• Welcome to The Olive Odysseys
  • Call us at 1-440-804-5062
  • Contact Us
  • Luxury Guided Small-Group Tours
  • Customized Private Tours
  • Personalized Trip Planning
  • Privacy Policy
1-440-804-5062
  • Welcome to The Olive Odysseys
  • Call us at 1-440-804-5062
  • Contact Us
  • Luxury Guided Small-Group Tours
  • Customized Private Tours
  • Personalized Trip Planning
  • Privacy Policy
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Magical Greece
May 2026
​
Your dream Greek adventure awaits!
Sun-drenched islands, ancient wonders and hidden gems.
Choose your itinerary and make this May, unforgettable.

Itinerary #1
​
Day One – May 13
Depart the U.S. Overnight on your flight.

Day Two – May 14 | Athens
Arrive in Athens. Private luxury transfer to your hotel. Afternoon private, skip-the-line guided walk of the Acropolis. Overnight in Athens.

Day Three – May 15 | Aegina, Poros
Private driver to the Temple of Aphaia for a guided visit. Midday ferry to the island of Poros. Check in and enjoy beachside time. Overnight on the Island of Poros.

Day Four – May 16 | Hydra
Day trip to the island of Hydra with a private guided tour. Ferry transfers included. Return to Poros in the evening. Overnight on the Island of Poros.

Day Five – May 17 | Epidaurus & Nafplio
Private driver and ferry to the mainland. Visit the Epidaurus Theatre and Asclepion with a private, skip-the-line guided tour (UNESCO). Continue to the charming town of Nafplio. Overnight in Nafplio.

Day Six – May 18 | Mycenae & Nemea
Visit the UNESCO World Heritage Site of Mycenae and the region of Nemea. Enjoy a wine tasting and light lunch at a renowned winery, with an optional olive oil tasting. Overnight in Nafplio.

Day Seven – May 19 | Mykonos
Private transfer back to Athens and flight to Mykonos. Airport pickup and transfer to your luxury hotel. Time to enjoy the spa. Dinner recommendations and reservations provided. Overnight on the Island of Mykonos.

Day Eight – May 20 | Delos
Semi-private guided tour of Delos, including boat transfers and an expert guide. Afternoon free for shopping, beach time, or relaxing by the pool. Overnight on the Island of Mykonos.

Day Nine – May 21 | Santorini
Private transfer to the port and ferry to Santorini. Private pickup and transfer to your hotel in Oia. Afternoon at leisure. Overnight on the Island of Santorini.

Day Ten – May 22 | Santorini
Walk along the caldera from Oia to Fira. Optional private catamaran cruise to the volcano, hot springs, and island beaches. Overnight on the Island of Santorini.

Day Eleven – May 23 | Athens
Private transfer to the port and fast ferry to Piraeus. Transfer to your Athens hotel. Afternoon private, skip-the-line guided walk of the Acropolis. Overnight in Athens.

Day Twelve – May 24 | Delphi
Morning bus trip to Delphi. Semi-private guided tour of the archaeological site and museum. Return to Athens for a curated self-guided foodie walk. Overnight in Athens.

Day Thirteen – May 25 | Athens
A day at leisure. Choose from a cooking class, Cape Sounion, museums, shopping, or café hopping. We’re nearby to assist. Overnight in Athens.
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Day Fourteen – May 26
Private transfer to the airport for your return flight to the U.S.

Itinerary #2
​
​
Day One – May 13
Depart the U.S.
​
Day Two – May 14 | Athens
Arrive in Athens. Private luxury transfer to your hotel. Afternoon private, skip-the-line guided walk of the Acropolis. Overnight in Athens.

Day Three – May 15 | Delphi
Travel by private driver to Delphi with scenic stops along the way. Check into your hotel in the village center and enjoy lunch at your leisure. Afternoon private guided tour of the Delphi ruins and museum with skip-the-line tickets. Dinner recommendations provided. Overnight in Delphi.

Day Four – May 16 | Meteora
After breakfast, depart for Kalambaka and Meteora. Lunch en route. Afternoon guided tour of the monasteries with a local expert offering insider insight. Dinner recommendations provided. Overnight in Meteora.

Day Five – May 17 | Thessaloniki
Morning visits to additional Meteora monasteries. Afternoon transfer to Thessaloniki, one of Greece’s most distinctive cities. Check into your harborside hotel and enjoy sea views and free time. Overnight in Thessaloniki.

Day Six – May 18 | Mykonos
Fly to Mykonos. Private airport transfer to luxury accommodations in the heart of town. Explore the winding back streets, shop, and enjoy the island’s vibrant dining scene. Overnight on the Island of Mykonos.

Day Seven – May 19 | Mykonos
A full day at leisure. Relax poolside or spend the day at iconic beaches such as Paradise or Super Paradise. We’ll assist with any plans you choose. Overnight on the Island of Mykonos.

Day Eight – May 20 | Mykonos & Santorini
Enjoy a relaxed morning before your ferry to Santorini. Private transfers at both ports. Check into your caldera-view hotel, then relax by the pool or explore the shops. Dinner recommendations provided. Overnight on the Island of Santorini.

Day Nine – May 21 | Santorini
Weather permitting, enjoy a catamaran cruise through the caldera and hot springs. Sail the Aegean, visit hidden beaches, and enjoy food and drinks on board. Overnight on the Island of Santorini.

Day Ten – May 22 | Santorini
Choose between a winery tour with tastings or a hands-on cooking class. We’ll handle all arrangements. Overnight on the Island of Santorini.

Day Eleven – May 23 | Athens
Fly back to Athens. Private transfer to your hotel in the historic center. Afternoon private, skip-the-line guided tour of the Acropolis. Dinner at a restaurant with Acropolis views. Overnight in Athens.

Day Twelve – May 24 | Athens & Cape Sounion
Private drive along the Athens Riviera to the Temple of Sounion. Guided visit of the site. Lunch nearby. Afternoon free in Athens for spa time, shopping, or cocktails. Overnight in Athens.

Day Thirteen – May 25 | Athens
A final day at leisure. Options include museums, shopping, a cooking class, or café hopping. We’re nearby to assist. Overnight in Athens.
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Day Fourteen – May 26
Private transfer to the airport for your return flight to the U.S.
Itinerary #3

Day One – May 13
Depart the U.S.

Day Two – May 14 | Athens
Arrive in Athens and transfer by private luxury coach to your hotel. Enjoy a private, skip-the-line guided walk of the Acropolis. Overnight in Athens.

Day Three – May 15 | Athens & Delphi
Travel by bus to Delphi for a semi-private guided tour of the archaeological site and museum. Return to Athens for a curated self-guided foodie walk. Overnight in Athens.

Day Four – May 16 | Athens
A flexible day to explore at your own pace—options include a cooking class, Cape Sounion, museums, or shopping. We are nearby to assist. Overnight in Athens.

Day Five – May 17 | Mykonos
Private transfer to the port and fast ferry to Mykonos. Transfer to your hotel, time to enjoy the spa facilities, and curated dinner recommendations. Overnight in Mykonos.

Day Six – May 18 | Mykonos & Delos
Today, visit the sacred island of Delos, once considered the center of the ancient world. Enjoy a guided exploration of this extraordinary archaeological site before returning to Mykonos for a relaxed afternoon and evening. Overnight in Mykonos.

Day Seven – May 19 | Crete (Heraklion)
Private transfer to the port and fast ferry to Heraklion, Crete. Settle into boutique accommodations near the Venetian harbor and enjoy dinner at a traditional Cretan taverna. Overnight in Heraklion.

Day Eight – May 20 | Crete (Heraklion)
Private guided visit to Knossos with skip-the-line tickets. Evening free with restaurant recommendations provided. Overnight in Heraklion.

Day Nine – May 21 | Crete (Rethymno)
Private transfer to Rethymno with scenic stops along the way. Settle into a beachside hotel and enjoy the medieval old town. Overnight in Rethymno.

Day Ten – May 22 | Crete (Rethymno)
Guided walk through Rethymno’s Venetian harbor and old town, with time for shopping and cafés. Cocktails by the sea, followed by dinner and an evening beach walk. Overnight in Rethymno.

Day Eleven – May 23 | Crete (Chania)
Transfer to Chania with an olive oil tasting en route. Guided exploration of Chania’s Old Town, with time for shopping, cafés, and swimming. Overnight in Chania.

Day Twelve – May 24 | Crete (Chania)
A full day to explore Crete with a private driver—choose from beaches, hiking Samaria Gorge, boat excursions, or local food and wine experiences. Overnight in Chania.
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Day Thirteen – May 25
Private transfer to the airport for your return flight to the U.S.



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The Olive Odysseys 
46 Shopping Plaza
​Drive # 107
Chagrin Falls, Ohio
​44022 U.S.A
Phone: ​1-440-804-5062
​
[email protected]
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A member of the
​American Society of Travel Advisors
  • Welcome to The Olive Odysseys
  • Call us at 1-440-804-5062
  • Contact Us
  • Luxury Guided Small-Group Tours
  • Customized Private Tours
  • Personalized Trip Planning
  • Privacy Policy