⚡ Before You Go — Sicily & Milos Essentials
Flights In
Rebecca: Tallinn → Catania via Riga (airBaltic, ~€150). Bernard: Austin → Catania via Frankfurt (Lufthansa, ~$850). Both arrive June 12.
Flights Out
Catania → Athens (Aegean, ~€50–80/pp) then Athens → Milos (Olympic Air, ~€50–170/pp). Book ATH→MLO ASAP — small planes sell out fast.
WiFi & Work Setup
Get an EU eSIM (Airalo or Holafly) before landing. Hotel WiFi is your main work connection — confirm speed at booking. Bring a portable hotspot as backup for work days.
Currency
Euro (€) in both Sicily and Greece. Most restaurants take cards but keep €50–100 cash for smaller spots and taxis. ATMs widely available.
Getting Around Taormina
Taormina's centro storico is entirely walkable. Use the funivia (cable car, €3 each way) to reach Mazzarò Beach. Taxis to Catania airport ~€60–80. No car needed in town.
Work Schedule Note
9am–5pm CT = 4pm–midnight Sicily time. This means mornings are completely free for activities! Plan big dinners on free days (Days 1–3), quick lunches on work days (Days 4–6).
Arrive, Settle In & Your First Sicilian Sunset
You're both arriving from different continents — Rebecca from Tallinn, Bernard from Austin. Today is about getting to Taormina, checking in, and easing into la dolce vita. Don't overplan. The town is small enough that a casual evening stroll covers the highlights.
Catania Airport → Taormina
From Catania (CTA), take a taxi or pre-booked transfer to Taormina (~50 min, €60–80). Alternatively, the Interbus/SAIS shuttle runs to Taormina bus station (~€8/pp, ~1h15). Coordinate arrival times — if you land within an hour of each other, share the taxi.
Check into your hotel. Drop bags, freshen up, and head out for a first walk along Corso Umberto I — Taormina's main pedestrian street that runs the length of the old town.
Piazza IX Aprile & San Domenico Palace Aperitivo
Walk Corso Umberto to Piazza IX Aprile — Taormina's main square with panoramic views of the bay and Mt. Etna. Watch the sunset from here, then head to the San Domenico Palace (Four Seasons) for aperitivo on the terrace. Yes, it's splurge-priced, but the views are unreal and you're on vacation. Make a reservation — they don't allow walk-ins.
Ancient Ruins, Hilltop Villages & the Best Dinner of the Trip
Your first full free day — no work, no constraints. Pack in the big sights today: the iconic Greek Theatre with its Etna backdrop, the medieval hilltop village of Castelmola, the stunning beach at Isola Bella, and a fine dining experience that Reddit calls "the best meal of my entire trip."
Teatro Antico di Taormina (Greek Theatre)
Built in the 3rd century BC and expanded by the Romans, this is one of the most dramatically sited ancient theatres in the world. The stage frames Mt. Etna and the coastline — go early (opens 9am) to avoid tour groups and get the best photos. Allow 1–1.5 hours.
Castelmola — The Village Above Taormina
A 30-minute uphill walk (or quick taxi/bus) to this tiny medieval village perched above Taormina. The views from up here are even more spectacular — you can see Etna, the coast, and Taormina below. Wander the narrow lanes, peek into the ruined castle, and stop at the piazza for an espresso.
Isola Bella
Head back down to Taormina and take the funivia (cable car, €3) down to Mazzarò Beach, then walk south along the waterfront to Isola Bella — a tiny island connected to the mainland by a narrow sand strip. The water is crystal clear and the snorkeling around the island is excellent. Rent a beach chair or just lay out on the rocks.
After dinner: Walk back along Corso Umberto at night — the town is magical when the crowds thin out and the lights come on. Stop at Osteria Rosso Divino for a nightcap and an excellent wine selection.
Boat Day Along the Sicilian Coast
Your last fully free day before work starts tomorrow. Spend it on the water — a private or group boat tour along the Taormina coast is one of the top experiences in Sicily. Grottoes, hidden coves, Isola Bella from the sea, and lunch on the water.
Taormina Coast Boat Experience
Book a half-day or full-day boat tour departing from Mazzarò or Giardini Naxos. Options range from €50–80/pp for group tours to €300–500 for a private boat (4–6 hours). You'll see:
- Grotta Azzurra (Blue Grotto) — swim through sea caves with blue light
- Isola Bella from the water — entirely different perspective
- Hidden coves only accessible by boat
- Snorkeling stops in crystal-clear water
- Views of Taormina's clifftop position from below
Morning Beach, Afternoon Work 💻 Work 4pm–12am
First work day! But here's the silver lining of working US hours from Sicily: your workday doesn't start until 4pm local time. That gives you a full, glorious morning to hit the beach, have a proper Sicilian lunch, and still be at your laptop by 4pm. Work until midnight, sleep in, repeat.
Mazzarò Beach Morning
Take the cable car down to Mazzarò Beach. The morning is the best time — less crowded, cooler, and the light on the water is incredible. Rent a lounger (€10–15) or find a spot on the free section. Swim, read, do absolutely nothing. You've earned it before a work shift.
Work Session
Back to the hotel by 3:30pm. Set up your workspace — hotel terrace, room desk, or lobby lounge. If WiFi is shaky, tether to your eSIM hotspot. Work 4pm–midnight Sicily time (9am–5pm CT).
Morning Culture, Afternoon Work 💻 Work 4pm–12am
Another work day, another free morning. If you didn't fully explore the Greek Theatre on Day 2, go back — mornings here are quieter and the light is different. Then browse the shops and grab lunch before logging on.
Morning Walk: Villa Comunale & Hidden Taormina
Start with the Villa Comunale (public gardens) — a beautiful terraced garden with sea views, originally built by a wealthy English woman. Then wander the side streets off Corso Umberto that most tourists skip. Every turn reveals a new view, a tiny church, or a local nonna hanging laundry.
Pop into La Pignolata for exquisite cannoli — Reddit says they're the best in town.
Work Session
Same drill — hotel workspace, eSIM backup, work 4pm–midnight. Quick dinner option tonight:
Castelmola Morning Hike, Final Work Day 💻 Work 4pm–12am
Last work day and last full day in Taormina. Make the most of the morning with a hike up to Castelmola via the old footpath — different from the road you might have taken on Day 2. Then a farewell lunch at one of your favorites and one final work session.
The Saracen Footpath to Castelmola
Take the old footpath from Taormina up to Castelmola (~45 minutes uphill). It's a mix of stone steps and dirt paths through terraced hillsides with wildflowers and olive trees. The views get better with every switchback. Much more rewarding than driving.
At the top, reward yourself with a view from the castle ruins and an espresso in the piazza. Stop at Al Saraceno on the way back for the panoramic views.
Last Work Session & Pack
Work 4pm–midnight, pack between meetings. Tomorrow you're flying to Greece! Quick dinner tonight:
Arrivederci Sicily, Yassou Milos!
Travel day! Catania to Athens to Milos. It's a full day of transit but you end it on a Greek island. Allow plenty of time for connections — especially the ATH→MLO leg on small regional planes.
Catania (CTA) → Athens (ATH) → Milos (MLO)
Leg 1: Taxi Taormina → Catania Airport (~50 min, €60–80). Flight CTA → ATH on Aegean Airlines (~1h45).
Leg 2: Athens → Milos on Olympic Air or Sky Express (~45 min). If you booked separate tickets, leave at least 3 hours between flights for any delays and terminal transfers.
Alternative: If you prefer a scenic route, fly CTA→ATH, then take a ferry from Piraeus to Milos (high-speed ~3h, regular ~5–6h). Book at ferryhopper.com.
Arrive & Settle In
Milos airport is tiny — you'll be in your accommodation within 20 minutes. Drop bags, shower off the travel day, and head out for your first Greek dinner.
🏝️ What Awaits in Milos
Milos is a volcanic island in the Cyclades with over 70 beaches, colorful fishing villages, and some of the best seafood in Greece. Here's your preview — your full Milos itinerary will be a separate page.
🏖️ Don't-Miss Experiences
- Sarakiniko Beach — Lunar-white rock formations meeting turquoise water. The most photographed spot in Milos.
- Klima Fishing Village — Colorful boathouses (sirmata) carved into the cliff. Dinner at Astakas here is magical.
- Boat tour to Kleftiko — Inaccessible by land, these sea caves and rock formations are the island's crown jewel. Half-day tour essential.
- Plaka Sunset — Watch the sunset from Plaka's hilltop with cocktails at Utopia Café.
- Paleochori Beach — Volcanic hot springs on the beach + food cooked in volcanic sand at Sirocco.
- Konstantakis Winery — Local wine tasting with island varietals.
🍽️ Top Restaurant Picks for Milos
💰 7-Day Budget Breakdown (Per Person)
Estimated costs for Sicily portion. Milos budget will vary based on accommodation and activities.
| Category | Daily Estimate | 6-Night Sicily Total |
|---|---|---|
| 🍽️ Food (meals + snacks) | €40–80 | €240–480 |
| 🚕 Transport (taxis, cable car) | €10–20 | €60–120 |
| 🎟️ Activities (theatre, boat tour) | — | €100–250 |
| 🍷 Drinks / Aperitivi | €15–30 | €90–180 |
| 🛍️ Misc (souvenirs, tips) | €10–20 | €60–120 |
| Total (excl. hotel & flights) | €75–150 | €550–1,150 |
✈️ Flight Estimates
| Route | Airline | Est. Price |
|---|---|---|
| Tallinn → Catania (Rebecca) | airBaltic via Riga | ~€150 |
| Austin → Catania (Bernard) | Lufthansa via Frankfurt | ~$850 |
| Catania → Athens → Milos (both) | Aegean + Olympic Air | ~€150/pp |
| Total Flights | ~€1,300 combined |
💼 Remote Work Tips for Sicily
Working US hours (4pm–midnight local) from Taormina is actually ideal. Here's how to make it seamless:
- 📶 WiFi: Confirm hotel WiFi speed before booking. Villa Belvedere explicitly lists "high-speed WiFi" and is "business-friendly."
- 📱 Backup: Get an EU eSIM with decent data (Airalo 10GB ~€15). Use as hotspot if hotel WiFi drops.
- 🔌 Power: Italy uses Type C/L plugs. Bring a universal adapter with USB ports.
- 🍕 Work dinners: Stritfud (arancini), La Focaccia (sandwiches), and Villa Zuccaro (pizza) are all quick, cheap, and steps from your hotel.
- ☀️ Morning routine: Your mornings are 100% free. Beach, hike, culture, granita. Work doesn't start until 4pm. This is the dream schedule.