This lot benefits: Mental Health Association of Okaloosa and Walton Counties

Perched on the high side of Taormina, just steps away from the town's center, Giano Penthouse boasts sweeping views over the picturesque town roofs and the enchanting sea below. Contemporary in design and style, this property allows three couples to experience upscale living in Sicily's most popular summer resort town.

The contemporary-styled living room welcomes you with its floor-to-ceiling glass panels that flood the space with natural light. The dining area provides comfortable seating for all guests and the kitchen area is fully equipped. The hushed palette was chosen to ensure that the eye is drawn to the view and not distracted by the clean-lined furnishing in the room. A wellness area equipped with TV, fitness machine, and bathroom with emotional chromo therapeutic shower are also included.

The real luxury of Giano can be found in its panoramic oceanfront terraces facing the Ionian Sea. Here you can enjoy sunbathing and relaxing in the outdoor jacuzzi while taking in the stunning views. The enchanting starry nights will be a dreamy backdrop while drinking perfectly chilled wine. Composed of both white and black sand and fringed with orange and lemon orchards, Sicily provides a beach experience unlike any other.

The largest island in the Mediterranean, Sicily is also one of the most culturally and geographically diverse regions of Italy. Your days are your own while in Sicily. Wander the narrow medieval streets of Palermo, where you'll get a flavor for local Sicilian life. Climb the lava dunes of Mount Etna, Europe's highest active volcano at approximately 3,350 meters, and marvel at its moonlike surface. Partake in a cannoli making class or Italian cooking class. Spend an evening immersed in Sicilian cuisine and culture on a food and wine walking tour of Taormina. Led by a local guide, travel to the city's top spots to sample fresh fish, bruschetta, sweet Sicilian cakes, and other regional specialties while sipping on a glass of prosecco.

This lot includes:

• Seven (7) nights for three (3) couples in a three (3) bedroom four (4) bathroom villa in Taormina, Sicily
• On-site concierge service
• Daily housekeeping
• Daily activities and dining based on the preference of the winning bidders

Restrictions: Must be booked in advance on mutually agreeable dates and is subject to availability. Some blackout dates may apply. Activities are at the discretion of the winner and cannot exceed $3,000. Expires April 30, 2020.

This lot benefits: Mental Health Association of Okaloosa & Walton Counties

A lively town known for its cafe?s, lemon trees, and history, Sorrento has been a must-see destination on grand European tours for generations. Appropriately named "the jewel" or il gioiello of Sorrento by the original owner and last descendant of a prestigious Neapolitan family, the Count de Mario Caracciolo, your home for seven nights is located in the heart of Sorrento.

The 4,845 sq. ft. home is designed over several levels, offering plenty of room for you and your guests. With five double bedrooms and four and a half bathrooms, Villa Il Gioiello comfortably accommodates four couples. An onsite villa manager offers a wealth of local knowledge on Sorrento restaurants and excursions. Three hours of daily maid service are also included in this package.

Our friend and Head Sommelier at the famed La Sirenuse Hotel and La Sponda Restaurant, Cristian Fusco, will lead you on a customized wine tour through your choice of Tenuta San Francesco, Montevetrano, or Antonio Caggiano. Finish your day as a guest at the Michelin star restaurant, La Sponda.

This lot includes:

• Seven (7) nights at Villa Il Gioiello, a five (5) bedroom, four and a half (4.5) bath home in Sorrento, Amalfi Coast, Italy for four (4) couples
  
• Customizable Amalfi wine tour with Cristian Fusco
  
• Dining credit to La Sponda in Positano

Restrictions: Based on availability of villa, tour guide, and restaurant reservations. Restaurant gift card not to exceed $500. Expires December 31, 2020.

This lot benefits: Children's Volunteer Health Network

Located in central Italy between Tuscany and Marche, Umbria offers a timeless glimpse into what Italian life is all about: beautiful scenery, great food, incredible wines, and wonderful friends.

Four couples will spend a full week in a four-bedroom, 17th-century farmhouse and stable that has been carefully restored to offer all the modern conveniences you would expect in a luxury property. Surrounded by beautiful countryside views, this incredible property includes open common spaces, a covered terrace, private swimming pool, and beautiful landscaping inclusive of a thriving herb and vegetable garden.

The large open courtyard offers the perfect environment for dining al fresco and is ideal for your dinner with Dina, a charming, talented local cook and Nona (grandmother) who will prepare an authentic Umbrian dinner at the villa. She can fire up the wood- burning oven for pizza, make pasta from scratch, or roast lamb on a spit.

Enjoy a full day of wine tours with Stefano, the charming local driver who will also deliver a rental car for your use throughout your stay. Visit the Fratelli Pardi Linen Factory and Winery in Montefalco. First, view the shop and then enjoy a tour and tasting lunch at the Pardi family's Cantina.

Immerse yourself in the culture of authentic Italian cooking when you partake in a hands-on morning class with Noni and Tita from within the comfort of your villa. You'll learn all about the theory, history, and techniques of traditional Umbrian dishes that will result in a four to five-course meal as well as recipes for each dish to take home with you.

Continue to taste your way through the Italian countryside with a variety of wine tours and tastings. Begin with a three-course lunch followed by a wine and olive tasting at Enoteca Properizo in the charming village of Spello, before moving on to a Palazzone wine tour and tasting in the Orvieto region with winemaker, Giovanni. Full concierge services will be provided by the villa owner to meet your every need.

This lot includes:

• Seven (7) nights for eight (8) people in the four (4) bedroom luxury villa of Fondo Le Tegile in Umbria, Italy
  
• Dinner with Dina
  
• Wine tour with Stefano
  
• Cooking lesson at the villa with Noni and Tita
  
• Fratelli Pardi Linen Factory and Winery visit for eight (8) people
  
• Three (3) course lunch with wine and olive tasting for eight (8) at Enoteca Properizo
  
• Palazzone wine tour and tasting for eight (8) people
  
• Rental car for seven (7) nights
  
• Airport/Rome transfers

Restrictions: Available April 2019- July 31, 2020. Must be booked at least 90 days in advance on mutually agreeable dates and is based on availability. Expires July 31, 2020.

This lot benefits: Emerald Coast Autism Center

Five couples will enjoy seven nights under the Tuscan sun on this wine-centric excursion to the Italian countryside. Wine lovers will find much to appreciate at Villa Montepulciano. Located on an Italian estate that still produces boutique wines and olive oils, the villa offers guests the chance to taste wines grown just beyond the door.

Built in the 1850s, Villa Montepulciano has five bedrooms complete with en suite bathrooms and features panoramic views of the Italian countryside. It also includes a private pool, outdoor dining area, and barbecue.

Enjoy a five-course traditional Tuscan dinner at the villa with wonderful wine pairings for each course. Dinner will be prepared from scratch by a local professional chef using fresh, seasonal ingredients.

You will meet Maurizio Dal Pino, the owner of the estate, for a tour of the vineyard and a private tasting of his wines grown on the property. Maurizio will also provide a wine tasting of different Montepulciano regional wines.

Embark from the villa on a wine tour with Maurizio Dal Pino as your guide and transportation for the day. Your first stop is an exclusive tour of Fanti San Filippo winery in Montalcino complete with a five-course lunch with Brunello wines. After lunch, Maurizio will guide you to another winery in Montepulciano where you will taste the best of Vino Nobile di Montepulciano, along with the full range of wines provided by that winery. Your guide will also illustrate differences in the way wines are produced in Montalcino and Montepulciano, as well as the differences between the winemaking in Tuscany, France, and California.

Ciao Bella!

This lot includes:

• Seven (7) night stay for five (5) couples in Villa Montepulciano, a five (5) bedroom, five (5) en suite bath private home in Tuscany
  
• Private five-course chef dinner with wine in the villa for ten (10) people
  
• Private wine tasting for ten (10) people at the villa including a vineyard tour with estate owner Maurizio Dal Pino
  
• Full day, private tour of two (2) local wineries and lunch for ten (10) people
  
• Walking tour of Montepulciano for ten (10) people
  
• Handmade pizza dinner in the villa on the final night for ten (10) people

Restrictions: Based on mutually agreeable dates and subject to availability. Expires April 30, 2020.