A Sail Through Greece's Cyclades Islands


A Seven Day Voyage through 5000 years of Mediterranean culture

Start Date

June 11, 2021

End Date

June 18, 2021




We’re embarking on Bolt’s second week-long journey through the Cyclades Islands in Greece. Sailing from Paros, a 3 hour ferry ride from Athens, we’ll visit a half dozen islands to the west, with a focus on less visited (and less crowded!) ports and beaches on Antiparos, Sifnos, Milos, and Kimolos. This will be a voyage marked by natural anchorages in hidden coves, relaxing days at beachside clubs, architectural exploration through ancient towns, a couple of spirited nights out on the town, and lots (and lots) of delicious food. 

Waking up in the Mediterranean

Home to Feta cheese, Democracy, and more than 6000 islands, Greece is a jewel of Southern Europe. The Greek Archipelago comprises almost half of the country’s coastline, with each stretch of sand more spectacular than the last. This trip mixes plenty of laid back beach hangs with exploration of towns and cities. Sailing gives us the freedom to explore more secluded spots, and we visited a range of different sized islands.

Our pace will be moderate, balancing relaxation with the opportunity to see the best of the islands. Pulling into harbors in our floating hotel gives us a home base right in the middle of the action, typically in a marina at the center of town.

Exploring the Cyclades Islands

Southeast of Athens in the middle of the Aegean Sea, the 220 Cyclades islands are peaks of a submerged mountainous terrain, with the exception of two volcanic formations, Milos and Santorini. Many of the smaller islands are uninhabited; read, perfect for pulling up onshore to our own private beach.

Our Home For The Week

We’ll sail a mix of catamarans and monohulls through the Cyclades. These are the perfect platforms for our adventure, with a swimming deck off the stern, and space for our crew to sprawl. After a safety briefing and a short sail, we’ll come together the first evening for a welcome dinner ashore. Three or four more nights will be spent in port, where you’ll disembark to explore, deciding whether to venture solo or join newly made friends for a meal. Two more nights will be spent on anchor, in secluded natural harbors. The majority of breakfasts, lunches, and dinners will be prepared on the boat. All members will share in food prep and cleaning - we’ve found this brings the squad closer together.

Exploring the Cyclades

The Cyclades center around Delos, one of Greece’s most sacred sites, and have been inhabited since 4000 BCE. We’ll have ample time to dive into this history across the Archipelago, including a visit to the castle on Sifnos, ancient villages on Paros and Milos, and much more.

Hiking the Hills and Exploring Ancient Towns

The Cyclades provide ample opportunity for exploration, including from our departure port of Paros. Bring your boots for moderate hikes up 2000-3000 foot summits - your reward will be panoramic views extending out into the ocean. On other islands, walks through town will lead up steep staircases past white-washed houses and temples. And when we reach Milos, we’ll anchor just off the coast under stunning cliffs.

Sampling Nightlife and Traditional Greek Dining

Our voyage takes us past a variety of islands, where we’ll have the opportunity to enjoy the finest that Greek nightlife has to offer. It’s summer and time to celebrate! Throughout the trip, we’ll also sample plenty of delicious Greek cuisine, from dolmas and gyros to moussaka and spanakopita, along with just the right amount of ouzo, the traditional Greek spirit.

A Map of Our Itinerary

Departing and returning to the island of Paros, our itinerary took us to Antiparos, before sailing east towards the Lesser Cyclades Islands of Schoinousa and Koufonisia. From there, we navigated to Naxos, one of the largest islands in the region. Next was Delos, one of the most important historical sites in all of Greece, and then Syros, the capital of the region. After a two night stay on this larger island, headed back south to Paros to complete the journey.

Activity Level:

The pace of this trip will be mixed, with time to relax on the boat and in port, along with optional activities each day - join other Bolt members or hang back and explore at your own pace.

What’s Included:

  • your spot on a boat, based on double occupancy (ie, you'll be sharing a cabin and a double bed with someone of the same gender).
  • all food provisions onboard - delicious breakfasts, lunches and dinners.
  • a welcome dinner onshore
  • one activity per day (snorkeling, hiking, photography, kayaking, etc)
  • endless games of Spikeball© and Cards Against Humanity©.
  • an awesome, experienced captain to guide your boat
  • all fees associated with the boat, including taxes, port fees, and fuel

Not included:

  • flights to/from Greece
  • meals onshore (apart from welcome dinner). Budget an additional $100-200 to cover these meals on land.
  • alcohol and soft drinks, both on the boat and onshore

Getting There

This 7 day Experience is designed to showcase the best of the Cyclades Islands. It involves substantial amounts of sailing each day, alongside time to explore. Our route and islands we intend to visit aren’t set in stone; sailing in a small group gives us options to change course and itinerary in the event of adverse weather.

Direct flights to Athens are available from some US cities, as well as easy connections via major European cities. From Athens Piraeus port, it’s a 2.5 - 4 hour ferry journey to the island of Paros and our starting and ending points. Paros is at the dividing line between the North and South Cyclades. Consider extending your trip, venturing north to Mykonos and other islands.

Sample flights from $750 round-trip: NYC, SF, LA, DEN.

Bolt's trips are only available to members of the community who have gone through our Discovery Process and invested in our community. Learn more:

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