Tailor Made

Customized Sailing Holidays in Greece. Your dates. Your route.

5/5 (420 reviews)

Private departures with maximum flexibility (in route, duration and boat type) that will match any private group of friends or family and any back to back travel arrangement. Ideal for private groups of 4-11 persons

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SailwithGeorge Tailor Made Private Sailing Holidays

Highlights

Ideal for bigger groups or families

Booking a whole yacht you get the chance to enjoy flexibility and privacy. Share the fun with your beloved ones, in an uncompromised and unforgettable way

Starting anywhere in Greece

Define your own route anywhere in Greece. Commonly used starting or ending points are Lavrio, Alimos, Syros, Paros, Mykonos, Santorini, Corfu, Porto Heli and a few more.

Well thought route and activities

The Greek islands is our backyard and we will carefully engineer your route and list of optional activities, including the best of the best.

Sailing Yacht or Catamaran? Your choice!

From our carefully selected luxury catamarans to our in-house monohull yachts, the uncompromised comfort and safety is the key.

Smart and versatile layout with 4 or 5 cabins + skipper cabin will accommodate your comfortably your group.

Itinerary

Define your own sailing route, anywhere in Greece. The Greek islands is our backyard and we will carefully engineer your route and list of optional activities, including the best of the best.

Commonly used starting or ending points are Lavrio, Alimos, Syros, Paros, Mykonos, Santorini, Corfu, Porto Heli and a few more.

Common duration is 7, 14 or 21 days of charter each time. But we can most of the times serve special inquiries starting from 3 days, up to long term chartering for the whole summer.

What is included

Yacht & Skipper

One of our 56' sailing yacht together and one of our four professional carefully selected skippers

Fuel + Port fees

Fuel, port fees, local taxes are all included in the price

Accommodation

Accomodation on board for the whole trip duration, with fresh linen, towels and the end cleaning included.

Water, Tea and Coffee

A start pack of water, tea and coffee is included. You can also bring your own drinks on board from local shops.

Learn how to sail

Our standard service includes, on your option, a Learn How to Sail light program with our professional skipper.

Not included

Food supplies & Meals
Food Allowance for your skipper
Land Transfers, car rentals (if any)
Crew gratuities

Calculating your overall travel budget

Food is usually not included in our quotation.

Provisioning from the local market with fresh fruits, salads, snacks for breakfast and light lunch on board is highly recommended during the trip to make the most out of the day and not spend too much time in the kitchen.

Dinners take place in chosen quality places on land. Usual spendings are approx 30-50€/person for the whole trip’s provisioning and usual dinner cost approx 25€/person for each dinner.

Final figure depends on the group’s appetite and spending style. Food allowance for the skipper is 40€/day, alternatively he shares meals with group.

Tipping the skipper (and the hostess, if applicable) is customary when you receive excellent service during your holiday. Our crew are dedicated professionals who rely on this work to support their families, and gratuities represent an important part of their income.

The amount is entirely at your discretion. As a guideline:

Private departures: €300–€1,500, depending on the level of service you have received

Physical rating

The physical demands of sailing trips naturally vary based on the itinerary and activities included.

Standard trips requires a moderate level of physical ability, such as navigating around the yacht or managing steps.

Participating in any included activity may involve not only swimming and snorkeling but also hiking, which can significantly increase the activity level. While the hikes are not technical, safe participation requires the ability to walk for 2-3 hours with considerable elevation changes without becoming overly fatigued.

Although no prior experience is typically necessary, maintaining a basic level of fitness and mobility will help you fully enjoy the adventure.

Weather

The sailing season features mostly sunny days, with temperatures ranging from 20°C to 30°C (68°F to 86°F). Winds are typically steady and predictable but vary by location, offering great conditions for sailing enthusiasts of all levels. The season starts mid-March and finishes at the end of November. Peak of the season is mid-July to end of Aug.

From mid June to start of Sep we have north prevailing winds which can be strong for a few days (eg 2-3 days) in a row. These winds are locally known as ‘meltemi’ and are very predictable. We always adjust the itinerary of the trip to maximize the fun and comfort factor for everyone onboard.