Sailing Planner: A Guide For Your Next Journey

General Info

It is winter. It is probably raining outside. You have not even had dinner, yet already, it has been dark outside for hours. To maintain just a small sense of enjoyment in your life, your mind will undoubtedly wander towards those warm summer days.

Chipping away on the waves in beautiful azure waters in a loose shirt unbuttoned down to far below the chest. A cold beer always within reach.

Dinner at gorgeous small seafood restaurants. Finishing of with a glass of wine in the sunset. 


To sailors. This is what it is all about. And to get through that dreadfully long off-season,planning your next summer trip will feel like a much needed patch on an open wound.

Actually. If done right. The planning may be as fun as the trip itself. Of course that is not true but it is a nice thing to tell yourself as you undertake this task.

Truth is, that even with copious amounts of planning, its not always easy to tell how things will play out. But to set out with a good starting point is always a strong beginning. So let us take a look at the sailing planner check-marks you need to focus on ahead of your trip.


Planning For A Sailing Trip

Determine your budget

We all know sailing is expensive and your budget will set the stage for your trip right from the start.

To get your funds to reach as far as possible, you should consider how many companions you would like to bring along. In general, the more members in the crew, the cheaper the cost will be per person.

However, you should also keep in mind that a boat can feel a little crowded when it is filled with people. There is not that many places to go in order to get some time alone.

And if you end up spending 2 hours in the bathroom every day, you will probably have the rest of your crew worried and you may have to face some questions.

Therefore, consider the possibility of including some extra people for your trip but make sure that you know them really well before you do so. And make sure that they enjoy the same type of vacation as you do.

If you would rather fall over on a bike than to visit a museum, you should probably think twice before you invite that couple from down the street that always choose the history questions for game night.

Thus, before you continue planning, you should definitely try to align your expectations as much as possible.

As a minimum, you need to discuss how many hours of sailing you wish to do per day, what type of stopovers you are interested in and how much time you wish to spend together when you are onshore. Even though you bring along relatives or close friends, it may be nice to spend a bit of time apart when you have the opportunity to dodo.  



Once you have your crew assembled, you need to agree on your destination. It does not need to be any exact location. Actually, to reap the full benefits from travelling by sail, instead you should consider just narrowing in on a region that you would like to visit. From then on, you can start researching which specific locations you find interesting. 


Popular regions for sailing adventures will often be coastlines or archipelagos (island groups).For coastlines, we popular choices are the southern coast of France (the Riviera), the coast of Croatia and the southern coast of Sweden to name a few.

For archipelagos, the Caribbean is by far the most famous but among other options we can highlight the Galapagos (Ecuador), French Polynesia, the Spice Islands (Indonesia), the Cyclades (Greece) and Key West (Florida, US).

sailing planner


Despite of all your meticulous planning, you should always keep in mind that wind and weather eventually will be likely to interfere. Or you may find a location so interesting that you feel the need to spend more time there. In general, we advise that you are flexible and willing to adapt to the interests of your crew.

There is no need to force an uncomfortable day of upwind sailing in rough conditions just to keep a schedule. The schedule should be regarded as a template that is able to change day by day.

However, this doesn't mean that it is a waste of time to prepare your route.

In order to get the most out of your trip, it will require a great deal of research on your targeted region. As it is likely you will find more interesting attractions that you have time to visit, you should try to lay down a route that will allow you to reach as many attractions as possible.

At the same time though, keep in mind that you need to leave enough time on location to actually enjoy it. Think about it in this way. The only reason you will ever bundle a beer is to get that buzz going as fast as possible.

Actually enjoying the beer takes a bit of time. The same thing when you travel. You may get all the photos you need by hurrying from one place to another but you will only really enjoy it if you let things take their time.

You may want to check out our favorite places to sail for your next trip too.


Chartered versus Owned

If you want to go on a sail without owning a sailboat yourself - and without any intention to change that - you are not left with many options. You will need to charter. But even if you have your own boat, you might still want to entertain the idea of chartering.

The most obvious benefit of chartering is that your starting location can be everywhere. If you sail in your own boat and have a specific destination in mind , you are likely to need a couple of days (or even more) of “transport sailing”.

Not only when sailing to the destination but also upon return. To skip this diligent part of your trip, you can charter a boat on location. Particularly, this makes sense if you do not have many days for your trip.

As another benefit,you will have the opportunity to sail another boat than your own. Especially if you are planning to travel as a larger group than what would fit in your own,the size of your own boat will no longer be a limitation. Also, it is just plain good fun to try another boat every now and then.


For chartering, there's many many options to choose from. Particularly around popular destinations.

Advice from friends within the sailing community is always useful but otherwise make sure to have a chat with the leasing company by phone. Make sure all documents are properly signed and that you have insurance in place as needed.

Also, chartering may require that you are certified to handle the specific type of boat. This will in many cases be relevant for larger boats and motored vessels.  


On the other hand,the benefit of bowing out in your own boat is mainly that you know it inside out. You know how to sail it. How to dock it. In what conditions it will struggle, how much room is available for luggage, and in tough conditions, you will definitely feel more confident in your decisions.


Also, and at this point you might want to roll your eyes and claim us to be some romanticists. That may very well be. But over the years, we do feel that boat-owners develop a special relationship with their sailboats. And there will be something special about reaching far destinations in a boat that you have personally nursed and taken care of for years on end.


What to bring for the journey

These considerations will slightly depend on your choice of destination. If you are planning to reach an remote archipelago in the West Indies, your main concern should be food supplies and water.

This video will also help: 

If you have picked a coastline near civilization, you will probably be able to dock into a harbor everyday to restock. In this case,you can focus more on items to help your company spend time while sailing,clothes and equipment for onshore leisure activities and so on.


For entertainment while sailing, some popular choices will be board games, books, movies,podcasts and music. WiFi is an issue while sailing. If you have kids this is particularly relevant as they are often allergic to being offline.

Symptoms will vary, but as a minimum they will begin to relentlessly ask how much time is left until the next destination. Fortunately, the symptoms can often be managed by ice cream, and these days most harbors offer WiFi access to guests-when they are docked in. 


For food supply, a convenient but perhaps also non-culinary option would be canned food. And there are multiple reasons for that.

First and foremost, it does not go bad even though it is exposed to a large variety of temperatures. Second, it does not occupy too much space. And finally, a lot of canned food contains a lot of calories.

This is actually important because you naturally burn a lot during sailing. Even though, there is not a lot of room to move, just being outside and being consistently active - pulling a rope here and there - will make you burn a lot more than a trip to the gym.

So to keep energy levels high during along trip, it is important to make sure that a sufficient amount of calories are being consumed. 

If your destinations less remote, you do not need to worry as much about food and water supplies.Many modern yachts today is equipped with fully-fledged kitchens with oven,hotplates, pots, pans and so on. If this is the case, we recommend that you explore the local food markets wherever you go to get your supplies. 


In terms of clothing, you almost need to bring the same outfits regardless of the destination. Even warm destinations will feel cold in showers and breeze and you need to be prepared for that. And even though you may end up spending two full weeks just in your speedo’s, you will be more comfortable knowing that you have your offshore suit ready. Just in case.


Finally you should not forget that travelling by sail to some extent is similar to any regular form of travel. There is a million items that you should not forget.

This includes Passport, Travelers Insurance, Credit Card, Medication, sunglasses(polarized), hats, sailing suits, sailing gloves, camera, sunscreen, snorkeling equipment, fishing gear, and so on.

However, the list is likely longer than what you have space for, so consider making a limit in terms of how many kg each person is allowed to bring.


Preparing for sailing

If you are planning along-distance offshore sail, and particularly if you are expecting to bring along a few inexperienced sailors, we highly recommended that you spend a weekend of sailing before you dock out on your great adventure.

This will be a perfect time to go through the safety procedures. How to work with the safety-lines and what to do if one falls overboard. It will also be a great opportunity to introduce inexperienced sailors to the basics of sailing.Specifically, how to execute basic maneuvers and how to sail the boat controlled in a straight line.  


And there you have it. Going through our sailing planner steps above will hopefully get you through those long months of winter while at the same time help you set yourself and your travelling partners up for an amazing adventure. 

You might also want to prepare for sailing in a storm or brushing up on your fire safety skills. Better safe than sorry. If you are very new, you might also want to ensure you're aware of boating at night but most of you reading this will understand.

Sailing is unquestionably one of the very best ways to explore the world. No other means of transportation offer travelers the same degree of freedom as a sailboat.You can set sail, whenever you want from wherever you are and you can point your bow to whichever direction your heart desire. That is sailing.