2026 Cheeky adventures by land + sea
Linda Sarris organizes a limited series of carefully-curated group trips throughout the year, mostly based in Sicily. Our programs offer a great blend of experiences by land or sea, always with a focus on everything delish. Sign up for one of these programs (as a solo traveller, couple or bunch of friends) or send us a request to book something special just for your own crew of family/friends.
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30 MAY - 6 JUNE, 2026
13 - 20 JUNE, 2026
20 - 27 JUNE, 2026
CHEEKY CHARTERS — PRIVATE SAILING TRIPS IN SICILY
Aeolian Islands, Sicily | Fly in/out of Palermo Airport | Boat check in/out: Capo d’Orlando
Sicily is known for incredible food, but we are taking you off-the-beaten path to a very special volcanic oasis between Persephone’s island and Italy’s main boot. We’re headed to THE AEOLIANS — a chain of seven Mediterranean islands that boast some of the best swimming, fresh seafood, and night life in Sicily.
Chef Linda Sarris has organized this adventure and will be onboard along with a certified sailboat captain here in Italy. Linda will keep the Cheeky cocktails flowing through the week while she prepares all of our family meals when we are at sea. Menus will feature freshly-caught seafood, light pasta dishes with seasonal vegetables, natural and volcanic wines, and exceptional desserts like cannoli and granita!
We will try to hit at least 4 islands during this weeklong adventure. Weather and wind are always factors when you plan a sailing trip. Our well-seasoned captain knows this area like the back of his hand. We’ll follow his lead to plan the best route, and might make some changes to the itinerary to make sure we have time for a few stops among the islands, free time for dinners and drinks off of the boat on your own, and relaxing mornings/afternoons catching some sun and enjoying “la dolce vita” aboard your own private catamaran.
Your Greek-American guide and Chef Linda Sarris has organized this adventure and will be onboard with you for the week. She'll keep the Cheeky cocktails flowing while preparing family meals aboard when we are at sea.
PRIVATE SAILING TRIP — OPEN TO ALL
AVAILABILITY: there are 4 single/double cabins on our boat. Each with one double-sized bed and a small bathroom, Guests must privately book the boat.
WHAT'S INCLUDED
7 nights on-board
a few restaurant meals/drinks out
groceries/bevs + all family meals on the boat
46-foot catamaran with captain, chef, dinghy tender boat, gasoline + docking fees, sheets, bath towels + end of week cleaning fee
NOT INCLUDED IN THE PROGRAM PACKAGE
Airfare and any pre/post trip adventures on your own
Extra meals on shore, excursions, shopping, snacks outside of the itinerary
OUR AEOLIAN ISLANDS
Vulcano (sizzling + steaming)
Filicudi (remote + wild)
Panarea (chic + delicious)
Stromboli (mystical + moody)
Salina (lush + boozey)
Lipari (calming + clear)
11–18 JULY, 2026
18–25 JULY, 2026
CHEEKY CHARTERS — SAILING IN GREECE
Ionian and Echinean Islands, Greece | Fly in/out of Preveza Airport | Boat check in/out: Lefkada
There's nothing quite like discovering off-the-grid destinations that aren't filled with crowds, especially in summertime. These are NOT touristic islands, maybe you've never even heard of most of them. That's actually what we love most about it.
During this weeklong adventure, we will be traveling around the west coast of Greece. We’ll follow our captain's lead to plan the best route to make sure we have time for stops among the islands, dinners and drinks off of the boat, and relaxing mornings/afternoons catching some sun and enjoying “i glykiá zoí” (the sweet life) aboard a beautiful catamaran.
Your Greek-American guide/chef Linda Sarris has organized this adventure and will be onboard with you for the week. She'll keep the Cheeky cocktails flowing while preparing family meals aboard when we are at sea.
Greece is world-famous for their history, longevity, 6000 islands, and their healthy food and wine-fueled diet. Menus will feature freshly-caught seafood, great seasonal meals for vegetarian guests, feta-stuffed flakey pastries, hearty greens/grains, roasted and stuffed vegetables, mountain tea refreshments, meze platters, big heaping salads, and honey-topped everything!
SAILING TRIP — OPEN TO ALL
AVAILABILITY: 4 cabins — each has one double-bed and a small bathroom
PRICING
Solo Cabin: €4350
Double Cabin: €2900 per person
WHAT'S INCLUDED
transfer from Preveza airport
7 nights on-board
a few restaurant meals/drinks out
groceries/bevs + all family meals on the boat
44-foot catamaran with captain, chef, dinghy tender boat, gasoline + docking fees, sheets, bath towels + end of week cleaning fee
THE IONIAN ISLANDS
Lefkada (hidden gem, beautiful beaches, lush forests and wineries)
Kalamos (mountainous, protected marine reserve)
Kastos (off-the-grid, crystal-clear waters great for snorkeling)
Ithaca (the island of Homer's Odysseus, relaxing, natural beauty)
Kefalonia (fishing villages, the setting of Captain Corelli's Mandolin film, wineries, and Linda’s auntie Dimitroula)
5–10 OCTOBER, 2026
VINO VOLCANICO — LADIES-ONLY WINE TASTING RETREAT IN PANTELLERIA
Pantelleria, Sicily | Fly in/out of Pantelleria Airport, by way of Palermo/Trapani/Catania
Discover “the black pearl of the Mediterranean” during my best-selling wine lovers trip on the island of Pantelleria.
Chef Linda Sarris will lead a small group of guests on a whirlwind of flavors from wild mountain herbs and freshly made túmma cheese to seasonal meals featuring capers, wild fennel, veggies and seafood. Learn about grapes, raisins, extreme agriculture, and DOC Passito di Pantelleria sweet wines, as well as traditional and natural winemaking techniques from the island.
This all-inclusive 5-night adventure takes place during the harvest season and we’ll have plenty of surprises in store for you! Follow the grapes from their volcanic soils and terraced vineyards to the cantinas with guided tours and epic all-day wine tastings. There will also be free time to soak up the magic each night with communal family meal dinners at our dammusi houses overlooking the sea.
WINE TASTING RETREAT — LADIES ONLY
AVAILABILITY: 3 guest rooms remaining for single/double/triple occupancy
PRICING
All of the 2-bedroom houses have indoor/outdoor spaces to be shared with other trip members. Double and Triple occupancy rooms need to be filled with your own travel partners. Each guest should register on their own and list your travel partners names in the signup notes.
Solo Traveller (private room/bathroom x1) €2800
Double Room (shared bedroom/bathroom x2) €1900 per person
Triplo Room (shared bedroom/bathroom with 3 single beds) €1500 per person
WHAT'S INCLUDED: All activities/excursions, tastings, and meals listed in the itinerary are included in the cost for this trip.
5-night dammusi accommodations at Le Case del Principe Pantelleria
Vineyard visits with lunch + wine tastings
A visit to a local caper producer
Daily breakfasts + special lunches
Communal dinners prepared by The Cheeky Chef
A visit to a traditional giardino pantesco lava stone-walled garden
Light hike + picnic in Pantelleria’s national park
Relaxing dips in natural hot springs + free time to swim in our private beach cove
Local transportation provided for excursions included in the itinerary
Round-trip van transfers from the Pantelleria island airport PNL to the dammusi
NOT INCLUDED IN THE PROGRAM PACKAGE
Airfare + any pre/post trip adventures on your own