header cover
sailsquare logo

Log in

Aegean sea adventure sailing trip from Naxos to Rhodos

Greece:

Cyclades

Duration:

7 days - 7 nights

Max number of passengers:

6 people

Available:

May - June

Suitable for travellers:

18 - 50 years

Boarding from:

Naxos

What's included

Cancellation policy

avatar image

Organised by:

Moritz W.

Member since 2019 -

Organisation

German

English

French

This experience, in a nutshell

Set sail from Naxos on a true Aegean adventure that leads deep into the heart of the Cyclades and Dodecanese, ending in legendary Rhodos. This route is made for solo travelers aged 20 to 45 who are looking for more than the usual island-hopping — a journey to places most visitors never reach, guided by wind, curiosity, and the spirit of exploration.

Leaving Naxos behind, we head toward quieter Cycladic islands such as Iraklia, Schinoussa, Koufonisia or Amorgos,


anchoring in remote bays where the water is impossibly clear and the nights are silent except for the wind in the rigging. Further east, the landscape becomes wilder as we cross into the Dodecanese, with stops on less-visited islands like Astypalea, Kalymnos, Leros, Lipsi or hidden anchorages near Patmos — places rarely included in standard ferry routes or package tours.


Life on board blends adventure and freedom. Days are filled with long open-sea passages, sunrise swims straight from the boat, snorkeling in untouched coves, paddleboarding along dramatic cliffs, and learning real offshore sailing skills with the skipper. Ashore, you’ll hike to hilltop monasteries, climb limestone walls on Kalymnos, explore sleepy harbor villages, and share simple meals in family-run tavernas where tourism still feels personal.


What makes this trip special is access: reaching remote beaches, uninhabited islands, and anchorages without roads or crowds, arriving by sail long before or after the ferries come and go. Some nights are spent tied to a tiny pier, others at anchor under a sky full of stars, far from any light pollution.


As you approach Rhodos, with its medieval old town and lively waterfront, the contrast feels rewarding — from hidden corners of the Aegean back to one of its great ports. This is a voyage for independent travelers who want real sailing, authentic islands, and the rare pleasure of discovering Greece from the water — quietly, socially, and far beyond the usual routes.

€581

7 days - 7 nights

experience image 0experience image 1
experience image 2
experience image 3

13+

Show all

Boat & Classes of Service

Dufour 43 Classic - 1999

Type

Sailboat

Length

13.2 m.

Toilets

2

Cabins

4

boat image 0boat image 1
boat image 2
boat image 3

5+

Show all

Our itinerary

Our trip starts here:

Naxos.

Check-in: 9:00 AM

Our trip ends here:

Rhodes town (Ródos).

Check-out: 9:00 AM

Our itinerary

We start in Naxos and sail east toward Rhodos, with possible stops on Iraklia, Koufonisia, Amorgos, Astypalea, Nisiros, Tilos or Simi.


The route remains flexible and is adjusted daily to weather conditions, crew experience, and group wishes, allowing us to choose the safest and most enjoyable path through the islands.

The itinerary may be subject to changes due to weather conditions and/or technical or logistical reasons, in order to ensure safety and a pleasant sailing experience for all participants.

What's included in the price

•

Boat equipment and facilities

    Final cleaning

    Tender and outboard

•

Onboard staff

    Skipper

•

Taxes, fees and moorings

    Embarkation and disembarkation mooring fees

What you'll have to pay during the experience

Below are the additional expenses you will incur during the experience.

Common Fund

€150 - €250 Per person

We do clean the boat at the end with each crew member helping 15-30 minutes. I provide a clean set of beddings and towels for free but it is washed at the end of the trip from the commong fund.

    Galley

    Food for the skipper

    Food for the crew

    Alcoholic drinks

    Mooring fees

    Fuel (boat/tender)

What's NOT included in the price

Below are the services that are not included in the price of the experience, including any available optional services that you may pay directly to the organiser (we advise you to inform the organiser prior to departure in case you wish to purchase such services and arrange the payment terms directly with him).

Excluded

    Bedding kit

    Towels kit

    Meals/drinks consumed ashore

Frequent questions

The organiser reviews

avatar image

Organised by:

Moritz W.

Member since 2019 -

Organisation

German

English

French

5.0/5

out of

1

review

Skipper

avatar placeholder

Coves stroll in Menorca

08/20/2019

Hamischa D.

-

Germany

Very relaxed trip, experienced skipper. Looking forward to the next trip together!

Let's talk Sailsquare!

HuffpostSailing todayYahoo!

Secure payments

MastercardVisaGoogle PayApple Pay

© 2025 Sailsquare Srl SB • All rights reserved - VAT IT07860990964