Sicily, Eight Different Ways

Written By Krista Nannery

If you’ve been thinking about visiting Sicily, consider this your sign. Whether you’re dreaming of a land-based deep dive into the island’s food and culture, a cycling adventure through lemon groves and along the coast, or a refined cruise with archaeological stops and vineyard tastings—Sicily is having a moment. And it’s easier than ever to go! In fact, I’m planning my own trip in 2026! Track this and my other travel adventures on my new Instagram account.

Here are some of the most interesting ways to explore Sicily in 2026. (And yes, some of them are still available for 2025.) Ready to book? Book a complimentary vacation consultation here.

⛵ By Private Yacht: The Custom Way to Island Hop

Looking for a completely private way to experience Sicily? I can help you charter a crewed yacht for you and your guests. Sail the southern coast, anchor off the Aeolian Islands, enjoy chef-prepared meals on board, and explore tucked-away beaches and historic ports at your own pace. Whether you want to snorkel, shop, or just sip wine on deck, I’ll handle the details—from provisioning to itineraries to booking your captain and crew.

Palermo, Sicily

🌍By Land: Fully Guided Tours

I am a preferred partner with a number of vetted package tour suppliers. What’s in it for you? Well, I’ve done all the training and know how everything works, and if anything does go wrong, I’ve got your back. (I have the numbers of all the Business Development Managers for these tour operators on speed dial.) Yes you could Google yourself senseless but why do that when I speak to all these companies regularly?

Plus I provide AirTags to track your bags and can help with pre- and post-trip travel, which clients really appreciate. Prices below are for 2026 travel.

Tauck - A Sicilian Odyssey
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10 days | From $9590 pp | Max of 24 travelers
This 10‑day small‑group tour weaves through Sicily’s iconic landscapes—from the ancient Greek temples of Agrigento and Roman‑era theatre in Taormina to the Baroque splendor of Noto and Ragusa—immersing travelers in the island’s rich tapestry of history, art, and architecture.

Collette – Sicily and Its Isles
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14 days | From $4,999 pp | Max of 24 travelers
A comprehensive overview of Sicily with stops in Palermo, Taormina, the Aeolian Islands, and more. Includes expert guides, historical deep dives, and a focus on local culture.

G Adventures – Highlights of Sicily
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14 days | $3949 pp | Up to 16 travelers
A small-group tour that blends cultural highlights with a more casual, immersive vibe. A great option for younger or budget-conscious travelers who still want quality experiences.

🚴️ By Bike: For the Active Traveler

Backroads – Sicily Bike Tour
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6 days | From $5,099 pp | Max of 26 guests. Private options available.
Pedal through the Val di Noto, roll past vineyards and seaside villages, and end your days with farm dinners and Mount Etna views. Backroads trips are known for high-end support and well-planned routes for a range of fitness levels. When booking with Backroads, I can provide support on pre- and post-trip stays.

The Sea Cloud Spirit

🚢 By Cruise Ship: Circumnavigate in Style

Sea Cloud Cruises – Sicily's Rich Cultural Heritage
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Sail on a historic windjammer with a refined guest list and stop at ancient sites like Agrigento and Syracuse. This is intimate, luxurious sailing at its best.

Ponant – A Circumnavigation of Sicily with Smithsonian Journeys
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Cultural enrichment meets luxury cruising. Onboard experts bring Sicily’s history to life as you sail around the island on a small expedition ship with high-touch service.

Remember with all cruise bookings, I can provide onboard credits and other amenities that aren’t available by booking direct.

🧳 Want Something Even More Tailored?

I can also plan a fully private tour of Sicily with top-tier guides and drivers, customized to your travel style and interests. Honestly, this is what I do best. Think: fabulous hotels like San Domenico Palace Taormina (Four Seasons), Villa Igiea (Rocco Forte), Grand Hotel Timeo (Belmond), private cooking classes, vineyard tastings, and VIP access to ancient sites—with no group tour in sight. Perfect for families, friend groups, or honeymooners who want a little more control (and a lot more comfort). I can do this at the 4-star or 5-star level.

Why Go in 2026?

Sicily continues to rise in popularity thanks to its mix of affordability, authenticity, and cinematic good looks. The infrastructure is strong, the food is exceptional, and the travel providers are responding with more options than ever. If you’re ready for island life—but with Roman ruins, Baroque towns, and the best cannoli of your life—Sicily should be on your 2026 list.

Need help picking the right itinerary for your style? I’m happy to help match you to the right tour or cruise. Book a complimentary vacation consultation here.

About Krista

I’m a Virtuoso luxury travel advisor based in West Palm Beach, Florida. Prior to moving to Florida to take care of my elderly mom with Parkinson’s Disease, I spent over 11 years living and working in London, England. My career and personal travel have taken me all over the world. To date, I’ve been to 78 countries. Now I bring the joy of travel to others as a Virtuoso travel advisor. I offer a 30 minute complimentary vacation consultation for anyone looking to plan their next trip.

Ways I Can Help You

Krista Nannery
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