Day 1: Rome

Since there aren’t direct flights to Sicily from the US, break up your trip with a night in Rome.

Hotel de Russie

From the chic suites and lush secret-garden courtyard where you can enjoy an aperitivo to the impeccable service and prime location (right by the Spanish Steps and Villa Borghese), this is the classic.

Photos courtesy of Hotel de Russie

After-Hours Vatican Tour

This VIP tour is beyond worth it. You’re escorted by two knowledgeable guards to view both the museum and the Sistine Chapel—alone.

La Terrazza

This decadent Michelin-starred spot on top of the Hotel Eden has stunning 360-degree views of the city. Come for the mouthwatering veal-broth ravioli with horseradish and stay for the epic sunset.

Da Enzo al 29

If you love a no-frills, wait-in-line-for-two-hours kind of restaurant magic, don’t miss this one. I dream about the rigatoni.

Days 2–4: Sciacca, Agrigento, and Menfi

Verdura Resort

About an hour outside the capital city of Palermo, Verdura is a sweet oceanfront respite set among acres of olive and orange groves. It’s perfectly located in Sciacca to make day trips—to Agrigento, Menfi, and more—super convenient and easy. And the Irene Forte spa is stunning: The outdoor thalassotherapy pool cured the last of my jet lag.

1. Sicily Is Sunny—Bring Provisions

   Resign yourself to going through a lot of sunscreen; I packed my favorites in full sizes.

2. For Face

   

   Saint Jane
   Luxury Sun Ritual Pore Smoothing SPF 30
   goop, $38

   SHOP NOW

3. For Body

   

   Dr. Dennis Gross
   Lightweight Wrinkle Defense SPF 30
   goop, $42

   SHOP NOW

4. For Hair

   

   Supergoop
   Poof 100% Mineral Part Powder SPF 35
   goop, $34

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5. For Hands

   

   UnSun
   Hand Cream SPF 15
   goop, $27

   SHOP NOW

Valley of the Temples

In Agrigento, the stunning, pristinely preserved examples of Doric architecture at the Valley of the Temples have been a UNESCO World Heritage Site since 1997. The Temple of Concordia (built in the fifth century) and Temple of Heracles are especially fantastic.

Walking Tour of Sciacca

Quaint and filled with shops selling local fabrics and ceramics, Sciacca’s city center is amazing for shopping. Oro di Sciacca, a beautiful family-run jeweler, makes jaw-dropping pieces from gold and locally sourced coral.

Cooking Class with Fulvio Pierangelini at Verdura Resort

Verdura Società Agricola, Verdura’s sprawling organic farm, supplies the entire resort. First harvest your own herbs in the picturesque fields, then learn to make red prawn salad with fresh string beans and oranges, a delicious Bolognese, and more.

Ristorante da Vittorio

For the freshest seafood you’ve ever tasted, stop at this seaside spot on the way to Agrigento (the view is sensational whether you sit indoors or out). Get the pasta alla Vittorio with shrimp, mussels, clams, and calamari.

Planeta Ulmo Winery

Forty-five minutes by car from Verdura near the smaller town of Menfi, Planeta Ulmo is a family-owned vineyard, winery, restaurant, and outdoor viticulture museum. The wine tasting and lunch alfresco—we tried five wines and ate charcuterie, olives, a Sicilian pasta cake, and fresh bread with the winery’s own homemade olive oil—is just incredible.

Cocciu di Luna

This restaurant is the best place to have a drink (I loved the Sicilian Spritz, with grapefruit seltzer, orange peel, and St-Germain) because of its spectacular view of Castello dei Luna, a medieval castle in Sciacca.

1. What to Pack

   You walk everywhere, so pack to look chic (and feel comfortable) doing it.



Crown Affair
The Mini Shampoo, Conditioner, and Oil Set
goop, $60

This three-step routine gives me the silkiest, softest hair with the best-ever texture—a guaranteed great hair day, even on vacation.

SHOP NOW



Tata Harper
Vitamin-Infused Cream Blush in Lovely
goop, $45

This dusty-pink cream works—and looks so good—on lips and cheeks. I just love it.

SHOP NOW



Natalie Martin
Jasmine Maxidress with Sash
goop, $388

This flowy 100 percent silk maxidress took me from exploring temples to aperitivos at dusk.

SHOP NOW



Birkenstock Arizona
Big Buckle
goop, $160

I lived in these Birkenstocks: easy and so comfortable.

SHOP NOW



Tower 28
Beauty SunnyDays SPF 30 Tinted Sunscreen Foundation
goop, $32

The most flattering barely-there makeup coverage and SPF in one.

SHOP NOW



goop Beauty
GOOPGLOW Microderm Instant Glow Exfoliator, 15 mL
goop, $42

My holy grail for sloughing all the travel dirt, sweat, and grime away.

SHOP NOW

Days 5–7: Palermo

Villa Igiea

At the foot of Mount Pellegrino and facing the Gulf of Palermo, this 13th-century palazzo was a long-ago hot spot for royalty and film stars and later renovated and restored to its former grandeur by hotelier Rocco Forte in 2021. It’s absolutely gorgeous and perfectly balances history—the Sala Basile reception room is wall-to-wall with Art Nouveau frescoes by Ettore De Maria Bergler—with a sleek, modern sensibility.

Photos courtesy of Villa Igiea

Teatro Massimo

The beauty of this grand opera house (it’s the biggest in Italy) has to be experienced, whether you’re in it for the excellent acoustics (the performances are legendary) or you just want to marvel at the gorgeousness.

Quattro Canti

This Baroque town square dates to the early 1600s, with ornate fountains made to represent each season and statues of the Spanish kings of Sicily and the patron saints of Palermo etched into the walls.

Cappella Palatina

One of the most well-preserved examples of Byzantine art and architecture, the Cappella Palatina was built in 1140. The walls are covered in colorful mosaics, precious stones, and gold.

Cattedrale di Palermo

Constructed in 1185, this grand cathedral has been renovated and restored by different religious groups over hundreds of years, leaving it with a unique mix of Norman Romanesque, Gothic, Moorish, and Neoclassical architecture, along with religious relics and precious objects—including, most notably, the tiara of Constance of Aragon.

Capo Market

There’s no better way to experience the deliciousness of Sicilian street food than this open-air market. I loved the just-fried arancini and the sfincione (a sort of Sicilian pizza) and searching for the perfect cannoli, which turned out to be even more delicious than I imagined.

Trattoria Altri Tempi

Furtuna Skin founder and COO Agatha Relota Luczo, a Sicily transplant, recommended this amazing spot—the place is crowded with locals who come for the outstanding pastas and fish.

Days 8–10: Taormina

Villa Sant’Andrea

Serene, enchanting, and glamorous, the Villa Sant’Andrea manages to feel both grand and intimate at once. Soft neutral tones offset charming 19th-century marble staircases and Baroque paintings throughout. Set directly on the white-pebbled beach, it’s pretty much paradise.

Photo courtesy of Belmond Villa Sant’Andrea

Corso Umberto

Between the two gates of the city—Porta Messina and Porta Catania—this walkable street has tons of charming stores, pastry shops, cafés, and more to explore.

Mount Etna

The active volcano is part of almost every view in Sicily; it’s also famous for hiking. The Alcantara Gorge, carved out by ancient lava flows, is spectacular; so is Valle del Bove, a horseshoe-shaped valley that protects the populated areas from future eruptions.

Teatro Antico di Taormina

This ancient Greek theater is set directly on the sea—it’s hard to overstate how beautiful it is.

Principe Cerami

This Michelin-starred spot in the San Domenico Palace (hello, White Lotus, season 2) serves quail with green asparagus and black truffle, risotto with anchovies, and more deliciousness, all from chef Massimo Mantarro. It has a breathtaking view of Taormina Bay.

Morgana

With staff in hot-pink patterned blazers and the sofas in plush orange velvet, this wildly entertaining cocktail bar—the people-watching is next-level—is a great spot for a drink (or two).