Italy has always topped my bucket list, and I was thrilled to finally have the chance to visit! Our journey began at a gala for the Reed Charitable Foundation, an organization we became involved with after discovering our daughter had dyslexia in grade school. This remarkable foundation trains teachers to help all children learn to read. During the gala, a live auction featured a trip to Tuscany, offering a seven-night stay in a Tuscan villa!

We eagerly bid alongside friends and won the trip! The certificate allowed us up to two years to book the villa, and we decided to go in the summer of 2025. The rest, as they say, is history.

Even though it was two years away, I enthusiastically started planning to make the most of our vacation. Plus, if you know me you know I’m obsessed with all things travel HAHA, researching destinations, and discovering unique restaurants, accommodations, excursions, and more!

We reserved the villa for mid-June, which I had heard was a fantastic time to explore Italy, though it’s also busy! We arrived in Rome by mid-morning and rented a car for the 2.5-hour drive to Cortona. The journey felt really quick, thanks to the breathtaking scenery along the way. Starving, we decided to stop at a gas station for a bite to eat. In America, I would have been disappointed, but in Italy, oh my goodness! They offered a gourmet selection of foods, and we all opted for pizza. That gas station pizza turned out to be some of the best I’ve ever tasted. Plus, you could even order wine! WIN! WIN!

after the amazing gas station lunch we headed to the villa. I am not kidding when i say that when we drove up to the villa, it was like being in a dream. you are welcomed by cypress trees as far as your eye can see, tuscan gardens surrounding the entire property & the owner coming out to greet you as you arrive along with their dog lucky! the villa was everything i thought it would be and more. the villa has stone covering the outside, and dark wood paneling inside with terra cotta floors. there is a stunning porch that you can wake up to every morning with the beautiful sunrise and sunset in the evenings that make you feel like you are in absolute paradise!

we had opted to get the villa’s welcome buffet because we were so tired from the flight and WOW was i glad we did. the owner made the food from scratch and it was creamy pasta, fresh baked bread, a charcuterie plate of the best meats and cheese i have ever tasted, local italian wine & delicious dessert! we loved it so much that we asked to get another home cooked meal for our last night in tuscany.

On our first day, we set off for one of the hill towns (there are several, but we could only explore a few due to time). Assisi was our first stop, and I’m so grateful we chose it, as it is rich in history and brimming with Italian charm. Our primary motivation for visiting was to see the Assisi Cathedral, where many, including St. Francis of Assisi, were baptized. The cathedral is absolutely breathtaking, both outside and inside. Built in the 13th century after St. Francis's passing, it features an upper and lower basilica, and it houses his tomb in the crypt. Assisi invites you to stroll through its ancient cobblestone streets, enjoy panoramic views of the surrounding valleys, and indulge in the delightful Umbrian food and wine!

After visiting Assisi, we made a stop in the picturesque hill town of Spello. This medieval gem, located in Umbria, is renowned for its enchanting atmosphere and stunning cobblestone streets, lined with houses adorned with vibrant flower boxes. It's the perfect destination for leisurely strolls, where you can appreciate the beauty while savoring Umbrian cuisine and wine. We enjoyed some gelato as we wandered about, but I truly wish we had more time to explore this delightful town. I hope to return someday! If you're in the Tuscany area, I highly recommend adding Spello to your itinerary!

That evening, we spent our time in Cortona’s main square, known as Piazza della Repubblica. Cortona is one of Italy's oldest cities, even pre-dating Rome, and is among the earliest hill towns in Tuscany. This area is famous for its extraordinary Italian cuisine and wines, particularly their Syrah blends. Strolling through the streets of Cortona felt like taking a step back into Italian history.

Perched high in the Tuscan hills, the town offers breathtaking views. We loved our walks in this charming area over several evenings and even returned to a restaurant we absolutely loved, eagerly wanting to indulge in more of their incredible dishes. Cortona is also renowned for its truffles and truffle hunting, with many local restaurants serving delectable truffle dishes that you simply cannot miss.

Make sure to wear comfortable walking shoes, as there are steep paths to navigate from the parking lot to the main square.

tuscan hill towns:

Spello- old umbrian town with some of the most beautiful cobblestone streets with houses lined with flowerbed boxes
assisi- beautiful & ancient umbrian town and birthplace of st. francis
orvieto- set on a rock cliff in umbria-known for incredible views & incredible restaurants
san gimignano- known for history, art-medieval towers & homes, delicious food and wine
montepulciano- stunning medieval tuscan town nestled among vineyards with incredible panoramic views of tuscany

The next day, we spent our time exploring two vineyards in Cortona, with the tours included as part of our gala package winnings. I had only experienced one other vineyard tour in my life, which was in Napa Valley, but this experience was entirely different. We found ourselves in the heart of Tuscany, renowned for producing some of the most famous wines in the world.

I gained a wealth of knowledge about winemaking and how Italy adheres to strict regulations in the production process. They follow a rigorous protocol to ensure that the wine is as pure as possible, avoiding added sulfates and sugars. Their stringent quality control systems guarantee that only the finest wines are produced.

Each vineyard offered fantastic wine tastings accompanied by charcuterie boards, allowing us to pair the wines with various foods. We had an amazing time at the vineyards, and I was really surprised by how smooth the wines tasted, lacking the strong "alcohol" taste often found in others. I also noticed that while in Italy, I could enjoy a couple of glasses of wine late at night without feeling terrible the next morning, unlike with American wines. I believe this is due to the high quality of Italian wines, which do not contain added sulfates. We loved the wine so much that we have started ordering directly from one of the vineyards.

*vineyards that we visited- specifically the one we order our wine from is in our italy itinerary in our store section on our website

we headed out to florence the following day and this was one of the places i have always dreamed of going one day. florence is where renaissance was born and i was so excited to see all of the architecture and art! it was raining when we arrived but i just kept telling myself who cares…you are in florence, FLORENCE!! what was incredible is it stopped raining right when we started to walk up to see the david in the galleria dell’ accademia di firenze. we had the most incredible day in florence visiting the museums, the duomo and just walking the incredible streets and trying the incredible food! florence was such a vibrant and fun area and i absolutely loved it. do yourself a favor and grab a gelato and overlook the Arno river. make sure to add florence to your must see while in italy!

my top 3 florence must-do’s:

the david- i have seen many pictures of the david but it is incredible to see the sculpture in real life and just what a magnificent piece of art it is!
vivaldi- this was the best gelato i had in italy (and i had gelato daily) get the pistachio & nutella-apparently there is one at disney springs and i need to go try and see if it tastes the same!
the arno river- beautiful river that is a historic landmark in florence

Arno River Florence — Arno River, Florence

Florence was absolutely amazing, but I was really looking forward to our next adventure in Cinque Terre. My sister-in-law had raved about how breathtaking Cinque Terre was during her trip to Italy, and wow she was so right!

On our journey to Cinque Terre, we made a stop at the Leaning Tower of Pisa. I genuinely believe it’s an ideal place to pause and admire the tower en route to another destination. Pisa is a vibrant college town, home to the University of Pisa, one of the oldest universities in Europe, founded in 1343.

Walking up to the Leaning Tower was surreal, especially considering how many times I had seen photos of it. Experiencing it in person was truly unforgettable! A quick tip: remember to bring water and wear a hat, as it can get incredibly hot and crowded, but witnessing such a remarkable piece of history is well worth it.

After visiting the Leaning Tower, we made our way to La Spezia, a charming port city recognized as the gateway to Cinque Terre. We decided to spend a night there to ensure an early start for exploring all five towns of Cinque Terre.

In my research, I found a beautiful boutique hotel conveniently located across from the train station serving the Cinque Terre area. The hotel was adorable, and our stunning room offered a breathtaking view of the city of La Spezia. A huge bonus was the comfortable American king-sized bed! If you've traveled in Europe, you know how luxurious it is to find a hotel with a king-size bed. We truly enjoyed wandering through the city center of La Spezia and discovering the local area. We had made reservations at a unique and highly recognized restaurant, but since we were starving and our reservation was at 7 PM, we had to wait. Many restaurants in Italy, particularly in less touristy areas, open later in the evening. *When looking for restaurants in Italy, do not go to ones that have pictures of the food on the menu...literally run, I warned you! We made this mistake and will never again. The food was so bad, we had to leave without eating!!

La Spezia offers a wealth of attractions, from being one of the largest naval bases to its charming streets, local markets, and exceptional seafood. You could easily spend an entire day soaking in the experience there.

La Spezia Italy — La Spezia-view from room

Early the next morning, we headed to the train station, eager to arrive in Cinque Terre before the crowds. It’s a quick train ride to the first stop, Monterosso. The five towns are 5 minutes apart by train or you can choose to hike them. although we didn’t have time to hike, i have heard the hikes are amazing with incredible views! Always check with the train stations for potential strikes and their schedules; on the day we visited Cinque Terre, the trains were scheduled to strike later that afternoon, and you don’t want to get stuck, especially in the towns because it would be difficult to find other transportation.

As we approached Monterosso, I was utterly amazed by the water's color—it was a shade of blue unlike anything I had ever seen! As a Florida girl, I know beautiful blue waters, but this was a striking deep emerald blue that took my breath away!

Monterosso exudes a beautiful, resort-like ambiance, featuring a long sandy beach adorned with colorful umbrellas and delightful cafes that overlook the water. The town has an old-world charm while providing modern conveniences. It's a place where you could easily spend an entire day or even a week, immersed in the full beachside Italian experience.

Unfortunately, we had only one day to explore all the towns, and I truly wished for more time. There was so much to discover in Monterosso! I could easily imagine myself lounging under one of those beach umbrellas, looking at the stunning ocean with an Aperol spritz in hand!

Monterosso Italy — monterosso-Cinque Terre

Our next stop was Vernazza, a picturesque village embraced by breathtaking blue waters, vibrant kayaks, and a backdrop of colorful houses. In my opinion, this fishing town is one of the most charmingly rustic places, retaining its small-town feel...I even read there are only about 600-700 residents.

The main square, as you stroll down to the water, is full of delightful cafés, trattorias, and gelato shops. There are also numerous vendors perfect for picking up souvenirs. I personally enjoy seeking out boutique shops that offer sweaters or shirts known for their durability, often featuring unique, one-of-a-kind items.

One of my favorite highlights of Vernazza was the historic 14th-century Church of Santa Margherita, which you can walk through, situated right by the water's edge. I wish we would have had more time in Vernazza because it was so beautiful and charming, and hoping one day to visit again!

We had planned to visit Corniglia, a charming fishing village that uniquely stands as the only one of the five towns not located right by the sea. Positioned high on a cliff approximately 100 meters above the Ligurian Sea, it offers breathtaking views of the coastline. However, we decided against visiting this village due to the numerous steps required to reach it, opting instead to proceed to Manarola. Based on what I had read and advice from friends, Corniglia was the town often recommended to skip if necessary.

Manarola quickly became my favorite among the five towns. It truly feels like stepping into a painting brought to life, with its stunning beauty. We wandered down to the water and watched people jumping off the cliffs into the sea, a sight both exhilarating and picturesque. As we climbed back up, we found the perfect spot to capture a photo of the beautiful turquoise waters below, framed by the colorful homes in the background. The village is compact and charming, lined with delightful trattorias, wine shops, and boutiques.

For me, Manarola encapsulated the essence of Cinque Terre: gorgeous ocean views, delectable wine and food, and a vibrant, endlessly captivating atmosphere!

Riomaggiore, the final stop on the Cinque Terre train line, truly exceeded my expectations! This picturesque Italian village cascades down steep cliffs into the Ligurian Sea, showcasing beautifully stacked pastel houses. It embodies the charm of a quaint Italian fishing town.

As you get off the train and head towards the town, you’ll notice a rushing sound beneath the sidewalk—it’s the nearby waterfall, which was such a beautiful and peaceful sound as you walk up. The path to the town involves navigating a steep walkway.

To access the restaurants and shops, be prepared for plenty of walking up and down narrow steps and hallways. When you reach the main area, you're greeted by stunning views of colorful boats gently bobbing in the water, the delightful aroma of fresh seafood, and balconies overflowing with vibrant flowers.

We thoroughly enjoyed our time in this town, sitting high on a hill overlooking the water while savoring some of the best pizza I’ve ever tasted! On our way back to the train, we stumbled upon a local artist with a charming shop, where we couldn’t resist purchasing some of her beautiful paintings of Cinque Terre.

Visiting the Cinque Terre towns is an absolute must if you're in the area, even if just for a day like we did. The natural beauty of the region left a lasting impression, and reminiscing about it feels almost dreamlike. I can’t wait to return one day and spend a few more days soaking it all in!

Riomagiorre Italy — cinque terre-riomaggiore

On our final day in Tuscany, we drove to Montepulciano, a town that left me breathless with its stunning panoramic views of the Tuscan landscape. Perched high on a ridge, Montepulciano is enveloped by lush vineyards and charming cypress-lined roads.

We dined at Ristorante Ai 4 Venti, a favorite from our trip that offers a delightful view of the piazza. The food was delicious—my gnocchi was bathed in a creamy sauce and sprinkled with cheese, reminiscent of a gourmet mac and cheese. My husband’s ravioli was equally impressive. Make sure to visit this restaurant when in Montepulciano!

Post-lunch, we explored Piazza Grande, feeling transported back to the Renaissance as we wandered the cobblestone streets flanked by grand palaces and churches.

Montepulciano is famous for its Vino Nobile di Montepulciano, one of Tuscany's most celebrated wines. The town boasts numerous underground cellars where you can savor these exquisite wines.

After our day in Montepulciano, we returned to the villa to soak in the view on our final night in Tuscany. We inquired if we could enjoy another home-cooked meal from the owner, as she prepares the most delicious Italian dishes! Honestly, I believe her cooking surpassed some of the fine dining restaurants we visited.

She treated us to homemade ravioli, steak with veggies, fresh Italian bread, and a delightful whipped ricotta topped with raspberries. To top off the meal, we savored a bottle of local Tuscan wine!

This was the perfect way to conclude our time in Tuscany and build excitement for our next adventure in Italy—Rome. Tuscany exceeded all my expectations with its stunning vineyards, charming hill towns, exquisite wine, and incredible food. We absolutely cherished our time there and look forward to returning to indulge in the food and wine once again!

Rome…oh rome! i absolutely fell in love with rome. the vibe, the culture, the food, the art & museums, shopping…i could go on and on. we dropped our friends off at the airport, and my husband and i took a taxi to our hotel. a friend of mine had given me information on this hotel and it was the perfect location for us…just blocks away from the spanish steps and trevi fountain.

the hotel was located in the art district kind of tucked back away from all the noise of rome. we fell in love with the hotel the moment we walked in. it is a beautiful boutique hotel offering spacious rooms with american king beds and the hotel and rooms are decorated beautifully.

the staff is incredible willing to help with anything you may need and they go above and beyond to make your stay amazing. the breakfast buffet is out of this world too literally anything you would want is there to eat and my husband was excited because they had american drip coffee lol

*i cannot recommend this hotel enough-details and an advisor only discount when you download our italy itinerary!

We had about three days to enjoy Rome. After settling in, we ventured out to indulge in delicious food, explore our surroundings, and, of course, relax with a glass of Italian wine while people-watching!

The next day, we got up early to visit the Trevi Fountain before the crowds arrived. However, we still arrived too late, getting there at 6:30 AM! I highly recommend going even earlier if you want to capture stunning photos or simply enjoy the fountain without being surrounded by a sea of people.

We absolutely loved visiting the Trevi Fountain and, true to tradition, tossed a coin into the water. Legend has it that doing so ensures you'll return to Rome one day!

The next day, we had a tour scheduled for the Colosseum, so we woke up early, enjoyed a wonderful breakfast, and set out. We opted to walk most places due to the heavy traffic, and you never know what interesting sights you might encounter along the way!

Unfortunately, our tour ended up being quite disorganized, but I was relieved to receive a refund. However, the timing got a bit mixed up. A great tip for you is that you can simply walk to the front and purchase tickets from booths if you just want to enter and explore the Colosseum, which turned out to be perfect for us!

The Colosseum was breathtaking and much larger than I had imagined. It felt a bit eerie to walk through and visualize all the gladiators and animals that once entered, never to return, all in the name of entertainment! I'm truly grateful we had the chance to visit; it’s remarkable to see such a historic structure still standing and to appreciate the rich history it embodies.

On our final day in Rome, we devoted our time to exploring Vatican City. Brace yourself for the crowds in this area; I was unprepared for how busy it would be. Strolling through the city was an extraordinary experience; the sheer scale was almost overwhelming. As we meandered along the cobblestone streets, it felt as if we had traveled back in time, enveloped by Renaissance architecture, centuries of faith, and the area's rich artistry. I truly wish we could have spent a few more days discovering the various museums, as there is so much to see.

However, we opted to concentrate on St. Peter’s Basilica and the Sistine Chapel. St. Peter’s Basilica left me in awe with its magnificence. The enormous doors and ceilings, paired with the stunning dome and artwork, made me speechless as I marveled at its beauty. Experiencing Michelangelo’s ceiling in the Sistine Chapel was nothing short of surreal! It had always been a dream of mine to see it, and witnessing it in person is a memory I will treasure forever. If you're planning to visit solely for the Sistine Chapel, be prepared for at least an hour's walk through the museums to reach it. Additionally, keep in mind that it can get quite hot during the summer, so don’t forget to bring water!

For our last night, we enjoyed an amazing dinner and then took a magical nighttime walk through Rome. Naturally, we grabbed gelato one final time before heading to our ultimate tourist destination: the Pantheon.

The Pantheon is a stunning engineering marvel, constructed over 2,000 years ago and still standing strong! It's incredible to see the concrete dome, which remains the largest unreinforced dome in the world, and the towering front doors that reach nearly 24 feet in height!

I am so thankful for the opportunity to explore such a historic site and to wander through Rome at night. Do yourself a favor and experience the city after dark; seeing Rome from this perspective is truly special, and there’s something undeniably magical about the nighttime atmosphere.

Italy was truly everything we dreamed it would be and more-from our peaceful stay in the rolling hills of tuscany and the charm of visiting a small vineyard, to wandering through florence surrounded by history and art at every turn. the vibrant colors and quaintness of cinque terre felt straight out of a postcard, and ending our trip in rome-walking ancient streets and standing in awe of it’s timeless landmarks- was the perfect finale. every region offered something unique and unforgettable, leaving us completely in love with this country. we can’t wait to return and keep exploring more of italy’s magic, one breathtaking destination at a time.

for those curious about our italy trip, including accommodation Recommendations (we have special pricing with an italian hotel chain), what vineyard we visited, food & store recommendations, excursions, must see spots, check out our custom curated travel Itineraries in pdf format in our store section of our website that includes our full itinerary including links, custom map, tips, etc. (sign up for our email list, and receive a free pdf yosemite itinerary template download). additionally you can collaborate with me to create a personalized itinerary exclusively tailored to your vacation.

*I have special discounts with an italian hotel chain-message me for more information

Happy Travels!

Mandy

check out our link below for custom travel itinerary to Italy:

Italy Itinerary

Exploring the heart of italy: tips for an unforgettable trip!

tuscan hill towns:

my top 3 florence must-do’s:

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