Itinerary for Greece & Greek Islands

Updated: March 18, 2026
Greece › Itineraries for First-Timers
By Santorini Dave • dave@santorinidave.com

My advice on where to stay

• Athens – where to stay
• Corfu – where to stay
• Crete – where to stay
• Delphi – where to stay
• Hydra – where to stay
• Meteora – where to stay
• Milos – where to stay
• Mykonos – where to stay
• Nafplio – where to stay
• Naxos – where to stay
• Paros – where to stay
• Rhodes – where to stay
• Santorini – where to stay

The Acropolis and Plaka (my favorite neighborhood) in Athens. I recommend at least one full day in Athens for a first-time visitor to Greece.

First Time Visitors – My Advice

• Best Places for a First Trip: For most first-time visitors, I recommend some combination of Athens, Santorini, Naxos, Paros, and Crete. Add Mykonos if nightlife, beach clubs, and shopping are a priority.
• Best Destinations by Travel Style: Santorini is best for romance and iconic views. Naxos is best for sandy beaches and a relaxed pace. Mykonos is best for nightlife. Milos is best for dramatic scenery and boat trips. Crete is best for travelers who want a bigger island with beaches, towns, food, history, and road-trip freedom.
• Best Ancient Sites: The Acropolis in Athens is the essential first stop. Beyond Athens, the biggest historical highlights are Delphi, Meteora, Delos, and the Peloponnese (especially Mycenae and Epidaurus).
• Most Fun Activity: The Fira-Oia Hike along the caldera cliff in Santorini. It takes 3-4 hours, offers the best views in Greece, and it’s free. Boat tours in Mykonos, Milos, and Santorini are also a highlight.
• How Many Days in Greece: For a first trip, 10 to 14 days is ideal. That gives you enough time for 2 days in Athens plus 2 islands without turning the trip into a blur of ferry ports, packing, and hotel check-ins.
• Can You Visit for Just 3 Days? Yes, but only if you stay in one location. Spend the entire time in Athens or fly directly to one island and stay there. Do not attempt to island hop or combine Athens with an island on a 3-day trip.
• Do Not Try to See Too Much: This is the most common mistake first-time visitors make. Every island change takes time: checking out, getting to the port or airport, waiting, boarding, arriving, and getting to your next hotel. For most trips, fewer stops means a better vacation.
• Ferries vs. Flights: Ferries are a big part of the Greece experience and work best for shorter, direct island-to-island routes. Flights make more sense when time is tight, when you are traveling between far-apart island groups, or when you want to avoid giving up most of a day to transit.
• Sequence Your Route Wisely: A logical route saves time and stress. For example, Athens → Paros → Naxos → Santorini works well because the islands connect naturally. Avoid mixing far-apart regions on the same short trip unless you are flying.
• Best Months to Visit: Late May, June, and September usually offer the best balance of warm weather, good swimming, and manageable crowds. July and August are the busiest, hottest, and most expensive months.
• Leave a Buffer Before Flying Home: Do not plan a ferry arrival in Athens and an important international flight home on the same day. If your flight really matters, spend the last night in Athens or fly out directly from your final island if that routing works well.
• Open-Jaw Flights Can Save Time: Consider booking a multi-city ticket instead of a round-trip to Athens. Flying into Athens and out of Santorini, Mykonos, or Crete can save a full day of backtracking.
• When to Rent a Car: A car is very useful on Naxos and Crete, helpful for parts of Paros, and unnecessary in central Athens. In Santorini, a car can be helpful for sightseeing, but if you are staying on the caldera and doing tours, a few taxis or Ubers might make a rental unnecessary.

Greek Island Itinerary – The Basics

• Santorini – Amazing volcano views, boat tours, wine tours.
• Mykonos – Great beaches and nightlife.
• Crete – History, good beaches, authentic Greek towns, good hiking.
• Naxos – My favorite beaches in Greece, good hiking, history, traditional Greek villages.
• Paros – Great beaches, trendy dining, nightlife.
• Corfu – Great beaches and scenery, wonderful historic Corfu Town.
• Zakynthos – Good beaches and scenery (just avoid the package tourism).
• Rhodes – Great beaches and wonderful medieval Rhodes Town.
• Kos – Very touristy but still enjoyable. Good for biking.
• Less-touristy Greek Islands: Folegandros, Milos, Sifnos, and Syros are my favorites.
• I’ve ignored most of Mainland Greece for this itinerary but it’s a wonderfully diverse area that could easily fill two weeks of incredible sights and experiences.

5 Days in Greece

• Athens – 1 Full Day
• Santorini, Mykonos, Paros, or Naxos – remainder of time

1 Week in Greece

• Athens – 1 Full Day
• Mykonos, Paros, or Naxos – 3 Days
• Santorini – 3 Days

10 Days in Greece

• Athens – 1 Full Day
• Mykonos – 3 Days
• Paros or Naxos – 3 Days
• Santorini – 3 Days

2 Weeks in Greece

• Athens – 2 Full Days
• Nafplio or Delphi day trip – 1 Day
• Mykonos – 3 Days
• Paros – 2 Days
• Naxos – 2 Days
• Santorini – 4 Days

3 Weeks in Greece

• Athens – 2 Full Days
• Nafplio, Delphi, or Meteora – 1 or 2 Days
• Mykonos – 3 Days
• Paros – 2 Days
• Naxos – 3 Days
• Milos, Folegandros, or Sifnos – 2 Days
• Santorini – 4 Days
• Agios Nikolaos (Crete) – 2 Days
• Chania (Crete) – 3 Days

Example Itinerary: 5 Days in Greece: The “Express” Highlights

This is a fast-paced trip. For a 5-day trip, flying from Athens to the islands makes more sense, though a high-speed ferry can still work if you are already staying in Athens and the timings line up well.

• Day 1: Athens. Land in Athens. Visit the Acropolis with a pre-booked timed entry, then do sunset from a nearby viewpoint or rooftop. Sleep in Athens.
• Day 2: Fly to the Islands. Take an early morning flight (Aegean/Sky Express) to Santorini OR Naxos. (Skip Mykonos for a 5-day trip unless partying is the priority; Naxos/Santorini offer more variety).
• Day 3: Island Exploration. If Santorini: Do the Fira-Oia hike in the morning. Sunset wine tasting. If Naxos: Rent a car. Drive to the mountain villages (Halki, Apiranthos) and end at Plaka Beach.
• Day 4: Boat Tour. If Santorini: The Sunset Catamaran Cruise is mandatory. It is the highlight of the trip. If Naxos: Day trip to the small Cyclades (Koufonisia) or a lazy beach day at Agios Prokopios.
• Day 5: Fly Out. If Santorini, best to depart directly from there or fly back to Athens to connect with your flight home.

Example Itinerary: 1 Week in Greece: The “Classic” First-Timer

This itinerary balances history with the two most famous islands.

• Day 1: Athens. Arrive, Acropolis & Plaka. Sleep in Athens.
• Day 2: Ferry to Mykonos/Paros/Naxos. Take the morning ferry (Blue Star or SeaJets) to your first island. Tip: Choose Naxos or Paros if you want beaches and relaxation. Choose Mykonos if you want nightlife and shopping.
• Day 3: Island 1. Beach day. Evening in the Chora (main town).
• Day 4: Island 1. Boat trip (Delos from Mykonos, or Antiparos from Paros).
• Day 5: Ferry to Santorini. Take the midday high-speed ferry (SeaJets) to Santorini (~2 hours). Watch the sunset in Oia.
• Day 6: Santorini. Fira-Oia Hike and Catamaran Cruise.
• Day 7: Santorini to Home. Fly out of Santorini (via Athens or direct).

Example Itinerary: 10 Days in Greece: The “Perfect Balance”

This is the most popular timeline. It allows you to see Athens + 2 Islands without rushing.

• Day 1: Athens. Arrive. Rooftop dinner with Parthenon view.
• Day 2: Athens. Acropolis, Ancient Agora, and Food Tour.
• Day 3: Ferry to Naxos (or Paros). Morning Blue Star Ferry (enjoy the deck). Arrive by lunch.
• Day 4: Naxos/Paros. Beach day (Plaka or Golden Beach).
• Day 5: Naxos/Paros. Mountain villages (Lefkes in Paros or Filoti in Naxos).
• Day 6: Naxos/Paros. Day trip to nearby island (Antiparos or Koufonisia).
• Day 7: Ferry to Santorini. High-speed ferry to Santorini (1.5 – 2 hours).
• Day 8: Santorini. Fira to Oia Hike.
• Day 9: Santorini. Akrotiri ruins + Winery Tour + Sunset Cruise.
• Day 10: Fly Home. Depart from Santorini.

Example Itinerary: 2 Weeks in Greece: History & Hopping

Adding the mainland (Nafplio/Delphi) transforms this from a beach trip into a cultural odyssey.

• Day 1: Athens. Arrive.
• Day 2: Athens. Sightseeing.
• Day 3: Day Trip (Nafplio or Delphi). Recommendation: Rent a car for the day and drive to Nafplio (2 hours). It is the most beautiful town on the mainland. Stop at the Corinth Canal and Mycenae on the way. Return to Athens or sleep in Nafplio.
• Day 4: Ferry to Mykonos. Morning ferry from Piraeus or Rafina.
• Day 5: Mykonos. Beaches & Nightlife.
• Day 6: Mykonos (Delos). Morning trip to Delos ruins. Afternoon ferry to Paros (45 mins).
• Day 7: Paros. Naoussa dinner and nightlife.
• Day 8: Paros (Antiparos). Day trip to Antiparos.
• Day 9: Ferry to Naxos. Short ferry (30 mins).
• Day 10: Naxos. Explore the interior villages and Halki.
• Day 11: Naxos. Beach day.
• Day 12: Ferry to Santorini. High-speed ferry (1.5 hours).
• Day 13: Santorini. The classics (Hike, Views).
• Day 14: Santorini. Boat tour & Winery. Fly out next morning.

Example Itinerary: 3 Weeks in Greece: The “Grand Tour” (Cyclades + Crete)

This route flows strictly North-to-South (Athens -> Western Cyclades -> Central Cyclades -> Santorini -> Crete). The Meteora is a mainland highlight.

• Day 1-2: Athens. Arrive. Acropolis and Plaka.
• Day 3-4: Meteora (Mainland). Train or tour to Meteora. Stay overnight. Return to Athens.
• Day 5: Ferry to the Western Cyclades. Take the morning ferry from Piraeus to Milos, Sifnos, or Folegandros. Why: These islands are on the direct “Western” ferry line from Athens. They are quieter and offer a gentle start to island life.
• Day 6-7: Western Cyclades. Explore your chosen island (e.g., Sarakiniko Beach in Milos).
• Day 8: Ferry to Naxos or Paros. Take the high-speed ferry (SeaJets) across to the Central Cyclades (~1.5 hours). Note: This cross-line connection is easy in summer.
• Day 9-11: Naxos or Paros. Enjoy the sandy beaches and lively villages. (Pick one; trying to do both and Mykonos and Santorini and Crete is too much).
• Day 12: Ferry to Mykonos (Optional). If Mykonos is a must, do a 1-night stop here. If not, add these days to Crete.
• Day 13: Ferry to Santorini. High-speed from Naxos/Paros/Mykonos to Santorini.
• Day 14-16: Santorini. The climax of the Cyclades. Caldera views, wine, and sunset.
• Day 17: Ferry to Crete. Take the high-speed ferry (SeaJets/Minoan) to Heraklion (2 hours). Pick up a rental car. Why this works: You are moving south, leaving the Cyclades behind for the grand finale.
• Day 18: Heraklio & Knossos. Visit the Palace of Knossos and the Museum. Drive to Chania (2.5 hours) to base yourself for the rest of the trip.
• Day 19-20: West Crete (Chania). Explore the Old Town, Balos Lagoon, and Elafonisi.
• Day 21: Fly Home. Fly directly out of Chania (CHQ) or Heraklio (HER) to a major European hub (London/Frankfurt/etc.) for your flight home. Do not fly back to Athens unless necessary.

Greece Itinerary: Top 5 Highlights

1. The Santorini Caldera

Santorini is the most magical and unique Greek island. A Santorini boat tour through the caldera is a highlight of any trip to Greece.

2. The Beaches of Naxos (and Many Greek Islands)

There are many Greek islands with fantastic beaches (Mykonos, Milos, Paros, and Crete) but no island has a better beach scene than Naxos.

3. The Parthenon and Acropolis in Athens

Athens has lots to see in a compact area. The Plaka, Acropolis and Acropolis Museum are where you should spend most of your time.

4. The Beach Clubs & Nightlife of Mykonos

Mykonos is the place to go for an ideal mix of great beaches, beach clubs, and nightlife.

5. The Town of Chania in Crete

Chania is a charming town on the island of Crete (the largest Greek island). Both Chania and Heraklio have many international flights to major European cities, making Crete a great place to start or finish your trip. And Crete has many amazing tours.