Rome
Oct 14 · Oct 20–22 · Based in Trastevere for the last three nights
Part Roman deli, part restaurant — and entirely extraordinary. The pasta is exceptional (cacio e pepe, amatriciana), the cured meats and cheese counter is one of Rome's finest, and the wine list is the kind that makes you want to linger for hours. Book well ahead — this is one of the most sought-after tables in the city. Worth every effort to make it work.
The quintessential Trastevere trattoria — small, warm, and flawlessly Roman. The cacio e pepe is among the city's best, the coda alla vaccinara (oxtail) is rich and deeply flavored, and the house wine keeps the bill honest. You'll be sitting close to your neighbors and loving it. One of the very best meals of the trip.
A genuine Roman institution that has somehow resisted the tourist trap fate of most Pantheon-adjacent restaurants. Family-run for decades, serving classic Roman cucina with real skill — rigatoni all'amatriciana, trippa alla romana, Roman artichokes in season. Tiny, in high demand. Book as early as possible. A perfect spot for the Pantheon day (Oct 22).
Testaccio is Rome's most authentic neighborhood for eating, and Felice is its most beloved trattoria. Order the cacio e pepe — it's tableside-finished, scooped into a giant parmesan wheel, and one of the great Roman pasta experiences. The tonnarelli cacio e pepe here is legendary. Worth a cab if you're staying in Trastevere (it's close). Book ahead.
The best seafood-focused restaurant in Trastevere, with a menu that leans into Roman-Jewish tradition alongside classic Roman pasta. Excellent spaghetti alle vongole, branzino, and some of the finest fried artichokes (carciofi alla giudea) you'll find. The setting is warm and unpretentious. Reservation recommended, especially on weekends.
Lively, loud, and fun — outdoor tables tumbling into a narrow Trastevere lane, solid Roman classics, and a relaxed energy that's perfect for an early trip dinner when you just want to soak in the neighborhood. Good cacio e pepe and carbonara. No reservation needed if you go before 7:30 PM; expect a wait later.
A dependable, unfussy Trastevere trattoria that punches above its weight. Solid Roman classics — gricia, amatriciana, abbacchio — in a room that feels genuinely lived-in. Good for a relaxed night when you don't want to fuss with reservations. Go early or expect a short wait.
Prati's most honest trattoria — fixed-price lunch and dinner, Roman classics only, house wine poured freely. Carbonara, cacio e pepe, rigatoni all'amatriciana. The kind of place where the owner knows half the tables by name. Perfect after a Vatican morning when you don't want to overthink lunch.
Old-school Roman trattoria that has barely changed in decades. Fixed-price menus, communal tables, and the kind of no-nonsense hospitality that Rome does better than anywhere. Extremely reasonable. Cash only. A great fallback if Roscioli is booked.
Fixed-price menu — you eat what they cook, house wine flows freely, and the bill is the same for everyone. No decisions required. The food is straightforward Roman home cooking, the energy is warm and slightly chaotic, and it's an experience as much as a meal. Perfect for a first night when decision fatigue is real.
Rome's iconic supplì — fried rice balls stuffed with ragù and melted mozzarella — done better here than almost anywhere in the city. Eat them standing on the street while they're hot. No seating, no fuss. Order the classic supplì al telefono and a suppli' cacio e pepe. Arrives perfect for a midday fuel stop near the historic center.
Gabriele Bonci's famous pizza al taglio — thick, airy focaccia-style crust with creative, seasonal toppings, sold by weight. Point at what you want, they cut and weigh it. This is genuinely some of the best pizza in Rome, from a chef who's been called the Michelangelo of pizza. Perfect post-Vatican lunch before the afternoon in Prati or Castel Sant'Angelo.
Right on the piazza — open early, cash only, always a small queue worth joining. The pizza bianca (white Roman flatbread, olive oil, salt) is extraordinary. Also excellent: pizza rossa (tomato), filled focaccia, and whatever pastry is behind the glass. One of those simple Rome pleasures that stays with you.
The Trastevere aperitivo institution. Order a Negroni or spritz (€8–10) and you get access to a generous spread of snacks and small plates that amounts to a light dinner. The crowd spills onto the piazza, the vibe is warm and social, and by 8 PM it's packed. Go at 6:30 PM for a good spot and a relaxed start. One of Rome's best evening rituals.
A rooftop wine bar perched above the centro storico with views over Rome's terracotta skyline. A drink here at golden hour — glass of local Frascati or a natural wine — is one of the more quietly spectacular things you can do in Rome. Good food too, if you want to stay for a light dinner. Worth planning an evening around it.
A proper Roman enoteca — shelves floor to ceiling, hundreds of bottles, cold cuts and cheese on the counter, and the energy of a neighborhood place that hasn't changed in forty years. Pull up a stool, ask for a recommendation, and spend an hour here before dinner. One of the more charming spots in the city.
Named after a Roman insult hurled at tourists, this tiny bar is one of the finest craft beer spots in Italy — rotating taps from Italian and international microbreweries, incredibly knowledgeable staff, and a crowd that's mostly locals. Great if you want a break from wine and an excuse to stand in a Trastevere alley for an hour.
The most local bar in Trastevere — cash only, marble tables, €1.20 espressos, and the kind of clientele that has been coming here every day for thirty years. No aperitivo spread, no DJ, no Instagram moment. Just a cheap beer or spritz in a Trastevere piazza among Romans. A necessary antidote to the neighborhood's more tourist-facing places.
A calm, beautifully designed café that works well for anything — morning coffee, mid-afternoon break, or early evening cocktail. Good Negroni, friendly staff, and a relaxed atmosphere that feels a cut above the surrounding touristy options near Campo de' Fiori. A solid default for any time of day.
Widely considered one of Rome's finest espresso bars — small, no seats, marble counter, and a coffee culture that has barely changed since 1919. The espresso is rich and perfectly pulled, the pastries are excellent, and the ritual of standing at the bar and drinking a coffee in under three minutes is exactly as it should be. Worth a detour on Vatican day.
Rome's most creative artisan gelateria — all flavors are naturally derived, gluten-free, and genuinely surprising. Expect things like Roquefort & pear, cinnamon & ginger, or basil & honey alongside more classical options. The quality is exceptional. Multiple locations; the Campo de' Fiori area branch is the most convenient for the historic center.
Florence
Oct 15–20 · Based in Via dei Servi, steps from the Duomo
October 19 is Meghan and Garret's 25th anniversary. They'll be in Florence — one of the most romantic cities on earth — on their last night before leaving for Rome. These three restaurants are worth the occasion.
Repeatedly named one of the world's best restaurants — not for the food alone, but for the entire experience. Set inside a sequence of connected medieval rooms in a historic Florentine palazzo, with vaulted frescoed ceilings and candlelight that makes the space feel genuinely otherworldly. The food is contemporary Italian done with real skill; the wine list is exceptional. It's a splurge, but the kind that earns its price. If there's one night to go somewhere truly memorable, this is it — and this is the place.
The highest-rated restaurant in Florence — three Michelin stars, one of Italy's most celebrated wine cellars (over 150,000 bottles), and a kitchen that has been producing extraordinary Italian haute cuisine since 1972. Set in a 15th-century palazzo with a beautiful inner courtyard. This is a longer, more ceremonial meal — multiple courses, wine pairings, the full experience. A serious occasion restaurant for a very serious anniversary.
The Four Seasons Florence occupies a Renaissance palazzo with one of the most beautiful private gardens in the city. Il Palagio — their main restaurant — is the more approachable option here: a Michelin-starred kitchen in a setting of real splendor, with tables in the garden on warm evenings. Slightly less austere than Pinchiorri, more restaurant and less ceremony. An exceptional choice if you want the occasion without the full tasting menu commitment.
Florence's most beloved old-school trattoria — founded in 1869, still run by the same family spirit, and entirely unchanged in the best possible way. The ribollita is the platonic ideal of the dish, the bistecca alla Fiorentina is enormous and spectacular, and the butter pasta (a buttery egg pasta tossed tableside) is a revelation. Reserve well in advance. One of the essential Florence dinners.
The neighborhood trattoria that every city wishes it had. Locals only — or it feels that way — with a menu that changes daily and cooking that tastes genuinely homemade. Perfect bistecca, ribollita, and pappardelle with wild boar ragù. The Oltrarno location makes it ideal for an evening after Bobboli or the Pitti. Reserve; it fills up completely every night.
Long communal tables, a room that never quiets down, enormous plates of Tuscan classics, and house Chianti that keeps appearing without being asked. This is dinner as a communal event — you'll end up talking to strangers, sharing dishes, and leaving two hours later slightly louder than when you arrived. Go early or expect a wait even with a reservation.
Florence's oldest restaurant — founded in 1886 — and one of its most reliably satisfying. No frills, no experimentation: just excellent Florentine cooking in a room that feels like it belongs to another century. Bistecca alla Fiorentina, ribollita, tagliatelle with ragù. Great when you want a relaxed, comfortable dinner without the energy of Il Latini.
A classic Florentine cellar restaurant near Ponte Vecchio — vaulted ceilings, candlelight, and cooking that takes the traditions seriously. The pappardelle al cinghiale (wild boar), bistecca, and house wine are all excellent. The location makes it an easy choice for an evening after the Uffizi. Reserve for evenings.
More refined than the average Florence trattoria — a serious wine list, beautifully executed Tuscan cuisine, and a room with some ambiance. Good for a nicer night out without veering into formal territory. The pasta is exceptional and the wine pairings are thoughtful. Worth a reservation if you want one elevated dinner in Florence.
The most convenient good option near Via dei Servi and the Duomo. Solid bistecca, ribollita, and pasta — nothing surprising, nothing disappointing. A reliable neighborhood option when you're tired and don't want to go far. Good value for the location.
Lunch only, cash only, communal tables, and a daily menu written on a chalkboard. Opens at noon and fills completely within 20 minutes — arrive at 11:45 AM and wait outside. The food is exactly what you'd want: ribollita, pasta al pomodoro, roasted meats, Chianti by the glass. One of Florence's most authentic and affordable lunch experiences. Do not miss this.
The most famous sandwich shop in Florence — schiacciata (Tuscan flatbread) split open and loaded with finocchiona salami, pecorino, roasted vegetables, and truffle cream. The queue is always long and moves quickly. Order confidently: "una schiacciata con finocchiona e pecorino." Eat it standing in the street, ideally near the Uffizi. One of the great cheap eats in Italy.
Florence's signature street food — lampredotto (the fourth stomach of a cow) braised for hours, then piled into a roll that's dipped in the cooking broth and finished with salsa verde. It sounds alarming and tastes extraordinary. This is what Florentines have eaten standing up for centuries. Order the panino con lampredotto and commit to it. No regrets.
The wine bar sibling of the acclaimed Santo Bevitore next door. Small plates, excellent natural wines, and a menu that changes with what's good that week. Good for a languid Oltrarno lunch — cured meats, cheese, a pasta, a glass of something interesting. Works just as well for an afternoon aperitivo before dinner.
A quiet Oltrarno lunch spot with a small garden terrace — exactly the kind of place you stumble across in Florence's left bank and want to return to. Seasonal Tuscan food, relaxed pacing, and a genuinely local crowd. Perfect for a slow lunch after Bobboli Gardens or Palazzo Pitti.
The upper floor of Florence's great covered market is a permanent food hall — dozens of stalls serving everything from lampredotto and pasta to pizza and gelato. Not the most authentic experience, but excellent for stocking the apartment (ground floor) or a quick, flexible lunch with options. Also great for a morning cornetto and cappuccino to start the day.
One of the Oltrarno's most relaxed and likeable aperitivo bars — mismatched furniture, a good music selection, and a crowd of young Florentines and students. The aperitivo spread is solid and the Negroni is properly made. A low-key spot for an early evening drink before dinner in the neighborhood.
A tiny, warm wine bar in the Oltrarno that draws a faithful local crowd. Good natural wines by the glass, small plates, and the kind of unpretentious atmosphere that makes you want to stay longer than planned. Great alternative to Volume if you prefer wine over cocktails for your aperitivo hour.
One of the best gelaterie in Florence — a long case of seasonal flavors, all made in-house, with real fruit and proper technique. The ricotta e fichi (ricotta and fig) is extraordinary in October when the figs are at their peak. Pistachio and dark chocolate are reliably excellent. A short walk from Santa Croce and worth the detour.
Sicilian-style gelato made by a family from Bronte — so the pistachio, made with the prized Bronte pistachios, is extraordinary. Also excellent: granita, brioche col tuppo, and almond flavors. Around the corner from the Accademia, making it a natural post-David stop. One of the best gelato shops in the city.
Siena
Oct 18 · Day trip from Florence — arrive around 1:00 PM, depart ~6:30 PM
No sign on the door, no menu, no credit cards — just a daily chalkboard of whatever was good at the market, a single room with a handful of tables, and some of the most honest Sienese cooking you'll find. The pici cacio e pepe is the dish to order if it's available. Cash only, lunch only, seats fill quickly. Arrive by 12:30 PM. One of the great hidden gems of Tuscany.
A family-run Sienese trattoria on a quieter piazza just off Il Campo — less discovered than the tourist-facing spots on the main square, and substantially better. Classic Sienese dishes: pici all'aglione, ribollita, pappardelle with wild boar. The terrace is lovely for a warm October afternoon. No reservation required for lunch if you arrive before 1 PM.
The bars ringing Il Campo are overpriced by Sienese standards — but one drink on one of the world's great medieval piazzas, watching the light go amber on the Palazzo Pubblico, is worth every extra euro. Order a Campari spritz, sit on the shell-shaped bricks, and stay for exactly as long as it takes to finish it. Then drive back to Florence.
- Reservations:
- Any spot marked "Reservation Needed" books up fast — especially in October, which is high season. Don't wait until you're there.
- Timing:
- Lunch is 12:30–2:30 PM; dinner rarely starts before 7:30 PM. Showing up at 6 PM will get you an empty room and confused looks.
- At the bar:
- At any Italian coffee bar, you pay less if you stand at the counter than if you sit at a table. Always order at the bar.
- The bill:
- In Italy, the check doesn't come until you ask for it — il conto, per favore. Sitting there waiting is one of the great tourist mistakes.
- Cash:
- Several of these spots are cash only. Keep €40–60 in small bills at all times.
- Coperto:
- A small cover charge (€1–3 per person) is standard and not optional. It's not a tip — tipping is appreciated but not expected.