Italy
Rome · Florence · Tuscany
There is a reason Italy has been the world's most romantic destination for centuries. It is the kind of place that makes you slow down without even trying. Where a glass of wine at dusk becomes a two-hour conversation. Where the food is an event, the architecture is art, and the streets were practically designed for wandering hand in hand.
I have been to all three destinations in this guide and I can tell you that Italy done right is one of the most unforgettable trips in the world. Here is everything you need to know.
Rome
Ancient, electric, and endlessly romantic
Rome is not just a city, it is two thousand years of civilization compressed into one place, and somehow it still feels completely alive. Ancient ruins sit next to espresso bars. Baroque fountains anchor neighborhood piazzas. The Colosseum is right there, in the middle of everything.
Rome delivers a specific kind of magic. There is romance in the chaos here, in the warmth of the people, in the ritual of the aperitif hour and the late dinner and the walk home through cobblestone streets at midnight.
What to do
The Pantheon and Fontana di Trevi
Start with the Pantheon, use the cash line for faster entry. The Fontana di Trevi is best visited early morning or late at night when it is illuminated and the crowds have gone home. One of the most beautiful things I have seen in any city.
The Colosseum, Palatine Hill and Roman Forum
Book a guided tour covering all three, early morning is essential for cooler temperatures and manageable crowds. Standing inside the Colosseum imagining what took place there is one of those genuinely humbling travel experiences.
Vatican City
Book the first available tour slot. The Vatican Museums, Raphael Rooms and Sistine Chapel reward early arrivals enormously. Michelangelo's ceiling is one of those things that photographs do not prepare you for.
Castel Sant'Angelo
Just across the Tiber from the Vatican, this fortress offers stunning views over Rome and the river. An underrated stop that most visitors skip entirely, do not make that mistake.
Trastevere
For a slower, more residential side of Rome. Cobblestone streets, local cafés, the beautiful Santa Maria in Trastevere church, and fresh produce markets. Find a table in Piazza Santa Maria as the day winds down and watch the neighborhood come alive.
Roman nightlife
Argot is a hidden speakeasy known for creative cocktails in an intimate setting. Jerry Thomas Speakeasy for Prohibition-era charm, book a reservation and get the password. The Eating Europe food tours are exceptional for experiencing the culinary culture of the city at night.
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.
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.