Positano, Naples, Amalfi Coast: An 8-Day Italy Itinerary

We begin your 8-day Italian journey in Naples, then leisurely float away for a quick excursion to the island of Procida before docking you in Positano. Insider scoop: It’s not always seamless to get to the Amalfi Coast, but this option offers a non-stop and more cultured/scenic journey to Positano. Those who stay in Sorrento will envy your approach. Andiamo!

Explore Naples
Spend the day at local sites like Castel Sant’Elmo. It’s situated on a hilltop so it has the best views of the city, Mount Vesuvius and the Bay of Naples. Walk 5 minutes to restaurant Renzo e Lucia where you’ll enjoy more panoramic views with drinks and light snacks.

Next, head to the oldest castle in Naples (and my favorite), Castel dell’Ovo. Although inside the castle is closed, wandering through the structure is joyful because it's right on top of the sea. Top off your day with a sunset walk along the Lungomare, which you can access just outside the Egg Castle.

Visit the UNESCO World Heritage site, Pompeii. Walk the ruins of this historic Roman city that was wiped out and buried in volcanic ash during the eruption of Mount Vesuvius in 79 A.D. After a few hours of exploring Pompeii, it’s possible to go to Mount Vesuvius and hike to the crater. If you prefer to skip the hike and immerse yourself in food & culture instead, a private guide will take you through the local neighborhoods and tell you more about the history of Naples.

Pizza e Vino

Naples would not be complete without indulging in pizza. It’s THE birthplace of pizza. Locals swear by Sorbillo, however, I prefer Pizzeria Sandropizzettata for their fluffy crust and top-quality ingredients or La Masardona’s fried pizza, a pocket full of yum.

After your ultimate pizza experience, head to Spuzzule, a small wine bar bursting with local flavor. If you’re hungry again, they've got you covered with tapas-style bites and charcuterie boards.

In the morning, hop aboard a 40-minute high-speed ferry to the island less-traveled. Named Italy’s Capital of Culture 2022 and one of my favorite islands in Italy, Procida (between Capri and Ischia) is the most charming island with colorful buildings and fresh-caught seafood.

From the ferry port, take a 30-minute stroll to Spiaggia del Postino (Pozzo Vecchio). Grab a drink at the beach bar and rent a lounge chair on this quaint beach. After you’ve had your fix of sun, sand and sea, head to Marina di Corricella, (another 30-minute walk). Lunch will be picturesque at La Lampara where you’ll enjoy the view and fresh local fish, caught daily.

There are a couple of ferry companies that go direct from Naples to Positano in-season. I can also recommend a private boat transfer or a scenic drive along the winding cliffside roads.

Check in at the cliffside hotel, Il San Pietro, and spend the first part of the afternoon at their private beach club. Or stay at the serene Villa TreVille, and lounge at the beach club I frequented most, Laurito Beach. If you wish to stay directly in town and close to the action, Villa Flavio Gioia and Le Sirenuse are my top choices!

Explore and Climb the Steps of Positano: Positano is a vertical town, so expect stairs everywhere you go. John Steinbeck makes mention of this in his 1953 "Positano" article in Harper’s Bazaar: "Everything else is stairs, some of them as steep as ladders. You do not walk to visit a friend, you either climb or slide." Your 8-Day Italy itinerary would be incomplete without getting lost among the steps, paths and beauty around every corner. With shopping at every turn, these are my top 5 local apparel and ceramic shops:

• Marilu - Women’s apparel & accessories. A favorite among the locals.

• Emporio Sirenuse - Located just outside the hotel Le Sirenuse, this shop offers men’s & women’s apparel, accessories and home decor.

• Theodora Moda - Women’s apparel & accessories with all the vibes of Positano.

• Ceramica Assunta - Handmade Italian pottery.

• Ceramiche Soso - Locally made whimsical ceramics and home decor.

Dinner at Le Tre Sorelle: For dinner, have a seat at my absolute favorite restaurant, Le Tre Sorelle. When I lived in Positano, I could be found here up to 3x a week for lunch or dinner. If you’re lucky, Gaetano will be your cameriere (waiter) and he’ll start you off with heart-shaped bread, oozing with melted cheese, arugula and tomato. Pick from the fresh catches of the day, hand-delivered to Tre Sorelle each morning by the town’s fish guy. End your dinner the Italian way with espresso or limoncello and the best Tiramisu you’ll find in town.

Locals say, the best way to see Positano is from the sea. Your captain will take you on a private boat tour that can be curated any way you like. Pro Tip: Head toward Li Galli (a private island), have a swim, then lunch in Nerano at the Michelin star restaurant, Taverna del Capitano. Cruise the Amalfi coast taking in the sites of Priano, Fiordo di Furore, Conca dei Marini, Amalfi, Atrani, Maori and beautiful grottoes along the way.

• Cooking Class: An intimate cooking class awaits you in a dream-like setting above Positano at La Tagliata. You’ll start by walking through the gardens of the restaurant and collecting fresh ingredients. Learn simple traditional recipes, drink wine, and devour your meal cooked with love as you sit on the terrace overlooking Positano and Li Galli.

• Hike the Path of the Gods (Sentiero degli Dei): The Path of the Gods (Sentiero degli Dei) is a must for any hiking enthusiast. You’ll want to start on the early side because depending on the route you choose, it could take 4 hours. I made a full day of this activity and hiked from Nocelle, up to Bomerano in Agerola, then back down. Most people will take a bus to Bomerano and hike down to Nocelle or Positano. Reward yourself at the end with drinks on the terrace at Il Chiosco del Sentiero degli Dei.

A few more towns along the Amalfi Coast are not to be missed on your 8-day Italy Itinerary. A private driver will take you to Ravello, Atrani and Amalfi, where you’ll spend most of your day. In Ravello, visit Villa Rufolo and its gardens. Next, you’ll drive down to Atrani, where you’ll have a relaxing Mediterranean lunch at the seaside restaurant, Le Arcate. Following lunch, rent a lounge chair and relax on Atrani’s beach while gazing into the sparkling blue waters. End in Amalfi and enjoy a refreshing Granita al Limone on the steps of the Duomo di Amalfi.

This is your last night in Positano and you’ll want to dance the night away with the locals at Music On The Rocks. This disco club is carved out of a cliff overlooking the sea. The night will end with Whitney Houston’s "I Wanna Dance With Somebody," and with that, you’ve had the complete Positano experience.

Your private transfer will take you for a stop in Sorrento to visit the lemon garden and do a limoncello tasting at I Giardini Di Cataldo.

As you make your way back to Naples for the flight home, don’t be sad to leave, but happy you came.