So, we arrived in Sorrento late at night, which—pro tip—is the absolute best way to arrive anywhere in Italy. There’s something magical about stepping into a city that’s already alive and buzzing while you’re still shaking off the airport exhaustion. The plaza was packed. Men in effortlessly stylish camp shirts and slacks, women in flowing dresses that looked like they belonged on the cover of a romance novel. Everyone looked like they had just stepped out of a fashion shoot. Meanwhile, I was lugging my suitcase across cobblestone streets, looking like I’d kicked it down three flights of stairs. I had packed an old suitcase, and by the time I rolled it from the Naples airport to the train station, the wheels had literally melted. My suitcase only had two functioning wheels, and of course, they were on opposite corners. So, I was balancing my 45-pound suitcase on one wheel, dragging it across the uneven, black cobblestone like a weary traveler holding on to their last ounce of hope.
Exhausted, we found ourselves in the heart of Piazza Tasso, the main square of Sorrento, at 12:10 AM. Every single restaurant’s outdoor seating was full. Midnight. On a weekday. And yet, people were drinking, eating, laughing, and somehow looking like they had just casually strolled out of a five-star resort. There was live music playing, of course—because it’s Italy, and they know how to set the scene.
Our VRBO was a pleasant surprise: modern, spacious, and with just the right amount of Italian charm. It was in a historic building with grand wooden doors right in the heart of Sorrento. The living room opened up to a private balcony that overlooked a garden, adding that little extra bit of magic to the experience, enough to make you feel like you’ve found your own secret spot in Italy. It was the kind of place that makes you think, “Huh. Maybe I could live here forever.” A spot so perfect, it makes you question all your life choices and wonder if you should drop everything to become a full-time Italian local.
The first morning in Sorrento hit like a lightning bolt. The excitement of the day ahead—and maybe a touch of adrenaline—kicked in faster than I could shake off the jetlag. Our private van was scheduled to pick us up at 8:30 AM in Piazza Tasso for a full-day tour of the Amalfi Coast, and though I wasn’t fully awake yet, I couldn’t help but feel a rush at the thought of what was to come. Our tour guide advised an early start to stay ahead of the crowds, and it definitely paid off.
We climbed into the van, ready to take on the legendary Strada Statale 163 Amalfitana (SS163), one of the world’s most famous coastal roads. Imagine this: winding roads hugging jagged cliffs, with the sea plunging into the Mediterranean below. It was like something straight out of a dream. As we headed toward Positano, I could already see the coastline stretching out before us, dotted with yachts and fishing boats, the deep blue water gleaming under the early morning sun. Our guide—who grew up not far away in Naples—was completely unfazed by the hairpin turns and narrow roads. I, on the other hand, was holding my breath every time we passed a bus coming too close for comfort. We’d accelerate on the straighter sections, the engine roaring as we gained speed, only to slow down—just a little—on the sharp turns.
If you’re thinking of driving this road yourself, I have one piece of advice: Don’t. Just don’t. The road is stunning, sure, but the reality of dodging buses and navigating tight corners while also trying to enjoy the view? Not worth it. Go for a private tour, get a bus pass, or at the very least, hire a driver. You’ll thank me later.
Instead of stopping in Amalfi, our guide took us straight to Ravello—an inspired move, since we arrived before the crowds. This town sits high above the coastline, tucked away from the chaos of the tourist-heavy spots below. It’s quiet. It’s picturesque. It looks like a painting. Flowers spill over balconies, vineyards stretch across rolling hills, and the entire place feels like it was designed specifically for people who use words like “charming” unironically.
The highlight? A small wine shop called Sapori Mediterranei, where we sampled the best local limoncello. It was sweet, tangy, and bursting with bright citrus flavor—worth trying at least once while you’re here.
Amalfi was our next stop, and here’s the thing—you’ve got to embrace the chaos. It’s busy. There are tourists everywhere. But it’s also breathtaking. The colorful buildings, the dramatic cliffs, the Mediterranean stretching out forever—it’s everything you imagine when you hear the words “Amalfi Coast.”
Quick history lesson: Amalfi was once a powerful maritime republic, competing with Venice and Pisa. The entire coastline is named after this one small town, which tells you how influential it was. Now, it’s mostly known for stunning views and being one of the best places in the world to consume obscene amounts of lemon-flavored everything.
Speaking of which—Nino & Friends. This store is dangerous. You walk in, and they immediately start handing you samples. Chocolate bars. Pralines. Limoncello-filled cookies. I blacked out somewhere around the third truffle and came back for seconds on the way out of town. No regrets.
Next, we were headed to lunch at Costa Diva Hotel in Praiano. This place is a gem. Imagine dining under a canopy of sparkling lights and hanging lemons, with an incredible view of the coastline and the Mediterranean below. It’s like stepping into a fairytale. The charm of the place is hard to put into words—the ambiance, the warmth of the staff, and the genuine Italian hospitality made it feel like we were the only ones there.
We had our first Aperol spritz of the trip, sitting in the shade of a lemon tree with the sea breeze in our hair. I had spaghetti with shellfish and cherry tomatoes, and I honestly can’t remember the last time I had seafood pasta that good. The seafood was fresh, the sauce was simple but perfect, and the flavors popped in a way that made every bite unforgettable. And yes, I paired it with wine and Aperol spritz together. Oops.
Our next stop was Positano, my favorite on the coastline. Our tour guide dropped us off near the top of the hill, and we were able to walk down the winding road with panoramic views of the city and the ocean. As we strolled down the sloped hill, we passed charming shops, art galleries, and dessert stores offering free samples (which, of course, I had to try). The whole town is lined with beautiful flowers and vines creeping along the walking paths. The unique stores and boutiques, along with the villas and hotels scattered throughout the city, made Positano feel like a dream.
Positano is expensive to stay in, and the listings for accommodations book up fast. If you’re thinking about staying there, definitely plan ahead. There are some cool Airbnb/VRBO options, including ones where you can sleep on a sailboat docked at the ocean. Can you imagine waking up every morning to the sound of waves crashing and the view of colorful homes on the cliffs? That would be an experience worth every penny.
Positano’s history goes way back, even to the ancient Roman period. The city is often called the “vertical city” because of the way it climbs up the steep cliffs. Its stunning views, colorful homes, and winding paths make it one of the most photogenic spots along the Amalfi Coast. The beaches here are iconic, even if the rocky shore makes lounging a bit harder than on a sandy beach. But the water was so clear, it more than made up for it. The big yachts floating in the water and the smaller boats lined along the shore gave the whole place a sophisticated, luxurious vibe.
We spent some time at the beach, but the heat was a lot to handle in August. After a bit, we decided to climb the steep hills to explore the city further. And that’s when we got lost. We somehow ended up climbing hundreds of feet and several flights of stairs before we realized we’d gone too far. We were huffing and puffing, but the views from the top were worth every bit of the climb. We finally found our way back down to our meeting spot for the tour van, a little late but grateful for the unexpected adventure.
On the way back to Sorrento, we were all tired from the long day of sightseeing, but the beauty of the Amalfi Coast was impossible to forget. We took a well-needed nap when we got back to our VRBO in Sorrento. The place was buzzing with life—people laughing, music playing, and the whole city coming alive at night as the temperature cooled off.
Around 8 pm, we headed out to the Piazza Gargiulo for a firework show to celebrate the Feast of St. Anne. The view from there was amazing. Overlooking the coast, you could see Naples, Mount Vesuvius, and even Pompeii in the distance. The fireworks lit up the sky, and we could feel the energy in the air.
After the show, we wandered the streets looking for a place to eat. It didn’t take long for a man standing outside a restaurant to greet us with a friendly “this is where you’ll have dinner tonight.” We didn’t need much convincing; 30 seconds later, we were sitting down at a table, ready to enjoy more pasta.
While we ate, a man walked up to our table and started singing to us. It was a little awkward, as he was only about five feet away, and we couldn’t understand everything he was singing. But it was part of the charm, and the experience definitely added a bit of authenticity to the meal.
We had ravioli and agnolotti with squid, delicious. After dinner, we went on a little shopping spree. We got the infamous lemon sorbet that everyone had been talking about. Walking through the streets of Sorrento, stopping at every store offering free chocolate or limoncello samples, was like living in a dream. There’s gelato on every block, chocolate on every corner, and well-dressed Italian men trying to lure you into their restaurants with charm. It’s all part of the fun.
As we walked through the lively streets, with music spilling out of every restaurant, I couldn’t help but think about how much of Italy’s charm comes from these little moments—the impromptu performances, the warmth of the people, and the beauty of the landscapes. It was like living inside a movie, and I was lucky enough to be part of it.
After an incredible day exploring the Amalfi Coast, we couldn’t wait for the next adventure that awaited us. The following morning, we traded in the cliffs and bustling streets for the tranquil waters of the Mediterranean as we set off for the stunning island of Capri. A boat day was just what we needed to unwind and explore the island’s dramatic coastlines and hidden coves. But Capri, as we soon discovered, is a whole different world and one that’s best experienced from the water.
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