Greek Islands Catamaran Sail with Captain and Hostess – Options for Athens and Crete

10 Days

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May 31, 2024 - June 9, 2024 Guaranteed $3,995 USD
8 Available

We sail the magical Greek Islands leaving from Paros and jumping from island to island in the Cyclades on our private 8-passenger luxury catamaran. We’ll have our own captain and our hostess/guide/chef. You and your captain map out an itinerary. In the pre-trip we explore the Greek mainland, including Athens and Delphi. We are also offering a pre-trip to Athens and a post-trip to the incredible island of Crete.


This is the trip that put us on the map, and this tour brings visitors back year after year. We have our own private 46-foot Lagoon catamaran. This luxury ship has 4 berths for 8 passengers, and plenty of space for gathering both inside and out. We’ll be able to sail into small coves and isolated beaches to explore the many sights the Cyclades has to offer.

On day one you’ll meet with the captain and map out your itinerary. Dying to see Mykonos? Tell him to set sail! You’ll also meet with your hostess/travel guide. She’ll ask about your food and alcohol preferences. Our recommendation: let her pick everything for days of authentic Greek meals. Breakfast will be a huge spread, and as you sail to the next island, lunch may be a Greek salad with local fish. You may decide to have dinner at one of the islands’ great tavernas and feast on the fresh catch of the day. Your hostess will be happy to arrange such meals ashore. Some of the islands even have an active nightlife if that’s your thing. Every day will be a postcard moment, and you’ll bring back memories to cherish for a lifetime.

Note: Ship cabins are small, and each cabin has the equivalent of a queen bed and a private bath with shower. We are happy to pair you with a potential roommate, but please be aware of the space limitations. And unfortunately we cannot accommodate single room upgrades. Please contact us with questions.


Day 1 :

Depart for overnight flight, arriving in Athens the next morning.

Lunch, Dinner

Arrive in Athens and transfer to the island of Paros, Greece. We will take a ferry from Athens to Paros as it is easiest. In the afternoon, meet with the captain and map your island itinerary. Meet with the cook to create a shopping list for her. We will stay in Paros the first night, and then set sail the next morning.

Breakfast, Lunch, Dinner
Days 3 - 8 :
The Cyclades

Your captain will follow the island itinerary you have requested. Recommended itinerary includes Antiparos, Sifnos, Milos, Folegrandos, Sikinos, Naxos. Arrive back in Paros on Friday evening.

Breakfast, Lunch

Disembark and transfer to Athens via ferry and then home.


What's Included

  • Due to fluctuating airfares, air will be booked for you at the prevailing rate
  • Most meals per itinerary
  • Accommodations for 9 days/nights
  • All tickets and passes for all tours and activities
  • Airport Transfers to/from Athens airport


Is a visa required to travel to Greece?

No, U.S. citizens do not need a visa to spend up to 90 days for business or tourism purposes.

What currency is used in Greece?

Greece is part of the European Union and uses the Euro.

Does Greece have any COVID restrictions?

No, all COVID travel restrictions have been removed. You may enter the country with no test or need to show a vaccination certificate. American citizens do not need to test or show documentation to reenter the US.

What type electrical outlets are used in Greece?

Greece uses the standard round two-prong outlet in use throughout the European Union.

What will the weather be like?

The average temperature in the Cyclades is in the mid to upper 70s. It is very moderate this time of year.

Pre & Post Trip Options

Day 1 – Leave home for an overnight flight to Athens.

Day 2 – Arrive Athens and transfer to the Acropolis Palace Hotel for 3 nights with spectacular views of the Acropolis from the rooftop restaurant. Relax, and explore Athens on your own, prior to a group welcome dinner at the hotel.

Day 3 – Today we take an all-day tour of ancient Athens, including the Acropolis and the Parthenon, the Acropolis Museum, and other ancient archeological excavations.

Day 4 – We journey today outside of Athens, probably to Delphi where you can ask the oracle your own questions about the future and visit the very temple where she sat. We can also discuss a different outing too.

Day 5, Saturday – As our time in Athens ends, we take a ferry to join our other travelers in Paros.

$1,200 double occupancy
$400 single occupancy upgrade

What’s Included:
3-nights lodging near the Acropolis
Tour of ancient Athens
Day tour to Delphi (or other outing depending on travelers’ choice)
Airport / Ferry transfers
Breakfast each day

Post-trip – Crete – 4 days, 3 nights

Day 1 – After disembarking in Paros we’ll head to Crete for 3 days of relaxation on one of the most interesting islands in the Aegean. After transferring to our boutique hotel in Rethymno, we’ll have the afternoon to explore on our own. That evening we’ll get together for a group dinner.

Day 2 – Today we will explore the charming streets of Chania Old Town. Stroll through the narrow alleys lined with Venetian and Ottoman architecture. We will visit the Venetian Harbor and admire the iconic Venetian lighthouse.

After lunch at a local taverna, we will visit the Archaeological Museum of Chania to learn about Crete’s rich history, including the Minoan civilization.

The evening will include a wine tasting and paired dinner prepared at our hotel.

Day 3  – There are two choices for today, one that is more adventurous and one that is more relaxed.

Option 1: Hike Samaria Gorge ($100 extra cost)

We will head out early, as this is a full-day excursion. Our local guide will pick us up from our hotel, and we will take a scenic drive to Omalos Plateau, the starting point for the Samaria Gorge hike. The drive itself offers stunning views of Crete’s mountainous terrain. We will also learn more about the Samaria Gorge, its history, geology, and the unique ecosystem it hosts.

We will begin our hike from the Omalos Plateau entrance. The trek through Samaria Gorge is approximately 16 kilometers (10 miles) long and takes around 5-7 hours, depending on our pace. Along the way, our guide will point out highlights such as the “Iron Gates,” the narrowest part of the gorge, and the “Gates of Heaven,” known for their impressive height. You’ll also encounter diverse flora and fauna, including the Cretan wild goat, kri-kri.

We will enjoy a picnic lunch along the way.

Our hike will end in the coastal village of Agia Roumeli, where we can relax, freshen up, and have some free time for swimming in the Libyan Sea.

From there, we will take a boat ride from Agia Roumeli to Chora Sfakion or Sougia, where we will be transported back to Rethymno. The boat ride offers fantastic coastal views and a chance to rest after the hike.

We will arrive back in Rethymno in the late evening in time for a delicious dinner prepared by our hosts.

Option 2: Explore Rethymno

This is an opportunity to spend the morning wandering through the picturesque streets of Rethymno Old Town. We can explore the narrow alleys, visit the Rimondi Fountain, and admire the Venetian architecture before visiting the Fortezza, the town’s Venetian fortress, for panoramic views.

We will enjoy a leisurely lunch at a traditional Cretan taverna in the Old Town. Be sure to try local specialties like moussaka, souvlaki, and stuffed vine leaves.

The afternoon offers time to relax at Rethymno Beach, which is just a short walk from the Old Town. We can spend our afternoon swimming in the clear waters or relaxing on the sandy shores.

Day 4 – We fly from Crete to Athens, before heading back to the US the following day


$1250 double occupancy
$450 single occupancy upgrade

$100 optional Samaria Gorge Hike

What’s Included:
Transfer from Paros to Crete (either by ferry or plane)
3-nights lodging in Rethymno
all tours and admissions
Van and driver
Airport transfers
Breakfast and dinner each day, lunch for Samaria Gorge hikers

From $3,995 USD
/ Shared Room (Double Occupancy)
From $1,250 USD
/ Pre-Trip to Athens
From $1,250 USD
/ Post-Trip to Crete
  • Small Groups of 8 - 15 people
  • Flexible Payments
  • Pre-trip Educational/Preparation Meetings
  • TravelAvidly Trip Leader
  • Immersive Experiences

Trip Information

Activity Level: Relaxed (see all ratings)

Curator: Jim Peacock

Trip Leader/CSR: TBD