Surprisingly affordable

Someone recently asked “what is something you always thought was expensive and it actually isn’t?”, for me the response was easy: sailing holidays.

Whilst sailing holidays give off the impressive of absolute luxury, they can be surprisingly affordable, particularly when split between groups of friends/family and factoring in that it includes transport, accommodation, entertainment, cooking facilities and most meals depending on the type of trip.

Depending on how luxe you go, I liken sailing to glamorous camping – the toilets and showers won’t be top notch and the space will be a bit cramped but you have a whole lot of nature and beauty surrounding you to enjoy.

This article is written for those who don’t sail themselves regularly (people who do should be all over how to charter etc).

Our yacht in Croatia in 2017

Types of sailing holidays

There are a few types of sailing holidays you can go on,  depending on your budget, interests and desire for privacy.

Generally you can consider choosing between either booking a boat, or booking a cabin, these could be organised independently, as part of a tour/flotilla. A flotilla is when a group of yachts travel together through a set itinerary.

Independent booking:

You can independently book a yacht/catamaran in your desired destination by looking for “skippered charters”. You can also look for “bareboat plus skipper” option but try to avoid “crewed charters” or charters with a chef as these tend to get quite expensive. The “Skipper” is the captain of your boat, who will manage the navigation and generally give you great advice on where to stop, what to eat and what to do.  They will help you select moorings, which are the places where you “park” your boat while you go out and explore.

You can also ask for a “host”/”stewardess” in some parts of the world, who will cook and clean for you. This sounds very luxurious so we didn’t have one on our group sailing trip, and looking back for the cost split across the group, I really regret not having one! Yachts are generally quite small and the kitchen area requires a bit of skill to navigate, there are generally no dishwashers either. If you are travelling with a group and want to feel like you a truly on holiday, I would say hiring a host is a worthwhile expense. On the younger types of sailing trips, the skipper and the host will sleep in the lounge area of your boat (it is common for the lounge area to convert into a type of bed) or if you have a spare cabin they will take that. In more sophisticated arrangements, the skipper will generally require their own cabin.

There are a few considerations when booking your own yacht/catamaran, but these tips are also useful when assessing your options for other sailing trips:


  • How people will be in your party, how many rooms do they need?
    • Some boats offer a mix of double beds and bunks so if you are travelling with all couples you may prefer to book a catamaran which is more likely to have more double beds.
    • The cost of your boat will generally be divided by the size of the group, so
  • Do you need A/C?
    • Have a look at the historic temperatures of your destination and the hours of sunlight. If you are travelling somewhere very warm with long daylight hours (in the peak of summer) you may prefer to have air-conditioning to enjoy your time on the boat. If you think you’ll be out in restaurants/bars/clubs into the evening then you can generally survive without it.
  • Does the cost include port/marina fees?
    • If this is not factored into the price, ask for a summary of expected costs
  • Does the cost include meals?
    • It is quite common for breakfast and lunch to be provided, with dinner generally an opportunity to explore the restaurants in the location, where you are moored. Alternatively, you should be able to use the kitchen on the boat.
  • Kitchen facilities?
    • Generally these are small but functional kitchens, the fridge area will be quite small and often accessed from above, they not as cold as a regular fridge. You should also have a cool box area on the deck where you can store drinks (and ice, when you have it). If you are planning on cooking a lot you should ask what kitchen facilities are provided, normally this will involve a stove and potentially an oven/microwave oven. There generally isn’t a huge amount of space in these kitchens so if you are making a big meal you will probably take over the dining table while you prepare. Luxe boats will have more facilities… obviously.
    • While asking about the kitchen, check about clean up and what is provided (do you need rubbish bags, extra toilet paper etc?)
    • Can you bring your own alcohol and are there any limits?
  • Bedrooms/linen and towels
    • How are the bedrooms set up? Do you need linen and towels etc?
    • Unless otherwise specified, I would bring your own shampoo, conditioner and a towel. I would always shower in my swimsuit on the back of our boat instead of the internal shower.
  • Itinerary
    • Ask if they have a suggested itinerary and request the destinations you want to visit for them to incorporate.
    • Ask how many hours sailing on any given day, how many stops throughout the day and where you’ll be mooring.
    • In most popular destinations boats run Saturday to Saturday during peak season, in that case there will be less flexibility on start date and duration. You will also likely spend your last night at the final port then have to disembark the following morning, some people choose to stay in a hotel that night and leave the boat early but if you’re on a budget you don’t want to lose that last night of cheap accommodation!
    • If you are travelling outside of peak season you should be able to negotiate a shorter trip.

Tour/Flotilla booking

This is pretty similar to the independent booking above, however, the itinerary will be set and there will be other boats in the flotilla following the same itinerary. This can be a great opportunity to see some amazing place, as the group will have bookings and events organised for you.

Cabin booking

Don’t have a group of friends to travel with? You can book a cabin (or two!) on a boat which will likely include other like-minded guests in the other cabin. Many companies try and get a gender balance so don’t be surprised if you are asked how many males/females are in your party. If you’re travelling alone, some companies will allow you to book a “spot” which generally means a bunk, you will then be sharing with someone of the same gender. If you want the room to yourself you will likely have to pay a supplement.

Types of trips around the world

Here is a mix of different sailing options around the world

Croatia Adventure Sail Week:

This is a well-oiled machine, taking the best bits of the traditional “Sail Week” without as much of the partying and a bit more time to be physical and explore the various locations. This is most popular with couples from mid-20s to late 30s. The crowd skews Australian, NZ, South African, German, Canadian.

Yacht Week:

Popular with the American late-20s-about-to-start-an-MBA crowd, yacht week is Sail Week’s fancier cousin – slightly more high strung and bougie. The also offer a Yacht Week in the British Virgin Islands during December/January.

Sunsail (Skippered: or Flotilla:

Globally one of the largest companies offering bareboat charter (that’s without a skipper), skippered charters, flotillas and cabin charters. This is a more ”grown up option”. It is common to have families in the flotilla trips (although they do offer a child-free one. They also offer some special interest tours including food themed ones like this one in Sicily:

Other companies:


Here is a video compilation of our joint bachelor/bachelorette in Croatia in 2017 (part of Sail Week Croatia):

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