2-Week Greek Islands Tour Packages
Dreaming of a little Greek island hopping? Check out Santorini’s volcanic scenery, whitewashed churches and blue domes, seafront tavernas, and Golden Beach snorkeling. Before you venture from the mainland, visit Athens’ Acropolis, Meteora monasteries, and Olympia tzatziki making. Two weeks covers multiple islands and you’ll see a slower pace that’s truly captivating. You’ll easily see why people return every year.
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
Join the volcano boat tour ($70) with hot spring swimming. Explore quieter villages like Megalochori and Pyrgos away from cruise ship crowds. Book the 6:30pm wine tasting at Santo Wines to end your trip with a sunset view.
13 Days in Greek Islands, incl. Athens and Santorini
A captivating 13-day adventure through Athens and 4 islands: Mykonos, Santorini, Crete (3 nights), and Rhodes. Features Acropolis tour, Oia sunset, Knossos Palace, and Rhodes' medieval town. All transfers and accommodations included at approx. $420 per day.
- Days 1-2
Athens
Begin in Athens at the Acropolis. Get there before 8:30 AM to avoid crowds and heat. Wear shoes with good grip since the marble steps can be slippery. After seeing the Parthenon, visit the Acropolis Museum. A recent visitor shared: "The glass floors showing ancient ruins beneath your feet add an incredible dimension to the experience."
- Days 3-4
Mykonos
Take the morning ferry (4 hours) from Piraeus port to Mykonos. Stay near Little Venice for easy access to both beaches and nightlife. Walk through the white lanes of Matogiania during the day but save your shopping for cooler evening hours. Visit south coast beaches like Platis Gialos in the afternoon when the strong meltemi winds usually calm down.
- Days 5-6
Santorini
A 2.5-hour ferry ride takes you to Santorini. Stay in Fira or Imerovigli to enjoy caldera views without Oia's crowds. If you want to watch the famous Oia sunset, get there an hour early. According to one visitor: "The best views aren't from the castle ruins where everyone crowds—walk a bit further along the caldera path for equally stunning vistas with more breathing room."
- Days 7-9
Crete
Take the morning ferry (2 hours) to Heraklion, Crete. Visit Knossos Palace early before tour groups arrive and spend time at the Archaeological Museum. Set aside a full day for the old towns of Rethymno and Chania with their beautiful Venetian harbors. Local buses work well but can get packed. Renting a car gives you more freedom to explore.
- Days 10-11
Rhodes
Fly to Rhodes from Heraklion (1 hour). Book a hotel in or near the medieval Old Town. The Street of Knights looks best in early morning or late afternoon light. Walking the walls takes some effort but offers great views of the city.
- Days 12-13
Athens
Fly back to Athens. Use your last full day to visit places you missed like the Temple of Olympian Zeus or the Plaka neighborhood. Stop by the Central Market in the morning to see local life and try Greek specialties.
Athens & 5 Greek Islands Tour - 13 Days - Standard
This 13-day island-hopping trip takes you through Athens and five Cycladic islands including Paros, Naxos, Ios, Santorini, and Syros with 12 nights in standard hotels. The Venetian Castle sits in Naxos's old town, while Magganari beach in Ios offers a great spot to relax. A sunset cruise in Santorini sails past the volcanic crater of Nea Kameni. Daily breakfasts come included, along with all ferry tickets connecting the islands, with most bookings happening in September.
Greek Islands 14 Day Tour Packages You'll Love
Greek Island Wanderer
Mykonos, Santorini, Crete & Rhodes: 13-Day Island Hopping Tour
Athens & 5 Greek Islands Tour - 13 Days - Standard
Classical Greece Plus Greek Island Adventure
Greek Isles Adventure with Crete
Gems of Greece: Athens, Naxos & Crete (2026)
Mykonos, Santorini, Crete & Corfu: 13-Day Island Hopping Tour
Athens - Naxos - Santorini - Crete ( Aegean Gems )
13 Days in Greece from Athens To Rhodes.
Incredible Crete, Santorini, Myconos (small group, Discovery, Culture, food)
What people love about 2-week Greek Islands tours
- Greek Island Wanderer
Our tour guide, Peter, was amazing! He was well organized and extremely knowledgeable! He was always alert to our needs; always willing to help us in any way. Peter's great sense of humor added to our fun! Our tour group all felt that the descriptions of the walks were not at all accurate! For example, an easy coastal walk was actually a pretty challenging hike on uneven, rocky, hilly terrain. It would be helpful if you provided 1-5 activity level ratings for the "walks".
- Athens & 5 Greek Islands Tour - 13 Days - Standard
good choice of hotels, and excellent pick-ups to and from ports. Thank you
- Greek Island Hopping | Semi guided Tour | 11 Days
Very well organized, didn’t have to worry about getting to and from hotels or the islands we visited.