Treasures of Taormina & the Aeolian Islands

  • Sample Itinerary
  • Experiences
  • Pricing
  • Featured Hotels
  • Custom Quote

Getaway to Sicily’s most stunning beaches on this coastal journey that will take you from the romantic panoramas of Taormina to the unspoiled beauty of the Aeolian Islands. Swim in azure waters beneath the dazzling Mediterranean sun, boat along the serene coves of Salina, and discover the intriguing island charms of Vulcano and Lipari.

Sample Itinerary

Day 1

Arrive to Catania Airport where your private chauffeur will be waiting to welcome you. Set off for the stunning hilltop town of Taormina for check-in to your five-star stay, a former monastery turned luxurious palace hotel. Savor an elegant welcome dinner of contemporary Sicilian cuisine at your hotel’s acclaimed two Michelin-starred restaurant.

Day 2

Your chauffeur will arrive in morning and you’ll depart for the tiny hilltop town of Castelmola, designated as one of Italy’s most beautiful villages. Home to exquisite Norman architecture, you’ll meander along its scenic cobbled streets while taking in extraordinary views of Mt. Etna and the coastline. Sample the locally produced Vino di Mandorla (Almond wine) before returning to Taormina for lunch at a charming trattoria in the heart of town. Enjoy a free afternoon to independently explore the city’s Roman amphitheater and shop along the many artisan shops that line Corso Umberto.

Day 3

Today be transported to Taormina’s stunning bay, punctuated by the lovely Isola Bella. Spend a free beach day sunbathing and enjoying the magnificent Ionian waters at your leisure.

Day 4

Travel by chauffeur to the port of Milazzo, located at the north of the island. Embark via ferry boat for the paradisiacal Aeolian island of Salina, known for its unspoiled waters, lush landscapes cascading toward the sea, and brilliant flora. Upon arrival to Salina your private driver will transport you to your luxurious island retreat for a relaxed afternoon at your leisure. In the evening enjoy dinner at your hotel’s gourmet restaurant.

Day 5

Whisk away for a day of private boating along Salina’s stunning Pollara Bay. Your boat captain will introduce you to some of the island’s most scenic coves for free time to swim in pristine waters and marvel at dramatic views of the rugged coastline. Along the way, savor a lunch of fresh fish and seafood specialties while on board. In the afternoon return to land and visit a boutique winery specializing in small batch Malvasia DOC wines. Top off your visit with a tasting of the winemaker’s golden vintages.

Day 6

Today you will experience the intriguing island of Vulcano by private boat. Your captain will help you discover the island’s signature black sand beaches and natural hot springs, and you’ll delight in free time to swim and sunbathe at your leisure. Enjoy lunch on board before returning to Salina for the day.

Day 7

Your private boat will arrive to transport you to lovely Lipari, the largest of the Aeolian islands. You’ll have a free day to peruse the town’s scenic streets accented by pastel hued buildings and artisan boutiques. Take time to visit Lipari’s impressive Museo Archeologico Regionale Eoliano, housing archaeological treasures found across the Aeolian islands, from amphoras recovered from ancient shipwrecks to Greek theater masks in miniature. You’ll return to Salina by private boat in the early evening.

Day 8

After a leisurely morning, your private car will transfer you to Salina’s port for departure via ferry boat to Milazzo. Upon arrival in Milazzo your chauffeur will be waiting to transport you back to Taormina for a free evening to relax and get ready for tomorrow’s departure from Sicily.

Day 9

Following breakfast, bid Taormina farewell and travel by chauffeur to Catania Airport, in preparation for your return flight or the next leg of your journey.

Experiences We Recommend

  • Visit to picturesque village of Castelmolo designated one of Italy’s most beautiful towns
  • Tasting of typical Sicilian almond wine at local tavern outside Taormina
  • Visit to organic caper farm on the island of Salina
  • Private, captain-led boat tour of Salina’s most scenic coves and stunning Pollara Bay
  • Exclusive small batch winery visit with tasting of Malvasia DOC wine
  • Private, captain-led boat tour to the black sand beaches & thermal springs of Vulcano
  • Scenic boat ride to Lipari with free time to explore the island at your own pace


The minimum trip length for a CountryBred Encounter is 5 Days/4 Nights

Pricing for our Italy Encounters begins at:

  • $850-$1,000/per person, per day* based on double occupancy and a travel party of two
Small group pricing available for travel parties of four or more

*The final price of your custom tour will be determined by your travel party size, departure dates, trip length, amount of meals included, percentage of guided time requested, cities chosen in your itinerary and signature CountryBred excursions selected. This sample itinerary can also be crafted for solo travelers.

Encounters Include

  • Stays at five & four-star boutique luxury hotels
  • Chauffeured transport for touring & transfers
  • Private touring with professional local guides
  • Engaging activities led by cultural experts
  • Signature experiences with insider access
  • Regionally authentic dining
  • Traveler Welcome Package
  • Taxes & base gratuities

Read Client Reviews

  • Gay B.

    Alentejo to Lisbon
    Above and beyond our expectations for an amazing well organized adventure for 26!!
  • Mark W.

    From Castilla to Basque Country
    Our third CountryBred travel experience guided us through the rich cultural history, food, wine & unique culture throughout central/northern Spain. Our selected experiences coupled with the region/city ambassadors throughout our trip were exceptional and made our experience GREAT! (hotels too!)
  • Barbara R.

    Getaway to Tuscany and Northern Italy
    CountryBred thought of every detail for our trip. We didn't have to think about or worry about anything because they had it all covered by professionals every step of the way. From the chauffeurs, to the private boats, to the ambassadors who were extremely knowledgeable and spoke good English, to the amazing hotels, to the selection of restaurants and wines...WOW!

Crafting the Experience

Experiential travel takes time, passion and local ingredients to make something truly special.

Read more


We turn travel inspiration into unforgettable journeys. Begin the trip design process by filling out the form below and a CountryBred specialist will contact you to get your next great adventure underway.


  • CountryBred Encounters begin at $750-$1,000/per person, per day
  • The minimum trip length for a CountryBred Encounter is 5 Days/4 Nights
  • All CountryBred Encounters are land touring experiences only and do not include airfare
  • Groups of four or more are eligible for small group pricing


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