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Best of Tuscany in 5 Perfect Days | Luxury Travel Guide

Best of Tuscany in 5 Perfect Days | Luxury Travel Guide

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 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, the best Tuscany restaurants to eat at and Luxury Tuscany hotels for an elegant holiday.

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.

Antinori Chianti Classico Tuscany late 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!

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, the signs look like this.

ZTL Traffic zone signs Tuscany ItalyZTL Traffic zone signs Tuscany Italy

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

We always do a ton of research and after decades of travel know what we like and what we don’t. When I was looking for a Tuscany hotel one of my prerequisites was that I’d always wanted to stay in a castle and this seemed an idyllic place to do so.

Como Castello Del Nero is a twelfth-century castle layered with Renaissance frescoes and contemporary design. One of many reasons for choosing this Tuscany hotel is that it has a superb location just 30 minutes from the airport and Florence. It’s also easy to get to Pisa, Montalcino, and San Gimignano while having the most breathtaking views and a Michelin star restaurant and spa.

Champagne check in Como Castello del Nero

As soon as we pulled into the driveway of Como Castello Del Nero I knew we’d made the right choice. We were greeted with a cool face cloth and glass of Prosecco while we checked in and started to get into vacation mode.

Castello Del Nero nails the decor; while keeping its historic heritage it manages to be the right amount of modern and comfort.

Wine and Views Como Castello del Nero

Como Castello Del Nero | The Accommodation

There are several different types of rooms to choose from. We stayed in the Tavarnelle Suite which was a peaceful oasis with it’s own private garden and separate living area (great for when one of you wakes before the other).

I made use of the private garden so I could jump around like a crazy woman doing my quick morning total body workouts. Relax in the elegant bath tub, make use of the large walk-in closet, and laze in the sumptuous bath robes on the couch over a bottle of red late at night. Some of the other 646 sq ft suites overlook the courtyard, Italian formal gardens, or rolling Tuscan hills.

Beautiful Tuscan views Como Castello del Nero

Como Castello Del Nero COMO Terrace Suite

If you really want to splurge, book the COMO Terrace Suite 968 sq ft with exposed wooden beams rising high over the airy master bedroom and spacious separate living room. I’m totally in awe of its enormous terrace offering panoramic views of the Tuscan landscape and estate’s Tuscan lakes.

Hotel Dining at Como Castello Del Nero | Best Tuscany Restaurants

Como Castello Del Nero has 2 restaurants. The first is La Torre Gourmand Restaurant, a Michelin* 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.

Book La Torre Gourmand restaurant.

Como Castello Del Nero’s other restaurant is La Taverna. A more casual dining option which serves estate-to-table authentic Tuscan lunch & dinner as well as drinks for when you’re poolside. They serve a mean Gin and Tonic perfect for cooling off in the afternoon.

It’s an intimate restaurant with very few tables so try to make a reservation. It’s also a great spot for a night cap and overlooks the rolling hills. I have to mention Jacopo at La Taverna restaurant as his service was exceptional. One of the highlights for me was that they serve white port which is hard to find at restaurants and I love, having lived in Porto for 10 months.

Romantic couple sunset Como Castello del Nero

Don’t miss breakfast! A leisurely breakfast is served inside as well as on the raised terrace. I definitely recommend their fresh scrambled eggs and prosciutto, as well as the chocolate croissants. They have a lot of variety from healthy to decadent both on the buffet and a la carte menu.

Hey, you’re in Italy, calories don’t count right?! Oh and for my caffeine loving friends, you can’t beat fresh black Italian coffee.

Breakfast Como Castello del Nero

Como Castello Del Nero ESPA Spa

The massages at the ESPA spa, while not in the most exceptional of facilities (lovely but not wow), my husband and I both agreed, were one of the best massages we’d had. We had the Como Shamabala massages. Get there early enough to use their jacuzzi and play with all of the jacuzzi buttons and areas.

The hotel also offers free wifi & parking.

This is not a sponsored post.

Pool Como Castello del Nero

Luxury Tuscany Sightseeing Experiences

COMO offers various experiences. Where better in the world to do a Truffle Hunting Experience than in Tuscany which was the highlight of our time there.

Read on for full details of the truffle hunting and pics with the Truffle Hunter and Ufo the truffle hunting dog as well as our full 5 day itinerary.

Views Como Castello Del Nero Hotel Tuscany ItalyViews Como Castello Del Nero Hotel, Tuscany

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.

Beautiful sunset views Como Castello del Nero Tuscany 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 one was in Florence, more about that in the next post. I got quite into Aperol Spritz during this trip. We ate at La Locanda di Pietracupa which I highly recommend. Full details in the dining section below.

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

Tuscany is famous for its wines and Tuscany is known for its Chianti, Montepulciano, and Brunello Di Montalcino. They’re 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 and also just exploring these scenic places. We didn’t do any 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 town (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 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 wineries to visit in Tuscany?

Barone Ricasoli: This is the oldest winery in Tuscany 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.

Views Tuscany Barone Ricasoli luxury travel blogger Eve Dawes

To find this 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: 45 mins SE of 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 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 which felt quite commercialized to be honest.

San Gimignano

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 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.

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.

San Gimignano Restaurants

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.

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!

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

Yes, you really can do them all in 1 day!

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; San Gimignano and Volterra ended up being our 2 favorite towns in Tuscany.

Exploring San Gimginano Tuscany Eve Dawes floral dress


(1 hr SW of hotel) 1 of the most beautiful hill towns in Tuscany. 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 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.

romantic couple steps Volterra Italy


I was the one who wanted to go here 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 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.

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 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.

Montecatini Terme

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. Its very elaborate Liberty style architecture 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.

Time to hit some more 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 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

Wine tasting Avignonesi Winery Montepulciano Eve Dawes and husband

An authentic and rural find 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. They have 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 wineries, we stopped at the charming town of Montalcino. 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!

See Also

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. You need to book tastings here. 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 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!

Castiligion Del Bosco red wine tasting Tuscany Italy vineyard views

Rosewood Castiglion Del Bosco Hotel

2 wineries was enough for us, 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 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.

DAY 5 Tuscany: Truffle Hunting in Tuscany

Tuscany vineyards truffle hunting dog Glamour Gains travel blog

Truffle hunting experience and lunch was the absolute highlight of our Tuscany visit. We booked this private tour through our hotel. This experience was beyond amazing and so memorable with our truffle hunter Jacopo and his truffle hunting dog Ufo (short for Tartufo meaning truffle). You might have thought it was pigs and not dogs but their use is banned in Italy because:

Their overeager rooting damages the truffles’ delicate mycelia, the spore-holding web necessary for the fungi’s reproduction. Also, it’s pretty dangerous to get between a 300-kilogram pig and a truffle it’s determined to eat. CNN Travel

Truffle Hunting in Tuscany Italy

On a bright sunny morning, we met with our truffle hunter Jacopo and his truffle hunting dog in Val Di Pisa. He led us out of the tiny village along the winding country road into the Tuscan countryside and forest where Ufo caught scent of the black truffles and they were off.

The 2 of them were clambering up and down the hills, talking with each other, carefully unearthing truffles. It was incredible watching and learning as Jacopo and Ufo worked together and the relationship they have. Wow, do they know what they’re doing and he’s incredibly passionate about what he does.

The dog starts the dig frantically where he catches the scent, then Jacopo would tell him to be gentle or stop and he’d go in and finish pulling up the black yumminess. They didn’t care if there was a huge ant hill or mosquitoes, they were all about finding the truffles whatever it took.

Truffle hunter dog finding truffles Tuscany tour

After he felt we’d exhausted that area we walked back to the Abbey of San Michele Arcangelo a Passignano/Badia di Passignano. A historic Benedictine abbey located on a scenic hilltop, surrounded by cypresses, and into the private park to hunt for truffles in the cool shade provided by the ancient trees.

Val Di Pisa Wine Shop

We collected so many black summer truffles my pockets were overflowing. After an hour or so of truffle hunting we headed across the road to the village wine shop (I say village because there’s only 24 residents here and that includes the monks at the working monastery). It’s how you imagine and idealize Tuscany minus any crowds.

After truffle hunting in the sun, the cold Prosecco was most welcome. I don’t normally like or drink Prosecco as it’s too acidic but wherever we went in Italy it was so good! It might be like Greece where they keep the good stuff for themselves! The wine shop owner was a wealth of knowledge. We discovered a few new wines we like, including the rosé wine ‘Alie’ which even my husband likes and he doesn’t like rosés. After this we headed next door to Antica Scuderia for the truffle and wine pairing lunch.

Black summer truffles proscecco Tuscany

Truffle & Wine Pairing Lunch, Val Di Pisa Tuscany

The truffle lunch blew our minds. Sitting there on the empty terrace overlooking Tuscany’s green and golden landscape, listening to the church bells and indulging in some of the best food in our lives was magical and memorable. When it comes to serving truffles, simplicity is key so you can really taste the flavors. Jacopo picked the best truffle from our haul for us to have on our table and to shave onto each course. The rest went to the kitchen for our feast. Burrata with truffle, pasta in a light cream and truffle sauce, seared steak with truffle and ending with gelato (not truffle flavor thankfully!). Thankfully we had no plans for the afternoon as a much needed poolside food siesta was in order.

We need to go back October to late December or early January for the elusive gold rush: white truffle season! It’s the mild Tuscan climate and soil rich in mineral salts which make it the perfect breeding ground for top quality truffles.

Neither of us were really hungry in the evening so we just called the hotel room service and enjoyed the living room of our room in bath robes and slippers with some more wine.

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

Avoid the main piazzas to avoid the main tourist traps and explore down narrow side streets or where looks packed with locals.

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 quaintist of towns 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 Tips

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.

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

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.

Helpful Maps: includes maps of each city

Tuscany Italy | Shop the Looks & book the hotels

Find all my looks & beauty faves in 1 feed on the app & follow: Liketoknowit Eve Dawes. How to use

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


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How to minimize jet lag

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 for Tuscany or doing your own research and are feeling overwhelmed, feel free to reach out to me. Whether to double check anything or ask my opinion on something, I’m happy to give my opinion.

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