Itinerary for Greece & Greek Islands

Updated: January 8, 2026
Greece › Itineraries for First-Timers
By Santorini Dave • dave@santorinidave.com

My advice on where to stay

• Aegina – where to stay
• Andros – 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
• Poros – where to stay
• Rhodes – where to stay
• Santorini – where to stay
• Spetses – where to stay
• Zakynthos – where to stay

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

First Time Visitors – My Advice

• Greek Island hopping is the highlight of a trip to Greece. The ferries are fast, efficient, family-friendly, and fun.
• Best Places to Visit: Athens • Santorini • Mykonos • Naxos • Paros • Crete
• Best Tours: Santorini Wine Tours • Santorini Sunset Catamaran Cruises • Delos Day Trip (Mykonos) • Athens Food Tours
• Best Ancient Sites: The Acropolis (Athens), Delphi, Meteora, Delos, and the Peloponnese (Mycenae/Epidaurus) are the historical heavyweights.
• Best for Honeymoon: Santorini is the undisputed king of romance. For a quieter, chic alternative, try Folegandros or Milos.
• Best Restaurants: Athens has a world-class food scene. Naxos is famous for its local agriculture (potatoes, cheese) and farm-to-table tavernas. Sifnos is the dedicated “foodie” island.
• Best Beaches: Naxos has the best sandy beaches in the Cyclades. Mykonos has the best organized beach clubs. Milos has the most dramatic, unique coastlines (like Sarakiniko).
• Best Nightlife: Mykonos (World-famous clubs) • Ios (Younger, party vibe) • Athens (Rooftop bars & late-night buzz).
• 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.
• Best Hotels: Santorini (Caldera views), Mykonos (Beach luxury), and Athens have the best 5-star properties.
• How Many Days in Greece: For most tourists, I recommend 10 to 14 days. This allows for 2-3 days in Athens and 3-4 nights on two different islands (e.g., Naxos and Santorini).
• Can you visit for just 3 days? Yes, but limit yourself to one location. Do a city break in Athens OR fly directly to one island (like Santorini) and stay there. Do not try to island hop on a 3-day trip.
• Travel Tip: The “Shoulder Season” Sweet Spot
  Late May, June, and September are the best months. You get warm swimming weather without the crushing crowds of August.
  
  Note: Greek Easter is April 12, 2026. It is a wonderful cultural experience, but ferries and hotels will be packed. Book well in advance if traveling this week.
• Travel Tip: Sequence Your Islands Wisely
  The ferries run in a loop. A logical route (e.g., Athens → Paros → Naxos → Santorini) saves hours of travel time. Do not try to jump between unconnected groups (like Corfu to Santorini) without flying back to Athens.
• Travel Tip: Fly “Open-Jaw” to Save a Day
  Do not book a round-trip ticket to Athens. Instead, select “Multi-City” on your flight search: Fly Into Athens and Out of Santorini (or Mykonos/Crete). This saves you the hassle and cost of backtracking to Athens for your flight home.

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 and 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. You must fly between Athens and the islands to save time; relying on ferries for a 5-day trip eats up too much of your limited schedule.

 
• Day 1: Athens. Land in Athens. Spend the afternoon at the Acropolis Museum and sunset at the Acropolis (pre-book your time slot online). Dinner in Plaka. 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.