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Sicily Tour with Tiffany Derry
September 14 – 20, 2026 | One Exclusive Departure
From Market to Table
Discover the heartbeat of Italian cuisine through hands-on experiences, local ingredients, and traditionally crafted meals
“Everything was delicious.”
Questions? Text or call us
+1 (855) 219-8018
$11,000
per person based on double occupancy

Award-Winning Celebrity Chef and Founder, Tiffany Derry
Beneath the Mediterranean sun, the rhythms of Sicily unfold slowly—sea spray in the air, terracotta rooftops stretching to the horizon, and markets perfumed with bergamot and basil. In the past few days, you’ve shaped pasta beside local cooks and wandered past weatherworn ruins into open-air stalls where arancini are served hot and golden. Up on Mount Etna, you swirled volcanic whites and earthy reds, listening to a winemaker describe the quiet science of fermentation. Yesterday you stood beside a shepherd as he stirred milk into ricotta, and tomorrow, the Ionian will carry you toward ancient temples tucked beside fishing coves. This is Sicily—mythic, grounded, generous.
Trip Highlights
- Explore historic Taormina
- Learn to roll fresh pasta
- Stroll the ruins of Agrigento
- Make Sicilian pizza alongside Tiffany
- Ascend Mt. Etna in Jeeps
- Taste distinctive Sicilian wines
- Picnic in the Valley of the Temples
- Experience Marsala’s salt flats
- Sample street foods in the Palermo market

3 Reasons to Travel with Tiffany Derry
Tiffany Derry is a force. A James Beard Award finalist, television personality, and co-founder of T2D Concepts, she leads purpose-driven restaurants including Roots Southern Table, Roots Chicken Shak, and Radici Woodfired Grill. Raised on her family’s Texas farm, she carries forward a belief that food is love, memory, and connection. Whether judging on MasterChef or lobbying for food equity in Washington, Tiffany’s presence inspires. She reminds us that the table is where dialogue begins and real change can take root.

Traveler at Heart
Tiffany’s first trip outside the U.S. was to France at just 18, when her love of travel and food first collided. Decades later, that spark continues to guide her. Whether sipping morning espresso in Sicily or cooking over a wood-fired grill back home at Radici, she sees each journey as a chance to discover what connects us across cultures.
Sicily is a Lifestyle
Italy has always tugged at Tiffany’s heart, but Sicily is something else entirely. From the volcanic soils that give Nerello Mascalese its edge to the sun-drenched markets brimming with citrus and seafood, Sicily carries its own rhythm. For Tiffany, it’s not just a region — it’s a lifestyle, one she embraces from espresso at dawn to Aperol at dusk.
A Force for Good
Raised on her family’s farm in Texas, Tiffany learned early that food is about care, seasonality, and never wasting what the earth provides. Today, she brings that ethos to her restaurants, to her advocacy for food equity, and to her role as the first Black full-time judge on MasterChef. In Sicily, she shares not just her passion for flavor, but her belief that food can spark joy, dialogue, and real change.
I loved how the little things were always taken care of.
Such a totally immersive experience. Incredible.
The trip was curated in a way that provided unique experiences we wouldn't have had if we traveled solo.
Where We Sleep

Beautifully curated accommodations—we’ll relax under the gaze of a volcano in Sicily, and feel like we’re part of the island's story.
*On rare occasions, our hotels will change. Our standards for luxury and authenticity will not.
Dimora Cottanera
CastiglioneNestled on the slopes of Mt. Etna, our historic hotel blends rustic charm with unique architectural flair. Originally owned by engineer Priolo and later acquired by Francesco Cambria, the property features a restored villa, a mill, and lush hazelnut groves. Enjoy a serene retreat with a touch of Sicilian nobility and contemporary comfort.

Grand Hotel et Des Palmes
PalermoWithin the hallowed halls of this palatial hotel, we walk among centuries of tradition and artistry. The high-frescoed ceilings and Art Nouveau stained glass make our stay in Palermo more of an immediate immersion into both the past and present of the urban heart of Sicily.


Book Sicily Tour with Tiffany Derry
Make It Private
We understand that certain dates can work better than others, or sometimes a more private experience is more appealing. We’d be happy to modify this departure so it fits the needs of you and your group.
Start HereQuestions?
That’s OK, we have answers.
Read our FAQs below. Or text or call us at +1 (855) 219-8018 to speak with a Modern Adventure Trip Specialist.
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What does the price include?
Six nights at unique four- and five-star accommodations; private travel for all day trips and excursions; departure airport transfer; private tours with local guides and cultural experts; exclusive VIP access and tastings; guided activities, adventures and expeditions; entrance fees; daily breakfasts, most lunches and dinners; local beverages with meals.
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What does the price not include?
International roundtrip airfare; travel insurance; transportation to the trip’s starting point; activities not included in the trip itinerary; hotel incidentals including room service, laundry service and hotel bar tabs; food and beverages not included in itinerary; gratuity for tour leader.
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Where does this trip start and end?
Our adventure begins in Sicily at the Dimora Cottanera hotel. The closest airport is Catania’s Fontanarossa Airport (CTA). We recommend arriving one day early to ensure you’re at our starting point on time. On our last day, the closest airport is Palermo’s Falcone-Borsellino (PMO) airport. Your flight should be scheduled to depart at 12pm or later from PMO airport.
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What travel documents are needed?
US citizens are not required to have a visa for stays in Italy of under 90 days. Just bring a valid US passport. For citizens of other countries, please check with the Italian embassy or consulate for information and requirements.
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Do I need to pay a solo traveler supplement?
For solo travelers, there is a $2,700 single-supplement fee paid at the time of booking to secure a private room. These spots are extremely limited and available on a first-come, first-served basis.
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Who is going on this trip?
Our adventures typically have between 10 and 20 guests, and our Modern Adventure Team. Our experiences are fun and inclusive and you can expect to be joined by a diverse group in terms of age, background and interests—including solo travelers, couples and friends traveling together. This adventure is for travelers age 18 and above.
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Who is leading this trip?
This trip is led by an expert Modern Adventure trip leader. They’re an experienced travel guide, a representative of Modern Adventure and your go-to person for questions or concerns on the trip. We’ll be joined throughout our adventure by local, expert guides who are deeply knowledgeable with respect to local cultures, customs and history and are passionate about sharing that with us.
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Do I need travel insurance?
We highly recommend purchasing travel insurance. Travel insurance allows you to seek reimbursement for your trip costs; if your trip plans change for unforeseeable reasons, or if you need to get medical help, emergency transport, and for theft, loss or damage of items while traveling. For best coverage, always insure the full trip cost within two weeks of your initial trip deposit and note that most ‘Cancel For Any Reason’ policies must be purchased on the date of your initial deposit.
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What is the cancellation policy?
You may cancel 120 days or more before departure and receive a full refund minus a $1500 per person service fee ($500 of which may be retained as a future travel credit, valid for one year after cancellation). If you cancel on or after 119 days in advance, there is a 50% cancellation fee. On or after 59 days in advance, there is a 100% cancellation fee. See our full terms and conditions for details.
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When will my trip be confirmed?
Because our trips are designed as small-group experiences, we need a minimum number of travelers for each departure. You will receive an email no later than 130 days prior to departure confirming your trip. If we don’t meet the minimum, you’ll have the option of a full refund, reinstatement of any applicable trip credits, transferring to a different departure date, or converting your booking to a private departure. Please see our terms and conditions for complete details.
Important: We strongly advise booking refundable flights and pre-trip accommodations, or waiting until you receive your trip confirmation.
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What is the Small Group Supplement?
Our trips are priced based on a minimum of 10 guests. If a departure runs with 9 or fewer travelers, a Small Group Supplement (SGS) will apply. The SGS ensures your trip is guaranteed to run with the full program intact while offering you a more intimate, exclusive group experience.
The supplement amount depends on the final group size and will be confirmed no later than 130 days before departure. If additional guests join after the SGS has been paid, it will be refunded. Please review our full terms and conditions for additional details.