Turning 50 is a milestone that deserved a grand celebration, and what better way to mark it than with a month-long adventure through Italy? This beautiful country, with its rich history, vibrant culture, and stunning landscapes, has always been on my bucket list. So, when the opportunity arose to spend 30 days exploring Italy everything from the enchanting coastlines of Sorrento to the bustling streets of Rome, the picturesque villages of Cinque Terre, the serene beauty of Lake Como, and the romantic canals of Venice, I couldn't resist. Here’s a detailed look at my unforgettable journey, packed with experiences that made this trip truly special.

30 Days Exploring Italy...

Sorrento: A Coastal Paradise

Stay: Hotel Antiche Mura

Sorrento, perched on cliffs overlooking the Bay of Naples, is a gateway to the Amalfi Coast. Known for its breathtaking views, lemon groves, and historic charm, Sorrento was the perfect place to begin our adventure. Staying at the Hotel Antiche Mura, we were right in the heart of the town, with easy access to all the major attractions. The hotel itself was a charming blend of old-world elegance and modern comfort, with friendly staff who made us feel right at home.

Day Trip to Positano

Our first big adventure was a day trip to Positano, often described as one of the most picturesque towns in the world. As we wound our way down the steep, narrow streets lined with pastel-colored houses, the view of the sparkling blue sea was simply breathtaking. Positano’s beach, Spiaggia Grande, is a bustling hub of activity, with sunbathers, swimmers, and boats coming and going. We spent the morning exploring the town, wandering through the narrow alleys filled with boutiques and cafes, each more charming than the last.

Lunch at La Tagliata

For lunch, we headed to La Tagliata, a family-run restaurant perched high on the cliffs overlooking Positano. This was one of the best meals of our trip. The food was incredible, made with fresh, local ingredients, and the view from the terrace was out of this world. We feasted on a variety of traditional dishes, from homemade pasta to grilled vegetables and succulent meats, all paired with local wines.

Semi-Private Group Tour of Capri and the Blue Grotto with You Know

Capri was next on our itinerary, and it did not disappoint. We booked a semi-private group tour of Capri with You Know, which included a visit to the famous Blue Grotto. The boat ride over was an adventure in itself, with stunning views of the coastline and the sparkling sea. The Blue Grotto, with its electric blue waters, was like something out of a dream. As our small boat entered the cave, the sunlight reflecting off the water created an ethereal glow that was simply magical.

Monte Solaro Chair Lift

Another incredible experience in Capri was taking the Monte Solaro chair lift. This rapid ascent to the summit offered spectacular views of the Gulf of Naples with Vesuvius in the background, the Gulf of Salerno, Anacapri, the Isle of Ischia, and the incomparable beauty of the sea's color. Monte Solaro is the highest point on Capri, and the views from the top were absolutely breathtaking.

Faraglioni Rocks

Our tour also took us to the famous Faraglioni rocks. The best way to view these towering rock formations is by sea during a boat tour of the island. Our skipper sailed right through the stone archway of the Faraglione di Mezzo, and as tradition dictates, we exchanged a kiss for good luck while passing through. It was a romantic and unforgettable moment.

Hiking the Path of the Gods

For hiking enthusiasts, the Path of the Gods offers one of the most scenic trails in the world. This hike, which runs along the Amalfi Coast from Bomerano to Nocelle, offers breathtaking views of the coastline and the sea below. It’s a challenging trek, but the vistas make every step worth it. We spent the day traversing rocky paths and steep inclines, stopping frequently to take in the stunning scenery. The sense of accomplishment we felt upon reaching the end was indescribable.

Rome: The Eternal City

Stay: The Inn at the Spanish Steps

From the serene beauty of the Amalfi Coast, we moved to the bustling metropolis of Rome, a city that seamlessly blends ancient history with modern life. We stayed at The Inn at the Spanish Steps, a luxurious hotel right in the heart of the city. Our room overlooked the famous Spanish Steps, and the location couldn’t have been more perfect for exploring the city.

Private Tour of the Roman Forum and Colosseum

Our time in Rome started with a private tour of the Roman Forum and the Colosseum, two of the most iconic landmarks in the city. Walking through the Forum, it was incredible to think about the history that had taken place there. Our guide was knowledgeable and passionate, bringing the ancient ruins to life with stories of emperors, gladiators, and the everyday citizens of ancient Rome.

The Colosseum, with its massive stone arches and imposing presence, was awe-inspiring. As we walked through the ancient amphitheater, it was easy to imagine the roaring crowds and the fierce battles that took place there. The history and grandeur of these ancient structures were truly humbling.

Visits to Trevi Fountain and The Pantheon

No trip to Rome would be complete without a visit to the Trevi Fountain and The Pantheon. The Trevi Fountain, with its Baroque architecture and cascading waters, was every bit as beautiful as I had imagined. Legend has it that if you toss a coin into the fountain, you will return to Rome someday. Naturally, we made sure to participate in this tradition.

The Pantheon, with its massive dome and ancient Roman architecture, was another highlight. The interior, with its marble floors and towering columns, was stunning. As we stood beneath the oculus, looking up at the sky, it was hard not to feel a sense of wonder at the engineering marvels of ancient Rome.

Shopping and Dining

Rome is a shopper’s paradise, with a mix of high-end boutiques and charming local shops. We spent our days wandering through the narrow streets, discovering hidden gems and unique finds. One of our favorite spots for meals was Ginger, a chic restaurant offering a taste of Italy with an American twist. The food was fresh and delicious, and the atmosphere was perfect for a relaxing meal after a day of exploring.

Tuscany: Cycling Through Picturesque Landscapes

Stay: La Bandita in Pienza & Il Falconiere in Cortona

DuVine Bike Tour through Tuscany Valley

One of the standout experiences was the DuVine Bike Tour through the Tuscany Valley. This four-day level 2 ride took us through picturesque landscapes, with rolling hills, vineyards, and charming villages at every turn. We stayed at the luxurious La Bandita in Pienza and Il Falconiere in Cortona, both offering stunning accommodations and breathtaking views.

Podere il Casale Farm

Celebrating my 50th birthday at Podere il Casale was unforgettable. We toured the farm, learning about their sustainable practices and the importance of farm-to-table dining. The meal we enjoyed, featuring ingredients grown right there on the farm, was one of the best I’ve ever had.

Italian Cooking Lessons

Cooking with Barbara at Villa Rosa deli was another highlight. Learning to prepare traditional Italian dishes in a beautiful setting was an experience I’ll cherish forever. Barbara’s passion for cooking was infectious, and the food we made was absolutely delicious.

Cinque Terre: A Quintessential Experience

Stay: Luxury apartment in Manarola

Cinque Terre, with its five seaside villages, is one of the most picturesque regions in Italy. Each village has its own unique charm, and exploring them all was a highlight of our trip. We stayed in Manarola, in a “luxury apartment” that wasn’t quite as luxurious as expected but did come with a washer—quite handy on a long trip.

Exploring All Five Seaside Villages

With a three-day train pass, we were able to travel freely between the villages, each offering its own unique charm. Monterosso, the largest of the five, was particularly captivating. The town is known for its beautiful beaches, historic churches, and lively atmosphere. We spent our days wandering through the narrow streets, discovering hidden gems, and enjoying the local cuisine.

Photoshoot in Manarola

One of the best decisions we made was to book a professional photoshoot in Manarola. Our photographer was fantastic, capturing the beauty of the village and the joy of our trip. The photos are a wonderful reminder of our time in Cinque Terre and the special moments we shared.

Wine Tasting at an Ancient Wine Cellar

Our wine tasting experience in Manarola was another highlight. We visited an ancient wine cellar, where we learned about the region’s winemaking traditions and sampled a variety of local wines. The atmosphere was intimate and charming, and the wines were absolutely delicious.

Hiking Between Villages

The hiking trails between the villages are some of the best in Italy, providing stunning coastal views and a sense of adventure. We spent our days traversing rocky paths and steep inclines, stopping frequently to take in the breathtaking scenery. Each village we reached offered its own unique charm, making the hikes even more rewarding.

Milan: The Fashion Capital

Stay: Doria Grand Hotel

Milan, known as the fashion capital of Italy, was a whirlwind of style and culture. We stayed at the Doria Grand Hotel, which was decent but not somewhere I’d necessarily stay again. The city itself, however, was fantastic, with its mix of historic architecture and modern flair.

Galleria Vittorio Emanuele II for Luxury Shopping

The Galleria Vittorio Emanuele II is a shopper’s paradise, with its stunning glass roof and high-end boutiques. We spent hours wandering through the elegant arcades, admiring the luxury shops and indulging in a bit of retail therapy. Milan is known for its fashion, and this was the perfect place to experience it.

Enjoying Chinese Food

After weeks of Italian cuisine, we decided to switch things up with some excellent Chinese food in Milan. It was a refreshing change and a reminder of the city’s diverse culinary scene.

Lake Como: Tranquil Beauty

Stay: Palace Hotel

Lake Como, with its serene beauty and tranquil waters, was a welcome escape from the hustle and bustle of city life. We stayed at the Palace Hotel, which offered comfortable accommodations and stunning views of the lake.

Boat Cruise to Bellagio

One of the highlights of our time at Lake Como was a boat cruise to Bellagio. The town is known for its beautiful villas, lush gardens, and charming streets. We spent our days exploring the town, enjoying the local cuisine, and taking in the stunning views of the lake.

Dining and Exploring Bellagio

Bellagio’s dining scene is fantastic, with a mix of traditional Italian restaurants and modern eateries. We enjoyed a variety of delicious meals, each one better than the last. The town itself is a joy to explore, with its narrow streets, charming shops, and friendly locals.

Funicular Ride to Brunate

Taking the funicular up to Brunate was another highlight. The ride itself offers stunning views of the lake and the surrounding mountains. Once we reached the top, we hiked to the lighthouse, where we were rewarded with breathtaking views of the snow-covered Alps. It was a perfect way to spend the day, surrounded by nature’s beauty.

Venice: A Romantic Finale

Stay: Palmetto Madonna

Venice, with its romantic canals and historic charm, was the perfect place to end our Italian adventure. We stayed at the Palmetto Madonna, a beautiful hotel with a prime location. Our room overlooked the canals, and the atmosphere was simply magical.

Gondola Ride

No trip to Venice would be complete without a gondola ride. Seeing the city from its waterways was a unique and unforgettable experience. Our gondolier navigated the narrow canals with ease, sharing stories and insights about the city’s history and culture.

St. Mark’s Square

St. Mark’s Square is the heart of Venice, and spending time there felt like stepping into a different era. The square is surrounded by stunning architecture, including St. Mark’s Basilica and the Doge’s Palace. We spent hours wandering through the square, taking in the sights and sounds of this bustling hub.

Wandering the Streets

One of the best parts of our time in Venice was simply getting lost among the winding streets. Every corner seemed to reveal another breathtaking view or hidden gem. We stumbled upon charming cafes, historic churches, and picturesque bridges, each one more beautiful than the last.

Reflections on Italy

Celebrating my 50th birthday with a 30-day journey through Italy was beyond my wildest dreams. Each destination offered its own unique experiences and memories that I will treasure forever. Whether it’s the coastal beauty of Sorrento, the historical grandeur of Rome, the rustic charm of Cinque Terre, the fashionable flair of Milan, the tranquil serenity of Lake Como, or the romantic allure of Venice, Italy has something for every traveler. If you ever have the chance to explore this incredible country, don’t hesitate—Italy will capture your heart and leave you longing for more.

xo, holly

P.S. Check out my collage from our amazing trip ↓