Greek Islands Escape

  • Sample Itinerary
  • Experiences
  • Pricing
  • Featured Hotels
  • Custom Quote

Voyage to the bewitching Cyclades Islands of Greece as you discover their Aegean allure from Santorini and Mykonos to Delos and Naxos. Boat along the sapphire waters of Santorini’s spellbinding Caldera and sip crisp Assyrtiko amongst ancient vines, before venturing to cosmopolitan Mykonos to traverse the whitewashed labyrinth of Mykonos Town and taste a slice of historic Mykonian life. Appreciate the sacred archaeological island of Delos and ruggedly beautiful Rineia by private boat, and journey to the lush landscapes of Naxos to be enchanted by its Cycladic charms.

Sample Itinerary

Day 1

Begin your Greek Islands escape with arrival to Santorini International Airport, on the island of Santorini. Be welcomed by your private chauffeur and set off for the spectacular village of Oia, a tumble of whitewashed dwellings carved majestically into the slopes of the Caldera. Your home away from home will be a sumptuous, five-star retreat renowned for its idyllic location offering stunning views of the sapphire waters of the Caldera. This evening you will be transported to a charming village to savor a gastronomic welcome dinner inspired by the flavors of the Cyclades, while toasting to Santorini’s legendary sunset from the unique vantage point of one of the island’s best restaurants.

Day 2

Today will be a salute to Santorini’s ancient viticultural heritage. Learn about the origins of winemaking on the island and experience some of its oldest vineyards with a private winery visit that will introduce you to native varietals and local cultivation practices, before delighting in a multi-course lunch highlighting seasonal produce and paired with the estate’s critically acclaimed wines reflecting Santorini’s volcanic terroir. Your day of wine appreciation will continue with a visit to one of the most contemporary wineries on the island, renowned for its exquisite vintages matched by scenic views. Enjoy an oenologist-led tasting flight showcasing the winemaker’s award-winning wines crafted from indigenous grape varietals, such as their exceptional Assyrtiko. The afternoon will lead you to a hidden gem of the island, a medieval village offering an authentic glimpse of historic Santorini. Dinner will be an elegant affair with a modern tasting menu revisiting traditional Greek flavors accented by the golden glow of sunset as twilight paints your panoramic view shades of tangerine and plum.

Day 3

This morning you will set off to appreciate local Greek culture through its most typical flavors and ancient heritage. A local family will welcome you into their traditional cave home for a chef-led cooking lesson of classic, home-style Greek recipes using locally sourced ingredients, and crowned with a convivial lunch of your handmade creations. You will next experience the vibrant town of Fira, the capital of Santorini, for some free time to discover its colorful clifftop swirl of shops, cafes and museums set high atop the Caldera. Your afternoon will be spent exploring the archaeological site of Akrotiri, one of the Aegean’s most important Bronze Age settlements, with the help of your Regional Ambassador. Destroyed during a volcanic explosion in the 17th century BC and thought to have inspired Plato’s description of Atlantis, Akrotiri’s intriguing past as an important port of the Minoan civilization can still be witnessed today as a result of its preservation in volcanic ash.

Day 4

Your sojourn to Santorini will continue with an exclusive day of private boating on the Aegean. During your captain-led journey, admire the striking volcanic landscapes of Santorini as you experience some of the finest secret beaches for swimming in the cobalt waters of the Caldera. Lunch will be a celebration of fresh fare prepared for you on board before enjoying more time to worship the sun and sea. The afternoon will lead you to breathtaking Ammoudi Bay, the historic fishing port of Oia, for a seaside sunset dinner of the freshest local catch at a beloved taverna. Following your chauffeured return to the hotel, enjoy a free evening to relax under the stars at your hotel’s breathtaking infinity pool overlooking the midnight blue waters of the Caldera.

Day 5

Your escape to the Cyclades will next take you from Santorini to the cosmopolitan island of Mykonos via an independently booked regional flight. You’ll be greeted in Mykonos by your private chauffeur and whisked away to your chic, five-star sanctuary with splendid sea views. Delight in free time to rejuvenate at your hotel’s luxurious spa or lounge at one of the property’s divine pools with views onto the azure waters of Mykonos. This evening you will savor an elegant dinner of contemporary creations at one of the island’s most sophisticated restaurants.

Day 6

Today be welcomed by your Regional Ambassador, an expert archaeologist, and set off by private boat for the sacred island of Delos, mythological birthplace of Apollo and Artemis, for an in depth exploration of its spectacular archaeological site. A compelling walk through the ages of Greek civilization, you will examine the island’s astonishing antiquities as you learn about its importance as a powerful center for trade, commerce and spirituality in the ancient Greek world. From Delos you will embark by private boat for a captain-led voyage to the ruggedly beautiful, uninhabited island of Rineia. Enjoy lunch hosted on board before spending the afternoon swimming in mesmeric turquoise waters and experiencing the island’s secluded beaches untouched by time.

Day 7

This morning you will appreciate a true slice of local life by visiting a traditional Mykonian village, far off the beaten track. From the village’s delightful square of white washed buildings and blooming bougainvillea, you’ll be transported to a family farm estate for a glimpse of how life once was for the historic inhabitants of Mykonos. Uncover the island’s agrarian heritage while visiting the estate’s vegetable garden, vineyard and stables, before rolling up your sleeves for a bread making experience using the farm’s traditional oven. Your time at the farm will culminate with a special lunch celebrating estate crafted wine and farm fresh produce. You will next experience stunning Chora, or Mykonos Town, with its whitewashed cubic dwellings and meandering stone lanes adorned with balconies, doors and shutters in vivid aqua, cobalt and crimson. Set off for a guided stroll along the town’s picturesque harbor and explore the old seafaring neighborhood of 18th century Little Venice, with its colorful seafront houses, before being inspired by sunset at the iconic Mykonos windmills. Your afternoon in Mykonos Town will end on a delicious note with dinner at a scenic fish tavern beloved for its fresh catch of the day.

Day 8

Luxuriate with a day of sun kissed fun at one of the island’s most sophisticated and serene beach clubs. Let the lush breezes of the island lull you into sublime repose as you enjoy your exclusive beach retreat and its privileged position along spectacular cerulean waters. Lunch will be light, fresh and accented by sea views at the beach club’s gourmet restaurant, before returning by chauffeur to your hotel in the afternoon, for continued relaxation at the spa or poolside.

Day 9

Today your Regional Ambassador will help you discover the gorgeous garden island of Naxos, rich with Cycladic charms and culinary treasures. Set off on a private boat voyage from Mykonos to Naxos, where you will admire its 6th century Portara, a marble gate that stands as a reminder of a former temple dedicated to Apollo. You will explore the medieval Chora of Naxos, an intriguing blend of Venetian and Cycladic architecture, followed by an examination of the island’s Mycenaean roots at a unique site. From the ancient soul of Naxos you will next discover one of its most enduring epicurean traditions, cheesemaking, with a visit to an artisan cheese farm to witness how island cheeses like graviera and mizithra are produced from local cow’s milk. Lunch will be a rustic countryside meal inspired by the fertile plains and verdant valleys of Naxos. Your afternoon will be spent enjoying some of the most pristine beaches of the island by private boat, before returning to Mykonos for the evening.

Day 10

Bid adieu to your serene island stay as you are transported by chauffeur to Mykonos International Airport for departure, or the next leg of your Encounter.

Experiences We Recommend

  • Private captain-led sailing day in Santorini’s spectacular Caldera
  • Vineyard visit to learn about ancient varietals and winemaker lunch with wine pairing
  • Expert-led exploration of Akrotiri archaeological site
  • Cave cooking experience hosted at home of local family
  • Archaeologist-led visit of sacred island of Delos
  • Private boating experience to island of Rineia
  • Cheese farm visit to discover local cheesemaking traditions on island of Naxos
  • Exclusive beach club experience on Mykonos


The minimum trip length for a CountryBred Encounter is 5 Days/4 Nights

Pricing for our Greece Encounters begins at:

  • $800-$950/per person, per day* based on double occupancy and a travel party of two
Small group pricing available for travel parties of four or more

*The final price of your custom tour will be determined by your travel party size, departure dates, trip length, amount of meals included, percentage of guided time requested, cities chosen in your itinerary and signature CountryBred excursions selected. This sample itinerary can also be crafted for solo travelers.

Encounters Include

  • Stays at five & four-star boutique luxury hotels
  • Chauffeured transport for touring & transfers
  • Private touring with professional local guides
  • Engaging activities led by cultural experts
  • Signature experiences with insider access
  • Regionally authentic dining
  • Traveler Welcome Package
  • Taxes & base gratuities

Read Client Reviews

  • Gay B.

    Alentejo to Lisbon
    Above and beyond our expectations for an amazing well organized adventure for 26!!
  • Mark W.

    From Castilla to Basque Country
    Our third CountryBred travel experience guided us through the rich cultural history, food, wine & unique culture throughout central/northern Spain. Our selected experiences coupled with the region/city ambassadors throughout our trip were exceptional and made our experience GREAT! (hotels too!)
  • Barbara R.

    Getaway to Tuscany and Northern Italy
    CountryBred thought of every detail for our trip. We didn't have to think about or worry about anything because they had it all covered by professionals every step of the way. From the chauffeurs, to the private boats, to the ambassadors who were extremely knowledgeable and spoke good English, to the amazing hotels, to the selection of restaurants and wines...WOW!

Crafting the Experience

Experiential travel takes time, passion and local ingredients to make something truly special.

Read more


We turn travel inspiration into unforgettable journeys. Begin the trip design process by filling out the form below and a CountryBred specialist will contact you to get your next great adventure underway.


  • CountryBred Encounters begin at $750-$1,000/per person, per day
  • The minimum trip length for a CountryBred Encounter is 5 Days/4 Nights
  • All CountryBred Encounters are land touring experiences only and do not include airfare
  • Groups of four or more are eligible for small group pricing


What do you appreciate most when you travel? (Check all that apply)

How would you best describe your ideal travel pace?

(Early start denotes 8:30 AM; Later start denotes 10:30 AM)

What has been one of your favorite hotel stays & why?

Will you be celebrating any special occasions while on your CountryBred Encounter? (Check all that apply)

Are there any other considerations that you feel are important for us to know?