A Cheeky Sicilian Sailing Trip
Stellavision returns to sea alongside the Cheeky Chef, Linda Sarris in 2025! This tour combines a nautical adventure with cultural and culinary exploration in a hard-to-reach island paradise. Setting sail from Palermo, Sicily we’ll be floating our way through the Aeolians, a group of volcanic islands off the northeast coast of the main Sicilian isola. Picture yourself chasing sunsets by sea, swimming, snorkeling and sunbathing in turquoise waters, complete with a private chef. As we dock at five different islands throughout the week, we’ll hop on land to show you the best spots, enjoy meals by locals and Michelin-starred chefs and meet some very special island friends. Ready to come aboard?
At A Glance:
Tour Dates:
June 14 - 21, 2025
Tour Length:
8 days & 7 nights
Where We Go:
Palermo, Sicily + Aeolian Islands: Vulcano, Lipari, Salina, Panarea, Stromboli
Price: (USD)
Reserve your spot for $995 with our multi-month payment plans.
$7345: single occupancy
$5345: double occupancy (how to get this rate here)
Itinerary please!
Just take me to straight to the good stuff.
Weather:
June in Sicily is gorgeous. In the middle of the Mediterranean Sea in summertime, expect hot days (avg. 30 ° C / 86° F) with many hours of daylight. On our boat the refreshing sea and mother nature’s breeze are our only air-conditioning but there is shade to be found on board.
Meet Your Host / Chef
We’re setting sail with The Cheeky Chef: Linda Sarris
Let’s Talk.
Boat life is the best but quite different from a vacation on land. Here are all the details about what to expect and what to consider before booking.
Only 7 cabins available… is one of them yours?
“Italy has many pleasures to offer but none so sublime as traveling with a group of kind, curious, progressive, badass [people]… seeing the country through your eyes was profound”
— Sara B.
“Exploring the Aeolian Islands is a treat. Traveling by boat, even better! Dive into the sea as soon as you wake up, island hop to a new destination each day, dine under the stars, wander through the small port towns, and feast on local specialties. It's the dolce vita... Sicilian-style.”
- Linda Sarris aka The Cheeky Chef
Itinerary
Day 1: Palermo to Vulcano
Our tour starts with a very exciting meetup in Palermo, Sicily where your Stellavision Guide will be on hand to ease the transition from the Italian mainland to Sicily to the islands off the island: the Aeolian archipelago. Together we’ll journey by train towards the port of Capo d’Orlando, taxi from the train station to the yacht harbor where our pair of private catamarans are docked (each catamaran has its own professional captain and we’ll be exploring the islands in tandem all week!)
After your journey you’ll have time to settle into your private cabin and meet the rest of your crew: our boat Captains who will give us the 411 on life at sea and Linda Sarris, our Sicilian Host and Private Chef. Your Stellavision guide not only meets you in Palermo but stays aboard for week-long TLC.
And then - of course you’ve earned an aperitivo spread! Before sunset, we’ll take off for the island of Vulcano. Tonight we’ll be getting to know our group with welcome bites, drinks and dinner on-board. Benvenuto! Welcome to your nautical adventure.
Day 2: Vulcano to Salina
After breakfast on-board we’re off! It’s time to get those toes (and everything else!) into the turquoise of the Mediterranean. Not long after, we'll stop in our first spectacular swimming spot where you can enjoy Caribbean-esque clear waters. Linda is already prepping a buonissimo lunch to be enjoyed all together as we sail around Lipari before moving towards the island of Salina. Here, we dock in the main port of Santa Marina where we'll have time to head out to explore the lush green island. Thanks to freshwater sources, Salina is uniquely lush even among the "seven sisters". From olive groves to grapes, olive oil, capers and the colourful prickly pear cacti, we’ll take in the tropical paradise.
After your free time, we’ll meet up on shore for a gorgeous dinner and following our seafood supper, the night is yours. There will be plenty of time to wander the sweet enclave of Porto Santa Marina for a digestivo or cocktail, some late night shopping, a hot shower… choose your own adventure.
Day 3: Salina to Panarea
Good news pals - the nights we sleep in port you can take advantage of the expansive and lovely shower facilities on dry land! (You have a private shower on board, but it’s defo smaller.) This morning we’re having our first traditional Sicilian breakfast: coffee and sweets! We’re headed to our favorite local bar for cappuccino, granita and cornetti. After lunchtime on board you’ll pick your pleasure: a deep relax and sunbathe? a dip in the water? shopping and wandering in the town of Panarea (we can never decide whether it’s island chic or isola cute - you tell us!) This evening’s sundowner is an epic one as we head for finely-crafted aperitivo cocktails and nibbles at the island’s coolest sunset-watching spot. Vibes? next level. VIP? you know it.! Volcanic Stromboli will be puffing in the distance. Our progressive dining continues with Sicilian sushi and as we take the water taxi back to the boats for the night, you never know - there might just be a midnight spaghettata in store. In Panarea, we'll sleep in the bay, under the stars at anchor. Side by side, swaying with the sea.
Image courtesy of Giulia Re Callegaris
Day 4: Panarea to Stromboli
The day starts in Panarea, where we arrived yesterday. Water taxis will bring us to shore for breakfast in the harbour before we link up with Flavia, a local resident and friend who will be unlocking the secrets of these volcanic islands for us. Panarea is the smallest and most stylish island with narrow lanes winding up from the port, golf-carts buzzing by, and bougainvillea cascading over the walls. In the early afternoon, our group is headed for lunch at our favorite (female-owned!) seafront restaurant on the island. After that, we’re setting off for Stromboli and there’s a spectacular night in store! She is the most mystical and dramatic island in the group, thanks to the active volcano, who has been erupting every 20 minutes or so, for the past 2,000 years. No biggie. During the day, even in the distance from Panarea, puffs of smoke fill the sky above Stromboli, but at night with zero light pollution the BIG show begins. After our afternoon swims we’ll be doing a nighttime cruise to the uninhabited side of the island to see the volcanic eruptions. We're talking bright, red lava exploding into the sky. As our catamarans bob in the open water, we can enjoy the most impressive view possible. Don't worry, we’ll be feeding your bellies as well as your eyeballs of course - Chef Linda is treating us to dinner at sea (we'll have the pizza party this night instead, depending on weather we might sail back to sleep in Panarea like last time.. should we mention a night sail?). We will head back towards the main town and "park" our boats on a buoy for the night.
Image courtesy of @provincia_di_messina
Day 5: Stromboli to Salina
Buongiorno! After a night in the middle of the Med, we’re having breakfast on board and a slow morning. Dip in and out of the water. Float on a floatie. Don a pair of goggles and fins to ogle what you can sea below the waves. Or just enjoy the book or tunes we recommend you bring along with you. Then, we’re having lunch on-board and sailing westwards, back to the multifaceted island of Salina where we absolutely need more time to enjoy all her pleasures.
So… there’s a treat in store tonight and an opportunity to put on your favorite ‘fit. We wouldn’t bring you to Italy without a vineyard visit would we?? We’re not playing around with this one… you’ll be doing a guided wine tasting at a seafront vineyard on a 5-star resort property where we’ll also be enjoying dinner. Then it’s back to the port of Santa Marina where we’re docked for the night. We can point you in the direction of a few spots for drinks, walkable from the boat.
Day 6: Salina
On days we’re in the port we get the pleasure of swapping our on-board showers (which totally do the trick) for longer and more luxurious hot shower facilities on terra ferma - solid land! After that moment, we’ll head into town for some last minute shopping (bank or pharmacy runs too) in Salina before we transfer to another village for our favorite pani cunzatu spot on the island. We arrive in style, via water taxi. Did you know that while all over Italy regional dialects can be found, Siciliano is its own language? That’s where the term comes from and this sandwich’s history is steeped in cucina povera - a poor man’s meal that is now deeply delicious and authentic. The "seasoned bread" is piled high with the freshest of ingredients. Sandwich meets salad, perfection. Following lunch and granita, we’re sailing towards the Bay of Pollara where ‘Il Postino’ was filmed.
We’ll be chasing the sunset before dropping anchor in the baia and enjoying a swim, seafood dinner, and overnight.
Day 7: Salina to Vulcano
While enjoying breakfast on-board, this morning we journey to even more picturesque spots in Lipari. By Day 7 you’ll be boat experts and deep into the flow of swimming and chilling that’s in store. Today we’ll be celebrating our beautiful week together with lunch at one of our favorite restaurants onshore along with our charming captains on Vulcano. We’ll have time for one last dip before sailing back to mainland Sicily. Today’s dinner will be our final creation by the Cheeky Chef - savor it! But the bragging rights for the time you had your own kick-ass private chef for a week? Those last forever. We’ll spend the last night in the port of Capo d’Orlando and pop into the bar for some farewell cocktails.
Day 8: C. d’Orlando to Palermo
This morning is an early start and brings the first goodbyes as we say arrivederci to Linda and our amazing catamaran captains. We’ll stop off in the yacht harbour where we’ll have a quick breakfast, suitcases in tow, then take a taxi to the train station. Before 9am your Stellavision guide and Linda will board the train with you to see you comfortably back to Palermo, waving goodbye to the islands silhouetted on the horizon through the train window as we pass by. Will you remember which one is which? We’re honestly tearing up a little already.
As we deposit you back at the Palermo Centrale station in Sicily’s capital city before midday the tour will end. But from hotel recommendations and Stellavision rates to more tips to explore Sicily or beyond, we’re here to finesse your final day/s in Italy. Until next time, we’ll leave you with an effusive Italian goodbye: Ciao amici, ciao amori, tanti baci!!!
Post-Tour FYI:
Our tour is 7 nights and 8 days. We will be traveling back to Palermo from Capo d’Orlando by train on Day 8 of the Cheeky Sicilian Sailing tour. The drop-off point will be at the Palermo Centrale train station around Saturday just after 11AM, at which point the tour will come to a (sniff) close.
We expect to arrive back midday but we want to ensure your flight turnaround is not rushed. We would strongly recommend that you plan on booking a departing flight that night (Saturday), on the following day (Sunday) or beyond. We’re here to help with your post-tour logistics, booking a hotel for Saturday (night 8) or a Covid-test should you require one. Let us know what you need and we’re here to assist. Please note - any pre or post-tour fees are not included in the price.
What’s Included
Private en-suite Cabin
Our tour sets sail on two catamarans that will sail in tandem and dock together throughout. You’ll have your own private cabin (aka single occupancy) on one of the boats for 7 nights. Each cabin has a small bathroom. For more info about cruising on a Catamaran, your room and on board facilities, just click here. Traveling with your sister? Friend? Partner? Find out more about double occupancy.
All Meals + Private Chef
You might have spied on our itinerary that we’ll be enjoying incredible restaurant meals and authentic island food/wine, and of course gelato & granita. Beyond that, we have a private chef on board! The Cheeky Chef will be bringing all her culinary prowess and experience to Sicilian family-style meals with freshly caught fish, seasonal Italian produce, and pasta deliciousness. All meals and snacks are included.
Alcohol
From chic cocktails to classic Italian aperitivi and wine with dinners, you’ll have plenty of reasons to say ‘Salute!’ Linda’s connections to Sicily’s best wineries and vintners mean we have a sailing sommelier too! Not a drinker? Not a problem.
All Activities
We’ve curated a range of both classic and creative experiences to offer a unique and immersive Sicilian island showcase. From culture to food, swimming, sunning and sightseeing, you’ll experience it all - and always with a chic twist. On this trip expect plenty of dips in the water and chilling time as we sail between the Aeolian islands.
All Internal Travel
Aside from our catamarans, all your trains, taxis and transfers are included in the tour price. You won’t need to whip out your wallet once while we’re together.
Sicilian Captains, Stellavision Host + Expert Local Guides
We’re taking care of all of the logistics so you can kick back and enjoy. Two of us will be on hand to host the tour, take care of everything you might need, and point out precious details you may miss. In addition to our Chef / Host, you’ll be joined by a Stellavision guide and we’ll be linking up with local experts too. The boats are sailed by expert English-speaking Captains with years of Sicilian sailing experience. We will eat all meals together but for overnights, each catamaran will always have their own captain and one of our two hosts to take care of you.
Welcome Kit
Merch, maps and a few surprises await you upon check-in! We’re also providing masks and hand sanitizer to navigate ‘post’-pandy travel, safely.
Memories to last a lifetime.
‘nuff said.
Not Included
International Flight
You’ll meet us in Palermo, where the tour starts (and ends).
We depart early on the 14th so you’ll want to ensure you arrive in Palermo on June the 13th . We can help you with a hotel the night before and share a Stellavision rate.
Travel Insurance
is mandatory on all Stellavision Tours. We’ve done a bunch of the legwork for you though, you can find suggestions here. It is imperative your insurance cover sailing trips too - be sure to check.
Personal Expenditures
Incidental costs, personal shopping and any expenses accrued during free time are not included in the tour price.
Professional Photographer
Stay tuned for more details.
Your Sicilian Host & Private Chef
Linda Sarris was raised in a big Greek-American family and trained at the French Culinary Institute in New York City. After a few stints in restaurants, she took off to sharpen her culinary skills in her own adventurous way, developing her own Mediterranean style of cooking, working on a farm-to-table wine estate in Sicily, spending summers private-cheffing in Tuscany, and consulting for restaurants in Romania and Colombia! Linda is a published author, food/wine travel designer, and private chef with a decade of experience cooking for clients in the music and fashion industries. Part translator, part hostess with the mostess and our local culinary guru, the Cheeky Chef is working side by side with your Stellavision guide to finesse your time at sea. She's known as the Queen of Ballarò and has charmed the hearts of the vendors in her wild neighborhood food market in Palermo. She is a cheeky one (well named for sure) and when you’re on board, you'll find out why…. wink.
Life on a Boat & Your Cabin Accommodations
We are so unbelievably excited to go on this journey with you! We also believe in total transparency: your enjoyment and experience are far more important to us than selling you a spot on a trip that may not be the right fit. Here are some things you might want to consider:
Sailing is not as predictable as driving.
Rough seas and strong winds are always factors with boat trips. We need to go with the flow. The captain has the final say on where and when we sail to keep us safe and sound. During the week, the itinerary may change slightly depending on the best sailing path around the Aeolian Islands but no matter what, you can count on a great time. The weather in Sicily in June is typically still gorgeous and we are rain or shine kinda folks. If we encounter a dose of bad weather, the experienced professionals on board always do their best to manage the situation. You’re in great hands.
Let’s talk about sea sickness for a moment.
We’ll be sending out a full packing list before your trip and on there, you’ll find that we recommend things you might need for the possibility of sea sickness. It’s important to remember that going out on a boat is different than living/sleeping on a boat. Even if you’re not normally susceptible to sea sickness, please brings some ‘just in case’ items along. Guests typically bring pills / patches. We cannot provide these to you.
Some FYIs about getting on and off the boats
There are three ways you’re getting off the catamaran. (Well four if you include jumping into perfect turqoise water!)
When we are docked in a port, you’ll walk the plank like the chicest pirate that ever there was! The catamrans are moored approximately 2-3 feet from the dock (we wouldn’t want wood and all that gorgeous fiberglass connecting). A solid, wooden plank is how we walk off the boat and onto the jetty. You will receive assistance with your luggage and when you’re carrying any small bags if you’d prefer to be hands free. And if you DO want to hold someone’s hand - our captains are there to ease that transfer.
When we are docked at sea (for a meal or overnight), we transfer to local docks via the water taxis / boat tenders that we travel with. These are small, motorized dinghys that are on the back of each catamran. There is usually a step-down and a crawl up but - we’re all buds here! There’s no judgement. Most of us prefer to do it by sliding on our bums - and we love that for you! And us. Ya, we fully slide into the water taxi on our bums too.
When you go swimming, you can do an aforementioned jump or descend into the water via the ladder at the back of the boat. This is a vertical, metal ladder, similar to what you’d find in a public swimming pool. You’ll need a tad bit of upper arm strength. Tits up!
By day two, most guests are comfortable with all these embarking and disembarking measures that are part of our week at sea. Our crew will always be on hand to offer assistance if you need it.
Communal living & conveniences:
Communal living requires flexibility and an easy-going attitude. Unless you’re opting for double occupancy, all of our travelers will have a private bedroom space (more on the cabin facilities in a minute) but a boat is not a hotel. Even though this is our tiniest tour to date, we’ll be sharing a small living room area. There will be limited fridge space and our illustrious chef will be calling the shots on what goes inside it, as well as working from a small kitchenette. You’re going to be amazed at the gourmet grub she whips up! It’s important to go into this experience with the utmost courtesy and respect for our Hosts, Captains, the locals we'll encounter, and each other as we enjoy the Aeolians in our floating living space. (There is also plenty of time to stretch legs and get off the boat too!)
There is no Wi-Fi connection on-board. Cell service at sea is in and out but an Italian SIM card will be helpful if you need to stay connected.
There is no air-conditioning on the boats but you can look forward to refreshing sea dips and mother nature’s breeze. There is plenty of shade to be found on board.
Each of our two catamarans has four cabins and unless you’re opting for double occupancy (see below), one of them is all yours! Inside your private space you’ll find a double bed with a window above for air flow. There are USB outlets by the bedside, a small closet to hang items and two drawers if you want to unpack - which we recommend. We’ll store your suitcase to give you more space in the room. Speaking of:
It’s important (and you’ll be happier!) if you pack as lightly as possible. One small-medium suitcase and a backpack or tote is your luggage allowance. But don’t worry - if you’re spending longer in Italy or traveling onward and need more gear, we’ll be sharing where and how you can store a second or bigger suitcase in Palermo while we’re at sea.
Each cabin has its own bathroom. These are small but it’s all yours! Expect a toilet, small cabinet, and sink with shower head. AKA the entire bathroom turns into a shower over the toilet - there is not a separate shower to step into. But, we have 4 nights out of 7 docked in proper ports (as opposed to anchored out at sea). At each port you’ll have access to the on-shore bathroom and shower facilities. Long, hot, spacious, shower time! There’s also a freshwater shower on the boat deck (which we’d recommend doing in your bathing suit, not nude!) Between these three options, you’ll be fiiiine and clean as a whistle. There are mandatory bathroom rules that will need to be followed, to be explained by our captains on check-in. Welcome to boat life!
If you’d like a few pictures to fully paint this scene, feel free to drop us an email and we’ll provide some photo evidence of your home-sweet-home-to-be: hi@stellavisiontravel.com
Your Cabin & Packing
Sailing vs. Cruising
Catamarans are infamous for motoring more than sailing, there are pros and cons to both. We opted for this kind of boat because of their more spacious cabins, inside/outside communal areas, and general steadiness. Everyone hopes for smooth seas which keep us comfortable on-board but no waves usually means no wind and therefore no sailing. Of course our catamarans have beautiful billowy sails and we’ll get them up when we can. It’s quite a romantic moment softly swishing through the water and having a little tryst with mother nature's breeze.
How does double occupancy work?
Easy! Our new booking software will allow you to sign up as a twosome if that’s your preference. Some things to note about double occupancy:
Our catamran cabins can comfortably fit two travelers; that’s what they were built for! The bed is a double so you would be sharing (and consensually snuggling)
If your double is family, friends, romantic partners - all pairs are perfect! Please remember on Stellavision tours we welcome self-identifying women and non-binary folks who are comfortable in female spaces.
Travel Style
What can you expect from a Stellavision Tour? From journeying with a professional photographer to our travel values, find out how we do Italy:
Booking Terms & Conditions
All the fine - and not so fine -
print can be found here:
