Southern Italy

Taormina, Sicily

“Why Sicily?” is a question we’re asked a lot. Ben’s grandparents were from Sicily and immigrated on the last boat over to America before WWII. We knew we wanted to go to Sicily to find their homes while they were still there - a trip that Ben’s parents had taken a few years prior. With Sicily being our main purpose, we quickly discovered that places likes Venice would not be in the cards and we needed to stick to Southern Italy.

If you only have 1-2 weeks for vacation, I personally believe you either need to choose between Northern Italy or Southern Italy - this was also the advice we received from our travel agent. It gives you an opportunity to really experience a destination without feeling super rushed.

10-DAY ITINERARY IN SOUTHERN ITALY

DAY 1: Depart on a red-eye for Taormina Airport in Sicily
DAY 2: Check-in at Monaci delle Terre. Enjoy your arrival cocktail poolside and relax before dinner at Nerello, the hotel’s restaurant, recognized for the slow-food movement.
DAY 3: ATV on Mt Etna. Go back to the hotel to take advantage of their wine tasting. Opt for car service to have dinner on the water at Trattoria La Grotta in Acireale
DAY 4: Shopping and lunch in Taormina. Dinner at the hotel’s wine bar
DAY 5: Depart for Naples. Arrive and take a private guided tour of Pompeii. Check-in at Relais Regina Giovanna in Sorrento. Relax for dinner at the hotel’s restaurant, Pane E Olio
DAY 6: Explore the Amalfi Coast (Positano, Amalfi, Ravello) and have a cliffside lunch at Ristorante Da Ciccio Cielo Mare Terra Amalfi. We had a private driver which made the coastal drive more enjoyable than nerve-racking.  
DAY 7: Sail around Capri to see one of the blue grottos, and then “beach” at the hotel’s private beach. Dinner at Ristorante Museuo Caruso
DAY 8: Depart for Monte San Pietro, a town outside of Bologna by taking a train from Naples to Bologna, then take a private care service from the Bologna airport. Check into your airbnb. Dinner in the Medieval Town of Valsamoggia at Trattoria del Borgo.
DAY 9: Enjoy a day at the wineries - Tenuta Bonzara and Botti Vini. Then, head to dinner on a vineyard farm, Corte d’Aibo
DAY 10: Explore Modena; Balsamic Factory Tour, Ferrari Museum (for car lovers), and if you can, reserve lunch or dinner at Osteria Francescana.
DAY 11: Depart for Florence. Check into Hotel Antica Torre Tornabuoni, private walking tour with Academia, and dinner at I’Parione Restaurant 
DAY 12: We flew home; I would recommend another day in Florence. I left wanting to see more of this beautiful city.

The hotel pool bar at Monaci delle Terre - made from molten lava

SOUTHERN ITALY

Where to Stay:

Monaci delle Terre (Mt. Etna, Sicily) - It’s 19th century monastery turned into an eco-bio farm. Everything is fresh from the land. They have 21 unique rooms - we stayed in a Superior King which was essentially a private villa with a patio and chaise lounge chairs. My heart was originally set on staying in Taormina but after seeing the craziness of the tourists, we knew we made the right choice!

Relais Regina Giovanna (Sorrento) - A farm hotel on the coast of Italy with its own private beach access. We found this hotel to be a retreat from the tourists on the Amalfi Coast, and probably half the price. It was well worth it!

Cherry Cat Airbnb or Casa Sassolo 1713 (Monte San Pietro/Bologna) - Two unique airbnb homes with the most hospitable families; Cherry Cat is a mid-century modern home, while Casa Sassolo is a historic home from the 18th century across the hill. If you choose to stay in the Cherry Cat airbnb, I highly recommend allowing the family to make you dinner during your stay.

Hotel Antica Torre Tournabuoni (Florence) - A medieval tower turned into a boutique hotel with a historic address. We stayed in a Grand Deluxe Room with a private terrace and sweeping views of the city.

Where to Eat:

SICILY

Locanda Nerello - At Monaci delle Terre, you’ll find this beautiful restaurant with a 0km menu, set in the main monastery. Opt for a seat on the terrace to see the Mediterranean Sea off in the distance and the beautiful farm landscape.

Convivium Bar - Inside Monaci delle Terre’s main building, you’ll find this charming spot. From the lava molten rock walls to the lighting and cute bar, I couldn’t wait to spend an evening here relaxing. I’ll always remember the beautiful sounds of the Sicilian mouthpiece played by our bartender.

Trattoria La Grotta in Acireale - On the coast, you’ll find this cute restaurant with the freshest seafood possible; in fact, your dinner still be moving when you go to order it.

SORRENTO/AMALFI COAST

Pane E Olio - a hidden restaurant set on the Relais Regina Giovanna property. They make their own olive oil which you’re given different varieties to taste at the beginning of the meal.

Ristorante Da Ciccio Cielo Mare Terra Amalfi

Ristorante Da Ciccio Cielo Mare Terra Amalfi - it could possibly rank as one of the most stunning restaurants on the Amalfi Coast.

Ristorante Museuo Caruso - down the alleys of historic Sorrento, you’ll find this restaurant and museum dedicated to the singer Enrico Caruso. The live musician playing Caruso’s songs from table-to-table felt so special.

MONTE SAN PIETRO

Trattoria del Borgo - in the medieval village of Monteveglio Valsamoggia, this restaurant dates back to the 1600’s.

Corte d’Aibo - an organic farm with a restaurant serving organic food in the middle of their vineyard.

Osteria Francescana - A three star Michelin restaurant and one of the World’s Top 50 Restaurants (reservations open 3 months in advance). We brought toddlers in tow and they were so accommodating. We opted for the tasting menu but after trying one of the toddler’s pasta dishes, I wish I stayed with the basic menu.

FLORENCE

Parione - this restaurant was within walking distance of our hotel. We ordered the steak but to be honest, I would not recommend this restaurant; it was one of our least memorable meals in Italy.

We would love to return to Sicily and Northern Italy next time. Sicily and Monte San Pietre were our absolute favorite - it was so raw, untouched and real. Our Sicily-Italy itinerary and trip was orchestrated with the help of a Virtuoso travel agent and friend, Hannah Roth of Where To Next travel agency.