< Designed Trips

The Trip

Step away from the crowds of Santorini and Mykonos to explore some of the Cyclades lesser known islands. Take in the history of Athens, the otherworldly coastline of Milos, the white villages of Paros, and the dramatic landscapes of Crete as you cruise along the calm blue waters of the Aegean Sea. Begin in bustling Athens, the capital of Greece, the oldest city in Europe and the birthplace of democracy. Get acquainted with 3400 years of culture with a sights and bites tour, and step back in time 2500 years with a tour of the jaw-dropping Acropolis. Next, hop over to the island of Milos, the original home of the Venus de Milo statue, with its moon-like landscape and small island vibes before taking to the Aegean as you cruise to the small island of Paros. With its gorgeous beaches and incredible cuisine, it’s known as being one of the most romantic islands of the Cyclades, and an ideal place for a Greek cooking class and a hop over to the neighboring island of Naxos. The final stop on your Greek adventure is the expansive island of Crete where you can stroll through the Venetian harbor in Chania, explore wild beaches on a sailing trip, and visit ancient olive groves and wineries. 

The Details

Price: 
  • From $3,157 per person
Duration:
  • 12 days
Inclusions:
  • Highly-rated boutique hotels
  • Transportation within Greece
  • Small-group experiences
  • Curated destination mini-guide
  • Trip preparation & support

The Itinerary

Athens
  • Day 1: Welcome to the capital of Greece and the birthplace of democracy. Head to your boutique hotel in the historic center of Athens. In the afternoon, delve into Greek cuisine, culture and customs on a small-group food tour around the ancient city center.
  • Day 2: Rise and shine and enjoy a relaxed morning in one of the oldest cities in the world. Spend the morning exploring the quaint streets of Plaka, or opt to explore the award-winning Acropolis Museum. In the afternoon, step back in time with a small-group tour of the incredible hilltop Acropolis, built 2500 years ago. 

Milos
  • Day 3: Wake up to one of the world’s most iconic views. After breakfast, either relax on a 2+ hour ferry, or take a short flight southwest to the island of Milos, famous for being the location where the Venus de Milo statue (now displayed in the Louvre) was discovered in 1820. Pick up your rental car and navigate to your boutique island hotel. Check in, get settled and head to the beach for a cold beer, some mezze and an epic sunset after your travel day. 
  • Day 4: Awake to sunshine and the relaxed energy of this lesser-visited island. Milos is home to one of the most unique coastlines in the Cyclades, with chalky white cliffs, dramatic beaches, and natural Bentonite clay that is often used in local beauty treatments. The most impressive part of the island (on the west side) is largely inaccessible by car and best explored by boat, so head to the water to board a small-group cruise around the island. Enjoy a day of swimming, snorkeling, relaxing and exploring the turquoise water and otherworldly landscapes. 
  • Day 5: The morning is yours to explore. Maybe grab your towel, and a good book and hit one of the island’s 70 beaches. In the afternoon, swing by Kostantakis Estate, a local winery set in a natural volcanic cave, for a tour of the vineyard, cellars, and a tasting of 7 different wines along with a plate of appetizers and local cheeses. Depending on where you end up at sunset, find a table on the terrace of a relaxed taverna, and order a few mezze before making your way back to your hotel for a good night’s sleep.

Paros
  • Day 6: In the morning, make your way to the port and board the ferry to the island of Paros. This small island (13 miles by 10 miles) is best known for its beautiful whitewashed towns and incredible beaches. Once settled in your boutique hotel, the afternoon is yours to explore. Take a relaxing dip in the Aegean, order a couple cocktails and enjoy the sunset.
  • Day 7: Today is all about Greek food. On a half-day cooking class in the village of Ambelas, you’ll learn how to prepare a seasonal Greek meal, from appetizers to desserts, including tzatziki, marinated octopus, dolmadakia, loukoumades (Greek donuts) and more, all accompanied by local wine, of course.
  • Day 8: After a relaxed breakfast, it’s back to the ferry for a quick, 40-minute hop over to Naxos, the largest of all the Cycladic islands. Here you’ll find incredible archaeological ruins of the Castle and Apollo Temple, and beautiful beaches to discover. Spend the day swimming and exploring before taking the short ferry back to Paros in the early evening. 

Chania, Crete
  • Day 9: After a delicious Greek breakfast, relax on the 1 hour, 45 minute ferry to the impressive island of Crete. Take in the scenery of this (much) larger island as you drive to your boutique hotel in the seaside village of Chania. Explore the historic center and its famous Venetian harbor before heading out for a delicious Cretan dinner.
  • Day 10: Hop in your rental car and drive west to Kissamos Port. With a small group, board a 36-foot yacht and sail toward Balos Beach, one of the island’s most famous stretches of sand. Enjoy snorkeling, a local lunch, and cold drinks before returning to the port at the end of the day. If you’re feeling up for even more exploration, take a road trip south to one of the Crete's most famous locations; Elafonisi Lagoon or Samaria Gorge.
  • Day 11: In the morning, meet your guide who will take you on a full-day exploration of Cretan culture, food and drink. You’ll tour the Melissakis Olive Oil Mill, Dourakis Winery and honey bee hives of hilltop villages, sampling exquisite produce and feasting on a seasonal lunch along the way before returning home in the late afternoon ahead of your final Cretan dinner.
  • Day 12: Wake up and eat your final bowl of Greek yogurt. It’s the last day of your trip - head to the airport to hop on the plane for your flight home. Or if you’re not done traveling yet, ask us about adding another destination to your European adventure!

Pricing & Inclusions

Boutique
  • Athens, 2 hotel nights: InnAthens, The Marblous Athens, or equivalent
  • Milos, 3 hotel nights: Phos Milos, Psaravolada Hotel, or equivalent
  • Paros, 3 hotel nights: Paros Cape Suites, Parian Boutique Hotel, or equivalent
  • Chania, Crete, 3 hotel nights: Alcanea Boutique Hotel, Malmo Hotel, or equivalent
  • Small-group Athens food tour
  • Small-group Acropolis tour
  • Athens to Milos ferry or flight
  • Milos full-day sail
  • Milos winery experience
  • Milos to Paros ferry
  • Car rental on Paros
  • Small-group cooking class
  • Paros to Naxos RT ferry
  • Paros to Crete ferry
  • Car rental on Crete
  • Balos sailing trip
  • Full-day wine, olive oil and honey tour
  • Curated destination mini-guide
  • Trip preparation & support

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​Exclusions
  • Flights to/from Greece
  • Meals & activities not listed
  • Travel insurance

Boutique Pricing
  • From $3,157 per person

​*Pricing based on double occupancy and may vary depending on travel dates and total number of travelers. ​
Luxury Boutique
  • Athens, 2 hotel nights: Gatsby Athens, Coco-Mat Athens BC, or equivalent
  • Milos, 3 hotel nights: Cave Suites Milos, White Pebble Suites, or equivalent
  • Paros, 3 hotel nights: SeeSoo Paros, Hotel Senia, or equivalent
  • Chania, Crete, 3 hotel nights: Azade Chania, Scala de Faro, or equivalent
  • Private airport transfer
  • Small-group Athens food tour
  • Small-group Acropolis tour
  • Athens to Milos ferry or flight
  • Milos full-day sail
  • Milos winery experience
  • Milos to Paros ferry
  • Car rental on Paros
  • Small-group cooking class
  • Paros to Naxos RT ferry
  • Paros to Crete ferry 
  • Car rental on Crete
  • Balos sailing trip
  • Full-day wine, olive oil and honey tour
  • Curated destination mini-guide
  • Trip preparation & support

Exclusions
  • Flights to/from Greece
  • Meals & activities not listed
  • Travel insurance

Boutique Luxury Pricing
  • From $3,994 per person

*Pricing based on double occupancy and may vary depending on travel dates and total number of travelers. ​
Luxury
  • Athens, 2 hotel nights: Hotel Grand Bretagne, Monument Athens, or equivalent
  • Milos, 3 hotel nights: Domes White Coast, Milos Breeze, or equivalent
  • Paros, 3 hotel nights: Cove Paros, Andronis Minois, or equivalent
  • Chania, Crete, 3 hotel nights: Domes Zeen, Casa Delfino, or equivalent
  • Private airport transfer
  • Small-group Athens food tour
  • Small-group Acropolis tour
  • Athens to Milos ferry or flight
  • Milos full-day sail
  • Milos winery experience
  • Milos to Paros ferry
  • Car rental on Paros
  • Small-group cooking class
  • Paros to Naxos RT ferry
  • Paros to Crete ferry
  • Car rental on Crete
  • Balos sailing trip
  • Full-day wine, olive oil and honey tour
  • Curated destination mini-guide
  • Trip preparation & support

Exclusions
  • Flights to/from Greece
  • Meals & activities not listed
  • Travel insurance

Luxury Pricing
  • From $5,022 per person

​*Pricing based on double occupancy and may vary depending on travel dates and total number of travelers. ​

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​This Designed Trip was developed based on our personal travels, with local contacts, favorite hotels and authentic activities we've experienced first-hand.
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FAQs

WHAT IS A DESIGNED TRIP?
A Designed Trip is a pre-designed travel plan based on our personal, first-hand travel experiences in each destination. As they are pre-designed, our Designed Trips have been created as a turnkey travel option and can be booked and delivered in as little as one week. ​
CAN I MAKE ANY CHANGES TO A DESIGNED TRIP?
Absolutely! Pre-designed doesn’t mean there isn’t any flexibility. Whether you want to shorten or lengthen your trip, switch out a destination or change an activity, let us know. If, however, you want a trip built around your specific desires, a Custom Trip might be more appropriate. We can help you decide, so get in touch.
HOW LONG DOES THE PROCESS TAKE?
Once you’ve selected your Designed Trip and chosen between a Boutique, Luxury Boutique or Luxury experience, your trip can be booked and delivered in as little as one week. If you would like to make some changes to your trip, such as including an alternative activity, shortening or lengthening your trip, then this can take a bit longer.
HOW DO I KNOW HOW MUCH MY DESIGNED TRIP WILL COST?
Once you have decided on your Designed Trip, your dates, and any adjustments we will provide a personalized itinerary and pricing for your trip. We have included base pricing on each Designed Trip page to give you an idea as to what the final cost might be, but prices can fluctuate depending on time of year and any personalization. Get in touch and we can help.
If you have any other questions, feel free to check out more FAQs or send us an email.