2-Week Greek Islands Tour Packages
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Insider tips: Recommended 2-week Greek Islands tour itineraries
Compiled by

MelissaGreek Islands travel expert at TourRadar
14 Days in Greece, incl. Athens and Santorini
A grand 14-day Greek adventure spans 18 destinations across 4 major islands. The itinerary takes you through Athens' Acropolis, Syros's coastal walks, Paros's Byzantine path, Naxos's mountain villages, and Santorini's caldera trail. Includes 13 breakfasts and English-speaking guide throughout.
- Days 1-2
Athens
Start in Athens and arrive early to adjust to the time change. Get to the Acropolis by 8am before cruise ship crowds fill the site. One traveler notes, "The Acropolis is best visited first thing - get there by 8am before the cruise ship crowds arrive." Wander through the Plaka district's narrow streets and stop at local tavernas. Book your Acropolis tickets online to avoid long entrance lines.
- Days 3-4
Syros
Take the morning ferry from Piraeus Port. Get there 45 minutes early since the port gets busy. The trip takes about 4 hours to Ermoupolis. Visit the medieval area of Ano Syros, where white buildings stack up to the Capuchin Church. The coastal walk from Kini to Galissas takes 2 hours at a moderate pace. Wear good shoes since the path is rocky.
- Days 5-6
Paros
Take a 90-minute evening ferry to Paros. Stay in Drios to be close to the beaches. A TourRadar reviewer shares about the ancient Byzantine road from Lefkes to Prodromos: "The path is lined with wild herbs and offers spectacular valley views." Walk early in the morning to stay cool. Join the cooking class at Hotel Anezina, which many visitors rate as their favorite activity.
- Days 7-8
Naxos
Take a 1-hour fast ferry to Naxos. Watch the sunset at the Apollo Temple portal. Visit authentic mountain villages like Halki and Moni. One traveler notes, "The Tragea Valley walk offers a completely different perspective of Greek island life." You can take an optional day trip to Delos and Mykonos for $50 plus a $12 entrance fee.
- Days 9-11
Santorini
Take a 2-hour morning ferry to Santorini. Stay in Fira for easy access to everything. The Fira to Oia hike takes 4 hours. Start at 7am to avoid crowds and heat. A reviewer advises, "Bring plenty of water and sun protection; there's no shade on the caldera path." Visit Akrotiri archaeological site early before tour groups arrive.
- Days 12-14
Santorini
14 Days in Greece, incl. Athens and Greek Islands
Three iconic Greek islands unfold over 14 days: Crete's ancient ruins and local bougatsa pastries in Heraklion, Naxos's Venetian castles and traditional citrus spoon desserts, and Paros's famous white marble heritage and 'Church of a Hundred Doors'. High-speed ferries connect islands, offering local dining experiences and stunning Aegean beaches.
- Days 1-2
Athens
Begin your trip with two full days in Athens. Visit the Acropolis early at 8 AM to avoid crowds and heat. You'll need 3-4 hours for the archaeological sites. Spend your afternoon exploring the Plaka neighborhood. Take the metro from the airport instead of a taxi - it's 45 minutes and costs €10, while taxis often get stuck in Athens traffic.
- Days 3-4
Peloponnese
- Days 5-7
Delphi & Meteora
The drive to Delphi through the mountains takes about 3 hours. Visit the Oracle site early before tour buses arrive. Head north to the Meteora monasteries. A traveler shares: "Getting there early is crucial - by 10 AM the summer heat and crowds can be intense. Wear closed shoes with grip as the stone steps can be slippery, and bring a light scarf to cover shoulders inside the monasteries." The monasteries close at 5 PM and some require climbing up to 300 steps. Visit the Thermopylae battlefield on your way back to Athens.
- Days 8-9
Crete
- Days 10-11
Naxos
- Days 12-13
Paros & Return
- Day 14
Depart
13 Day Greece Itinerary, incl. Athens and Greek Islands
The 13-day tour at approx. $250 per day showcases 5 key destinations: Athens' Acropolis, Mykonos' Little Venice, Santorini's caldera, Heraklion's Palace of Knossos, and Chania's Old Town. Includes daily breakfast, English guide in Athens, and stays at 4-star hotels like El Greco Resort.
- Days 1-2
Athens:
Land at Athens International Airport and head to the city center. Book your airport transfer ahead of time since Athens taxis aren't always reliable in peak season. On day two start early at the Acropolis. Get there by 8 AM to avoid crowds and heat. Wear shoes with good grip since the marble steps can be slippery. Visit the New Acropolis Museum in the afternoon when it's hottest outside - you'll appreciate the air conditioning.
- Days 3-5
Mykonos:
Take the morning ferry from Piraeus Port to Mykonos. The trip takes about 4 hours. Pick seats on the port side where there's less wind. Stay in Mykonos Town so you're close to everything. Want great photos of the windmills? Go at sunset but arrive early for a good spot. Paradise Beach fills up quickly so get there before 10 AM. Skip the tourist restaurants by the harbor. The best local food is in the family tavernas in Little Venice.
- Days 6-8
Santorini:
The fast ferry from Mykonos to Santorini takes about 2.5 hours. Stay in Fira or Imerovigli for amazing caldera views without the huge crowds of Oia. Walking from Fira to Oia takes about 3 hours. Go early and take lots of water. Book an afternoon catamaran cruise to the volcano when it's less busy than evening trips. Visit Perissa's black beach in the morning before the sand gets too hot.
- Days 9-11
Crete:
Ferry from Santorini to Heraklion is around 2 hours. Stay in Heraklion to be near Knossos Palace. Visit the palace before 9 AM to beat the tour buses. Get a rental car to see more of the island. Elafonisi Beach is 2.5 hours from Heraklion but its pink sand makes the drive worth it. Want to hike Samaria Gorge? Start at 6 AM for the best experience.
- Days 12-13
Return to Athens:
What people love about 2-week Greek Islands tours
- Greek Island Wanderer
The tour materials and routes chosen were just what we needed and the accommodations were generally just right - not fancy but nice people, clean and comfort room and all basics required. Just right for our demographic (65+).
- Athens & 5 Greek Islands Tour - 13 Days - Standard
Overall was very good I made a mistake in the first question. All accommodation was very good except Paros Island as the hotel was very far out of twin with no facilities around it. A 1.6Km walk along a windy dark road was very inconvenient. The hotel itself was fine. The Gotta hotel in Naxos was the friendliest hotel I ever stayed at excellent.
- Athens & 5 Greek Islands Tour - 13 Days - Premium
We highly recommend it!! In Athens we stayed very close to the historical center, the plaka area and syntagma square, clean comfortable room and wonderful hospitable staff!! The sunset is a must if you are visiting Santorini. Seeing the sun go down and the white houses on the mountain. A magical sight. We loved parikia with the many small streets in Greek style. The hotel in Syros was close to the beach, small and very clean with attention to detail. The drivers were always on time.