From Ligurian Coastlines to the Heart of Tuscany
I recently returned from an incredible familiarization trip through northern and central Italy, and I’m still daydreaming about seaside aperitivi, vineyard lunches, and the warm hospitality we experienced along the way. My journey blended iconic Italian highlights with slower, more authentic moments, something we always strive to incorporate in our clients’ itineraries.
Over the course of 10 nights, my best friend and I explored the Ligurian coast, Emilia-Romagna, and Tuscany, staying in Sestri Levante, Portovenere, Parma, and two beautiful countryside properties in Tuscany. From swimming in the Gulf of Tigullio to wine tastings in Montalcino, every stop offered something completely unique while still feeling authentically Italian.
Sestri Levante: The Italian Riviera Without the Rush
Our journey began in Sestri Levante, a colorful seaside town that immediately felt more local and relaxed than some of Italy’s busier coastal destinations. With pastel buildings lining the golden sandy beach and locals gathering in the piazzas each evening, it was the perfect introduction to Ligurian life. What I loved most was how authentic everything felt: no rushing crowds, just a slower rhythm centered around good food, beautiful scenery, and enjoying the moment. Locals told me Italians in Northern Italy have been vacationing in Sestri Levante for generations.
One of the highlights of our stay was a boat tour through the Gulf of Tigullio to Portofino and Camogli with our skipper, Massimo. The coastline was stunning from the water, with dramatic cliffs and charming seaside villages around every corner. We even had the chance to swim near the famous Christ of the Abyss statue, which has been suspended underwater off the coast for the last 72 years. It sits 55 feet underwater, and we did not make it all the way to the bottom! We had fun gazing at it and swimming with a large school of small, striped fish.
Must-See & Do in Sestri Levante
- Take in the Baia del Silenzio at sunset with a spritz
- Take a Gulf of Tigullio boat tour to Portofino and Camogli!
- Swim near Christ of the Abyss
Sestri Levante – Baia del Silenzio
En route to Portofino on a private Gulf of Tigullio Boat Trip
Portovenere: A Storybook Coastal Escape
After Sestri Levante, we continued south to Portovenere, which truly felt like stepping into a postcard. Colorful homes stacked along the harbor, narrow medieval lanes, and dramatic cliffs overlooking the sea made this one of the most magical stops of the trip for us. While many travelers focus solely on the Cinque Terre towns, Portovenere is calmer, more romantic, and deeply connected to its history.
Portovenere was named after a temple to Venus (Portus Veneris) that once stood on the rocky promontory overlooking the sea. For centuries it inspired writers and poets drawn to the dramatic beauty of the surrounding bay, especially Lord Byron, who swam across the gulf from nearby Lerici and helped make the area famous among Romantic artists. Today, there is a stunning rocky cove located just beneath Portovenere’s medieval castle called Byron’s Grotto.
The Church of San Pietro quickly became my favorite spot in town. Perched dramatically on the rocky edge of the coastline, it offered sweeping views of the Ligurian Sea and some of the most breathtaking sunsets we experienced. We spent our evenings wandering the harbor, enjoying incredible seafood dinners, and hopping on ferries to nearby Cinque Terre villages during the day. One evening, after dinner, we sat by the water listening to church bells echo through the harbor while locals gathered nearby for a night out. Although it is a small town, Portovenere is rich with life and authentic Italian culture.
Must-dos in Portovenere include eating seafood at any of the amazing restaurants in town (we loved Antica Osteria del Carugio), swimming in Byron’s Grotto and climbing to the Church of San Pietro, especially at sunset.
Portovenere’s Harbor
Sunset over Bryon’s Grotto
Parma: Italy’s Culinary Heart
Next, we traded the coastline for the culinary capital of Parma in Emilia-Romagna. Parma felt elegant yet understated, with beautiful piazzas and historic architecture. The city itself was charming to wander, but the real highlight was our small group Emilia-Romagna food tour through the surrounding countryside.
Throughout the day, we learned about the traditions behind Parmigiano Reggiano, Prosciutto di Parma and authentic Balsamic Vinegar led by our amazing guide, Marika. We met passionate local producers who have been preserving these methods for generations. One cheesemaker explained how every wheel of Parmigiano is inspected by hand, and hearing the pride in his voice made us appreciate every bite even more.
Must-See & Do in Parma
- Join an Emilia-Romagna food tour
- Taste authentic Parmigiano Reggiano
- Explore Parma’s historic center and shopping
Baptistery in Parma
Cheese Wheels
Tuscany: Rolling Hills & Family Traditions
From Parma, we drove into the heart of Tuscany, where the landscape transformed into rolling vineyards, cypress-lined roads, and golden countryside views. We spent two nights in a peaceful countryside retreat located between Siena and Florence.
One of the standout experiences here was a winery lunch hosted by Riccardo and Silvano at their vineyard at the estate. Riccardo’s knowledge of the vines, harvest process, and regional wines made the experience feel deeply personal rather than overly polished. Even more unforgettable was the meal prepared by his mother, featuring homemade pasta, local olive oil, and dishes that tasted like they had been perfected over generations.
Setting for winery lunch
Montalcino & La Dolce Vita
Our final stop brought us deeper into Tuscany to a stunning family-owned countryside property surrounded by vineyards. Between the infinity pool overlooking the hills and the peaceful atmosphere, this was the kind of place where time seemed to slow down completely. The property felt warm and welcoming from the moment we arrived, largely thanks to the manager, Minnie, and the Losappio family who own and run the property. The attention to detail and excellent taste made every room seem like something out of Vogue. Their charming cat, Tamino, quickly became everyone’s favorite unofficial host.
The villa offered onsite wine tastings and convenient shuttles into nearby Montalcino, making it easy to explore the area without worrying about driving. Evenings here were especially memorable: watching sunset over the vineyards with a glass of Brunello in hand felt almost cinematic. Tamino often joined guests for pets and relaxing evenings watching the sunset.
Must-See & Do Nearby
- Relax at the infinity pool
- Visit Montalcino
- Enjoy onsite wine tastings
- Watch the sunset over the Tuscan hills with Tamino
Tamino keeping things under control
View from our Villa
This trip perfectly captured the diversity of Italy, from colorful coastal villages and historic harbors to culinary traditions and peaceful Tuscan vineyards. What stood out most wasn’t just the scenery, but the people we met along the way: the local guides sharing stories, the families welcoming us into their homes, and the moments that felt completely unplanned yet unforgettable. Italy has a way of making you slow down, savor every meal, and appreciate the beauty in simple experiences.
As I reflect on this trip, what lingers most isn’t any single view or meal, but the way each destination allowed us to experience a different rhythm of Italian life. If you’re ready to experience Italy in a way that feels more personal, more immersive, and more memorable than anything you’ve done before, our team would be delighted to help design it with you.
