Southern Italy Itinerary

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Advisor - Janelle Smith
Curated By

Janelle Smith

  • Italy

  • Positano

  • Naples

  • Capri

  • Sorrento

  • Food & Wine

  • Arts & Culture

  • Sightseeing

  • Local Food

  • Outdoors

A view of the village of Cortona, Italy and the countryside.
Curator’s statement

Travel to Southern Italy, where the warm and welcoming nature of the people makes visitors feel like family. I journeyed to Southern Italy's Amalfi Coast region to celebrate an unforgettable 40th birthday adventure, complete with majestic mountain views, azure waters and stunning natural beauty. Southern Italy is renowned for delicious cuisine, boasting its famous Neapolitan pizza and traditionally prepared fresh seafood dishes where cherished and preserved recipes are handed down through generations. The region's culinary delights are a testament to its rich gastronomic traditions, making Southern Italy truly special and a delight for food lovers. Incorporating a Hub and Spoke strategy from Sorrento was a perfect way to experience a variety of historical, cultural and natural wonders of the Amalfi Coast region of Southern Italy.

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Day 1: Arrival to Sorrento

A view of a wooden staircase leading down to a body of water and rocks in the surrounding areas.

Set yourself up for a week of travel adventures ahead by taking it easy after a long journey. Once settled into your hotel, stretch out by walking around the hotel and grounds to see where the pool, spa, restaurants and fitness center are located. This is a good opportunity to visit the concierge desk to say hello and see about any local "must sees and hidden gems" not already on your agenda.

Mid-afternoon is a perfect time to explore Old Sorrento, the historic center of this charming coastal town. You will find numerous artisan shops showcasing local products such as intricate woodwork, lacework and ceramics. They offer a glimpse into the traditional crafts that have been passed down through generations.

Don't miss Piazza Tasso in the heart of Old Sorrento. The vibrant square, named after the famous poet Torquato Tasso is a bustling hub filled with cafes, shops and restaurants.

Old Sorrento boasts breathtaking views of the Bay of Naples and Mount Vesuvius. Grab some dinner and take in the breathtaking scenes before heading back to the hotel for a well-deserved good night's sleep after a long day of travel and arrival in Sorrento.

Before you know it, you will hear the local roosters ushering you into Day 2.

Personal Note: It was in Old Sorrento that I purchased a beautiful hand-crafted portable chess board. I use it often and it reminds me of my wonderful Italian adventure.

Day 2: Capri, Anacapri, Blue Grotto & Pizza Class

La Fontelina is an iconic beach club and restaurant located on the scenic coastline of Capri. Picture is of blue and white umbrellas on a beach with rocky outcroppings in the distance.

Capri, Anacapri & Blue Grotto 8-Hour Day Trip Tour

From Sorrento, your local guide and your group will board an express ferry to the beautiful island of Capri. Once on Capri, you will shuttle around the island learning about its rich history as you travel to the natural caves of the Blue Grotto. Next up is the charming town of Anacapri, where you will have free time to shop, catch a cup of coffee and explore Mount Salaro via chairlift before heading back to Sorrento for the evening.

Evening Authentic Neapolitan Pizza Making Class

Grab a glass of local wine as you learn the secrets of Neapolitan pizza making. Enjoy a traditional dessert of Tiramisu before heading back to your hotel.

Night Cap before Bed

Wind down and enjoy a glass of wine or cup of sleepy tea on the patio recapping the day with your loved ones.

Personal Note: The view from Mount Salaro was breathtaking. This full day was so enjoyable for me, offering a terrific mix of land, sea and culinary fun.

Insider Tip: Ask many questions of your shuttle driver, bartender, tour guide and store clerks. Learn as much as you can from the locals to enhance your experience as you show gratitude for their knowledge and expertise.

Day 3: Pompeii, Mount Vesuvius National Park, Wine Tasting & Dinner at Nino's

Beautiful Pompeii vineyards and mountains in the distance.

Pompeii, Mount Vesuvius National Park, Wine Tasting 7-Hour Day Trip Tour

Visit and learn about the deep history of the extraordinary city of Pompeii, where time stands still after the devastating eruption of Mount Vesuvius in 79 A.D. Next on the tour, you will visit Vesuvius National Park and a vineyard tucked into the side of Mount Vesuvius before heading back to Sorrento.

Dinner at Nino's

Enjoy dinner and craft cocktails at this top-ranked Sorrento restaurant offering a terrace with a view of the Gulf of Naples.

Personal Note: As a history lover, Pompeii really impressed me. I was in awe of this ancient city the entire tour. I cannot wait to visit again. I know you will enjoy it as much as I did.

Day 4: Positano, Amalfi, Limoncello & The Three Tenors Inspired Opera Show

Visit Positano coast and see the village near the ocean. Beautiful coastline with houses built into the mountain side.

Positano & Amalfi Scenic Boat 8-Hour Trip Tour

Depart the marina on a scenic boat trip visiting Positano and Amalfi, where you will visit each town for local shopping, refreshing swim time and snacks. Top off the tour with a sip of a Southern Italy favorite - Limoncello, before sailing back to Sorrento along the spectacular Amalfi Coast.

Sorrento: The Three Tenors Inspired Opera Show

After a short rest back at the hotel and dinner out, head to the Three Tenors Inspired Opera Show. The highly rated Southern Italian show will leave you full of emotion, located at the concert hall of the Correale museum of Terranova.

Watch the new video of The Three Tenors Video!

Personal Note: I loved climbing the rocky roads of Positano to one of the many hilltop restaurants for a glass of prosecco and light snack overlooking the fairy tale hillside city. Simply breathtaking!

Day 5: E-Bike, Oil & Lemon Tour/Tasting & Pool Time

View from the Lemon Path in Minori. The coastline and foliage in the distance.

E-Bike, Oil & Lemon Tour with Tasting 3-Hour Tour

Discover Sorrento via E-Bike. Explore the rolling hills of Sorrento while enjoying the panoramic views of the peninsula below. Visit the oldest oil mill in the area and learn about the ancient art of oil production. Taste and learn about Southern Italy's staples such as olive oil, lemons, truffles as well as local goods such as limoncello, marmalade, honey and much more!

Pool Time or Spa Massage

Enjoy your hotel amenities like the hotel pool or a spa massage for relaxation before a sumptuous dinner out.

Pro Tip: Use TripAdvisor to search for top-ranked restaurants, where you can filter specifics that are of interest to you and the group. For instance, you can filter by price, customer ranking or cuisine style. See the below link specifically for restaurants in Sorrento. Buon Appetito!

Restaurants in Sorrento on TripAdvisor

Advisor - Janelle Smith

Travel Advisor

Janelle Smith

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Looking for more travel inspiration? Check out Fora's article: 9 Best Hotels in Southern Italy.

This guide is part of our ongoing series on travel to Italy.