DATES: March 6-14, 2027

TRIP LENGTH: 9 days / 8 nights

GROUP SIZE: up to 14 people

Experience Sicily on a small group trip filled with beautiful coastal towns, ancient history, incredible food and wine, and some of the most spectacular scenery in Italy.

We’ll begin in Catania, where we’ll explore the historic center, experience the city through its food on a local food tour, visit the Cathedral and ancient Bellini Theatre, and stroll along lively Via Etnea.

From Catania, we’ll venture out on two unforgettable day trips. We’ll spend a day in Taormina, one of Sicily’s most beautiful towns, perched above the Ionian Sea with charming streets and incredible views. We’ll also explore Mount Etna, taking in the volcanic landscape and stopping at a local winery before ending the day with a hands-on Sicilian cooking class.

Then we’ll travel south to Syracuse, our second home base for the trip. We’ll take to the water for a boat tour with swimming and lunch, explore the beautiful island of Ortigia on a walking tour, and enjoy a special rooftop dinner overlooking the sea.

We’ll also take a half-day trip to Noto, famous for its beautiful Baroque architecture, with plenty of free time afterward for the beach, shopping, wandering the streets of Ortigia, or simply slowing down and enjoying Sicily.

Throughout the trip, we’ve planned a balance of historic sights, beautiful scenery, local food and wine, special experiences, and free time, so you’ll experience some of the best of eastern Sicily without feeling like you’re racing from place to place.

With just two main hotel bases - Catania and Syracuse - we’ll be able to settle in and truly enjoy each destination while using them as our base for exploring more of Sicily. 🇮🇹

*Activities, accommodations, and itinerary are subject to change with similar substitutions if necessary.

This trip is perfect for couples, solo travelers, and friends who want to experience the best of Sicily without rushing through it.

It’s perfect for those who love beautiful places, incredible food and wine, fascinating history, charming towns, and time to simply enjoy where you are. We’ll see some of eastern Sicily’s most memorable sights, but we’ll also leave room for long meals, wandering picturesque streets, shopping, relaxing by the sea, and discovering places on your own.

This trip is a great fit if you:

• Prefer small group travel over large tour buses and packed itineraries

• Want the ease of having the details planned for you while still having free time and flexibility

• Love experiencing a destination through its food, wine, culture, and local traditions

• Enjoy a mix of guided experiences and independent exploring

• Want to see Sicily’s famous sights along with beautiful smaller towns and local experiences

• Appreciate a comfortable pace with only two main hotel bases instead of constantly packing and changing hotels

• Want to travel with a group while still having time to do your own thing

If your idea of a great trip includes sipping Sicilian wine near Mount Etna, wandering the streets of Taormina and Ortigia, taking a boat ride along the coast, enjoying a rooftop dinner overlooking the sea, and having enough free time to actually enjoy Sicily, this trip was designed for you.

• Explore the historic streets and lively atmosphere of Catania

• Taste your way through the city on a Sicilian food tour

• Visit Catania Cathedral and the historic Bellini Theatre

• Spend a day in beautiful Taormina, with its charming streets and spectacular coastal views

• Experience the dramatic landscapes of Mount Etna

• Visit a Sicilian winery with views of the volcano

• Learn to prepare local favorites during a Sicilian cooking class

• Stay in Syracuse and explore the beautiful island of Ortigia

• Cruise the coast on a boat tour with swimming and lunch

• Take a guided walking tour of Ortigia

• Enjoy a special rooftop dinner overlooking the sea

• Visit the Baroque town of Noto

• Have plenty of free time for beaches, shopping, cafés, and exploring on your own

• Experience Sicily at a relaxed pace with only two main hotel bases and a small group

Hotel accommodations are subject to change, with comparable accommodations provided if necessary.

There will be approximately 12-14 people in the group. Expect enjoyable, well-paced days with a mix of guided experiences and free time, balanced so you can take in everything Sicily has to offer without coming home exhausted.

This trip is designed to let you experience Sicily, not just see it. We’ve combined the places you won’t want to miss with local food and wine, beautiful scenery, memorable experiences, and plenty of time to slow down and enjoy it all.

You’ll wander through historic cities and charming seaside towns, taste authentic Sicilian specialties, visit a winery on the slopes of Mount Etna, learn to cook Sicilian dishes, cruise along the coast, and enjoy dinner overlooking the sea.

And because we believe the best trips shouldn’t feel rushed, we’ll stay in just two main locations — Catania and Syracuse — and take day trips from there. That means less packing and unpacking, fewer travel days, and more time actually enjoying Sicily.

With a small group, thoughtfully planned experiences, and free time built in, you’ll have the ease of a group trip without feeling like you’re on a traditional group tour. We’ll take care of the planning so you can simply show up and enjoy Sicily.

• Cost per person:  $3999 (based on double occupancy)

• A $500 non-refundable deposit secures your spot.

• See payment options below.

We require you to have travel insurance that covers:

• Emergency medical treatment

• Evacuation and repatriation

• Personal injury

We also highly recommend coverage for trip cancellation, delays, and lost or stolen belongings.

Note - You will see an option to add travel insurance at checkout with a company I have no affiliation or experience with. I recommend insurance with Faye, but you are welcome to purchase anywhere you prefer.

Our Sicilian adventure begins! 🇮🇹

Today, you’ll depart the U.S. on your overnight flight to Catania, Sicily.

Get some rest on the flight because tomorrow we’ll arrive in Sicily and begin an incredible week of beautiful towns, delicious food and wine, coastal scenery, and unforgettable experiences.

Welcome to Sicily! 🇮🇹

After arriving in Catania, we’ll transfer to our hotel and get settled in. You’ll have time to unpack, relax, and recover from the overnight journey before our first evening together.

Tonight, we’ll gather for a welcome dinner, where we’ll get to know one another and enjoy our first taste of Sicilian cuisine. It’s the perfect way to kick off our week together!

After dinner, settle in for a good night’s rest—we have an incredible week in Sicily ahead of us.

Included: Airport transfer

Today we’ll get to know Catania, a lively Sicilian city filled with beautiful Baroque architecture, historic landmarks, bustling markets, and incredible food.

We’ll begin with a local food tour, tasting our way through the city while learning about Catania’s history, culture, and culinary traditions. Along the way, we’ll experience some of the flavors Sicily is famous for and get a glimpse into everyday life in the city.

Afterward, we’ll visit Catania Cathedral and the historic Teatro Massimo Bellini, followed by time to stroll along Via Etnea, Catania’s main shopping and pedestrian street.

The remainder of the day will be yours to explore at your own pace. Browse the shops, stop for an espresso or gelato, wander the historic streets, or simply relax and enjoy the atmosphere of Sicily.

Included: Breakfast, Food Tour, cathedral and theatre entry

Today we’ll take a day trip to Taormina, one of Sicily’s most beautiful and beloved towns.

Perched high above the Ionian Sea, Taormina is known for its spectacular coastal views, winding streets, colorful balconies, charming cafés, and beautiful piazzas.

We’ll spend the day exploring the town and taking in the scenery that has made it one of Sicily’s most iconic destinations.

We’ll visit the impressive Ancient Greek Theatre, where the ruins are surrounded by incredible views of the coastline and Mount Etna.

Afterward, you’ll have free time to enjoy Taormina your way—wander along Corso Umberto, browse the boutiques, find a café for lunch, enjoy a gelato in the piazza, or simply explore the beautiful side streets.

Later in the afternoon, we’ll return to Catania with the evening free to relax or head out for dinner on your own.

Included: Breakfast, Guided day trip to Taormina

Today we’ll experience some of the flavors and landscapes that make Sicily so special.

We’ll head to Mt Etna, Europe’s largest active volcano, where we’ll take in the dramatic volcanic landscape and incredible views surrounding the mountain.

Next, we’ll visit a local winery on the slopes of Mount Etna. The volcanic soil here creates some of Sicily’s most distinctive wines, and we’ll have the chance to taste them while enjoying the beautiful countryside.

Later, we’ll roll up our sleeves for a hands-on Sicilian cooking class. We’ll learn how to prepare traditional local dishes before sitting down together to enjoy what we’ve made.

With volcanic scenery, Sicilian wine, delicious food, and plenty of time around the table, this is sure to be one of the most memorable days of the trip!

Included: Breakfast, Winery Experience, Cooking Class with dinner

Today we’ll say goodbye to Catania and travel to Syracuse, our home for the next few nights.

Once we arrive, we’ll experience Syracuse from one of the best vantage points - the water! We’ll head out on a boat tour along the coast, taking in views of beautiful Ortigia and the surrounding coastline from the sea.

Along the way, we’ll have time to swim in the clear Mediterranean water, relax on board, and enjoy lunch together. It’s the perfect introduction to Syracuse and a chance to slow down and enjoy Sicily’s beautiful coastline.

After our boat tour, we’ll have time to settle in before heading out for dinner together.

Included: Breakfast, Transportation to Syracuse, Boat Tour with lunch

Today we’ll explore Ortigia, the beautiful historic heart of Syracuse. Surrounded by the sea and filled with winding streets, elegant piazzas, Baroque architecture, and centuries of history, Ortigia is one of the most charming places in Sicily.

We’ll begin with a guided walking tour, discovering the island’s most important sights while learning about the Greek, Roman, and Sicilian influences that have shaped it over the centuries.

After our tour, you’ll have free time to enjoy Ortigia on your own. Wander the narrow streets, browse the boutiques, stop for a coffee or gelato, enjoy the waterfront, or find a quiet piazza and simply take in the atmosphere.

Tonight, we’ll come together for a dinner by the sea, the perfect ending to a day in beautiful Ortigia.

Included: Breakfast, Walking Tour

Today we’ll take a half-day trip to Noto, one of Sicily’s most beautiful Baroque towns.

Known for its honey-colored buildings, ornate churches, grand palaces, and picturesque streets, Noto is a wonderful place to wander and take in the beauty of southeastern Sicily.

After exploring Noto, we’ll return to Syracuse for an afternoon of free time to enjoy however you’d like. Head to the beach, do some shopping, wander through Ortigia, stop for a leisurely lunch or gelato, or simply relax and enjoy our final full day in Sicily.

Tonight, we’ll come together for dinner and one last evening enjoying Sicily before our trip comes to an end.

Included: Breakfast, Tour of Noto

Sadly, our Sicilian adventure comes to an end today.

After breakfast, we’ll say goodbye to Syracuse and take the train back to Catania, where we’ll head to the airport for our flights home.

We’ll leave Sicily with wonderful memories of beautiful towns, Mediterranean views, incredible food and wine, and a week spent experiencing this unforgettable part of Italy together.

Included: Breakfast, transportation to airport