Sicily
Palermo · Cefalù · Taormina · Siracusa
Sicily is the kind of destination that stops you in your tracks the moment you arrive. The largest island in the Mediterranean sits at the crossroads of every civilization that ever passed through: Greek temples, Arab architecture, Norman mosaics, and baroque town squares all layered together in the most extraordinary way.
We flew into Palermo and out of Catania, rented a car, and drove across the island. That road trip through Sicily was one of the best travel decisions we have ever made. Here is everything you need to know.
Palermo
Vibrant, layered and completely its own
Palermo is one of Sicily's main gateways and it deserves more time than most travelers give it. The city is layered with centuries of Arab, Norman and Baroque influence and it wears all of it openly — in the architecture, in the markets, in the food, in the energy of the streets at night.
What to do
Via Maqueda
Essential at night. Lined with restaurants, full of people and life. Grab a seat, order whatever looks good and spend an hour watching Palermo do what it does best.
Palatine Chapel
The Byzantine gold mosaics covering every surface are among the most beautiful things I have seen in Sicily. Worth a visit without question.
Teatro Massimo
One of the largest opera houses in Europe and a stunning piece of architecture. Worth seeing from the outside even if you do not go in.
Dining in Palermo
Taverna dei Canti for outstanding seafood. Maccio Osteria Alcolica for authentic Sicilian cuisine with a modern twist. Mak Mixology for expertly crafted cocktails and a lively night out.
Where to Stay?
Hotel Indigo Rome - St. George
Preferred partner
Sleek luxury boutique hotel on a quaint cobblestone street with a rooftop terrace and full-service spa.
Hotel Chapter Rome
Preferred partner
A stylish boutique retreat blending vintage charm with modern design in the heart of the city.
Insider tip
Stay just west of the Pantheon. You are eight minutes from every major attraction and completely removed from the tourist noise. That neighborhood is where Rome actually lives.
Insider tip
Stay just west of the Pantheon. You are eight minutes from every major attraction and completely removed from the tourist noise. That neighborhood is where Rome actually lives.
Listed hotels are preferred partners, meaning Elavated Travel clients may enjoy benefits such as complimentary breakfast, upgrades when available, hotel credits, and VIP treatment.
Florence
Art, history, and the most beautiful food in Italy
Florence is compact, walkable, and one of the most artistically rich cities in the world. The Duomo dominates the skyline. Michelangelo's David is here. The Uffizi Gallery holds one of the greatest collections of Renaissance art anywhere on earth. And yet Florence never feels like a museum it feels like a city where people actually live.
The key to Florence is to get out early. Most of the major attractions reward early arrivals enormously and the streets in the morning before the crowds arrive are magical.
What to do
The Duomo
Pre-buy tickets for the Duomo climb, the interior is free but the climb to the top of Brunelleschi's dome is the real experience. The mural inside the cupola is unlike anything you will see anywhere else, and the views over Florence from the top are unforgettable.
Michelangelo's David at the Accademia Gallery
Book the 8:15am slot and go straight to the David. Seeing it before the crowds arrive is genuinely moving. The scale of it, the detail of it, the impossibility of it existing at all — it stops you completely. Worth planning your entire morning around.
The Uffizi Gallery
One of the most important art museums in the world. Botticelli, Michelangelo, Leonardo da Vinci, Raphael. Pre-purchase tickets and plan to spend at least an hour inside. Accademia in the morning, Uffizi in the afternoon; one of the great cultural days of any trip to Italy.
Ponte Vecchio and Piazzale Michelangelo
Walk across the medieval stone arch bridge lined with jewelers and linger on it. Then take a cab up to Piazzale Michelangelo for the panoramic views over Florence the Duomo in the center, the Tuscan hills behind it. Go at sunset.
Dining and drinks
Il Locale is one of the top bars in the world. FirstGlass Wine in front of Ponte Vecchio for wine tasting and perfect people watching. La Buchetta Food and Wine for dinner.
Where to Stay?
Hotel Calimala
Preferred partner
Historic meets glamorous with unparalleled service and an exclusive rooftop restaurant with views over the entire city.
Four Seasons Hotel Florence
Preferred partner
A 15th century palazzo with a private 11-acre garden in the heart of Florence — one of the most magnificent hotel settings in the world.
Listed hotels are preferred partners, meaning Elavated Travel clients may enjoy benefits such as complimentary breakfast, upgrades when available, hotel credits, and VIP treatment.
Hotel Continentale
Preferred partner
Chic contemporary design with stunning Arno River views — a stylish base for exploring all of Florence.
Tuscany
Rolling hills, vineyard sunsets, and the most extraordinary hotel
If Rome is the head of Italy and Florence is its heart, Tuscany is the soul. Rolling hills covered in vineyards and olive groves. Cypress-lined roads leading to medieval hilltop villages. Sunsets that look like Renaissance paintings.
Tuscany is not about sightseeing, it is about being somewhere so beautiful that you stop thinking about what to do next and simply exist in it. It is the destination that takes an Italy trip from great to unforgettable.
What to do
Castello di Casole — the highlight of the entire trip
The cypress-lined driveway sets the tone the moment you arrive. The property sits on a 4,200-acre estate in the Tuscan hills and has been here since the 10th century. The grounds are extraordinary especially in late spring when the flowers are in full bloom. The pool has rolling views of the Tuscan hills that make every other pool view feel slightly insufficient.
E-biking through the Tuscan countryside
The property has extensive hiking and biking trails. We rented electric bikes and spent a morning exploring the hills — the electric support makes the terrain effortless and the scenery is extraordinary. A visit to Mensano, the nearby medieval village, is worth the short trip for authentic Tuscan atmosphere with almost no tourists.
The Essere Spa
The hot tub, steam room, sauna and relaxation room are worth building an afternoon around. On our last day we chose the spa over a trip to Siena and it was absolutely the right call.
Sunsets and evenings at Bar Visconti
Do not miss the sunsets from the hotel terrace. With an aperitif in hand watching the sun go down over the Tuscan hills is one of those travel moments that you will spend the rest of your life trying to recreate. Bar Visconti often features a gentle musical duo in the evenings — an atmosphere you could not manufacture if you tried.
Where to Stay?
Castello di Casole, A Belmond Hotel
Preferred partner
A majestic 10th-century Tuscan estate on 4,200 acres. This is the property I recommend above every other in Italy — there is nothing else quite like it. $100 food and beverage credit, breakfast daily, and upgrades through Elavated Travel.
Listed hotels are preferred partners, meaning Elavated Travel clients may enjoy benefits such as complimentary breakfast, upgrades when available, hotel credits, and VIP treatment.