Sail the Greek Islands
with your own Captain and Cook!

All summer, 2022

We are restarting our popular Greek island cruise trips and we can't be more thrilled. There is a two-day Athens pre-trip stay, which includes all entry fees to the Acropolis and tours. There is also a 3 day post-trip to Santorini that is not to be missed. This trip is one of our small-group options and will be managed by members along with our overseas partners.

From my experience hosting these trips, the food is of course authentic, and to die for.


  • Round trip air from Nashville or larger Eastern hubs

  • 7 days/6 nights aboard a private luxury Catamaran with semi-private ensuite berths for 8 travelers plus captain and cook.

  • A dedicated captain who will be by your side throughout the trip and will assist with setting an itinerary for the week.

  • A dedicated cook available day and night to shop for food, prepare meals, and bartend. She will also help plan excursions, happy hours, and evenings out on the islands. Think of her as your private entertainment concierge.

  • A dedicated guide in Athens to support your trip, and to accompany you to the catamaran. As room permits, a club ambassador will accompany you onboard as well.

  • First night dinner at the Divani Palace.


  • $3,450 including round trip air and all accommodations onboard.

  • Roughly $100 PP for groceries onboard

  • $625 double ($755 single) for 3 day/2 night pre-trip extension in Athens at Divani Palace Acropolis Hotel with spectacular views of the Acropolis from the rooftop restaurant. Optional excursions to the Acropolis/Acropolis Museum, ancient Athens, and the ruins at Delphi are extra. Meals and excursions will be together as a group unless you opt to tour on your own.

  • Meals out on the islands. Some of our fondest memories have been at small tarvernas scattered in small towns and quiet coves  in the islands. Prices are usually very inexpensive.

  • $450 to reserve, and $500 per month till paid.


Sailing dates:

If you bring your own group of 7 or 8, the sailing will be yours. For smaller groups or singles, we will pair you with others. We'll obviously get everyone together for regular meetings prior to each trip. Currently the following sail dates are planned. These are dates we leave, so plan on 8 days unless you select one of the extensions.

  • April 30

  • May 11

  • May 22

  • June 2

  • June 13

  • June 24

Later sailings are available. We also have a few spots left for late summer 2021.



Let's spend a week exploring the Greek Islands with 7 other travel companions aboard your own private catamaran, complete with captain and cook! You and your captain will decide on your itinerary when you arrive. Pick from an island of ancient ruins one day, and a quaint fishing village the next. Sail into a picturesque cove for snorkeling or sun worship. It's all up to you. At each stop your cook will shop the local market based on your wishes for the next day's meals. Enjoy the most incredible fresh Greek salads, seafood, and lamb you've ever tasted, all while enjoying the most intoxicating views on earth. Your cook knows the islands and can be an excellent resource for what to see and where to eat.

Note on Santorini extension: One of the questions we often get is why we don't just go to Santorini on one of our island stops. The answer is that you can if all agree, but since it's at least a day's trip each way, you'll miss out on much that the other islands have to offer.  Ultimately, you'll decide on your itinerary along with your fellow travelers.


Our Home in the Islands

We'll sail the calm seas of the Aegean on this 8 person (plus crew) luxury Catamaran


Lagoon floorplan

We'll spend most of our onboard time on the back deck, or the comfy living room. Drinks and conversation seem sweeter in the Islands.


Onboard berth

This is one of the four passenger berths. And yes, you'll be good friends by the end of the week! Each berth is equipped with its own bath.


The Acropolis

The Acropolis, it's Parthenon, and the Acropolis Museum are of course the highlight of any visit to Athens.


Patio on Mykonos

Don't ask, don't tell. Right? :)

fishing village.jpg

Fishing Village

The Greek Islands are built around fishing. In every port you'll meet some salty and friendly fishermen mending their nets.



This is Naxos, an island near Paros that you'll likely visit. For the islands, this is a big city. Many islands may have a few homes, a fishing village, and a taverna, or restaurant.

lagoon island.jpg

Typical Island Cove

On the last trip we spent the entire day sunning and exploring the caves in this cove, then sailed around to the village for fresh-caught dinner.


The Aegean Sea

During May, June, and early July we'll take a ferry to Paros and sail from there. Later sailings may sale from Athens, as conditions warrant.