a distance with its 14 meter high fortified walls & 14 towers perched on a hill. Have a quick wander, grab an iced coffee or gelato (it’s never too early for ice cream) before heading to the first winery.

Some other smaller Tuscany villages that might be worth a visit if they’re closer to your hotel if you don’t stay where we did (but you’re missing out if you don’t stay there or at Rosewood Castiglion Del Bosco-another beautiful resort): Greve, Chiocchio & Panzano.

Which are the best Tuscany wineries to visit?

Barone Ricasoli

This is the oldest Tuscany winery and 55 minutes SE of the hotel. The castle is small but with good panoramic views. Unfortunately, the wines were disappointing to both of us but tastes are very personal. There was also no ambience in wine tasting room, it’s pretty stark and cold.

Tuscany winery Barone Ricasoli luxury travel blogger Eve Dawes

To find this Tuscany winery put the castle name into Waze but stop before you enter the castle gates. The wine tasting room is at the bottom of the hill before you enter the driveway to the castle.

We recommend eating before or after this winery as there are only 2 options here. A small cafe opposite the wine room with food I didn’t even find edible or a lovely looking Osteria within the castle gates. We could’ve eaten her and it gets good reviews but didn’t as the food was more like a dinner menu and too heavy for us on a hot day.

Castello di Ama Tuscany Winery

45 mins SE of Como hotel. This really isn’t so much of a castle and we couldn’t even find the winery so we just ate lunch which was great but a little out of the way.

Castello de Verrazzano

This castle Tuscany winery has 1 of the most ancient cellars in Greve and some great views. We weren’t able to see the wine cellars so just did a tasting on terrace. This felt quite commercialized to be honest rather than the authentic taste of Tuscany that we were hoping for.

Best of San Gimignano Tuscany Travel Guide

San Gimignano

San Giminignano is one of those Tuscan towns you’ll probably see in every Tuscany travel guide, as it really is a must see town. Whether you’re in Tuscany for 1 day or trying to schedule 5 perfect days in Tuscany, it’s a must see. After freshening up at the hotel it was time to explore again, I’m not good at sitting still for long.

With 14 medieval towers, ancient city walls, a bell tower, Palazzo Comunale and Piazza della Cisterna this Tuscan town checks all of the traditional Tuscan town boxes. Is it busy-yes! Is it worth visiting-most definitely and parking is easy in one of the main lots.

San Gimignano Restaurants

If you’re in San Gimignano for lunch both Winery Fattoria Poggio Alloro and Tenuta Torciano Vineyards were both recommended with their beautiful views back at city. However, since we were there just before sunset we wandered the streets before finding an Enoteca and sitting outside watching sunset with fabulous views of the lush Tuscan landscape.

We couldn’t get into the restaurant I wanted to dine in, Le Vecchie Mura as it was fully booked. My mistake! Be sure to call ahead and make a reservation as the views and ambience on the terrace are so romantic and beautiful. It’s inside the city walls and easy to find as its signposted from the main square, it’s a more upscale and elegant taste of Tuscany.

Instead, we had a casual dinner at Pizza at La Nostra Cucina E’Espresso and totally over ordered! Pizza, Calzone, and salad, which came out American portion sized. However, we still made room to squeeze in Gelato from a gelateria on the corner of Piazza della Cisterna and sat on the well listening to the live music. Just looking at these photos makes me want to go back already!

Tuscany 5 day itinerary DAY 3 – Exploring Authentic Tuscan Towns: Volterra, Pisa, Lucca & Montecatini Terme

Yes, you really can visit all of these Tuscany villages and towns in 1 day! If you’re doing less than a 5 day itinerary, skip Lucca and Montecatini Terme and do Volterra, Pisa and San Gimignano.

Volterra, Pisa, Lucca, and Montecatini Terme. It sounds like a lot in 1 day but it’s totally do-able. This was one of our favorite days besides the truffle hunting. San Gimignano and Volterra ended up being our 2 favorite towns in Tuscany as they felt the most beautiful, well preserved and gave us the authentic taste of Tuscany we were looking for.

San Gimginano Tuscany Eve Dawes exploring city floral dress


Volterra is one of the most beautiful hill towns in Tuscany and 1 hr SW of hotel if you stay where we stayed. A walled town with a well preserved Roman theatre. You can go inside the Roman theatre and visit but we got great views inside from walking around the road above. Other sights in Volterra include Piazza dei Priori with Palazzo dei Priori, Palazzo Pretorio w/Tower of the Little Pig, Cathedral & Baptistery.

Wear comfy shoes to explore Volterra as there’s a lot of steps from the parking lot into the town! We tend to just walk cities and explore wherever looks interesting to us rather than going into every church and museum.

Volterra Italy romantic couple steps


I was the one who wanted to go to the Leaning Tower of Pisa as Lewis has already been and was sweet with being ok about going again. Being so close, I couldn’t not check it off the bucket list. From hearing other people’s experiences, I went with really low expectations as I was just expecting the Leaning Tower in the middle of a field, some tourist shops, and lots of crowds. From the moment we drove in along the bustling scenic river I knew I was wrong. It’s a decent size Tuscan city and has lots of charm.

Beware of the ZTL here which means a little walk from wherever you park to the Leaning Tower of Pisa and Duomo di Pisa/Cattedrale De Pisa. I was so impressed with how scenic and clean it was. By this point, if you go in the Summer like we did, you’re probably hot and sweaty so stop and grab gelato by the leaning tower or for lunch a few blocks away.

Best of Tuscany travel tip: It’s a major tourist destination so be patient and polite taking your turn to take a photo and you’ll get a good one. Everyone’s pretty good about waiting their turn and not getting in each others shots, after all, we all have the same goal.

Leaning Tower Pisa Italy luxury travel blogger Eve Dawes


This Tuscan city was too touristy, dirty, and busy for me, I really wasn’t impressed. Yes, it has preserved walkable 16th century walls and is close to Pisa but that’s about it. Go if you really want but otherwise skip it, especially if you’re trying to see all of the area during your Tuscany 5 day itinerary.

Tuscany travel guide | Montecatini Terme Spa Town

Montecatini Terme is located in between Pistoia & Lucca and known for its thermal waters. It’s one of Italy’s top spa towns. This was a super cute, very relaxing, uncrowded spot. We started by taking the funicular railway up the hill to the old town of Montecatini Alto, even though you can drive. It runs every 30 minutes and costs 7 Euro for a return ticket.

There are several restaurants at the top and some fantastic panoramic views, if you don’t get rained on like we did. When you come back down, visit the historic spa Terme Tettuccio which is in the park.

Montecatini Terme has very elaborate Liberty style architecture which has Italians sitting, talking, and sipping on the different thermal waters, each of which offers different benefits. In saying that, just because they’re good for you, doesn’t mean they taste good. However, it was another taste of Tuscany not to be missed if you want to see how the locals do it and get a sense of authentic Tuscany.

Time to hit some more Tuscany wineries. After a good breakfast on the terrace and dousing ourselves in lots of bug spray we headed out with a plan. Which was to visit 3 Tuscany wineries in both the Montepulciano and Montalcino regions with a couple of stops to explore some towns en route. Put on your comfy shoes, because there’s lots of cobble stones and steep hills.

Starting at:

Avignonesi Winery, Montepulciano

best Tuscany wine tasting Avignonesi Winery Montepulciano Eve Dawes husband

An authentic and rural winery situated among its pretty vineyards. We are going to sound super picky but we didn’t love the wines but really enjoyed the experience and recommend visiting here. I liked the rosé and white white but neither of us enjoyed the reds.

Avignonesi has a special sweet dessert wine called Vin Santo which was probably our favorite, think white port as a comparison (but I still prefer white port).

Wine tasting flight Avignonesi Winery Montepulciano Italy


In between the Tuscany wineries, we stopped at the charming town of Montalcino, another historic taste of Tuscany that will take you back in time. Get ready to trek the steep hill of the main street inside the city walls. Lined with cute cafes and shops, we escaped the rain in a pizzeria overlooking the church. I won’t mention the name as the food wasn’t great and the service super slow. Better options looked to be as soon as you come through the cities main entrance.

After the rain stopped we walked or should I say hiked up to 14th century fort but didn’t go in as we didn’t really have the time (or desire). We’d walked so much the sole of my shoe came off! I wasn’t having much luck with my shoes as the sneakers I’d brought with me rubbed so I gave up on those. Luckily, we found a shoe shop and super comfy pair of slip ons that lasted almost the rest of the trip for me; until both soles split in half on the last day! I’m not kidding when I say we walked a lot, we were doing 7-8.6 miles a day.


Next stop, Montepulciano (90 minutes South of the hotel). We could’ve skipped this town as there are lots of other lovely towns that are more special and have more to see. We ended up just having iced coffee in the square as the rain and humidity was making us sleepy and we were having none of that as we still had lots to see!

Castiglion Del Bosco

Time to drive some more and head to Montalcino for a Brunello wine tasting at Castiglion Del Bosco in Montepulciano, Val D’oraia next to the Rosewood hotel. This was one of our favorite wineries and hotels and if you’re looking to do a luxury Tuscany itinerary you should consider going. You need to book wine tastings in advance.

At a certain point of the drive, the road turned into a dirt track but Waze said we still had another 7+ miles to go! My husband was convinced we’d taken a wrong turn and that a Rosewood hotel would never be located so far down something you really couldn’t call a road or so remote. I had faith in Waze and where it looked like it was located in the bigger scheme of things so we kept going. It IS the right road, keep going, the reward it worth it!

Castiglion Del Bosco is a gem of a Tuscany winery. We were the only ones sat outside on the terrace overlooking the gorgeous Tuscan scenery for leisurely wine tastings without a road or building in sight. Everyone else thought it was too hot, but we’re from Vegas, so this was great! Our sommelier was personable, knowledgable and guided us through our wine tastings in depth and we actually enjoyed the wines here!

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Castiligion Del Bosco red wine tasting Tuscany Italy vineyard views

Rosewood Castiglion Del Bosco Hotel

2 Tuscany wineries was enough for us in one day, so we skipped the 3rd and took a walk over to the elegant Rosewood Castiglion Del Bosco Hotel afterwards for Ruinart Rosé champagne (our favorite after visiting Ruinart’s cellars in Reims). As well as pizza for a late afternoon snack before heading back to the hotel. If you stop here for a drink be sure to explore the small but pretty castle at the hotel too.

Other highly rated Tuscany wineries include Castello Banfi whose wine bar closes at 8pm and Podere dei Ripi which closes at 6 pm.

I haven’t mentioned where we ate dinner that night as we were disappointed in both the service and food we had.

If you don’t stay at Como Castello Del Nero and don’t mind being in a remote location, Rosewood is another beautiful luxury hotel.

Luxury Tuscany 5 day itinerary DAY 5 best private tour: Truffle hunting in Tuscany

Tuscany travel guide Glamour Gains blogger rolling hills dog

If you’re planning a luxury Tuscany itinerary, you can’t not do a truffle hunting tour unless you don’t like truffles. It’s another must do tour and something every Tuscany travel guide should include is truffle hunting for an authentic taste of Tuscany. The private truffle hunting experience and lunch in the most beautiful and authentic Tuscany village was the absolute highlight of our Tuscany visit. So much so I gave it its own blog post. This tour really made our 5 perfect days in Tuscany perfect. Truffle Hunting Tour | If you only do 1 thing in Tuscany Italy do this!

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

When it comes to eating in Tuscany and finding the best restaurants, avoid the main piazzas to avoid the main tourist traps. Instead explore down narrow side streets or where looks packed with locals.

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 luxury Tuscany 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 | Shop the Looks & book the hotels

Find all my looks & beauty favorites not just from this 5 perfect 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.


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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. To make sure you get the most our of your 5 perfect 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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