Sicily South travel is all about having the trip you want.

We promise we won’t try to fit you into an ambitious 4 inch stiletto if what you’re looking for is a soft Italian leather ballet flat.

Why join a small group tour:

Join solo, with a friend or two, or your amore


See Sicily with your 11 new friends (we only take groups of 12 or smaller)


Enjoy as much or as little structure as you want - join day trips and meals only when you feel like it

Get pre-trip support to answer your questions, like "how many bottles of wine can I realistically bring back in my suitcase?"


Relax, knowing a personal, Italian-speaking Italy- enthusiast guide is available to assist


2020 Small Group Tours

Cities: Ragusa Ibla | Siracusa (Ortigia)

Highlights: partnership with Chattanooga School of Language, 15+ hours Italian language instruction by native speaker(s) | cooking class with Sicilian grandmother

APRIL 16 - 24, 2020

Cancelled due to COVID-19


Cities: Palermo | Agrigento | Ragusa Ibla 

Noto | Siracusa (Ortigia)

Highlights: two wine tastings | cooking class with Sicilian grandmother | boat trip around Ortigia island

MAY 9 - 18, 2020

Cancelled due to COVID-19


Fall 2020 Preview


Cities: Malfa (Salina) | Siracusa (Ortigia)

Highlights: total relaxation in the magical Aeolian Islands, wine tastings, boat excursion, shopping and food culture in fun, quirky Ortigia



Cities: Palermo

Highlights: full immersion into the incredible food culture of Sicily's capital city, wine tasting, behind-the-scenes with local producers






When we say that we want you to have the trip you want, we mean it. If one of our pre-arranged group trips sounds good but you already know exactly where you'd like to go and who you want to go with?

If you’re head-strong and independent and feel like you don’t need an Italian-speaking Italy enthusiast to accompany you on your journey but you’d like some expert guidance and recommendations to help you plan?

While our bread and butter (or maybe olive oil is more appropriate?) is small group tours of Sicily, we would love to help you design your dream Sicilian holiday. To see if we’re a good fit, schedule your free 10-minute consultation today!

we've got you!

we've got you!



“I don’t like group trips! But I love the idea of an incredible trip I don’t have to plan. Should I do this?”
The first thing I hear from the kind of people who join our group trips is, “I don’t like group trips.”
Me neither. I've created a group trip for people who don’t like group trips. This isn’t on-and-off-and-back-on the tour bus, file into mediocre tourist trap restaurants big enough to accommodate a group, kind of fare. It’s the specialness of a private trip with the ease of a group trip. Yes, you should come!

This trip needs to be THE trip to Italy. Does it have to be just Sicily?
Our group trip offerings are based in Sicily. BUT we also offer custom group trips, so if you’d like to hit up the other Italian highlights we can plan an itinerary around your Italian do or die list. 

On a group trip, do we have to eat every meal with the group?
Absolutely not. While we hope you’ll stick around for at least a few of the arranged dinners included in your trip (we take a lot of care to choose the perfect restaurants for our guests), you are more than welcome to venture off on your own, and we’d be happy to make recommendations.

What do your trip costs cover? Do we just pay one flat fee?
The trip cost covers all accommodations, arrival airport transfer, ground transportation, all breakfasts, several lunches, and most dinners. The cost also covers any special guides needed at historical sites as well as entrance fees to monuments included in the itinerary.

Have you been to all the hotels and restaurants you’ve picked out?
Yes! We looove our clients, so we wouldn’t dare put you up in skeezy accommodations or feed you sub-par Sicilian food. 


What level of “luxury” are your group trips? I like nice hotels.
When we look for hotels, we’re looking for the unique. We want maximum comfort for our clients but equally important to us is finding places with a strong charm factor. We are not into big resorts or sterile-feeling, chain hotels.

How dressy do we have to get for meals? 
This is your vacation. Dress however you are most comfortable! When choosing restaurants we don’t focus so much on how elegant a locale it may be but, first, how great the food is and, second, if it’s the type of place that will help us have the magical, out-of-a-movie, Italian evening we’re going for. If we do ever choose a restaurant that would require you to “gussy up” a bit, we will tell you well in advance.

Do you book flights for us?
No. I’ll handle just about everything else but you are responsible for getting yourself to your trip’s starting point. I am more than happy to make suggestions for trusted travel agents who can help you book your airfare.

If we’re going on our own to Sicily, do we need a car? 
This is kind of a tricky question: 1) Sicily’s rail and public transport infrastructure isn’t quite up to par with the rest of Italy. You can get a lot of places by train ( but some of the smaller, lesser known towns are not accessible by train or bus. 2) Driving in Sicily means driving with no rules. It’s a free-for-all. For me personally, the only way I’ll get in a car in Sicily is if someone else is driving it. But ultimately the choice is yours.

Do you pick places to stay that are walkable to a town, restaurants, etc?
Yes. We love to encourage our clients to explore the itinerary destinations on their own, so we book places that are within walking distance to most everything worth seeing. There may be the occasional exception if we’re staying on-site at a winery or a special agriturismo but we’ll always let you know and help arrange transportation “into town” if you want to wander.

Do we need to know Italian if we’re going to Sicily by ourselves?
It is very helpful to know a few words of Italian if you’re going to Sicily on your own. It’s not a 100% necessity but I would suggest carrying at least a good dictionary or having a translating app on your phone.

On the custom group trip, is there an ideal number of people? And is there a limit?
If you want us to take just you to Italy we can do that! If our custom groups had a sweet spot, though, it’s usually about 6-8 travelers. Many of our preferred hotels and restaurants can’t accommodate huge groups, so we cap all of our trips at 14 guests.

Can the custom group trip be made affordable for a range of budgets? We’d like to include friends who don’t have a ton to spend.
Yes! We can work with a wide range of budgets to create a custom group trip to Italy with you and your friends. We’re also happy to make special payment arrangements if you’d like to gift a portion of the trip to certain people in your group.


Is Sicily dangerous?
Dangerously beautiful, yes. It might steal your heart.