Mykonos to Santorini

Thanks for deciding to come on an adventure with OTBT! We are very excited about the upcoming season and look forward to having you out on a trip with us. Every week will be a little different with as we have no set itinerary apart from our start and finish destinations. So you can plan for your holiday we've produced these joining instructions. Is there's anything we missed please email us:

We will most likely depart Mykonos on the Saturday evening (or Sunday morning after breakfast depending on your flight times) and head South. Through the week we have possibilities of visiting many islands including Rhinia, Syros Ios, Sikinos, Milos, Amorgos, Iraklia, Koufonisi, Naxos, Paros, Syros, Folegandros, Delos and of course Santorini. Your skipper will decide after taking into account the weather conditions to which island we will visit each day. We will try to visit at least 5 islands.


Unless otherwise agreed, please arrive at our rendezvous point which is Matthews Taverna on the road just above the New Port in Mykonos town at 2.00pm on the Saturday. The yacht will be moored at the marina in the New Port which is situated about 1 mile out of Mykonos town centre and is also known as the Ferry Port. The yacht is called IKAROS and will be flying either red or blue flags with the OTBT logo on. 

We always recommend spending a couple days in your start and finish destinations, to see all the Islands have to offer.



When you arrive at the boat we will need to go through some formalities. Your skipper will need your passport details to provide to the port authorities. The amount of time this bureaucracy takes can vary, so I’d therefore appreciate it if you could let me have details in advance to speed things along. 

There’s a form at the end of this page for each person sailing to complete complete. We will also need details of your travel insurance policy before we set off as you will not be able to sail without it. Before we set off there will be a safety briefing and a quick chat about plans for the week ahead. Depending on the weather, port authority red tape and a general consensus of what the group want to do, we will decide whether or not we leave that evening or if we stay the night in port and sail the following morning after breakfast. 

Safety & Accommodation 

Our Beneteau Cyclades 50.5 ‘Ikaros’ is fully licensed to charter for up to 10 passengers and is equipped with state of the art technology offering all travellers on board a safe and enjoyable experience. Find out more about the yacht by clicking the link below

Your OTBT skipper will be with you throughout your journey. The aim of the skipper is to take the hassle out of your travels and to help you have the best trip possible, as well as taking complete charge of the sailing, your safety on board and the safety of the vessel. 

As this is a real sailing adventure, our skipper might also request your help on board and will be more than happy to impart some of his sailing knowledge during the course of the journey. Our skipper is a fully licensed yachtmaster with seven years of experience sailing in the area. He will provide information on the places you are travelling through, offer suggestions for things to do and see, recommend great local eating venues and you can expect your skipper to have a broad general knowledge of the Greek islands you will visit. 

Space on board is optimised, sleeping quarters are snug, meaning that more of the boat is open for everyone to enjoy. Cabins are allotted by the skipper based on the gender and traveller make-up of the group. No particular cabins or berths can be guaranteed. Our skipper will pair up travel partners or if you are travelling single, with someone of the same sex. 

Please be aware that as this is a real sailboat and not a cruise vessel and although this is a large yacht the space on board is tight. You will be sharing a compact cabin with one of your fellow passengers or travel partner and sharing the three bathrooms on board. The sleeping quarters on sailboats are generally kept to a minimum size in order to maximise public space and performance. Please note that the skipper has his own cabin in the bow of the boat, but will also be sharing the yacht quarters and amenities with you. 

Our small group adventures bring together people of all ages. It is very important you are aware that, as a minimum, an average level of fitness and mobility' is required to undertake our easiest programs. Travellers must be able to walk without the aid of another person, climb 3-4 flights of stairs, step on and off small boats, and carry their own luggage at a minimum. 

Travellers with a pre-existing medical condition must ensure they have the necessary fitness and mobility to comfortably complete this trip and know their own limitations for shore excursions. While our skipper works hard to ensure that all our travellers are catered for equally, it is not their responsibility to help individuals who cannot complete the day's activities unaided. 

What to pack for your sailing holiday 

What people take with them when they go sailing varies by the kind of sailing they are doing, where they are sailing, their experience and personal preferences, but here we try and give those uncertain what to bring some guidelines on useful items to have with you during a sailing holiday with OTBT. 


As your holiday falls between mid-May and the end of September, you won’t need much in the way of clothes! See our suggested kitlist further down this page. 

It is preferable to pack in soft bags rather than hard suitcases as hard cases are more difficult to stow away in lockers on board. It’s a good idea to choose soft bags with wheels or have a collapsible trolley for ease of transport. 

Toiletries and medication 

Most brands of soap, shower gel, shampoo, sunscreen etc. are sold in Greece although they tend to be more expensive from the small harbour-side shops. If you take prescribed medicine, it is advisable to bring enough with you for the duration of your holiday. Although all our yachts have a basic first aid kit, it is a good idea to carry one of your own which should include travel sickness pills, antiseptic cream, insect repellent, antihistamine cream/gel for insect bites, after sun soother and anything else you personally may need. 

Documents & currency 

Don’t forget to pack your passport & EU medical card (which replaces the now defunct E101 form). If you are from a non-EU country you should check with your Greek consulate as to whether you need to apply for a visa. 

Although you don’t need sailing qualifications to sail with us, if you are qualified please also bring any sailing certificates, as they are sometimes requested by the Port Police. 

We may hire a car, motorbike or other vehicle whilst on holiday, so you should also bring your driving licence. 

Your personal holiday insurance documents should be included in your hand luggage. 

It’s a really good idea to have a photocopy of your passport and all other documents in a separate bag just in case you lose the originals. 

We recommend that you bring a combination of cash together with your debit/credit cards. Most of the time it is better to buy your Euros in Greece. You can use bank ATM cash machines in most places to obtain Euros so long as your bank card operates while abroad; not all cards do. 

Remember that the smaller and more remote ports we visit may have no banks and no ATMs and that in small tavernas cards may not be accepted. It’s therefore a good idea to carry enough Euros to buy daily supplies and pay for evening meals and drinks. 

Eating & Drinking Out 

Eating traditional foods and sampling the local brew is a big part of travelling. Breakfast and lunch are included in the price, but eating out for evening meals is not included in the trip price. When we stop over in a port the local tavernas or restaurants offer you a choice of eating options, giving you maximum flexibility in deciding where, what and with whom to eat. It also gives you more budgeting flexibility, though generally food is cheap. 

Our groups tend to eat together to enable you to taste a larger variety of dishes and enjoy each other's company. There is no obligation to do this though. Your Skipper will be able to suggest favourite restaurants during your trip. 

Ikaros is not licensed for the supply or provision of alcoholic beverages. However, you are welcome to buy and bring your own alcoholic drinks on board for your own or shared use. Due to the obvious dangers of living on a boat and restraints of being in close confines with others, it is important to drink sensibly so as to be able to move around the yacht safely and not be a nuisance to others. 


Through the week, unless we BBQ on the beach and sleep under the stars we will tend to dine out most evenings. Although service may not be what you are used to in your home country, tips are much appreciated by local tavernas and do get split between the whole service team. We recommend only tipping if you really enjoyed the meal and the atmosphere in the taverna. Just because one person tips doesn't mean everybody has to, as some people’s opinion on the meal or particular dishes may differ. Tipping in shops and bartering is not standard practice.

Tipping your Crew

If you are totally satisfied with your Off The Beaten Tack adventure experience then please feel free to show your appreciation to your Skipper and 1st mate. A standard tip in the marine industry would be up to 10% of the cost of your trip, but please only tip what you are able – and only if you think we’re worth it.

OTBT thrives on word of mouth recommendations by guests telling their friends and sharing memories and experiences of their sailing adventures on social media. Sharing a picture really can can speak a thousand words. We would massively appreciate your help by sharing your photos and leaving us a review on our facebook page at

May the wind always be at your back and the sun upon your face! 

Skipper Jimmy

Off The Beaten Tack founder


Please click the box and complete the form as soon as possible

Packing checklist 

To make things easy, here’s a kit checklist! All optional of course. 

  • Swimsuits 
  • Beach towels for sunbathing 
  • T-shirts 
  • Shorts 
  • Casual evening wear 
  • Windproof jacket 
  • Sun hat 
  • Sunglasses with lanyard 
  • Sunscreen/sun cream 
  • Lip salve/screen 
  • Toiletries (all-in-one shampoo/shower gels can be handy) 
  • Prescription medicines 
  • Ipod/music device – so you can play DJ (and charger) 
  • Passport / visa 
  • Driving licence 
  • Holiday insurance 
  • EU medical card 
  • Euros /credit or debit card 
  • Camera with batteries and 12v (car plug) charger 
  • Fleece or sweater 
  • Warm trousers 
  • Flashlight 

Laundry and on shore shower facilities are available at some ports. Hair driers draw a lot of current and may not work on the boat unless we are alongside with 220v hook ups. Try going without for the week. 


Knowing the Ropes 

You can play as much or as little a part in sailing the yacht, but here are some technical terms for you to learn to help you orient yourself aboard: 

Sailing Operations 

Tacking: turning the bow through the wind onto the opposite tack
Gybing: turning the bow with the wind onto the opposite tack
Round up: turning the boat exactly bow into the wind to stop moving forward
Leeway: the amount a boat is pushed off course by the effect of the wind
Anchor up: Drop the anchor and stop for a while
Moor: Tie up to a buoy or in a harbour
Lines: Lines, not ropes
Halyards: for pulling up and letting down the sails
Furling lines: to set and take away the sails
Sheets: to adjust the sails during sailing
Shrouds: the wire rigging either side of the mast holding it up
Forestay: the wire cable at the bow to the top of the mast
Backstay: you guessed it.... the wire cable from the stern to the top of the mast
Topping lift: the line supporting the boom from the top of the mast
Mooring line: line connecting the yacht to the harbour or pontoon
Ground lines: anchor line holding the bow when moored ‘stern to’

Parts of the Yacht 

Hull: the ‘body’ of the boat
Deck: upper level of the boat
Below: everywhere below deck
Galley: the kitchen
Heads: the toilet, shower and washrooms
Cockpit: area at the back from where we steer and operate the sails
Bow: the front of the boat
Stern: back of the boat near cockpit
Helm: steering wheel
Helmsman: Person at the helm, not necessarily the skipper
Starboard: right hand side of the boat when you are looking forward
Port: left hand side of the boat when you are looking forward
Mast: vertical pole supporting the sails
Boom: horizontal beam attached to the mast and bottom of the main sail
Mainsail: large sail fixed at the rear of the mast with boom at the bottom
Genoa: the triangular sail at the bow in front of the mast
Lazy jacks: the net of lines guiding the sail over the boom when it is lowered
Fender: inflated plastic bumper used to avoid damage of the hull when moored
Winch: drum to help pull in control lines for sails
Main Anchor: the anchor at the bow of the yacht
Kedge anchor: the anchor at the stern of the yacht. 
Cleat: a 'bollard' to secure a line to especially halyards and mooring lines
Clutch: a device to hold a line securely
Guard rails: the wire 'fence' around the deck