This is what happens when Italian Fix takes you on vacay. Meet the people, places and piazzas that make each experience extra special. Part 2 of a 3-week series.

Overnight tours in Italy are better when you’ve got the *right* kind of company.

Especially when it involves Sicily and Southern Italy, where many meals are al fresco and cocktails are best enjoyed under lemon trees, and where we stay in small hotels, with even smaller groups.

Here’s why these places are some of our faves:

  1. You get to go off-grid… With transportation to places you wouldn’t journey to on your own (our private drivers handle that).
  2. You. Get. To. Relax. Seriously. Lots of time for almond milk baths in copper tubs, dips in the ocean and poolside cappuccinos — rocking ‘em solo or with a new amica you’ve met on the trip.
  3. You’re on Italy Vacay Time. In the South, things are exotic. And they move to the pace of your favorite nonna. It’s where Italians go to vacation, so you know they mean serious lounging business.

Today, we’re going deep into the southern cellar of our tour tasting room and spilling the grappa on some of our mega foodie moments that make it all so gorgeous ‘n’ groovy.

Sicily Southern Italy Tours with amazing food and a beautiful view

Get wined and dined, the Michelin-starred way.  Sicily Tours 2020.

Our food choices are a mix of high and low. Sometimes it’s a mix of nibbles on plastic chairs outside our fave sidewalk haunt in the market, but sometimes we swing the other way. Big time. On one of our nights on the Aeolian Islands (read: the Hawaii of Italy) during our Sicily overnight tour (companies never take clients to this island  — we’re the only ones doing this), we treat our people to an extra-special evening at a restaurant headed up by the youngest female Italian chef to win a Michelin star (dining complete with view of a smoking volcano, yeah, not kidding). Our clients LOVED her cooking class last year — she just started giving them and we got our guests to the front of the line. Best part about a cooking class? Eating!

This spot rocks our Italian socks because:

You wouldn’t know about it if someone didn’t take you there. It’s oh-so-special and oh-so-intimate at the same time. You’re thinking, why isn’t the whole world here? Because it can seem like our group has the whole island to themselves! The tasting menu and cooking experience, created specially for our private group, focuses on traditional ingredients sourced from the area’s volcanic grounds, paired with local island wines (that many don’t know about). Um, dreamy much?

The Italian Fix Factor:

We book out our hotels and exclusive experiences like this WAY in advance. This isn’t the kind of island you can just stumble upon. It takes time, care and knowing the right people to score the spaces and places we treat our guests to. To get real access to things you wouldn’t get on your own. We invent all sorts of things (Francesco, can you take our clients out on your boat at sunset? They’ll need great snacks and and don’t forget the passito di Pantelleria!) It’s what memories are made of, and simple pleasures are best when they’re shared together, in an intimate group, led by a local who speaks Italian so that you feel safe and taken care of.

Sicily Southern Italy Tours Exclusive Cooking Classes with a Michelin Star Chef

Sicily Southern Italy Exclusive Cooking Classes

Cruise through the Puglian countryside. Southern Italy Tours 2020.

Halfway through our Southern Italy overnight tour, we show you what it’s like to venture deep into Italy beyond the usual suspects by whisking you away to the cute countryside in Puglia. We explore some of the smaller Puglian villages, like Ostuni, a crown of creamy white buildings spread out over three hills overlooking the Adriatic Sea. And here comes the foodie moment: you’re treated to a private lunch at a local masseria.

Dining in the Puglian countryside rocks our socks because:

It’s STUNNING. Everything out here feels warmer, slower, more ethereal. This deep pocket in the south is where 99% of Italy’s olive oil comes from. The tomatoes are juicier. The vibe is earthy, exuberant, luscious. And at our particular masseria (meaning country estate), we’re surrounded by endless rows of olive groves and vineyards. Your to-do list couldn’t feel further away.

The Italian Fix Factor:

First things first: cruising through the Puglian countryside sounds extra relaxing, but truth be told, it’s actually pretty difficult to get to if you don’t have a driver. Ok, let’s be real — it’s a pain in the arse! Our private transfers take care of you from hotel to masseria. We take all the stress out of planning how to get around to the best hidden spots.

Second: this private lunch experience includes a menu designed exclusively for our Italian Fix clients. You’re not just rolling up and choosing any ol’ a la carte thingamajig off the menu rack here! If you’re taking the time to come to Southern Italy with us, you’re only gonna have the best. The vibe of our trips is less about museum line-ups and more about feeling good. Which means being surrounded by great people in great places. It’s not science — it’s an art that sets us apart.

Sicily Southern Italy Tours at a Masseria and Winery

Sicily Southern Italy Tours in Taormina

Sicily Southern Italy Food Tours

Taste Taormina. Sicily Tours 2020.

A mega highlight of our overnight tour in Sicily is Taormina: a teetering town carved into cliffs overlooking the Ionian Sea. People come here for the ancient Greek theater, the mountains and sea. Obviously, we experience all of that. And we get up-close-and-personal with the Ionian Sea — on our last day, we make it extra-splendida with a private boat cruise of the bay, with lunch onboard.

Private boats in Taormina rock our Italian socks because:

You haven’t experienced Sicily until you’ve a) been in the water b) been on the water and c) been guided across the water by locals who know how to score the best views. Because Taormina is tucked away up in the cliffs, the best way to take it all in is when you’re cruising on the bay. All those dreamy photos of Taormina — they’re taken from the water!

The Italian Fix Factor:

We know the locals and we know ‘em well. This boat trip is guided by one of our favorite private local captains who whips up a mean feast *and* shows us a good time. Italian Fix is all about the access — not just to the right places, but the best faces who help you feel like a local. Even in a spot that people love to descend upon, we keep every experience intimate, high-quality and exclusive. We’re gunning for “best trip of my life” reviews, and we get ‘em. And “Oh, I have to tell you about that private boat lunch in Sicily!” = you making your friends back home a tad bit jelly post-trip.

Keep one eye cracked open for Part 3 of this series next week, where we’re dishing on more opportunities to live a bigger life in 2020! Not already on our list? Hop on it and be the first to know.

Sicily Southern Italy Tours on an exclusive boat tour

Sicily Southern Italy Tours on the water

Sicily Southern Italy Tours in Taormina

In the meantime, you can find out about dates and prices for our tours here:

Would you love to spend a day doing any of the above with us? Tell us which one’s pulling at your OMG-gotta-go-here strings in the comments below.


All photos except 2, 11 credit: Danielle Rubi

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