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 specialties, 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 favourite 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 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 a 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 of 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 the 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 favoured 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 amphitheatre 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 theatre was later remodelled 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 revelling 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 as 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.”

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