Signature Sicily

The dates: May 9-18, 2020

The cost: $3495/person

The highlights: see Sicily west to east, eat gelato, cooking class with Sicilian grandmother, two fabulous wine tastings, boat excursion

"Hands down, best travel experience ever. Sicily South offers a perfectly curated tour of Sicily from the best bed and breakfasts down to the carefully chosen food menus. Can't wait to do it again!"

Sicily is a seriously magical place, steeped in tradition and… delicious things like pistachio gelato. With everyone from the Greeks, Arabs, Normans, Germans and Jews - at one time or another - making their mark on the largest island in the Mediterranean, Sicily’s culture and atmosphere are totally different from mainland Italy.

Sicily South benefits. You’ll get the benefit of traveling with people who speak Italian and know Sicily. Plus, we’ve planned everything for you. All you need to do is find yourself in Palermo on May 9th and we’ll take it from there (for the next 9 nights).

The itinerary. From May 9-18, 2020, come live out your Godfather La Dolce Vita fantasy in Sicily. If you’re thinking a group trip isn’t for you - think again. We keep things small and open our trips to only 10 guests. This means no giant tour bus and no ball-cap-wearing-guide wielding an embarrassing umbrella and headset. 


If you want to stick with us during our free afternoons, we can’t wait to hang out! But if you’d like to wander on your own, we’ve booked the most centrally-located accommodations in each of our destinations so you’re close to everything worth seeing. Sicily is your oyster.

Day 1 Get your behind to Palermo and we’ll pick you up from the airport and hightail it to our stylish downtown hotel on a gorgeous pedestrian street in the historical city center. We’ll welcome you with cocktails and nosh before putting you and your full belly to bed early. Tomorrow we’ll do the city!

Day 2 We start today with an expert-guided walking tour of Palermo - which won’t be hard. Our hotel is minutes from all the city’s most important monuments. We’ll get a street food-ucation and enjoy lunch in one of Palermos vibrant, historic markets. The afternoon is yours to explore or rest before joining us for a spectacular Sicilian dinner at a local restaurant where the executive chef is one of our good friends!


Day 3 We bid arrivederci to Palermo and begin the day with a little winery visit for tasting and lunch in the Sicilian countryside. Since a wine tasting really takes it out of you (it’s hard work!), we’ve decided to stick to the country for just the night, staying in a converted farmhouse masseria where we’ll enjoy an honest-to-goodness farm to table dinner.

Day 4 Our morning starts by traveling back in time with a guided visit to stunningly intact Greek ruins in the Valley of the Temples just outside the town of Agrigento. After lunch, kick back and enjoy the scenery during the trek to our next destination, Ragusa, where we’ll check in to our fabulously restored b&b before enjoying a dinner of local specialties.

Day 5 Today is a day to kick back and relax in this little gem of a town. Stroll Ragusa’s quaint lanes and visit its churches. We’ll meet up for a smorgasbord lunch featuring local meats and cheeses. The evening is yours to enjoy. Stake out a table in the piazza, enjoy some wine-flavored gelato (we’ll show you where to find it!), and live your evening like the Sicilians do!

Day 6 We have a special treat planned for you today - a visit to a private residence overlooking the Mediterranean Sea where we’ll learn how to make Sicilian food from a real Sicilian grandmother! After we enjoy the lunch we make with Giovanna, we’ll head back to Ragusa where you’re free to spend the evening however you like!

Day 7 Today we leave Ragusa behind and continue making our way east. We’ll stop in Noto for a lunch break where you can enjoy their spectacularly Baroque cathedral and magnificent gelato from a little caffe’ featured in Volume 4 of the Netflix series Chef’s Table. We’ll then head to the final destination of our Sicilian adventure, the tiny island of Ortigia. After we check in to our historic hotel, we’ll enjoy a pizza dinner before turning in for the evening. 

Day 8 Enjoy a leisurely morning then join us for a magical wine tasting and lunch on the grounds of a castle at a stunning family-run winery just outside of Ortigia. The rest of the day is yours to explore and enjoy every nook and cranny of this special place. 


Day 9 Let’s soak in every last ounce of Sicilian magic on our last full day together. We’re going to take full advantage of being on an island and embark upon a little boat trip to enjoy a new view of Ortigia. Take the afternoon to wander the tiny lanes and buy those last few gifts for friends and family back home. We’ve got a spectacular farewell dinner planned at one of our favorite restaurants in Ortigia.

Day 10 Savor your last caffè with us this morning as we bid you arrivederci and send you on your way. Whether it’s the airport or train station you need, we’ll help you get where you need to go.

Who's in charge here?

We are!

I'm Sarah Cate and that handsome, "make you an offer you can't refuse" type on the right

is my Sicilian husband Benedetto (Benny for short). The littlest one is Enzo, who joined our team in May 2018.

We work tirelessly to create spectacularly authentic experiences for our Sicily South travelers.

Our knack for hospitality and insider knowledge combined with the expertise of local providers is our secret sauce.

Benny, Enzo, and I, along with a local guide, will accompany you on our adventure!

Who this trip's for:

  • People who value quality over quantity.

  • People who love to eat, and learn about, food.

  • Easy-going people who love to have fun.

  • People who enjoy charming, thoughtfully curated, locally-run accommodations

Who this trip's not for:

  • People who want to see as many destinations as possible in one single trip.

  • People who want a cookie cutter travel experience.

  • People who have a bad attitude, aren’t fun to be around, and like to travel by a hard and fast, minute-by-minute schedule.

  • People who are looking for white glove service in 5-star resorts.

Have questions? Check out our FAQ or email us at!

The cash money + what's covered.


per person


  • 9 nights in great hotels and bed & breakfasts (accommodation is in a shared room - 2 people -, if you're coming solo and would like a single room, please let us know. We can accommodate a limited number of single occupancies for an additional fee)

  • Transfer from Palermo airport

  • All ground transportation

  • All breakfasts, 6 lunches, and 7 dinners with vino.

  • Two wine tastings

  • Boat excursion around Ortigia

  • Transfer to Catania airport (one transfer is arranged at 9am on the final day of the trip, transfers to the airport outside of this will incur an additional charge)

"Sicily South planned one of the best trips we've ever taken. Every day contained the perfect balance of activity, food/wine tasting, and leisure. We felt so well taken care of and were exposed to all the hidden jewels of Sicily, with a group that felt like family by the end of the trip."


  • Airfare to Italy (click for more details)

  • Travel insurance (we highly recommend you purchase this)

  • Anything else not specifically mentioned above

We also can't guarantee you have a good time. That one's on you!

But we'll let Adam Sandler & SNL handle this one:

Book your trip today for just $500!


$500 non-refundable deposit due at registration + $2995 due 90 days before departure date


$500 non-refundable deposit due at registration + equal monthly payments


Sicily South does not book airfare for our travelers.

For this trip, you'll want to fly into Palermo (PMO) on May 9, hopefully in time to join our welcome happy hour at 7pm.

You will fly out of Catania (CTA) on May 18. Please note that on the morning of May 18 you will be in Ortigia, which is approx. 1 hour from the Catania airport. Group transportation is provided at 9am on May 18. If you need to leave earlier or later than that, you will be responsible for the additional cost.


Have questions? Check out our FAQ or email us at!