< Designed Trips

The Trip

Uncover a few of the Cyclades’ most beautiful and authentic islands on this unique 10 day trip across the Aegean Sea. Developed to offer the perfect balance of stunning landscapes, pristine beaches, and idyllic Greek villages, this Designed Trip is the ideal escape for anyone seeking a genuine Greek island hopping adventure without all the crowds. Begin with a few days in the small, rugged island of Folegandros with its incredible cliffs and charming mountaintop Chora. Explore the island’s best beaches on a private, half-day boat tour, hike scenic trails across the windblown hills, stopping at tiny white chapels. Next, it’s a short ferry to Folegandros’ much larger neighbor, Sifnos, renowned for its traditional villages, incredible cuisine and ceramic studios. Stroll the coastal paths past the 17th century Chrisopigi Monastery, swim in the turquoise seas, and learn how to make traditional Manoura cheese at a local goat farm before sitting down to a delicious dinner at sunset. From here it's on to the tiny, circular island of Koufonisia, with its unbeatable beaches, rocky coves, and calm, see-through waters. Small enough to walk the circumference, long summer days here can be spent hopping over to the uninhabited Kato Koufonisi island, swimming at the crescent white sand beach of Paralia Pori, and taking in the sunset from the hilltop windmill. With three of the Cyclades' most spectacular hidden gems, this trip is for anyone who values authentic and off-the beaten path travel, with long lunches at family-owned tavernas, quiet walks past local goat farms, and hidden coves with lapping waves.

The Details

Price: 
  • From $2,449 per person
Duration:
  • 10 days 
Inclusions:
  • Highly-rated boutique hotels
  • Transportation within Greece
  • Small-group experiences
  • Curated Greece mini-guide
  • Trip preparation & support
Exclusions:
  • International flights to Greece
  • Meals & activities not listed
  • Travel insurance

Greece FAQs

Where should I fly in and out for this trip?
The trip starts in Folegandros and ends in Koufonisia, so you can either connect through Athens and take a long ferry or short flight, or Santorini or Mykonos, with short ferries from either island. Once you book the trip, we’re happy to provide recommendations for the most cost effective and efficient flights from your home town based on your travel dates.
When is the best time to visit Greece?
Greece has a long summer season, lasting from late May through early October. Expect sea water to be chilly through June and summer ‘Meltemi’ winds in July & August.
Will I have a hard time communicating?
Although far more Greek is spoken on these smaller islands, most people who work in tourism (especially at hotels and restaurants) will speak English. 
Will I need a car on these islands?
Folegandros and Koufonisia are both quite small and can easily be navigated by local bus or on foot. You could rent a car or ATV in Sifnos if you would like to explore the island more independently. 
What are ferries like in Greece?
​Ferries range from large, multi-storey vessels that carry cars and trucks, to smaller passenger only boats. The boat type typically varies based on the route and local schedules. We will always book the most efficient ferry available.
How active or adventurous is this trip? 
​If you enjoy hiking, swimming, and/or cliff jumping, this is a great trip for you. However, if you would rather relax on a boat or at the beach, these activities are absolutely not required.

The Itinerary

Folegandros
  • Day 1: Step off the ferry on to the stunning island of Folegandros and hop in a private transfer to your charming boutique hotel. Small but spectacular - 12 square miles in total - this island is truly one of the Aegean’s best hidden gems. With an intensely rugged landscape, a handful of beautiful beaches, and a cliffside Chora (main town) with views that rival its more famous neighbors, Folegandros packs a serious punch, offering all of the beauty and charm of the Greek Isles without the crowds. Your first day is free to explore the island, catch sunset from the awe-inspiring Church of Panagia, and sit down to an authentic Greek dinner in Chora.
  • Day 2: Wake up to views of the deep blue Aegean, a shaken freddo espresso, and freshly baked spinach pies. After a relaxed morning, head to the port of Karavostasis for a half-day boat tour to the island’s best hidden coves and most famous beaches, only reachable by sea. Experience the awe of the towering cliffs from the water as your captain expertly navigates the rocky coastline stopping for swims in protected turquoise coves. The rest of the afternoon is free to enjoy a long seafood lunch or before relaxing at the beach or by the pool. 
  • Day 3: With two main towns less than 2 miles apart and a bus that runs every hour to connect them, Folegandros is as laid-back and easy to explore as it gets in the Mediterranean. Covered with hiking trails that pass by little white chapels and lead to a series of cove-shaped beaches with shallow, warm water, today is wide open. Head to Agkali beach and dig your toes in the sand, swim in the calm, shallow waters, discover the endless views from Chora, or simply relax and embrace the art of doing nothing at all.

Sifnos
  • Day 4: After a quiet morning, a driver will take you to the port for a short afternoon ferry north to Sifnos. Larger than Folegandros, but still maintaining a wonderfully authentic appeal, Sifnos is known for having some of the best cuisine in the Cyclades, along with a coastline dotted with incredible beaches, and charming villages with traditional Cycladic architecture. Head south to Platis Gialos and the best part of the island where you’ll check into your boutique hotel before sitting down to dinner at one of the many great local tavernas. 
  • Day 5: Start your day with a bowl of thick Greek yogurt and endless sea views. The morning is free to discover the best beaches of Sifnos’ southern coast. Hike the coastal trail from Platis Gialos to the charming seaside village of Faros, stopping to swim in the clear turquoise waters along the way. Visit the 17th century Chrisopigi Monastery, set perfectly on a small peninsula extending out just south of Apokofto Beach. In the late afternoon, delve into the traditions of rural island life in Greece, visiting a local goat farm for a unique experience, feeding and milking the friendly goats, before learning how to make the local Manoura cheese. You’ll then sit down to an authentic homemade, farm-to-table vegetarian dinner, made with all of the delicious produce from the farm. 
  • Day 6: Wake up to a frothy freddo cappuccino and a free day ahead to explore more of the island. Continue beach hopping, or head inland to Kastro and the Church of Seven Martyrs, Sifnos’ most famous and picturesque village and church. Alternatively, if you’re feeling adventurous, consider a no-license boat rental for a day on the water cruising along calm waters and into idyllic coves along the coast. 
Koufonisia
  • Day 7: Enjoy your final morning on Sifnos before being picked up for the short drive to Kamares, where you’ll board an afternoon ferry to one of Greece’s most epic and under-the-radar islands, Koufonisia. It’s a longer journey to Koufonisia, as the ferry makes stops at larger and busier islands along the way, but you’ll get there by late afternoon with plenty of time to take a dip in the unbelievably blue waters of Ammos Beach, just steps from the port. Spend the evening getting settled in to your boutique hotel, grabbing dinner, and catching an unbelievable sunset from the island’s one main village. 
  • Day 8: Located just south of one of the Cyclade’s largest islands, Naxos, which acts as a barrier from the northerly Meltemi winds, Koufonisia benefits by having some of the calmest, most pristine waters in all of Greece. A tiny speck of land (just 2 square miles), the island can be traversed in an hour or so, but with all the best beaches to the south, everything is seemingly within arm’s reach. There’s no better way to spend a day here than to stroll leisurely along the coastal paths from beach to beach. Head northwest, to Paralia Finika and Paralia Italida, on your way to the famous crescent white sand beach of Paralia Pori. In the evening, stroll the tiny streets of the main village, sitting down to dinner at one of the hillside restaurants while gazing out to sea.
  • Day 9: Wake up to fresh, salty air and the sound of the sea. After a relaxed morning and delicious Greek breakfast, walk down to the port to catch a water taxi to the rugged, nearly deserted island of Kato Koufonisi, just 10 minutes away. There’s almost nothing on the island, aside from a local taverna, some goats, and a handful of mind blowingly beautiful beaches. Spend a couple of hours at Paralia Nero or Hawaii Beach before hopping back on the boat to the main island of Koufonisia. Stop by the crystal clear waters of Ludiko Beach before calling it a day and heading out to your last dinner in the Cyclades.
  • Day 10: Savor your final Greek Coffee and island breakfast, before checking out of your hotel and getting ready to head home. Choose to extend your island adventure, or add some time in Athens, before heading home.

Pricing & Inclusions

Boutique
​
​Exclusions
  • International flights to Greece
  • Meals & activities not listed above
  • Travel insurance

Boutique Pricing
  • From $2,449 per person

​*Pricing based on double occupancy and may vary depending on travel dates and total number of travelers. ​
Luxury Boutique
  • 3 hotel nights in Folegandros: ANEMI Folegandros, Anemomilos, or equivalent
  • 3 hotel nights in Sifnos: Eleonas Residences, Nival Boutique Hotel, or equivalent
  • 3 hotel nights in Koufonisia: Utopia Hotel, or equivalent
  • Private round-trip port transfers on each island
  • Ferry from Folegandros to Sifnos
  • Ferry from Sifnos to Koufonisia
  • Private Folegandros boat trip
  • Small-group Sifnos farm experience & dinner
  • Curated destination mini-guide
  • Trip preparation & support

Exclusions
  • International flights to Greece and home
  • Meals & activities not listed above
  • Travel insurance

Boutique Luxury Pricing
  • From $3,264 per person

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

Optional extras

  • Car or ATV rentals on each island

​​​---
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, check out more FAQs or send us an email.

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