Our Top 10 Tips for a Stress-Free Voyage with Family or Friends
Traditional sailing trips are ideal as a group getaway. Once you’re on board there’s no accommodation or food to worry about, and as for activities to keep you busy the professional crew will definitely have that covered! Working on deck together can be a fantastic way to reinforce relationships, and you’ll have adventures to chat about for years to come.
Each member of the party can enjoy life on board in a way that suits them, be that monkeying around the foredeck from dawn till dusk or spending more time relaxing and enjoying the view; you don’t have to split the group to each take the expedition at your own pace. The crew are all well practised in working with everyone from novices to experienced sailors, ensuring everyone learns something and has fun.
That’s all well and good, but getting organised for a group trip can be like herding cats, so here are our top tips for taking a successful and enjoyable sailing holiday together.
We are in no way affiliated with any of the apps mentioned below, and our recommendations are based purely on what’s proved practical for us in the past.



1. Get Your Group Organised
Everybody hates a WhatsApp group (other messaging platforms are available!), but they are indispensable for planning a group holiday. If you’re reading this, chances are you are the Chief Cat Herder, so it’s your job to keep the chat on track, and make it as efficient as you can for your own sanity! The ‘Polls’ feature is particularly helpful for collating everyone’s availability and getting quick responses for questions about destination, duration, price etc. Just set up a poll with the possible options and get everyone to vote. The key thing is to make sure people vote for EVERY option that would work for them, not just their favourite. This way you can quickly find a result that suits the majority of the group without having to trawl through hundreds of messages and decode cryptic fence-sitting.
Hang on to the group chat even after the trip is booked. It can be useful for real time travel trouble-shooting as you all make your way to the ship, as well as being the perfect place to share photos afterwards.
2. Get Informed
It’s vital that everyone understands what they’re getting into when joining a traditional sailing voyage. Some of you might have been sailing before, some might not. Share your experiences and maybe a few articles from our archive (such as the ones suggested below). If someone steps on board expecting deck chairs and cocktails, and you’ve booked a hands-on tall ship passage across Biscay, this might cause some friction!
Top Tips for Your First Traditional Sailing Holiday
Classic Sailing’s Voyage Packing List
First Time? No Experience Required
Sailing at Night: Common Beginners’ Questions

3. Cater to the Least Experienced and Least Confident…
The point of a group adventure is to have fun together, not to alienate anyone. While some of you might be keen for an ocean epic on a square rigger, this might be anxiety-inducing to others.
The joy of a traditional sailing holiday is that you can all take what you need from it, so choosing a shorter and seemingly less adventurous voyage can still tick the boxes of the adrenaline junkies amongst you. Instead of riding big ocean swells, why not take advantage of calmer waters to climb right to the top of the mast, or out onto the bowsprit? Instead of the challenge of night watches and days out of sight of land, enjoy learning some coastal navigation skills and swimming from the ship.
If the most nervous person in your group is having a cracking time, you all will.
4. …Also Cater to the Least Flush
Tension around money sets things off to a terrible start on a group holiday, and it’s awful feeling excluded from a group because you don’t have the cash to get fully involved. Be sensitive to these concerns from the very start, and make sure that shorter and cheaper voyages are among the options you present to the group. There are a few things to bear in mind to help keep it affordable:
-Pick a round trip rather than an ‘A to B’ voyage, as this makes travel planning easier and cheaper.
-Consider a voyage with more sea time and fewer port stops, as this will reduce the inevitable shore-side spending.
-Sail close to home. You don’t need to travel halfway around the world to have an amazing adventure. Exploring familiar territory from a completely new perspective can be even more rewarding.
-Don’t go for too long. Not everyone can afford the time off work, and you’ll be amazed how much fun you can fit into a long weekend at sea!
-There’s no need for everyone to go out and buy lots of sailing gear. Use your group chat to find out what everyone has, and what everyone needs, and share stuff out. All the ships provide life jackets and all other safety equipment, and many of them have wet weather gear available to borrow, so check the kit lists carefully. If anyone does need to buy anything, there is no need for sailing-specific kit. Hiking waterproofs are absolutely fine for most trips and are often much cheaper, plus more readily available second-hand. Check out our packing list for more advice on what to take.



5. Be Clear on Costs
Money’s a big one, so here’s another hint- don’t let any grey areas emerge about who’s paying for what. Arguing about who-owes-what while you’re on the train home can leave a sour taste after an otherwise fantastic trip.
One of the big benefits of going sailing as a group holiday is that, once on board, things are pretty all-inclusive. Food and accommodation are taken care of. However, there are the travel costs to work out, as well as additional spending such as restaurant meals ashore and visits to the pub. Make it crystal clear in advance which costs will be shared and which will be taken individually. It’s lovely if someone offers to buy the next round, but not if they’re expecting everyone to chip in afterwards.
Apps like Splitwise, which handle multiple currencies, are a really useful way to keep track. They enable you to quickly record who paid for what, and at the end will work out exactly what everyone owes and to whom. This avoids the eruption of atmosphere-killing maths-chat every time someone goes to the bar or books a taxi.
6. Book Early
Voyages can book up amazingly quickly. It’s heartbreaking if you’ve gone through all the decision making with the whole group and found your perfect trip, only to discover that there aren’t enough bunks left for everyone.
For groups of more than four, it’s wise to plan a season ahead. Spring/summer is often when the ships release their schedules for the following year, so try and get organised by this point if you can.
Larger groups looking for whole-boat charter are wise to explore a ship’s current sailing schedule as early as possible to see the areas and kinds of voyages they operate. If a particular trip on a particular ship appeals to you, there is a good chance they’ll be running it again next year. You could secure it for your group before it’s even launched to the general public. Get in touch and we can help you with this.
If you’re happy to sail in the ‘shoulder seasons’ of Spring and Autumn, these voyages can take longer to sell, so you might find something for the current sailing season. The easiest way to find voyages with enough space for your group is to drop us an email with your requirements. We can check the most up to date availability with each ship in turn, and potentially also put a temporary hold on bunks for you while final decisions are made.

7. Don’t Get Hung Up on the Destination
Usually, when planning a holiday, the ‘where’ is the key. Not so with a sailing voyage, which is more about the process of getting somewhere than the somewhere you’re getting to. A round trip isn’t about getting somewhere at all, rather it’s about enjoying being on board, surrounded by sea, sky and sails.
Of course geography has an impact, most notably on climate and the scenery in the background. These things make a difference, but are nowhere near as important as the ship, the length of voyage and the cost when it comes to planning a group getaway. Choose a vessel that suits your group, make sure nobody is overstretching themselves financially or physically, and you’ll have a fab time wherever you are.
8. Make a Decision and Stick to it
The final decision on which voyage to pick might be tricky, and it can be tempting to tentatively apply for several voyages to keep your options open, stringing along the payment of deposits for as long as you can. Please don’t do this. Talk to us as much as you like before making the booking, so you feel confident it’s the one for you and your group, and once you’ve booked, follow through. The traditional sailing ships we work with operate on tiny margins, maintaining some of the most beautiful and historic vessels in operation. Bookings which fall through are not only frustrating, they can often lead to a loss of income as ships miss out on other potential sailing guests.



9. You’re Part of the Crew Now
Unless you’ve booked out a whole ship for your group (which is a distinct possibility- get in touch and we can talk you through some options!), be conscious of those fellow sailors who aren’t part of the group. You might have arrived together, but once on board you are all part of the crew at large. Clique-y behaviour is a disaster for the atmosphere on board ship, and if you’re open and friendly with everyone you’ll have a much better time.
10. Talk to Us!
We’ll say it again- get in touch! We would love to help you find a trip that would suit you and your group, and might have some ideas for locations and vessels that you haven’t considered. Plus we can help arrange whole-boat charter voyages with the vessels we work with, enabling you to have the ship to yourselves. This is an amazing experience and a fantastic way to celebrate a special occasion.
Whole-boat charter can be anything from a day sail to a voyage of a week or more, and many of the ships in the Classic Sailing fleet offer discounted rates for group bookings. ‘Off the peg’ trips are usually available for private charter only up to the point of the first individual booking, and bespoke voyages have to be fitted around a vessel’s other commitments, so the earlier you can arrange your trip the better. It’s never too early to start the conversation, so get in touch and we’ll help you find an adventure to suit your group’s own particular circumstances.