italy
It all begins with an idea.
as someone who studied abroad in Rome, I get it — planning a trip to Italy can feel like a full-time job. Between the Amalfi Coast, Tuscany, Rome, Florence, Milan, Lake Como, Sicily, Sardinia, the Dolomites (deep breath)... it's overwhelming. i’m going to do my best to help you navigate the most iconic cities, pick the right hotels, find the best food, and map out the perfect 10-day itinerary for you. think of it as the ultimate Italian Choose Your Own Adventure.
rome
Rome is chaotic, romantic, historic, and electric — and a perfect place to start.
Where to stay
W Rome — Ludovisi — $$$ — Trendy, buzzy, rooftop vibes. Young, cool crowd and a killer rooftop bar.
Donna Camilla Savelli — Trastevere — $$ — Historic monastery turned boutique hotel. Quiet, romantic, walkable to everything.
Hotel de Russie — Near Piazza del Popolo — $$$$ — Classic luxury. Lush garden, spa, and great for celeb spotting.
The Hoxton — Parioli — $$ — Hip, modern, local feel. Great cafe and interiors, away from tourist zones.
Residenza Napoleone III — Centro Storico — $$$$ — Lavish and regal. Feel like royalty in a 16th-century palazzo.
Chapter Roma — Regola — $$ — Edgy, design-focused. Artsy and youthful in a central location.
Where to eat
Roscioli ($$) — Iconic Roman deli meets restaurant; cacio e pepe heaven.
Da Enzo al 29 ($) — Cozy, classic Trastevere trattoria.
Pierluigi ($$$) — Elegant seafood spot with a gorgeous piazza.
Taverna Trilussa ($$) — Pasta served in pans. Enough said.
Pizzarium Bonci ($) — Cult-favorite pizza by the slice.
tip! Seek out Aperitivo hours. Many Roman bars offer free small bites — chips, olives, bruschetta, or mini sandwiches — with the purchase of a glass of wine or cocktail. Head to Trastevere or Monti for local favorites like Bar del Cinque or Freni e Frizioni around 6–8 p.m.
florence
Florence is Rome’s more polished, artsy younger sister — a little smaller, a little sweeter, and always dressed to impress. Just a quick train ride away and the gateway to Tuscany, Florence is full of art, romance, and Renaissance magic.
Where to stay
Portrait Firenze — Arno River — $$$$ — Ultra-luxury, design-forward. Run by Ferragamo family, stunning views.
Hotel Brunelleschi — Historic Center — $$$ — Classic meets modern. Views of the Duomo and great breakfast.
Velona's Jungle Luxury Suites — Santa Maria Novella — $$ — Quirky boutique B&B. Maximalist and fun interiors.
Hotel Calimala — Centro Storico — $$ — Cool and contemporary. Rooftop terrace is a must.
AdAstra — Oltrarno — $$ — Chic guesthouse with gardens. Feels like a local hideaway.
Where to eat
Osteria Vini e Vecchi Sapori ($) — Small, traditional, family-run. Cash only.
Trattoria Cammillo ($$) — Old-school favorite, especially for bistecca.
Il Santo Bevitore ($$) — Stylish but unfussy Tuscan food.
La Giostra ($$$) — Romantic and theatrical; great for a special night.
All'Antico Vinaio ($) — Iconic paninis that are worth the hype.
tip! The panini battle is real. Florence is home to two legendary sandwich shops: All'Antico Vinaio, known for its overflowing schiacciata sandwiches (prepare for a wait), and SandwiChic, a slightly lesser-known gem with quality ingredients and quicker service. Honorable mention: Antico Noè, a cult-favorite tucked under an archway — the kind of local panino stop that turns into a craving long after you’ve left. Try them all and pick your winner.
tuscany
Rome is chaotic, romantic, historic, and electric — and a perfect place to start.
Where to stay
Hotel Castelfalfi — Montaione — $$$ — Resort-style, vineyard escape. Golf course, spa, winery — it’s a Tuscan dream.
Borgo Santo Pietro — Chiusdino — $$$$ — Romantic countryside luxury. Organic farm, world-class spa, and elegance.
Villa Cora — Near Florence — $$$ — Baroque villa luxury. Lavish interiors, pool, views of the city.
Locanda Rossa — Maremma — $$ — Boutique farm-chic. Hidden gem with a cozy vibe.
Where to eat
La Rocca di Castelfalfi ($$) — Elegant Tuscan fine dining with vineyard views.
Osteria di Passignano ($$$) — Michelin-starred with Chianti wines.
Dario Cecchini's Officina della Bistecca ($$) — Famous butcher, unforgettable meat experience.
Il Falconiere ($$$) — Refined flavors in Cortona’s countryside.
Trattoria Omero ($$) — Classic Tuscan with a view near Florence.
amalfi coast
if you choose to go south after Rome, enter: the Amalfi Coast. Dramatic cliffs, turquoise seas, and citrus everywhere and in every form.
Where to stay
Le Sirenuse — Positano — $$$$ — Iconic, elegant, cinematic. The Amalfi Coast fantasy come to life.
Hotel Marincanto — Positano — $$ — Romantic, great value. Amazing views, walking distance to everything.
Casa Angelina — Praiano — $$$ — Sleek and minimal. Peaceful and refined with killer sunsets.
Monastero Santa Rosa — Conca dei Marini — $$$$ — Cliffside spa retreat. Former convent turned wellness oasis.
Palazzo Avino — Ravello — $$$$ — Historic pink palace. Intimate and luxurious above it all.
Where to eat
La Sponda ($$$$) — Candlelit magic at Le Sirenuse.
Chez Black ($$) — Classic Positano beachfront trattoria.
Il Pirata ($$) — Cliffside seafood with local charm in Praiano.
Ristorante Max ($$$) — Art gallery meets fine dining.
Da Adolfo ($) — Beach shack bliss only accessible by boat.
lake como
Where to stay
Mandarin Oriental Lake Como — Blevio — $$$$ — Jaw-dropping setting, lakeside spa, and polished luxury.
Hotel du Lac — Bellagio — $$ — Classic and charming with views that don’t break the bank.
Grand Hotel Tremezzo — Tremezzo — $$$$ — Lavish, iconic, and colorful with a floating pool on the lake.
Il Sereno — Torno — $$$$ — Sleek, modern design with private boat access and stunning views.
Hotel Belvedere — Bellagio — $$$ — Family-run charm with a quiet atmosphere and panoramic views.
Palace Hotel — Como Town — $$ — More accessible, centrally located option for exploring the town.
Where to eat
Giardino dei Sogni at Grand Hotel Tremezzo ($$$) — Worth a stop if you don’t stay here, romantic and scenic with garden-to-table fare.
Locanda La Tirlindana ($$) — A hidden gem right on the water in Sala Comacina with unbeatable lake views.
Ristorante Mistral at Villa Serbelloni ($$$$) — Michelin-starred with refined cuisine and jaw-dropping views.
Ristorante La Punta ($$) — Laid-back seafood and pasta spot with a beautiful terrace in Bellagio.
Materia ($$$) — Modern fine dining in Cernobbio from a young Michelin-starred chef.
Il Gatto Nero ($$$) — Clooney-approved and wildly romantic, perched in the hills of Cernobbio with elegant, old-school service and unbeatable views.
tip! Consider Lake Garda for a quieter, just-as-beautiful experience. While Lake Como gets all the love, Lake Garda is larger, less touristy, and perfect for relaxed lakefront stays. Check out Hotel Bellevue San Lorenzo in Malcesine — an adults-only retreat with unbeatable views and old-world charm.
Suggested 10-Day Itineraries
Itinerary 1: Classic Romance
Rome → Florence → Lake Como
Rome: Stay at Chapter Roma, dine at Roscioli
Florence: Stay at Hotel Calimala, dine at Cammillo
Lake Como: Stay at Mandarin Oriental ($$$$) or Hotel du Lac in Bellagio ($$), dine at Giardino dei Sogni at Grand Hotel Tremezzo ($$$)
Itinerary 2: Coastal Dream
Florence → Amalfi Coast → Sicily
Florence: Stay at Velona's Jungle, dine at Santo Bevitore
Amalfi Coast: Stay at Hotel Marincanto in Positano ($$), dine at La Sponda ($$$$)
Sicily: Stay at Belmond Grand Hotel Timeo ($$$$), dine at Ristorante Locanda Don Serafino ($$$)
Itinerary 3: Countryside Escape
Rome → Tuscany → Dolomites
Rome: Stay at Donna Camilla Savelli, dine at Taverna Trilussa
Tuscany: Stay at Hotel Castelfalfi ($$$), dine at La Rocca di Castelfalfi ($$)
Dolomites: Stay at Forestis in Brixen ($$$$), dine at their alpine fine dining spot ($$$)