Summer 2027 · A Mediterranean Odyssey
John’s Italy & Greece Adventure
June 18 – July 3, 2027 · 15 Nights
🇮🇹 Sicily
🇬🇷 Greece
🇮🇹 Rome
Your Journey at a Glance
An epic arc from the American heartland through the ancient Mediterranean
Day-by-Day Itinerary
Tap a day to jump straight to it.
Day 0 · Travel Day
June 18, Thursday — CVG → Catania
Overnight transatlantic crossing
🌆 Evening
- ✈️ Air France via Paris CDG (recommended): Depart ~5:30 PM CVG, arrive CTA ~12:30 PM next day (~19h total with layover)
- ✈️ Alt: Delta via JFK: Depart afternoon CVG, arrive CTA next day
⭐ Transit Tip
Book Air France CDG connection — fastest routing. Overnight flight — bring neck pillow, eye mask, compression socks.
Day 1 · Catania
June 19, Friday — Arrive Catania, Sicily 🇮🇹
Arrival & first Sicilian sunset
☀️ Morning / Noon
- 🛬 Land Catania Fontanarossa (CTA) ~midday
- 🚕 Taxi or Alibus shuttle (€4) to city center (~20 min)
- 🏨 Check in — Hotel Katane Palace or Una Hotel Palace Catania
🌤️ Afternoon
- 🚶 Gentle orientation walk through the city center
⭐ Piazza del Duomo — the famous Lava-stone Elephant Fountain & Basilica Cattedrale di Sant’Agata
🌙 Evening
- 🍝 Dinner near A’ Piscaria (fish market area). Try: pasta alla Norma, arancini, cannoli
- 🌆 Stroll Via Etnea — Catania’s grand boulevard
Day 2 · Catania
June 20, Saturday — Catania City Day
Baroque splendor & Sicilian cooking
☀️ Morning
⭐ Monastero dei Benedettini di San Nicolò (€10, guided tour required) — underground Roman ruins, monk kitchens, breathtaking Baroque architecture. One of Europe’s largest monasteries.
- 🏔️ Gravina di Catania — scenic hillside viewpoint over Etna foothills and Catania bay (5km from center)
🌤️ Afternoon
- 🏰 Ursino Castle (museum, free entry)
- 🎭 Teatro Massimo Bellini exterior
- 🛍️ Via Etnea shopping stroll
- 🐟 Fish market (A’ Piscaria) for lunch snacks
🌙 Evening
⭐ Sicilian Cooking Class — 3-hour hands-on class. Make pasta alla Norma, arancini, cassata. Book via Airbnb Experiences or La Norma Cooking School.
Day 3 · Catania · Day Trip
June 21, Sunday — Day Trip: Ragusa & Modica
UNESCO Baroque gems & chocolate paradise
🚗 Transport: Rent a car or join guided day tour (~2h south of Catania). Depart 8 AM.
☀️ Morning
⭐ Ragusa Ibla — UNESCO Baroque gem. Cathedral of San Giorgio, Giardini Iblei park, labyrinthine stone streets.
- 👣 Ragusa Superiore connected by 200+ steps — panoramic Baroque views
🌤️ Afternoon
- 🍫 Modica (30 min from Ragusa) — famous for cold-process chocolate. Visit Antica Dolceria Bonajuto, Sicily’s oldest chocolate shop (since 1880)
- 🚗 Return to Catania by 7 PM
Day 4 · Taormina · Transfer Day
June 22, Monday — Mount Etna + Transfer to Taormina
Conquer Europe’s tallest active volcano
🌅 Very Early Morning
⭐ Mount Etna guided excursion (depart 6:30 AM!). Cable car from Rifugio Sapienza (1,900m) to 2,500m, then authorized 4WD jeep to 2,900m crater rim. Cost: ~€60–80/person.
Dress in layers — summit is 15–20°C cooler. Wear hiking boots.
🌤️ Midday / Afternoon
- 🏨 Return to Catania hotel, check out, light lunch
- 🚌 Transfer Catania → Taormina by car (~45 min) or InterBus (€5, 1h)
- 🏨 Check in — Grand Hotel Timeo or Hotel Isola Bella
🌙 Evening
⭐ First golden hour in Taormina — Corso Umberto I stroll, Piazza IX Aprile terrace (jaw-dropping Etna + sea view at sunset). Rooftop dinner with volcano view.
Day 5 · Taormina
June 23, Tuesday — Taormina Highlights
Ancient theatre, island beach & hilltop village
☀️ Morning
⭐ Teatro Antico di Taormina (Greek Theatre) — 3rd century BC, still used for summer concerts. Etna as backdrop is extraordinary. Arrive before 9 AM. Entry ~€10.
🌤️ Midday
- 🚡 Cable car down to Isola Bella — tiny island nature reserve connected by sandbar
- 🏖️ Swim in crystal water. Lunch at beach café
🌤️ Afternoon
- 🏔️ Castelmola village (15 min drive or 45-min hike). Bar San Giorgio for famous almond wine. Panoramic views of both coasts of Sicily.
🌙 Evening
- 🍸 Aperitivo at Wunderbar Café (Truman Capote’s favorite)
- 🍽️ Dinner on the terrace
Day 6 · Taormina · Day Trip
June 24, Wednesday — Day Trip: Catanzaro, Calabria
Cross the Strait of Messina into Calabria
🚗 Transport: Drive to Messina (~45 min), ferry across Strait of Messina (~15 min), drive to Catanzaro (~1.5h). Total: ~2.5h.
☀️ Morning / Midday
- ⛪ Cathedral of the Assumption
- 🎨 Museo Marca (modern art)
- 🚡 City’s famous funicular — views over the Gulf of Squillace
- ⛪ Byzantine church of Sant’Elia
🍽️ Lunch
- 🌶️ Calabrese cuisine — ‘nduja spread, pasta e patate, pitta ‘mpigliata pastry
🌤️ Afternoon
- 🚗 Drive back via scenic coastal SS18. Return to Taormina by 7 PM.
💡 Transit tip: This is a long travel day — consider renting a car specifically for this day.
Day 7 · Athens · Travel Day
June 25, Thursday — Fly to Athens 🇬🇷
Sicily farewell, Greece awaits
☀️ Morning
- 🏨 Check out, drive to Catania airport (~45 min)
✈️ Flight
- ✈️ Catania CTA → Athens ATH — ~2h35m. Ryanair or Aegean Airlines. ~€60–170
- 🚇 ATH → city center by Metro Line 3 (€9, ~40 min)
- 🏨 Check in — Hotel Grande Bretagne or Electra Metropolis (Syntagma)
🌙 Evening
⭐ First Athens night — Monastiraki Square, Plaka neighborhood. Rooftop dinner with illuminated Acropolis view. Try: souvlaki, tzatziki, horiatiki salad.
⏰ Time zone note: Athens is 1 hour ahead of Italy (EEST, UTC+3).
Day 8 · Athens
June 26, Friday — The Acropolis & Ancient Athens
Walking in the footsteps of Socrates
☀️ Morning
⭐ MUST — Arrive Acropolis at 8 AM opening! (€20, book in advance). Parthenon, Erechtheion, Propylaea, Temple of Athena Nike. Stunning panoramic city views.
⭐ Acropolis Museum (€15, world-class) — original sculptures, Elgin Marbles context gallery.
🍽️ Lunch
- 🍽️ Plaka taverna — try moussaka, spanakopita, fresh calamari
🌤️ Afternoon
- 🏘️ Anafiotika — tiny Cycladic-style white-washed village hidden on Acropolis slopes
- 🏛️ Ancient Agora & Stoa of Attalos museum
🌙 Evening
- 🍷 Thisseio rooftop restaurant with Acropolis night view. Greek wine tasting: Assyrtiko, Xinomavro
Day 9 · Athens
June 27, Saturday — Athens + Cape Sounion Sunset
Museums, markets & the Temple of Poseidon at golden hour
☀️ Morning
- 💂 Syntagma Square — changing of Evzone guards (every hour on the hour)
- 🌿 National Garden stroll
- 🏛️ National Archaeological Museum — Bronze Poseidon, Antikythera mechanism
🌤️ Midday
- 🛍️ Monastiraki flea market (Sundays are biggest — plan to visit tomorrow for peak atmosphere)
🌅 Afternoon / Evening
⭐ Cape Sounion excursion (70km south, ~1h). Temple of Poseidon perched on sea cliff. Arrive 1 hour before sunset for golden light over the Aegean — one of the most spectacular sights in all of Greece.
Seafood dinner at seaside taverna near Sounion.
Day 10 · Rome · Travel Day
June 28, Sunday — Athens → Fly to Rome 🇮🇹
From Greek splendor to the Eternal City
☀️ Morning
- 🛍️ Monastiraki flea market (Sundays are biggest!)
- ☕ Final Greek coffee and koulouri (sesame ring bread)
✈️ Midday Flight
- ✈️ ATH → FCO ~2h. Arrive Rome Fiumicino early afternoon.
- 🚄 Leonardo Express train to Roma Termini (€14, 32 min)
- 🏨 Check in — Hotel de Russie (Piazza del Popolo) or Trastevere boutique hotel
🌙 Evening
⭐ Trastevere — cobblestone alleyways, Santa Maria in Trastevere basilica. Dinner at Da Enzo al 29 (cacio e pepe, coda alla vaccinara). Evening stroll to Tiber River.
Day 11 · Rome
June 29, Monday — Ancient Rome
Gladiators, ruins & secret keyholes
☀️ Morning
⭐ Colosseum (book weeks ahead! ~€20) — underground gladiator tunnels tour if available. Roman Forum & Palatine Hill included in ticket. Arrive at 9 AM opening.
🍽️ Lunch
- 🍕 Testaccio neighborhood — Rome’s authentic food market. Try supplì (fried rice balls), porchetta sandwich.
🌤️ Afternoon
- 🏟️ Circus Maximus, Aventine Hill
⭐ Knights of Malta Keyhole: perfectly frames St. Peter’s dome through the keyhole of a gate. Queue is short.
- 🌸 Campo de’ Fiori market area
🌙 Evening
- 🍸 Aperitivo in Campo de’ Fiori, dinner back in Trastevere
Day 12 · Rome · Day Trip
June 30, Tuesday — Day Trip: Florence
Renaissance masterpieces in a single glorious day
🚄 Transport: Frecciarossa high-speed train Roma Termini → Firenze SMN (~1h25m, €20–50). Depart 7:30 AM.
☀️ Morning
- ⛪ Florence Duomo & Baptistery (book dome climb for extraordinary views)
- 🏛️ Piazza della Signoria, Loggia dei Lanzi sculptures
🌤️ Midday
⭐ Uffizi Gallery — book timed entry. Botticelli’s Birth of Venus, da Vinci, Michelangelo.
🌤️ Afternoon
- 🌉 Ponte Vecchio, Oltrarno neighborhood
- 🏔️ Piazzale Michelangelo viewpoint
- 🍦 Gelato at Gelateria dei Neri
- 🚄 Return train ~6:30 PM → back in Rome by 8 PM
🌙 Evening
- 🍽️ Pantheon area dinner — Ristorante Fortunato al Pantheon
Day 13 · Rome · 🙏 Papal Day
July 1, Wednesday — Vatican + Papal Audience + Frascati
The most extraordinary day of the trip
🌅 7:30 AM
⭐ PAPAL AUDIENCE — Free tickets (request in advance at vatican.va). St. Peter’s Square. Pope Francis addresses pilgrims. Starts ~10 AM — arrive 7:30 AM for good seats. Deeply moving experience.
☀️ Late Morning
⭐ Vatican Museums & Sistine Chapel — book early entry (8 AM slot, €33–42). Michelangelo’s ceiling, Gallery of Maps, Raphael Rooms. Allow 3–4 hours.
🍽️ Lunch
- 🍕 Pizzarium (Bonci) — Rome’s best pizza al taglio, Via della Meloria
🌤️ Afternoon
- ⛪ St. Peter’s Basilica (free entry) — climb dome for panoramic Rome views (€6–8)
🌅 Late Afternoon / Evening
⭐ Frascati Wine Tour — 45 min to Castelli Romani hills. Visit a local cantina (Cantina Gotto d’Oro or Villa Simone). Taste Frascati DOC white wine with local porchetta and pecorino. Romantic hilltop vineyard views over Rome.
Return to Rome by 9 PM.
Day 14 · Rome · Day Trip
July 2, Thursday — Day Trip: Assisi
Pilgrimage to St. Francis’s medieval hilltop town
🚄 Transport: Train Roma Termini → Assisi via Foligno (~2.5h, ~€15). Depart 7:30 AM.
☀️ Morning
⭐ Basilica di San Francesco d’Assisi (UNESCO) — twin basilica with stunning Giotto frescoes. Upper and lower churches. Crypt with St. Francis’s tomb.
🌤️ Midday
- 🏛️ Piazza del Comune, Tempio di Minerva (Roman temple facade)
- 🍝 Lunch: Umbrian cuisine — truffle pasta, wild boar
🌤️ Afternoon
- ⛪ Basilica di Santa Chiara
- 🏔️ Walk the medieval walls, panoramic Umbrian valley views
- 🚄 Return to Rome ~7 PM
🌙 Evening
- 🍽️ Final Rome dinner — Ristorante Il Sorpasso or rooftop at Divinity Restaurant
Day 15 · Finale · Travel Day
July 3, Friday — Rome Finale + Fly Home
Last Roman morning — arrivederci!
OPTION A — Final Rome Morning (Recommended)
⭐ Trevi Fountain (toss your coin for return!), Spanish Steps, Pantheon interior (€5). Gelato from Giolitti.
- ☕ Piazza Navona farewell espresso
- ✈️ Transfer to FCO airport ~2 PM for evening return flight
OPTION B — Add Ischia (requires extra night)
- 🚄 Train Rome → Naples (1h), hydrofoil Naples → Ischia (~45 min)
- ♨️ Poseidon Thermal Gardens (~€30), Sant’Angelo village, Gardens of La Mortella
- 💤 Overnight Ischia, next day to FCO
📋 Booking Checklist
Tap items to check them off as you book — progress is saved on this device.
Book Immediately (12+ months before)
- ✈️ Flights CVG → CTA (via CDG preferred) — June 18, 2027
- ✈️ Flights CTA → ATH — June 25, 2027
- ✈️ Flights ATH → FCO — June 28, 2027
- ✈️ Return flight FCO → CVG — July 3, 2027
- 🙏 Papal Audience free tickets (vatican.va)
- 🏨 Hotel reservations: all 4 destinations
- 🏟️ Colosseum tickets (sells out months ahead)
Book 3–6 Months Out
- 🌋 Mount Etna guided tour
- 🎨 Uffizi Gallery Florence (timed entry)
- 🎭 Vatican Museums & Sistine Chapel
- 🏛️ Acropolis timed entry tickets
- 👨🍳 Sicilian cooking class
- 🍷 Frascati wine tour cantina booking
- 🚄 Florence Frecciarossa trains
- 🚄 Assisi train tickets
Book 2–4 Weeks Out
- 🌅 Athens Cape Sounion sunset tour
- 🌙 Rome night walking tour
- 🍫 Modica chocolate workshop
- 🚗 Car rental for Catanzaro day trip
💡 Travel Tips & Essentials
Everything you need to know for a seamless Mediterranean journey
Trip Insurance
You don’t need trip insurance until you need it. Most policies have a pre-existing condition waiver as long as the policy is purchased within 10 days of the initial payment for any portion of the trip. Cerchio Travel is a sales agent for a variety of insurance providers such as Allianz, Travel Guard, and Berkshire Hathaway. Read more on travel insurance here.
🌡️ Weather
Sicily in late June is HOT (30–35°C / 86–95°F). Athens similar. Bring lightweight linen, sun hat, SPF 50. Etna summit is 15–20°C cooler — pack a light jacket. Rome can be humid.
💶 Money
Italy and Greece use Euro (€). ATMs widely available. Notify your bank before travel. Contactless payment accepted almost everywhere. Budget: €30–50/day for food if eating local; €80–120 mid-range restaurants.
🚌 Getting Around Sicily
Rent a car or get a driver for the Ragusa and Catanzaro day trips — public transport to these destinations is inconvenient. Within Catania and Taormina, walk or take local buses.
🕐 Time Zones
Sicily/Italy = CEST (UTC+2). Greece = EEST (UTC+3). Remember: Athens is 1 hour ahead of Italy. Both are 6–7 hours ahead of Cincinnati (EDT).
📱 Connectivity
Get a TIM or Vodafone Italy SIM at Catania airport. Switch to a Greek SIM in Athens or use an eSIM (Airalo app recommended) for seamless coverage across both countries.
👟 Footwear
Pack comfortable walking shoes — you’ll walk 8–15km/day. The Acropolis and Colosseum involve uneven ancient surfaces. Sandals fine for evenings.
🎭 Papal Audience
Apply at vatican.va under “Office for Papal Audiences”. Free tickets. Arrive at St. Peter’s Square by 7:30 AM for good position. Dress code: covered shoulders and knees. Very moving even for non-Catholics.
✈️ Packing Essentials
Travel adapter (Type F for Italy/Greece, same plug), lightweight scarf (for churches), refillable water bottle, portable charger, EU travel insurance.
🍷 Food & Drink Highlights by Destination
🇮🇹 Sicily
Arancini, pasta alla Norma, granita, cannoli, Etna Rosso wine
🇬🇷 Greece
Souvlaki, horiatiki, baklava, Assyrtiko wine, Greek coffee
🇮🇹 Rome
Cacio e pepe, supplì, artichokes Roman style, tiramisu, Frascati white wine
🇮🇹 Florence
Bistecca alla Fiorentina, lampredotto sandwich, Brunello di Montalcino