June · July 2026

Mike & Ashley
do Italy

Eleven days. Three cities. Let's go!

Wheels down in Florence in

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The Journey

The whole trip on one map.

✈️ 🛬 Florence Rome Puglia Tyrrhenian Sea Adriatic Sea
  • Florence · 6/29–7/2
  • Rome · 7/2–7/5
  • Puglia · 7/5–7/9

Tap any pin · 91 places, all linked back to the source

Stop 01

Florence

Jun 29 – Jul 2 · 3 nights

Day 1 Mon · Jun 29

Arrive & Alone in the Duomo

  • Land in Florence, train to hotel, drop bags
  • Light wandering / lunch depending on arrival time
  • 5:45 – 7:45 PM: "Alone in the Duomo" private after-hours tour Booked
  • Evening: grab a pizza and head to Piazzale Michelangelo for a sunset picnic (or save for another night if Duomo runs late)
Day 2 Tue · Jun 30

The Big Sights

  • Lunch in Piazza della Signoria
  • 2:30 PM: Uffizi & Accademia Gallery tour — Michelangelo's David + Renaissance masters Booked
  • Ponte Vecchio — old bridge with shops
  • Flex: hunt for wine windows, leather shopping
  • Evening: dinner near hotel
Day 3 Wed · Jul 1

Chianti Wine Day

Driver: Marco Bonucci · 8 hrs · Booked · cash on the day

No deposit required · reconfirm a few days before · send him our hotel address for pickup

  • 9:00 AM: Marco picks us up at the hotel, drive south out of Florence
  • 10:00 AM: Casa Emma (Castellina in Chianti) — first wine tasting · small charming family-run winery
  • Late morning: Short stop in a little Chianti village on the way to Sant'Appiano
  • Lunch: Cellar tour, lunch & second wine tasting at Sant'Appiano — second small family winery, food & wine both very good per Marco
  • Afternoon: Scenic drive back to Florence
  • Back to hotel by ~6 PM, dinner near hotel
🚄

Jul 2 · Frecciarossa 9591 · Firenze SMN 7:05 AM → Roma Termini 8:35 AM
1h 30m · Booked · PNR AA3YFN

Stop 02

Rome

Jul 2 – Jul 5 · 3 nights

Day 4 Thu · Jul 2

Easy Arrival in Rome

Frecciarossa 9591 · PNR AA3YFN

Day 5 Fri · Jul 3

The Vatican

Day 6 Sat · Jul 4

Ancient Rome

  • Morning: open / TBD
  • Lunch near the Vatican
  • 1:00 PM (1.5 hrs): Colosseum Underground Tour — Palatine Hill + Roman Forum Booked · non-refundable
  • Late afternoon: Piazza Navona — historic square
  • Pantheon
  • Dinner in Testaccio — best authentic Roman food
🚄

Jul 5 · Frecciarossa · Rome Termini 4:30 AM → Bari Centrale 9:23 AM
4h 53m · Booked · Booking ABZPZN

Stop 03

Puglia

Jul 5 – Jul 9 · 4 nights

Day 7 Sun · Jul 5

Arrive in Puglia

Frecciarossa from Rome · Booking ABZPZN

  • 4:30 AM: Depart Rome Termini
  • 9:23 AM: Arrive Bari Centrale (4h 53m on the Frecciarossa)
  • Pick up rental car at Bari, drive to Polignano a Mare (~45 min)
  • Check in to San Michele Suite, settle into the cliffside hotel
  • Afternoon / evening: relax + wander Polignano a Mare
Day 9 Tue · Jul 7

Ostuni & Alberobello

  • Day trip to Ostuni (the white city) and/or Alberobello (trulli houses)
  • Wine & olive oil tastings around town
  • Afternoon: cooking class
  • 8:30 PM: Dinner at Grotta Palazzese — cliffside cave restaurant in Polignano (reservation required)
Day 10 Wed · Jul 8

Lecce — "Florence of the South"

Day 11 Thu · Jul 9

Fly Home 😢

United · Confirmation L77CV6

  • Drive to Bari (BRI) airport — return rental car with buffer
  • 10:05 AM: BRI → EWR · UA 381 · 10h 10m transatlantic
  • 2:15 PM EDT: Arrive Newark · 2h 40m layover
  • 4:55 PM: EWR → MCO · UA 1900 · 3h flight
  • 7:56 PM EDT: Arrive Orlando 🍊

Tour Guide

Brush up on the history before each tour — the more you know walking in, the more you'll see.

Day 1 · Mon Jun 29 · 5:45 PM

Alone in the Duomo

Florence Cathedral · Santa Maria del Fiore

A small-group, after-hours tour of Florence's cathedral — climb the terraces, watch the keymasters lock up, and have the place essentially to yourselves.

Did you know?

  • Construction started in 1296 and took 140+ years to finish.
  • Brunelleschi's dome (1436) is still the largest brick dome in the world — built without a wooden support frame using a self-locking herringbone brick pattern he invented.
  • The interior fresco "The Last Judgment" (Vasari + Zuccari, 1572–1579) covers over 3,600 m² — one of the largest frescoes ever painted.
  • Brunelleschi is buried inside the cathedral, sealed into a column — at his own request.
  • The pink, green, and white marble exterior is from three different Italian quarries and is mostly 19th-century — the original facade was never finished and was torn down in 1587.

What to look for

  • The herringbone brick pattern between the inner and outer dome (you'll be able to see it on the climb)
  • Dante and Lucifer in the Last Judgment
  • Brunelleschi's tomb in the crypt
  • The view of Florence from the lantern at the very top

Tips

  • 463 stairs to the top of the dome — wear comfortable shoes
  • Even in summer it's cool inside; bring a light layer
  • Cover shoulders and knees (active church)
Day 2 · Tue Jun 30 · 2:30 PM

Uffizi & Accademia Galleries

Renaissance art at its peak

Two of the most important art museums in the world, on a combined ticket. Together they tell the story of the Italian Renaissance from beginning to peak.

Uffizi — did you know?

  • Built 1560 by Giorgio Vasari as uffizi ("offices") for Cosimo I de' Medici's magistrates.
  • Became one of the world's first modern museums when opened to the public in 1769.
  • The Vasari Corridor — a kilometer-long elevated passage — connects the Uffizi to Palazzo Pitti so the Medici could walk between palaces without touching the street.

Uffizi — must-see rooms

  • Botticelli (Rooms 10–14) — Birth of Venus, Primavera
  • Da Vinci — Annunciation, Adoration of the Magi
  • Michelangelo — Doni Tondo (the only panel painting by him in Florence)
  • Caravaggio — Medusa, Bacchus
  • Raphael — Madonna of the Goldfinch, Self-portrait

Accademia — did you know?

  • Italy's first art academy, founded 1784. The museum was built around David.
  • Michelangelo carved David from a single block of Carrara marble between 1501 and 1504, when he was 26.
  • The statue is 17 feet tall, weighs 6 tons.
  • His hands are deliberately oversized — the statue was originally meant to sit on a roofline of the Duomo, viewed from far below.
  • His left and right eyes look in slightly different directions — a deliberate optical correction for the original 30-foot pedestal at Piazza della Signoria.

Accademia — must-see

  • David — circle the entire statue, not just the front
  • The Prisoners / Slaves hallway — Michelangelo's unfinished sculptures appearing to emerge from the marble (the non-finito technique)
  • The Plaster Casts gallery — overlooked but fascinating

Tips

  • Both museums close Mondays
  • Photography allowed without flash
  • Allow 2–3 hours for Uffizi alone if you're going at this pace
  • Keep the combined ticket together — same booking covers both
Day 3 · Wed Jul 1 · all day

Chianti — Casa Emma + Sant'Appiano

Marco's route through small family wineries between Florence and Siena

Two small, family-run Chianti wineries that Marco curated based on customer feedback — both charming, both serving food and wine. Less famous than the castle-and-art-collection circuit, more in the "you're a guest at the family's estate" mode.

Chianti — context

  • "Chianti Classico" is a specific region between Florence and Siena, demarcated since 1716 — one of the world's earliest legally defined wine zones.
  • The famous black rooster (Gallo Nero) on every Chianti Classico bottle goes back to a 13th-century border dispute settled by which town's rooster crowed first at dawn.
  • Tier system: Annata (basic) → Riserva (24+ months aged) → Gran Selezione (top tier, 30+ months).
  • Sangiovese is the backbone grape — at least 80% of any Chianti Classico bottle.

Casa Emma · Castellina in Chianti

  • Small family-run estate in the heart of Chianti Classico territory, just outside Castellina in Chianti.
  • Produces Chianti Classico Annata, Riserva, and Gran Selezione, plus a Vin Santo and an IGT Merlot ("Soloìo").
  • 10:00 AM tasting — first stop of the day, when palates are fresh.
  • Marco books this in advance.

Sant'Appiano · the lunch stop

  • Second small family winery — Marco's pick for the longer afternoon stop with cellar tour, lunch, and the second tasting all on-site.
  • Per Marco: "food and wine are very good." Charming, small-business feel.
  • Plan on this being the unhurried part of the day — eating slowly with multiple pours.

Day flow

  • 9:00 AM · Marco picks us up at the hotel
  • 10:00 AM · Casa Emma tasting
  • Late morning · short stop in a Chianti village along the way
  • ~1:00 PM · cellar tour + lunch + tasting at Sant'Appiano
  • Afternoon · scenic drive back to Florence (~6 PM hotel)

Tips

  • Cash for tipping at wineries (€5–10 per tasting) and cash for Marco at the end of the Chianti day.
  • Don't drink and drive — that's the whole point of a private driver. Lean in.
  • Taste, don't chug — long day, Italian alcohol percentages are real.
  • Ask to taste their olive oil at both stops — many Tuscan estates produce excellent oil too.
  • Reconfirm with Marco a few days before — that's his standing protocol.
Day 5 · Fri Jul 3 · 8:00 AM

Vatican Museums · Sistine Chapel · St. Peter's Basilica

2.5 hour priority-access tour

The world's smallest sovereign country (109 acres) holds the world's largest treasure of Christian art. You'll walk ~3 km through 4 millennia of human history.

Did you know?

  • Vatican City has been a separate country since 1929 (the Lateran Treaty) — total population ~800.
  • The Vatican is built on top of a Roman necropolis where St. Peter (the apostle) was crucified upside down and buried in 64 AD. The current basilica's altar sits directly above what's believed to be his tomb.
  • Construction of the current St. Peter's Basilica began 1506 and took 120 years. Architects included Bramante, Raphael, Michelangelo (designed the dome), and Bernini (the colonnade and altar).
  • The Sistine Chapel is named after Pope Sixtus IV who built it (1473–1481). Michelangelo painted the ceiling 1508–1512 — 4 years on his back, age 33–37.
  • Michelangelo painted The Last Judgment on the altar wall 23 years later (1535–1541), at age 60. He included a self-portrait — his own face on the flayed skin held by St. Bartholomew.
  • The Sistine Chapel is also the site of every papal conclave since 1492 — the cardinals are literally locked in until they elect a new Pope.

What to look for

  • Sistine Chapel: The Creation of Adam (the famous touching fingers); The Last Judgment on the altar wall; the prophets and sibyls along the side panels
  • Raphael Rooms (in the museums, before the chapel): The School of Athens — Plato is modeled on Leonardo, Heraclitus on Michelangelo, and Raphael painted himself in the corner
  • Gallery of Maps — frescoed maps of Italy from the 1580s, fascinatingly accurate
  • St. Peter's Basilica: Michelangelo's Pietà (carved at age 24, his only signed work — encased in glass after a 1972 attack); Bernini's bronze Baldachin over the altar
  • Bernini's colonnade in St. Peter's Square — find the two marble disks in the pavement; from each one, the four columns line up perfectly into one

Tips

  • Cover shoulders AND knees — strictly enforced, even in summer. Bring a light scarf or shirt to throw on.
  • No talking in the Sistine Chapel (everyone whispers anyway)
  • Photography allowed in the museums; not allowed in the Sistine Chapel
  • Route is one-way: Museums → Sistine Chapel → St. Peter's. Don't try to backtrack.
  • If you have energy after the tour, climb the dome of St. Peter's (551 steps, or take the elevator to the roof and climb the last 320). The view is among Rome's best.
Day 6 · Sat Jul 4 · 1:00 PM

Colosseum Underground · Roman Forum · Palatine Hill

1.5 hour full-access tour with hypogeum

Three sites, one ticket — the heart of ancient Rome. Your "Underground" version goes into the hypogeum (the substructures beneath the arena floor) which most tourists never see.

Colosseum — did you know?

  • Built 70–80 AD by Emperor Vespasian and finished by his son Titus. Original name: the Flavian Amphitheatre (after their dynasty). The "Colosseum" nickname came from a giant statue of Nero — the Colossus — that stood next door.
  • Could seat 50,000–80,000 spectators, comparable to a modern NFL stadium.
  • Used for ~400 years for gladiatorial games, animal hunts (they imported giraffes, elephants, lions from across the empire), executions, and even mock naval battles when they flooded the arena.
  • The velarium was a massive retractable awning operated by 1,000 sailors of the Roman navy.
  • Roman tickets were marked I–LXXVI matching the numbered entrances — same system as a modern stadium.
  • Largely intact for 1,000+ years; the marble cladding was looted in the Middle Ages to build St. Peter's, Palazzo Venezia, and other Roman buildings.

What to look for

  • The hypogeum — the underground tunnels and animal lifts. You'll be standing where gladiators waited to be hoisted up to the arena floor.
  • The partially reconstructed wooden arena floor
  • The travertine blocks with holes drilled in them — those once held iron clamps that locked the stone together (looted later for the iron itself)
  • The Arch of Constantine outside (315 AD) — built celebrating Constantine's victory and the legalization of Christianity

Roman Forum — context

  • The political and commercial heart of Rome for nearly 1,000 years. Originally a marshland between the Palatine and Capitoline hills, drained around 600 BC.
  • Caesar's funeral pyre was here in 44 BC. The Senate building (Curia Julia, partially reconstructed) is where he had been stabbed days earlier.
  • Fell into ruin after Rome's collapse; in the Middle Ages it was a literal cow pasture called Campo Vaccino.

Palatine Hill — context

  • One of the seven hills of Rome. Tradition says Romulus founded Rome here in 753 BC; you can see the foundations of an Iron Age hut said to be his.
  • The aristocratic neighborhood — emperors lived here, including Augustus and Domitian. The English word "palace" comes from "Palatine."
  • Has the best view of the Forum below and the Circus Maximus on the other side.

Tips

  • Wear comfortable shoes — uneven cobblestones, lots of walking
  • Hat + sunscreen — minimal shade, July heat
  • Bring a refillable water bottle — Rome has free nasoni (drinking fountains) everywhere
  • Combined ticket is good for the entire day across all three sites
  • Best photo angle of the Colosseum: from outside on the south/Palatine side

Italy Travel Tips

Practical things you'll want to know on the ground — money, food, churches, driving, etiquette.

💶 Money & Tipping

  • Carry small euro coins. Public restrooms charge €0.50–1, espresso at a bar is €1–2. Cash matters.
  • Tipping is not expected like in the US. 5–10% at nice restaurants if service was good. Round up at cafes/taxis. The "service charge" / coperto on bills is a cover charge, not a tip.
  • Use credit cards in cities, but bring €200–300 cash for smaller villages, the Chianti driver, and tipping at wineries.
  • Notify your bank you're traveling. Visa & Mastercard widely accepted; Amex is hit-or-miss.
  • ATMs (bancomat) at banks have the best rates. Avoid airport / hotel currency exchange.

🍝 Food & Restaurants

  • Coperto (€2–5/person cover charge) is normal — covers bread & the table. Not a tip.
  • Italians eat dinner late. Restaurants don't open until 7:30–8 PM, locals don't show up until 9. Reservations recommended for anywhere good.
  • Espresso is consumed standing at the bar. Sitting at a table can double the price.
  • Cappuccino is a morning drink only. Ordering one after lunch tells everyone you're a tourist (it's fine, but they will smile).
  • Avoid restaurants with photos on the menu, hosts barking at the street, or English-only menus near major sights — that's the tourist trap signal.
  • House wine (vino della casa) is usually a bargain and totally good.
  • Drinking fountains (nasoni in Rome) are everywhere and the water is excellent. Refill your bottle.

🚆 Trains & Transit

  • Your Frecciarossa tickets are assigned seats, no need to validate. (Validation is only for regional/local tickets.)
  • For local/regional trains, validate paper tickets in the green/yellow machines on the platform before boarding — fines for unvalidated tickets are real.
  • Roma Termini is huge; allow 15 min from arrival to platform. Same with Firenze SMN.
  • For your 4:30 AM Rome → Bari, pre-book a taxi the night before — Rome's metro doesn't start until 5:30 AM. Hotel can arrange.
  • Public transit in Rome: a 100-min ticket is €1.50 and works on bus, metro, and tram. Validate when you board.

⛪ Churches & Museums

  • Cover shoulders and knees in churches — strictly enforced at the Vatican and the Duomo. Bring a scarf or light shirt.
  • Churches generally close midday (12:30–3:30 PM) and reopen for evening mass.
  • Most major museums close Mondays. Many are free the first Sunday of each month — but expect crowds.
  • No flash photography in most museums. The Sistine Chapel allows no photos at all.
  • Ticket prices are cheaper online in advance than at the door.

🚗 Driving in Puglia

  • ZTL zones (Zona a Traffico Limitato) are camera-monitored restricted zones in Italian old towns. Driving in one without a permit = €100+ fine, mailed home weeks later. Polignano a Mare, Ostuni, Lecce all have ZTLs in their old centers — park outside and walk in.
  • You'll pick up at Bari Centrale — most rental car desks are at the station or a short walk away. Confirm pickup location in your reservation.
  • Italian driving is more aggressive than American; lanes are suggestions, scooters weave, and tailgating is normal. Stay calm, don't over-react.
  • Highway tolls (autostrada) — green signs. Take a ticket on entry, pay on exit. Cards work.
  • Gas (benzina) — most stations are self-service. "Servito" = full service for ~€0.20 more per liter.
  • Park in marked spots: white = free, blue = paid (use the meter), yellow = residents only (don't).

📱 Phone & Connectivity

  • Easiest option: add an international plan with your existing US carrier for the trip duration (T-Mobile, Verizon, AT&T all have $10/day options).
  • Cheaper option: an eSIM from Airalo, Holafly, or Saily — €15–25 for the trip, activated by QR code before you leave home.
  • Free Wi-Fi at most hotels & cafes.
  • Download Google Maps offline for Florence, Rome, and southern Puglia before you go. Lifesaver in spotty coverage.
  • Useful apps: Google Translate (download Italian offline), Trenitalia, Free Now (Uber-equivalent for taxis).

🛡️ Safety

  • Italy is overall very safe. The main risk is pickpocketing at: Termini station, the Colosseum metro stop, around the Trevi Fountain, on Roman buses (especially #64).
  • Use a cross-body bag with a zipper, kept in front in crowds. No wallets in back pockets.
  • Common scams: people approaching with friendship bracelets, "free" roses, the "ring drop," fake petitions. Polite "no grazie" and walk on.
  • Italy emergency number: 112 (single number for police/ambulance/fire).
  • US Embassy Rome: it.usembassy.gov

🇮🇹 Cultural Notes

  • Greetings matter. Walking into a shop or restaurant: Buongiorno (until ~5 PM) or Buonasera. Leaving: Grazie, arrivederci. Costs nothing, dramatically changes how you're treated.
  • "Excuse me" = Scusi. "Sorry" = Mi dispiace. "Please" = Per favore.
  • Italians don't really "do" iced drinks. Water comes still (naturale) or sparkling (frizzante / con gas) — bottled, room temp by default.
  • Riposo (afternoon shop closure, ~1–4 PM) is real, especially in smaller towns and Puglia. Plan errands around it.
  • Sundays in southern Italy: most shops + many restaurants are closed. Plan ahead in Puglia.
  • Tipping the Vatican guard, the Colosseum guide, etc. is appreciated — a few euros, in cash, with a thank you.

Packing List

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Documents & Essentials

Clothes (Hot June/July)

Toiletries

Electronics

For the Plane

Nice to Have

Practical Info

Flights

Jun 28 → Jun 29 · Outbound · Delta · Confirmation GTYAWM · Booked · total 14h 35m

  • MCO Terminal B → ATL · 2:05 PM → 3:55 PM · DL 1030 · Airbus A321 · seats 12D, 12E (Delta Comfort)
  • Layover Atlanta · 1h 10m
  • ATL → AMS · 5:05 PM → 7:45 AM next day · DL 72 · Airbus A330-300 · seats 32J, 32H (Delta Comfort) · overnight transatlantic
  • Layover Amsterdam · 55m
  • AMS → FLR · 8:40 AM → 10:40 AM · DL 9388 (operated by KLM Cityhopper) · Embraer 195 · seats 20D, 20F (Europe Economy) · arrive Florence!

Jul 9 · Return · United · Confirmation L77CV6 · Chase points

  • BRI → EWR · 10:05 AM → 2:15 PM · UA 381 · 10h 10m transatlantic
  • Layover Newark · 2h 40m
  • EWR → MCO · 4:55 PM → 7:56 PM · UA 1900 · home!

Trains

Jul 2 · Firenze SMN → Roma Termini · 07:05 → 08:35 · 1h 30m · Frecciarossa 9591 · Booked · PNR AA3YFN

Jul 5 · Rome Termini → Bari Centrale · 04:30 AM → 09:23 AM · 4h 53m · Frecciarossa · Booked · Booking ABZPZN

Pre-Booked & Paid

  • Alone in the Duomo Tour (Day 1, 5:45 PM) — charges 6/26
  • Uffizi & Accademia (Day 2, 2:30 PM) — charges 6/27
  • Vatican / Sistine / St. Peter's (Day 5, 8:00 AM) — charges 7/1
  • Colosseum Underground Tour — Forum & Palatine (Day 6, 1:00 PM) — non-refundable
  • San Michele Suite (Polignano) — Partial paid 4/22 · Balance due 10 days before arrival

Driver & Car

Jul 1 · Marco Bonucci for Chianti — 8 hrs, 9 AM pickup · cash on the day, no deposit. Reconfirm a few days before and send him our hotel for pickup.

Jul 5 · Pick up rental car at Bari Centrale for the Puglia leg

Good to Know

  • Italy emergency number: 112
  • US Embassy Rome: it.usembassy.gov
  • Tipping: 10% nice restaurants, round up at cafes
  • Most museums close Mondays — verify before going
  • Carry small euros for restrooms & espresso
  • Validate train tickets before boarding (regional only)

What to Wear

Day-by-day outfit suggestions for Mike & Ashley.
Elevated Italian summer · linen-heavy · neutrals with one pop · Vatican-friendly when needed.

Photos are illustrative — Flickr Creative Commons via loremflickr. They show the vibe, not the exact piece. Each outfit also links to a Pinterest search for more inspiration.