Bespoke Stories:
A Singular Sicilian Adventure

Lorenzo Santamaria

B&R Guide
(and proud Sicilian)


Look at something lovely long enough, or often enough, and even the most astounding beauty will eventually come to feel ordinary.

As a native Sicilian, I grew up eating its incredible food, learning its storied mythology and surrounded by incredible views. After a lifetime spent immersed in Sicily, I assumed I had become immune to everything my island had to offer.

A similar thing happened when I became a B&R guide. All of a sudden, visiting Italy’s most incredible corners, eating at its most exclusive restaurants and meeting with its most renowned winemakers was my job.

It’s really good work if you can find it, but after guiding my fair share of trips, I figured I had seen it all, done it all, and had become far too spoiled to appreciate adventure as I once had.

Boy was I wrong.

Tailor-made to suit the unique tastes of the individuals on trip, Bespoke trips are custom designed to blow you away at every turn. Each trip is a unique expression of the regions and people that comprise it, but all Bespoke trips share the same goal: to give you the trip of a lifetime.

This is the story of how one Bespoke trip re-opened my eyes, reinvigorated my soul and really, really, really blew my mind. (And I was just the guide!)

What follows is my trip diary from what was probably my favourite trip of all time.


Day 1

A High Bar (and a Chocolatey Start!)

From the itinerary alone, I knew this trip was going to be special. Our travellers had been on multiple B&R trips before, and were looking for something that surpassed even our incredibly high standards.

“While in the planning stages of our trip to Sicily, I gave our planner the task of creating the most unforgettable bespoke trip B&R has ever designed…” says Tim Green, the traveller who helped arrange the trip.

So we knew the bar was set incredibly high when we picked up our travellers at the airport in Catania and earnestly began the trip in the Baroque town of Modica, in the stunning Hyblaean Mountains.

There we had our first proper Sicilian welcome lunch at Locanda del Colonello, where the flavors of southern Sicily made a tasty first impression on our travellers.

After lunch we got on our bikes and rode downhill through the old town, taking in the exuberant genius of its Baroque architecture.

But the architecture wasn’t our primary concern. Modica is particularly famous for its chocolate—said to be among Europe’s earliest recipes—and our travellers were more than happy to discover this local tradition and dive into decadent samples.

After our sugar high, we made our way into the countryside and settled into our hotel, the impressive Borgo Hedone, right in the middle of the Baroque Valley, a lovely luxury boutique hotel right by the town’s cathedral. Complete with a panoramic pool and a gorgeous view onto UNESCO-protected Scicli, it was the perfect home away from home for our first three nights.

In the evening we enjoyed an apertivo on the hotel’s awe-inspiring terrace, accompanied by live music, before settling into a family-style catered dinner underneath the stars at the Borgo Hedone. The relaxed tasting menu boasted only the finest locally grown food, and made for a sumptuous start to the trip.

Day 2

Incredible Rides (and Even Better Meals)

If the phrase “hotel breakfast” doesn’t exactly inspire, you probably haven’t started your day at the Borgo Hedone.

After a delicious morning meal, we started Day 2 with a ride through farmland, where our travellers found out first hand why Sicily is simultaneously Europe’s breadbasket and vegetable garden. Wheat, tomatoes, olive oil, grapes and oranges may as well be the currency of this part of the island, and each of them combines to make for incredible backdrops.

After moving through farmland we found the stunning coast—often used as a backdrop in the Italian TV series Inspector Montalbano—and stopped for a seaside lunch that allowed us to feast upon that morning’s catch.

Back at the hotel in the afternoon, our travellers enjoyed a little downtime before a drink in the centro storico.

For dinner we headed to Satra, where Sicilian-American chef Rita Russotto gave us a personal introduction to her unique approach to the local gastronomy.

Chef Rita Russotto of Satra

See Sicily Your Way

A cultural crossroads where Greeks and Romans, Phoenicians and Arabs, French and Spanish civilizations have left their mark artistically, architecturally and gastronomically, Sicily has long extended a welcoming hand to visitors. Discover the best of this incredible island on a Bespoke Sicily adventure tailored just for you.

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Day 3

A Unique (and Underground) Feast

The next day, we started with an easygoing morning ride out to the southern coast, where a local tomato producer told us all about the (big!) business of growing tomatoes in Sicily.

After another sumptuous lunch comprised of local specialities, we lingered a little longer on the coast before riding back to the hotel.

As the sun got low and a romantic aura settled into the sky, we made our way to Ragusa Ibla, a hilltop UNESCO World Heritage town in the Val di Noto with a historical centre prized for its Baroque architecture.

There an extremely personable local guide gave us a short tour of the ancient centre before we sat down for a spectacular dinner set inside a stunning cave, Yes, you read that right: inside a cave.

Set within the natural caves at Don Serafino, the two Michelin-starred Ristorante Locanda Don Serafino is easily the top table in Sicily—and we were more than happy to make a reservation.


I truly believe B&R’s involvement has brought about the most extraordinary travel experience to Sicily that wouldn’t have been possible otherwise. From the amazingly talented and knowledgeable trip planners, to the personable and unshakeable guides who NEVER skip a beat, B&R consistently delivers on putting their guests in the most talented hands in travel.

– B&R Traveller Tim Green

Day 4

Syracuse… and a Scavenger Hunt

The next day began with a leisurely drive east to a family-owned cheese farm, where we got a firsthand ricotta-making demonstration. (Good God I wish all days could start like this.)

Fueled by cheese and fired up from our visit, we hopped in the saddle and rode through the east-coast countryside to Marzamemi, one of the most charming and authentic seaside fishing villages in southern Sicily.

After lunch at our favorite spot in town, we rode to the Villa Romana del Tellaro, a Roman villa built in the first quarter of the 4th century that contains one of the richest and most complex collections of Roman mosaics in Sicily, where we lingered long enough to contemplate its immense beauty.

Next up we made our way to Siracusa, the 2700-year-old city situated on a limestone plateau that drops down to the sea and well known for its rich Greek culture and amphitheatres. In ancient times, Siracusa was the economic, political, scientific and cultural centre of Sicily, a history preserved by its status as a UNESCO World Heritage Site.

That evening, we had a special little surprise up our sleeves. We arranged a scavenger hunt through the historic city centre, Ortigia. But this wasn’t just any scavenger hunt. My co-guide Leah came up with an incredibly amusing quiz related to our travellers’ respective families, which also included some of the cultural things we had done/seen up until that moment.

Every correct answer was awarded with a B&R tag that needed to be worn, and we moved from bar to bar in Ortigia being welcomed by Sicilian-themed shots! It was great fun, brava Leah!

Day 5

Sailing the Bay of Siracusa

The next day we headed into the beautiful Anapo Valley and the entrance to the Necropolis of Pantalica, a series of cemeteries with rock-cut chamber tombs dating from the 13th century BC.

We visited prehistoric burial chambers that were later used as safe refuge during turbulent periods. For lunch we hopped on our bikes for a short ride to a family-run farm, where we were treated to a tour of the property followed by a fabulous lunch with ingredients straight from their garden.

That evening was a special treat, as we headed out on a traditional Caicco sailboat for a ride in the Bay of Siracusa, an incredible way to see Ortigia Island and the caves lining the shores.

Day 6

Soaring Through the Skies

Today was incredible. In the morning we drank in the views of Mount Etna and the Aeolian Islands—while hovering above them in a private helicopter!!

Seeing the sea spread out beneath us was incredible, and gave me a new appreciation for Sicily’s raw beauty that I couldn’t have gleaned from any earthly vantage point.

After leaving from Siracusa and spending about an hour in the air, we touched down on Panarea, the second smallest of the eight Aeolian Islands, but the one with perhaps the biggest reputation. Considered by many to be the most exclusive and picturesque, this is where the rich and famous flock, flooding the marinas with their yachts during the summer months.

After enjoying lunch and a dip in the crystal clear waters, we headed out for an easy afternoon walk to Capo Milazzo, an archeological site dating to the 14th century BCE. This Bronze Age settlement, destroyed in 1250 BCE, was excavated in 1948, when 23 huts were found, suggesting a population of about 100 people had settled here. The pottery discovered shows a distinctly Minoan influence, indicating a link between the Aeolians and Crete.

The visit was amazing, and a dramatic reminder of just how much history this island has. I couldn’t help but marvel at my B&R colleagues who designed this trip so spectacularly: while the morning saw us hovering above a mountain like some sort of celestial explorers, the afternoon brought us back down to earth in such a wonderfully intimate way.

After Capo Milazzo, some of the group splintered off for a fishing trip, while the rest regrouped at the hotel. In the evening we brought everyone back together at Hotel Raya’s panoramic rooftop bar, where we sipped our aperitivi and drank in the views throughout dinner.

This hotel is stunning—a wonderful five-star on different levels with its pools with different types of water in them, including a natural volcanic one.

We had an amazing meal on the restaurant’s terrace, with a breathtaking view on the Stromboli volcano. Luckily enough, that day was also the celebration of the Saint patron of the island, and there were insane fireworks taking place right on the dock in front of us!

It is a memory I will always carry with me.

Day 7

After dancing until the night turned into an early morning, the next day started with a leisurely breakfast and a short walk to the port.

From there we hopped on board our exclusive yacht and jetted off to explore the islands west of Panarea, Vulcano, Lipari and Salina. Along the way we stopped to snorkel and swim in some of Sicily’s most precious coves, which are only accessible by sea. (And while you don’t have to arrive at these coves via private yacht, I have to admit, it certainly helped make the whole experience feel even more special.)

After working up an appetite on the water, we feasted on a delicious melody of salads, cheeses and regional meats before making our way to Stromboli, an island that’s been called “the lighthouse of the Mediterranean” since the time of the ancient mariners.

And “light” is the operative word. Incandescent flames explode into the sky from the island’s volcano, which has continuously erupted for 2,000 years. We saved our acquaintance with the volcano until late in the afternoon, when a local expert guided us to a viewing area near the base of the volcano.

Afterwards, our walk continued on the magical black sand beach of Piscita, where our own private BBQ awaited.

Day 8

Not quite done soaring through the Sicilian skies, we took to the helicopters once again to whisk us to the foothills of yet another volcano, the fabled Mount Etna, where our bikes awaited us.

Riding through the verdant countryside just north of Etna, its billowing smoke provided a dramatic backdrop as we stopped for lunch and savoured the delicious products of Etna’s fertile soil.

From there it was off to the Alacantara Gorge, a dramatic gorge cut out of black basalt by the rushing waters of the Alcantara River (which runs from the Nebrodi Mountains and feeds into the Ionian Sea) and a marvelously compelling sight. There we ditched the bikes in favour of wetsuits, and embarked on a river trek. We spent the afternoon exploring on foot, swimming, sliding, and climbing through the gorge’s impressive expanse.

Several thousand years ago, Mount Etna’s lava blocked the river’s path and its ice-cold water cooled the lava, resulting in crystallization and the formation of unique ballast river columns. Over the years, as the river ran through the volcanic rock, it carved intricate paths along the way, most above ground. Today these paths offer the perfect natural playground for exploration, and we took full advantage.

After our adventurous afternoon, we rode the coach into chic Taormina, the beguiling and bucolic hill town that’s been a favored winter and summer retreat for more than a century, replete with flower-scented piazzas, charming streets, chic boutiques, subtropical gardens and endless sea views and mountain vistas.

We spent the evening enjoying a sophisticated dinner on the world-famous terrace of our hotel, the Timeo, where we delighted in southern Italian hospitality.

Day 9

Our final day began with an invigorating walk to Monte Veneretta in Castelmola, starting with the Greek Roman amphitheater next door to our hotel. We arranged to have the amphitheatre open early before all the crowds, so our travellers were able to explore it all on their own.

Originally built by the Greeks in the 3rd century BCE, the theater was later remodeled by the Romans in the 1st century AD. The original stage and orchestra pit created by the Greeks for performances were then converted into a circular arena for gladiator fighting.

After lunch, the ladies headed off for an afternoon of spa treatments while the guys lounged by the pool, then everyone reconvened for an unforgettable final night meal, and one last night spent dancing and reveling in true Sicilian style.

While this trip was full of highs, by far the best one was the words of appreciation received by the travellers, who thanked us for the trip of a lifetime.

In fact, I left you hanging earlier when I quoted Tim explaining how he challenged us on this trip. What he actually said was:

“While in the planning stages of our trip to Sicily, I gave our planner the task of creating the most unforgettable bespoke trip B&R has ever designed…

…and boy did she nail it. AMAZING!”

They were overjoyed with the experience, which made us feel incredibly good about all the hard work we did to make sure such a wonderful (but yet, very challenging to guide for us) trip ended up flowing like it should and delivering the best possible experience to our travellers.

Or as Tim put it, “Just when you think B&R can’t raise the bar any higher – you turn the corner and there’s yet another surprise that completely elevates the trip to new heights. You can’t make this stuff up if you tried.”


Ready to go on your own adventure? Have the perfect trip in mind? Whether it’s somewhere you’ve always dreamed of going or something you’ve always dreamed of doing, our expert Trip Designers specialize in turning fantasies into reality.

Email us at bespoke@butterfield.com to find out more.

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