Sorrento Women's Adventure

Sorrento Women’s Trip … with Pia Ruoppo 

Take a deep breath, and fall into the embrace of beauty. This is the Sorrento Coast, where jagged mountains plunge their way to the sea, colorful villas cling to cliff-sides and fishing boats bob atop impossibly turquoise waters. A land like this can’t be “seen”, it must be experienced – taken in with all of your senses.

With native Sorrentine, Pia Ruoppo, as your delightful host, you’ll visit Sorrento, Capri, Amalfi and Positano as a insider. 

Walk in the footsteps of Roman Emperors along seaside mule-trails that weave through Mediterranean forests and lemon-scented hillsides – offering stunning, panoramic views of the sparkling azure sea – sip Prosecco as the sun sets over the yacht-studded harbor, and meander the narrow alleyways  – lined with irresistible shops.

Each day brings just the right combination of invigorating walks, private visits, thrilling options and a healthy dose of spontaneity – so that you can fully immerse yourself in the regional culture and stunning beauty of the Sorrento Coast.

Stunningly Beautiful and Endlessly Fascinating

Our Sorrento Women’s Trip is led by Strada Toscana team member, Pia Ruoppo, and includes hands-on activities, behind-the-scenes looks into local culture and meaningful, shared experiences with Pia’s family – natives of the Sorrentine Peninsula for generations. Plus you’ll be immersed in the beauty of one of Italy’s most spectacular regions, all while staying at a historic, boutique hotel in the heart of Sorrento.


DAY 1: Arrival

  • Highlights: Arrival, welcome with Pia
  • Dinner

Benvenuti in Italia! Sit back and relax as you’re transported from Napoli Airport to the stunning Sorrento Coast and your four-star accommodations, in the heart of Sorrento’s historic center. Here you’ll be greeted by your delightful trip host, Pia, as you get settled in your elegant room. Afterwards, you’ll join Pia, and your fellow travelers, for a tour of neighborhood – including a walk to a stunning location for aperitivo overlooking the Bay of Naples, followed by dinner featuring regional specialties.  

DAY 2: Sorrento

  • Highlights: Private walking tour of Sorrento, shopping time, excursion to the “upper” Sorrentine Peninsula
  • Breakfast, Lunch, Dinner

This morning, after a delicious breakfast that includes freshly baked torte, breads and crostate, yogurt, fruits, eggs – and more – you’ll set out to explore Sorrento’s winding alleyways with our friend, Sasha (an exceptional local guide) where you’ll discover churches filled with stunning masterpieces and surprising historic sites. Afterwards you’ll have time to explore or shop on your own before our private driver takes you on a breathtaking excursion up the steep mountain that rises above the town of Sorrento. After a stop at our favorite, panoramic lookout, it’s on to Pia’s brother’s fattoria (farm) with stunning views of the sea. Here you’ll enjoy a tour of the family’s organic herb gardens, followed by a delicious lunch, featuring organic foods grown right here on the farm.

In the afternoon, it’s back to town for free time to relax or enjoy a passeggiata in Sorrento, before enjoying a rooftop aperitivo, and then dinner together at a favorite, family-run trattoria.

DAY 3: Isle of Capri

  • Highlights: Ferry to Isle of Capri, walking tour of Capri and Anacapri, optional chairlift ride to Mt. Solaro
  • Breakfast, Dinner

This morning, after breakfast, get your camera ready, as you’ll be joining Sasha for a scenic, 30 minute ferry ride to the famous island of Capri. Here you’ll explore the former mule trails, turned trendy avenues, as you take in views of the yacht-studded harbor and learn the ancient history of the island. Next you’ll shuttle to Anacapri  – on the opposite end of the island – where Sasha will take you to one of the most beautiful, tiny churches in Italy. Its hand-painted tile floors are simply stunning!

After lunch on your own, you might hop on the chairlift for a panoramic, 12 minute ride to the summit of Mont Solaro – or opt to shop your way through Anacapri instead. Either way, you’re in for incredible views that stretch across the sea. This evening, back in Sorrento, you’ll enjoy a relaxing aperitivo, followed by a Mediterranean inspired dinner at a family-run trattoria.

DAY 4: Pompeii

  • Highlights: Guided tour of Pompeii, family-style cooking lesson
  • Breakfast, Dinner

This morning, after another delicious breakfast, you’re in for a treat as our private driver transports you to famous archeological site of Pompeii. Here you’ll discover Pompeii’s fascinating history – along with plenty of mysteries – as you walk with Sasha along the ancient, stone avenues of this impressive Roman city  – frozen in time after the fateful eruption of Mount Vesuvius. After lunch on your own at the park’s outdoor cafe, it’s back to Sorrento to relax or take a walk along the seaside cliffs.

This afternoon you’ll don apron for a delightful cooking lesson with Pia’s family that includes regional specialties and traditional recipes. Learn how citrus – in particular, lemon – influences the cuisine of Sorrento, and why fresh and local is the secret to some of the best food in Italy. Aperitivo is woven into your cooking time, followed by dinner featuring your homemade dishes – of course!

DAY 5: Amalfi, Positano

  • Highlights: Private boat ride and coastal tour, visit to Amalfi and Positano, pizza night
  • Breakfast, Dinner

This morning, after breakfast, it’s off to Marina Piccola to begin a stunning boat ride along the Sorrento coast all the way to Amalfi. Along the way you’ll explore tiny, azure coves and discover magnificent villas that overlook the sea. As you arrive in Amalfi, take in the shape of this seaside village that spills from the mountains right down to the beach. Here you’ll have time to explore, shop, and have a look inside Amalfi’s must-see cathedral. Stunning! Grab lunch on your own, before returning to the boat as you continue to Positano. 

Positano’s steep, inviting avenues are lined with shops selling everything from jewelry to sandals to ceramics. Visit the town’s historic duomo, dip your toes in the sea, or cool your feet – and your taste buds – at a gelateria before your boat driver transports you back to Sorrento. This evening we’ll be enjoying pizza at a family-run pizzeria.

DAY 6: Sorrento & Environs

  • Highlights: Marina Grande, visit to private lemon grove, farewell dinner
  • Breakfast, Dinner

This morning ,after breakfast, you’ll head out with Pia from Sorrento’s historic center for a scenic walk along winding, seaside avenues, as you make your way to charming, Marina Grande, with its quaint fishing boats and inviting, seaside trattorie. Here you’ll enjoy lunch on your own, followed by free time to shop and explore on your own back in Sorrento. Don’t miss stopping in one of the hand-made sandals shops!

In the afternoon, you’ll visit a private lemon grove with Pia, where you’ll enjoy a fascinating tour, followed by an oh-so-fun limoncello-making lesson. Aperitivo is right here in the lemon grove, followed by a special, farewell dinner. 

DAY 7: Departure

Early morning departure to Napoli Airport or Napoli Centrale Train Station.


Your accommodation for the Sorrento’s Women’s Trip is 4 Star, Boutique Hotel Palazzo Guardati. Owned by a historic Sorrentine family, Palazzo Guardati is located in the very heart of Sorrento, overlooking the Gulf of Naples – and just a short walk to both Marina Piccola and Marine Grande. Surrounded by winding avenues, flanked by characteristic artisan shops and workshops, guests are immersed in the magic atmosphere of old Sorrento. From this elegant and convenient home base, complete with rooftop terrace and pool (the views of Mt. Vesuvius are incredible), you’ll explore Pompeii, Capri and the romantic Amalfi Coast.

See the Photo Gallery


  • 7 days/6 nights at Boutique Hotel Palazzo Guardati
  • Private group transportation to/from Napoli Airport on arrival and departure days
  • Private ground transportation for excursions included in the trip itinerary
  • All abundant breakfasts
  • All delectable dinners
  • One delicious lunch
  • Evening aperitivo
  • Family-style cooking class
  • Ferry ride to/from Capri
  • Limoncello lesson
  • Visit to private lemon grove
  • Guided walking tour Capri and Anacapri
  • Private, coastal boat tour to Amalfi and Positano
  • Private guided tour of Pompeii archeological site
  • Free time for shopping and exploring
  • Invigorating, guided walks and private visits

Not included: Airfare, meals, alcoholic drinks, buses, trains or boat transportation outside of that which is specifically listed in the trip package, gratuities for villa staff and drivers

The Unexpected is Part of the Journey: At Strada Toscana we weave amazing, authentic experiences into every trip, but sometimes unexpected things come up. If a site has an unscheduled closing, we improvise to include something equally as wonderful and interesting. The quality of the trip is never at risk, as our team is committed to excellence, along with our vast, local, Italian connections.


  • Dates:
    • MAY 5-11, 2024  – SOLD OUT
  • Prices:
    • $3,295 – $3,995 USD per person (based on room choice upon booking)
  • A $700 deposit is required to secure your space on this trip
  • Remaining trip balance payment is charged to the same credit card on file 120 days prior to the trip start date
  • Terms and Conditions