A 5-Star Summer Roadtrip: How to Spend 5 Days in Sicily
LAST UPDATED: FEBRUARY 18, 2025 | TRAVEL DATES: JULY 2024 | EST. READING TIME: 10 MIN
IN THIS GUIDE ✺
Wondering how to see the top sites in Sicily while indulging in this luxurious destination?
A quick flight over from the mainland, Sicily is a common island getaway visited for a dose of relaxing beach time during an Italian summer adventure. A less common European destination, this autonomous region is particularly well-suited for indulgence. With 5 days in Sicily, where to stay becomes a simple question, as ritzy 5-star resorts and Michelin meals are significantly cheaper here than in more prominent cities like Rome, making this the perfect place to splurge! With a host of quaint seaside towns dotting the coast, cruise around the island at your leisure while embracing the finer things in life.
From lounging on king-sized day beds under the Sicilian sun to devouring gourmet interpretations of the land’s native proposals, this carefully curated 5-star roadtrip hits the top resorts in each town while ensuring sumptuous leisure is the top priority each day.
How to Spend 5 Days in Sicily
In a hurry? Here’s a brief overview of the detailed what to do in Sicily for 5 days itinerary exploring the top three seaside towns you’ll find below:
Days 1-2: Cefalu
Days 3-4: Taormina
Day 5: Ortigia Island
Day 1: Land in Palermo - Your Roadtrip Begins!
LEARN MORE WITH A DETAILED TRAVEL GUIDE: 2 Days in Cefalu Itinerary
Assuming you’re traveling to Sicily by air—and not the train and ferry combo which takes at least 8.5 hours—you’re best suited to fly into the Palermo Airport. While this isn’t the biggest airport in Sicily, it’s closer to the northern town of Cefalu where your 5-star summer roadtrip begins. After traveling along the coast down the east side of the island by car, you’ll depart from the Catania Airport, which is the main international airport on Sicily!
Direct flights aren’t possible from the Americas, so account for at least 1 layover. Aim to touch down in Palermo during the late morning to make the most of your first day. If no such flight routes exist from your point of departure, consider spending at least 1 day in the connecting city—I spent 2 days in Paris before flying to Palermo.
Driving is the easiest, most efficient way to get around the island. At home and abroad, I’ve had the most seamless rental car experience with Sixt—each time their process has been a complete breeze, with the entire exchange lasting no more than 5 minutes. There are Sixt locations at both airports, so you’ll have a convenient way to pick-up and drop-off your rental vehicle.
Since this isn’t a given in Sicily, book an automatic vehicle if you can’t drive a manual stick-shift. The route to Cefalu from the Palermo Airport entails a 1 hr 20 minute drive along the easily navigable E90 highway.
For a truly lavish 5-star experience, Le Calette is the top stay in Cefalu. Tucked within the Caldura bay, this boutique resort charms with Mediterranean architecture in harmony with the natural landscape. Select between the terraced suites, rooms, or villas of Le Calette N°5 and 4-star Le Calette Bay. Both accommodation types are housed within the larger complex entailing restaurants overlooking the sea, bars, a beach club, and wellness areas like the spa and gym.
Check in after 2:00 PM and drop off your luggage, then head to the informal Calette Reef for an afternoon bite. This contemporary sea bistro underneath rattan fixtures serves Mediterranean dishes elevated by lush tropical scenery and spunky couch seating.
After filling up on fresh seafood, head directly down the restaurant steps to the Calette Reef Club. Overlooking a private turquoise inlet, there’s plenty of room to relax on the teak solarium full of luxurious king-sized sun beds with bar service. Sip a refreshing Aperol Spritz the Italian way.
To become one with the crystal-clear waters, book a rejuvenating Thai massage on a sea-view futon, glide on complimentary canoes and stand up paddle boards, or plunge in for an invigorating snorkel session.
Switch up your scenery with a dip in the panoramic pool as the sun sets, rinsing off any salty ocean residue before returning to the room to get ready for dinner.
You don’t have to go far for fine Michelin Guide dining, as Cala Luna is hosted on the property lawn with a view of the Via Presidiana port below. Inspired by traditional Sicilian recipes, the lively proposal is based on the territory’s naturally colorful cuisine. Great technique refines each simple ingredient, which can be tasted from a 5-course menu for €115, 7-course offering for €140, or an à la carte list.
Day 2: Cefalu - Le Calette Lounging
Begin your second day in Cefalu indulging in the complimentary breakfast spread, including sliced fruits, fresh squeezed juices, and local spreads. The undeniable highlight is a range of baked Sicilian goodies including pies, tarts, and cannoli.
Once sufficiently fueled, climb the massive limestone mogote from which the city took its name, derived from the Greek word “kephale” meaning head. La Rocca is 885 feet high and requires moderate trekking to climb, with the entire 2.1-mile out-and-back trail taking 1.5-2 hours to ascend, explore the top, and return to sea level.
Reward yourself after an active morning by lounging at Calette Beach, the resort’s soft sand club reachable via a complimentary shuttle service. Wade in the calm waters with views of La Rocca in the distance before lying down to tan on the front row chairs reserved for hotel guests.
Return to the room to freshen up, then walk through the streets of Cefalu’s historic center before dinner to discover cultural landmarks. The 12th-century Arab-Norman Duomo di Cefalu is a UNESCO World Heritage Site with a variety of paid tours offered, including one which ascends the cathedral towers up to a rooftop walkway with panoramic coastal views.
Catch the sunset from the jetty overlooking Molo di Cefalu to witness a golden hue wash over the coastal town behind the last swimmers splashing about in the sea.
Another Michelin Guide special, Cortile Pepe experiments with authentic Sicilian cuisine by enhancing the seasonal flavors of the land and sea, incorporating fresh produce straight from their organic garden. Feast under the dining room’s vaulted wine cellar ceiling or in the fading light of an attractive outdoor space.
Day 3: Cefalu to Taormina - Corso Umberto
LEARN MORE WITH A DETAILED TRAVEL GUIDE: 2 Days in Taormina Itinerary
Wake up bright and early to embark on the 2 hour 22 minute drive along the coast from Cefalu to Taormina. In regards to upscale accommodations, the NH Collection Taormina is a posh 5-star experience located minutes from every main attraction, yet it’s still 3x cheaper than the White Lotus San Domenico hotel!
Given the small size of Taormina, there’s no need to rush and cram in all the famous sites. While the entirety of town could easily be covered in an hour, instead embrace the ‘dolce far niente’ Italian philosophy after checking in—or the sweetness of doing nothing—by leisurely strolling down Corso Umberto I.
Eat, drink, shop, and be merry in this choose-your-own-adventure experience, popping in the stores and wine bars along the bustling main street that call to you. Nino and Friends offers free samples of exclusively Italian products like limoncello and truffles, while Le Bar Louis Vuitton hides behind the designer window with an elevated apéritif terrace overlooking the Mediterranean.
Piazza IX Aprile is the first square to be discovered, offering the best coastal views of Mount Etna flanked by the Torre dell'Orologio medieval clock tower and Baroque Church of San Giuseppe. Piazza Duomo comes next, home to an ornate fountain adorned with a 16th century stone lion. Don’t miss the San Domenico Palace Hotel steps away where season 2 of The White Lotus was filmed!
Enjoy a cool refreshing treat at the end of this stroll from Levante Gelato Artigianale. Serving up gelato, granita, and small pastries like cannoli handcrafted daily, be sure to add a scoop of freshly whipped cream on top of any order!
Finish today’s retail therapy by exploring fine Sicilian craftsmanship. Il Sandalo Caprese meticulously prepares the same leather sandals Emperor Tiberius wore when he arrived in Capri, custom made on the spot to your exact specifications. Managó Ceramiche Siciliane sells hand-painted ceramics with vividly intricate designs including Moorish head planters and local pine cone motifs.
Before dinner, stimulate your appetite with an apéritif from streetside wine bar Enoteca. Peruse an array of Sicilian wines by the glass while people watching as you sip your chalice to partake in this European social ritual.
Dine al fresco at Michelin Guide Vineria Modì to observe traditional quartet performances adding melodic ambiance to your evening. Previously an alleyway wine bar, this historic haunt boasts over 1,000 exclusive labels with a sommelier on site! An irresistibly charming culinary experience, enjoy elaborate fare from the €80 à la carte offering including 2 dishes plus dessert in the elegant dining room or outside on the pedestrian street.
Day 4: Taormina - Ancient Exploration
Start the next morning at Bam Bar, the #1 place in Taormina you can’t miss, famous for their sweet combination of granita with a warm brioche bun. Granita is a traditional Sicilian frozen dessert made from sugar, water, and flavorings like fruit juices or purees before being topped with sweet cream!
The Teatro Antico di Taormina 5 minutes away is an ancient theater dating back to the 3rd century BC. The construction is one of the best preserved Greek theaters in the world, showcasing blended Greek theatrical design with Roman engineering.
Villa Comunale di Taormina nearby is a lush 19th century garden commissioned by Lady Florence Trevelyan for her private estate. Manicured English and Mediterranean gardens comprising 87 plots of land were converted into the historic public park you’ll find today, complete with smattering of whimsical pavilions known as follies.
For lunch, visit the best street food shop in Taormina to try arancini. This traditional Sicilian dish consisting of stuffed rice balls is coated with breadcrumbs and deep-fried to a golden, crispy perfection inside Rosticceria Da Cristina 2, one of two popular sister restaurants that typically have a line at the counter.
Another day in Sicily means another opportunity to eat gelato. For dessert, find Gelatomania on Corso Umberto I, allowing you to taste up to 3 of your favorite Sicilian flavors for quite a reasonable price—only €5 for the largest cup and €6 for the largest cone!
Experience breezy seaside bliss by taking the cable car down to Isola Bella in the afternoon. This small island connected to the mainland by a narrow strip of sand is part of a protected marine reserve and can be accessed via a short walk during low tide or by boat. The surrounding water is teeming with marine life, making it a popular spot for snorkeling and diving.
For your final night in Taormina, embark on a culinary journey at the flagship restaurant of the gorgeous Grand Hotel Timeo, Ristorante Timeo, where you’ll be treated to scenic views of the town’s dramatic vistas. This striking location is complemented by a superb menu of locally-sourced Sicilian favorites with a tableside steak cutting service.
Day 5: Taormina to Ortigia - Minareto Magic
LEARN MORE WITH A DETAILED TRAVEL GUIDE: 1 Day in Syracuse Itinerary
Complete the final leg of this roadtrip around the Sicilian coast, cruising for 1 hour and 45 minutes from Taormina to the Minareto Siracusa just outside Ortigia Island. A place where luxury is a state of mind, the Minareto stands out on the international resort scene for the uniqueness of its proposal, offering an experience dedicated to all-round wellbeing.
After checking in, begin a day of utter relaxation on an embrace amongst water, earth, and sky: the multi-level rocky solarium. This private cliff—surrounded by crystal-clear waters in which to dive—offers a panoramic view of Ortigia Island across the way while calming with the soothing sound of waves and sea breeze.
After lounging around, pop into Nesos for lunch to taste native flavors, aromas, and colors which have made this island famous throughout the world. Depending on the conditions, enjoy your food on a sunny outdoor terrace overlooking the bay or inside the large informal dining hall.
Head to the enchanting Baia delle Latomie for a more traditional sand scene equipped with the same comfortable loungers and umbrellas as the solarium. For more adventurous types, SUP paddle boards are available to rent, or go all in on relaxation by reserving floating lounge chairs—which can be further elevated with a massage service added on top.
Return to homeostasis with a dip in the panoramic jacuzzi terrace. This always open wooden deck offers a romantic couple’s moment or relaxing reprieve in the two tubs accommodating four guests each—embellish the experience with a 1-hour champagne and bubbles reservation for your exclusive use.
Brave the waves once more by boarding the love boat from the rocky solarium. Pop an excellent bottle of local Prosecco while cruising along the coast of the Syracuse bay for an hour. A plate of freshly prepared, gourmet Sicilian bites like arancini is also provided on the covered speedboat fitted with comfortable cushions.
Cap off your last day in Sicily by watching evening descend from the panoramic sea view terrace overlooking Ortigia. Pair this mesmerizing sunset with an excellent apéritif in good company! The lounge becomes populated with servers during dusk, so you can place your drink order directly from a comfortable couch!
Depart from the main property in the evening to discover prestigious Area M on nearby Ortigia Island, a sister restaurant associated with the Minareto. Paying homage to its harbor location, find a menu stocked full of fresh seafood dishes rooted in Sicilian tradition yet infused with contemporary international influence.
Day 6: Fly Home From Catania
At long last, it’s time to return your rental vehicle to the Catania Airport and fly home. Plan to depart from Syracuse the next morning with a 55 minute drive representing the final trek to the eastern airport, thus concluding your 5 splendid days in Sicily.
How Much Does a 5 Day Trip to Sicily Cost?
Following the above what to see in Sicily in 5 days itinerary cost me $3,324.23 overall as a 20-something on a couples trip, omitting flight costs. Given this Sicilian summer roadtrip was full of Michelin Guide meals and only the finest 5-star hotels, I found my overall expenses to be quite reasonable for an all out luxury extravaganza—and certainly cheaper than a similarly fancy trip on the mainland!
I spent the most in Taormina at $1,230.61, which can be largely chalked up to the abundant artisan souvenirs I purchased along Corso Umberto I. Two days in Cefalu cost me $1,196.82, with our accommodations being the largest expense by far. However, this expense also included two all-you-can-eat brunch spreads, transportation, and water sport rentals at luxurious beach clubs. The single day I enjoyed at the Minareto outside Syracuse only cost me $896.80, with the love boat excursion being the one significant cost outside of the resort itself.
Many of the native delicacies across Sicily like arancini and granita are extremely cheap, with this street food and similar meals in casual eateries never exceeding a few euros. When traveling on a budget, prioritize those dishes rather than indulging in the gourmet culinary scene percolating around the island. Cutting out any Michelin Guide recommendations from above would help manage expenses as well.
Is 5 Days in Sicily Enough?
While no time abroad is ever enough, 5 days is a satisfactory amount of time to explore the top three seaside towns in northeast Sicily. Given the small size of these coastal stops, there’s no need to spend more than a day or two in each destination before moving along to the next. From the serene beach clubs of luxurious Sicilian retreats to gourmet culinary experiences, this itinerary delivers the perfect dose of summer indulgence.
If you have a few more days to spare, consider stopping in Palermo after your flight over before continuing along to Cefalu. The primary intent of each day described above is to relax under the sizzling sun, so without much action added in along the way I wouldn’t recommend spending more than a week in Sicily.
While this 5-star itinerary is packed with timeless stays and the best bites, it's flexible enough to adapt to varying budgets. Food connoisseurs prioritizing Michelin meals can save on less expensive stays, while resort enthusiasts can cut back on food costs with affordable Sicilian street fare to curate their own perfect adventure.
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