Private ocean charters, volcanic wine estates, and the unapologetic luxury of the Sicilian coast.
Sicily
September 9-15 2027
$500 Deposit To Join
Then pay in full or choose a flexible plan with monthly installments, milestone options, or buy-now-pay-later via Klarna and Affirm.
Day 1: Welcome to Taormina
Land in Catania, where a private driver whisks you up to the glamorous clifftops of Taormina After a brief welcome the evening is yours to wander and grab dinner.
Day 2: The Yacht Day
We’re spending the day on a private yacht cruising the coastline. Expect plenty of swimming and snorkeling near Isola Bella and hidden sea caves. Lunch and local aperitifs are served right on deck, leaving the late afternoon and night completely open for your own plans.
Day 3: Volcanoes & Vineyard Lunches
We hit Mount Etna in a fleet of Land Rovers, exploring old lava flows and volcanic caves with our guide. Afterward, we head to a stunning winery on the slopes for a long, boozy lunch paired with incredible local vintages.
Day 4: Do Whatever You Want
Today is 100% yours. No schedule, no rush. Sleep in, lounge by the pool, hit the spa, or shop the local boutiques.
Day 5: Cinematic Vibes & Vintage Cars
We’re heading into the hills to explore the timeless villages made famous by The Godfather. (Want to drive? You can upgrade to pilot your own vintage Fiat 500 for the day).
Day 6: Poolside Living
Your final full day to soak up the sun on your own terms. Keep it low-key by the water, or opt for the ultimate upgrade: a private helicopter flight directly over Etna’s smoking craters.
Day 7: Arrivederci
One last seaside breakfast before your private transfer back to Catania Airport.
Land in Catania, where a private driver whisks you up to the glamorous clifftops of Taormina After a brief welcome the evening is yours to wander and grab dinner.
Day 2: The Yacht Day
We’re spending the day on a private yacht cruising the coastline. Expect plenty of swimming and snorkeling near Isola Bella and hidden sea caves. Lunch and local aperitifs are served right on deck, leaving the late afternoon and night completely open for your own plans.
Day 3: Volcanoes & Vineyard Lunches
We hit Mount Etna in a fleet of Land Rovers, exploring old lava flows and volcanic caves with our guide. Afterward, we head to a stunning winery on the slopes for a long, boozy lunch paired with incredible local vintages.
Day 4: Do Whatever You Want
Today is 100% yours. No schedule, no rush. Sleep in, lounge by the pool, hit the spa, or shop the local boutiques.
Day 5: Cinematic Vibes & Vintage Cars
We’re heading into the hills to explore the timeless villages made famous by The Godfather. (Want to drive? You can upgrade to pilot your own vintage Fiat 500 for the day).
Day 6: Poolside Living
Your final full day to soak up the sun on your own terms. Keep it low-key by the water, or opt for the ultimate upgrade: a private helicopter flight directly over Etna’s smoking craters.
Day 7: Arrivederci
One last seaside breakfast before your private transfer back to Catania Airport.
- Premium Stays: 6 nights at a luxury boutique hotel perched in the cliffs of Taormina.
- 8 full meals plus a 2 curated food/drink tastings
- Private roundtrip airport transfers between Catania Airport and the hotel.
- A full day on a private boat cruising the coast, complete with swimming, snorkeling, and a local lunch with aperitifs on deck.
- Etna 4x4 Adventure: An off-road mountain trek with professional drivers and a naturalist guide.
- Volcanic Wine Tasting: A private estate tour, sommelier tasting, and multi-course lunch at a premier winery on the slopes of Mount Etna.
- All ground transport, drivers, local VAT, and entry fees for our scheduled group excursions are fully covered.
- On-call host support and our custom Sicily City Guide to map out the best spots for your unscripted solo days.
- Food & Beverages not specified above
- Passport
- International Airfare
- Visas (if applicable)
- Travel Insurance (required)
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