Vacations for Singles Over 40: Everything you need to know to have fun travelling alone


I did my first ever solo trip at 35. I was separated from my now ex-husband and I loved to travel. However, most of my friends were married so I really didn’t have anyone to go on holidays with – gosh did I feel like a bit of a loser! Added to that high self-esteem was the fact that I was terrified to go away on my own.

What if I didn’t speak to a single person the whole time? What if I got really depressed as a result? What if something went wrong? What would I do in the evening? The whole notion of singles holidays over 40 was daunting!

It’s almost funny to think back on that now – almost! I clearly remember those feelings. It is now 10 years later and I have done quite a few vacations for singles over 40, a lot more trips with people I have met along the way, organized trips, partners at the time, trips with friends and family – you name it.

Don’t miss my post on 30 Fantastic Solo Travel Groups Tour Options!

singles vacations over 40

Travelling alone doesn’t need to become the way you always travel – instead, it becomes part of the mix. Once you start traveling alone it is amazing how many people you meet as well as others in your life that come forward and issue invitations. Anyway, you’re not at this point yet but I wanted to offer comfort that you are not destined to do every holiday alone for the rest of your life!

So I am assuming going into this that you would probably like to meet other people on your singles vacations over 30. If you are annoyingly completely unconcerned about traveling on your own you are probably not reading this post!

So here are my top tips:

1. Vacations for Singles over 40: Do something organized

One of the best ways to do a solo trip is to do it with others. This doesn’t need to be other solos – it can be learning to scuba dive, a cooking trip, a photographic trip etc etc. A singles holidays over 40 that starts on a certain day means your first day will be the first day for other people – and this is one of the easiest ways to meet people.

Also, there will usually be something organized to introduce everyone to each other and there will usually be planned activities. If you do want to meet people I highly recommend attending as many planned activities as you can stand. Again doing a class or having a meal is one of the best ways to meet people.

best singles vacations for over 40

My first vacation as a single over 40 was an organized yoga week in Italy. Everyone arrived the same day and it was for a week. There was yoga every morning and then breakfast. Days were fairly free with potential activities. Then there was late afternoon yoga and dinners you could choose to attend or not. I met other people the first night and knew everyone by the end of the week. I also ended up staying in contact with three girls from the trip after I left.

For something a bit different why not try living a life Unsettled? In August of 2017 I spent a month living life Unsettled in Medellin Colombia and loved it! Unsettled is a fantastic concept. Essentially it aims to give people the experience of living in a city for a month rather than being a tourist.

singles holidays over 40s

The way it does this is that it has about 25-30 people sign up, organizes apartments and a coworking space and sets up activities that you can participate in as much or as little as you like. The other people on the trip are your community, the hosts act as your connection to local life and having an apartment and workspace means it feels more like living.

They choose brilliant locations from Buenos Aires to Cape Town to Barcelona. I highly recommend checking them out. If you decided to live life Unsettled then use the code “FRIENDSOFUNSETTLED”  and tell them that the Boutique Adventurer sent you for a discount of USD$150!

2. Singles Vacations over 40: Head to a spa/fitness/yoga etc retreat

Again it is ideal to arrive at one of these locations for a programme retreat/course. Many will have weeks that kick off on a certain day. However many do not. For those that do not have set weeks again, I would advise attending as many classes/walks/activities as you can manage. It continues to be the easiest way to meet other people in a natural construct.

Take a deep breath and introduce yourself to the person closest to you. A hi this is my name and I’m from x – how about you? Is all you need to get going. If you are feeling brave it is often good to say that you are travelling on your own for the first time and a bit nervous.

In the majority of cases, this will result in a come eat with us offer then or later. I am assuming you can say this without tearing up – that might put people off a bit J. And don’t feel you should only speak to others on their own. Couples, in particular, are great for a chat – and very likely to invite you to join them for meals. They are often getting a bit bored with each other and keen for some new company!

singles holidays over 40

Quite a few of these types of places now have talking tables at dinner. These are designed for those on singles holidays – and often frequented by non-solo travelers as they can sometimes be the most fun place to be at dinner! This is certainly the case at Kamalaya (see my key tip below). Most will have this on their website or ask about it when you are booking.

Click here for Great Deals on Spa Vacations


Read my complete post on Spa Holidays Solo here.

3. Singles Holidays over 40: Podcasts

I love a good podcast and there are SO many! However, podcasts are particularly great for the solo traveler for a few key reasons. Firstly I always find having someone in my ear makes me feel less alone. Secondly, you can download them on your phone and then play them anywhere – even without reception.

travel tours for singles over 40

Thirdly you can be sitting at a bar or a table and have your headphones in and people won’t know. This is good because most people won’t approach someone obviously reading a book. But if it is just headphones they won’t realise until they approach you that you have them in. It is always a good idea to sit at the bar/bar area rather than a formal table as it is much easier to chat to those nearby as it tends to be more relaxed and have the seats closer together.

One of my favourite Podcasts for travelling is Dear Sugar. This is by the wonderful Cheryl Strayed and is an online advice column. It is very absorbing and if you are feeling lonely it is always good to know that everyone is going through issues not just you.

Check out my favourite Books to Read When Travelling Solo!


single holidays over 40

4. Vacations for Singles over 40: Create a blog

This does not need to be a big full on blog. You can set up a free blog on word press easily and for no cost – for those of you that don’t know it is essentially an online diary. The great thing about doing a blog is that it gives you a sense of purpose when you are travelling on your own – you are doing research for great things to do/places to eat to write it up for your blog. Not because you are someone who has no one to go on holidays with  – you are almost like a glamourous journalist!

It is also a great conversation topic. I can’t believe how interested everyone is when I tell them that I am a travel blogger. You can also use it to start conversations. If you are at a bar/tourist site/class whatever when you say hi to someone you can say that you are a blogger and would be interested in their opinion of whatever it is that you are doing – whether you are or aren’t. It is also a great thing to tell say a bartender or a hotel owner as you can then find out more about the hotel/bar and get to know them better – and they are more likely to introduce you to other guests.

I also find blogging great fun but that’s me. Remember you can always be just starting one – it doesn’t need to be a full-blown blog with 100,000 followers.

singles holidays over 40

5. Single Holiday over 40: Consider the USA

America is very friendly – and I assume if you are reading this you speak English so it will be easy to communicate! Americans are much more likely to chat away to someone on their own and much more likely to keep a conversation going. This also holds for meeting Americans in other locations around the world. This is particularly true in bars – and if you are a single female traveller!

Heading to Europe? Check out this great post on 25 Tips for Solo Female Travel in Europe.

6. Tours for Singles over 40: Organised tours designed for solo travellers

I have excellent news – you are not someone who is doomed to travel alone forever and most likely die alone – you are at the crest of a hot new trend! You are a trailblazer! Travelling solo is the hottest growth area in the travel industry – and it is focused on those over 35!

I have been watching this sector for 10 years and in the last couple of years there has been an explosion in the number of companies offering single only tours, solo travel-based companies, no single supplement, solo weeks – you name it.

I will share my companies list in an upcoming post as it is quite long! For the moment just google trips for solo travellers and you’ll see the results coming through! A key tip here is don’t just limit yourself to your own country. Australia has quite a few solo travel-focused companies as does the UK.

Major travel organisations like Exodus also have special solo travel offers on many of their trips which mean that you can expect a larger percentage of the group to be travelling solo. I find this tends to increase the more physically strenuous the trip is as these are the hardest ones to find others who want to go eg cycling trips, climbing mountains.


There are the top 5 trips for solo travelers on Exodus:

Highlights of the Amalfi Coast – 8 nights

-Cycling Vietnam – 16 days

-Costa Rica – 16 days

-Discover Sri Lanka – 16 days

-The Inca Trail – 11 nights

Read my complete post on Tours for Singles over 40 which has a long list of specialised solo tour companies.

I went Everest Base Camp with Exodus – read all about it in Everest Base Camp Posts

7. Have loads of fun good books with you in case you start to feel lonely

There is nothing like a good book to keep you company when travelling solo! I keep adding to my list – please email me with more suggestions! [email protected] I keep them all in my amazon shop.

Explore Great Books in my Amazon Shop


8. My top tip – Kamalaya

I will be writing quite a few posts in specific places/hotels/spas/companies for solo travelers. But as this is my first in that series I thought I would share with you my single best place for solo travelers. This is where I would and have sent newly single friends who are terrified of travelling on their own for the first time. Kamalaya is on Koh Samui in Thailand. It is one of my favourite places in the world.

Read my Complete Post on Kamalaya Here


I have been twice – once solo which was my first trip. It is an absolutely stunning place (dedicated posts to come) and fabulous as a retreat. What elevates it for the solo traveler is the wonderful friendly feel of the place. Everyone is so welcoming and that extends to the guests. There are lots of classes and everyone tends to chat with those nearest to them – particularly before the class starts. Best of all there is a talking table in the evening that is the place to be in the restaurant. I have met many interesting people at Kamalaya. Oh and at any given time about 40% of the guests are traveling on their own. There are not many couples so it is also a great post break up place as well.

single vacations over 40

Travelling solo can be great fun – and also a bit addictive as you can do what you like when you like! But it is tough when you first start. Luckily I have been doing this and researching it for 10 years so I will be sharing more posts with you about company names, where to stay and lots lots more.

Compare Prices and Book Kamalaya Here


If you’ve got some outstanding questions Read my post on the Key Questions asked by people Travelling Solo.

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Frequently Asked Questions by those travelling solo over 40:

There are a few key questions that commonly pop up for the lone traveller no matter what type of trip you are planning. To be honest the right answer for most of these is very much about your personal preferences but I can at least highlight the questions and give you some views!

1. Do I stay in a hostel or a hotel or a boutique hotel or where do I stay????

Let’s face it – few people over 25 want to stay in a youth hostel. I never wanted to stay in one at any age! But we all know that youth hostels are chatty and provide a theoretically easy place to meet people (although this is not guaranteed!).

The good news is there is now a whole new segment of the youth hostel market that has gone premium! They are of course still youth hostels so many have shared rooms but they do have better sheets – or appear to! There is always the option of staying at a youth hostel and getting a private room eg the equivalent of the penthouse suite! This is a good article covering off lots of premium youth hostels. Northern Europe tends to be particularly good at these.

vacation for singles over 40

Generator Hostels is a chain of luxury hostels – all of them are currently in Europe – and I think offer one of the best options in this area.

It does appear like it is more difficult to find this new segment in South America. Australia has some good ones and I have also heard good things about Cape town in this area. Let me know any more you find out!

Let’s move on to the other end of the spectrum – 5-star hotels. Whilst I can’t guarantee anything I can tell you it is highly unlikely you will meet other people travelling alone easily if you stay at a 5-star hotel. Great if that isn’t your intent but please don’t book this if it is your first solo trip – unless you’re keen for room service and in-room movies (which is often a fab solo night!). Yes, people are travelling alone for business but they tend to get up early, sit at breakfast with their head buried in their phone or laptop and then go for dinner with people in their local office.

travel for singles over 40

In the middle is what I call boutique hotels. This is a broad definition – to me, this is about hotels with fewer rooms eg 20 or less and a bit more design focused than say a Holiday Inn (for mid-range big chain hotels same applies as 5 stars). There is not as high a chance of meeting people as there is in a youth hostel but it is a lot better chance than there is a 5 star hotel.

Here are a few tips for the lone traveller in boutique hotels:

  1. Choose a boutique hotel that has a roof terrace/outdoor area for a drink. Kicking back with a wine after a day exploring is a great time to meet people – especially if you have a full bottle/snacks and can share. Also even if you don’t meet anyone it is nice to have somewhere to sit other than your room when you are on your travelling alone

2. Go to breakfast at peak time. Breakfast is another great easy time to meet other people and chat – much easier than to ask them how their day was later on the roof terrace

3. Say hi and smile to everyone you walk past in the hotel – that is an easy thing to do and makes it a lot easier to then say something more at breakfast/terrace drinks

4. Become friends with the owner/person on reception. Firstly this is an excellent way to find out good local restaurants and places to go. Secondly, let them know that you are on your own and that you are keen to meet people. They may introduce you to other guests or help break the ice. Or they may even suggest you do an activity with someone they know – anything can and does happen!

5. The more exotic the location the greater the chance of chat. I have never had much luck with this strategy in Italy and France but I have always met people in places like Morocco, Istanbul, Burma etc. People who travel to more exotic locations tend to be a bit more curious – and when you are having a more extreme experience you tend to want to share and compare more.

over 40s singles holidays

Personally, I tend to go the boutique hotel option. However, I tend to limit it to a couple of nights and I always have Netflix/the kindle stocked up as my back up plan.

If you’re after examples of good boutique hotels when you are a lone traveller here are a couple:

Hotel Empress Zoe in Istanbul

The Apsara in Luang Prabang Laos

Dar Roumana in Fes Morocco

2. Do you get your own room on a group trip?

This is a tough one. Sharing a room gets you an immediate buddy. Most importantly you have someone with whom to go to meals. However, you could easily get a total dud and then be stuck with them. Or worse someone annoying. And it means you get no time on your own. So what do you do?

As I said there is no easy response. My advice is to get a roommate if you are new to solo travel and/or worried about travelling alone. If you are more experienced and used to showing up at dinner on your own and you can get a single supplement this would be my choice. I had a brilliant experience with a roommate I had never met before when god forbid I had to share a tent on Kilimanjaro but I do tend to get a single supplement whenever I can. Or I will share if it is only one or two nights.

singles travel groups over 40

3. How likely am I to meet a potential partner and/or someone for a fling?

If you’re a guy you probably have a good chance as there tend to be more women than men travelling solo – especially on organized trips and especially to more known locations.

If you’re female I would put your time into online dating in your home country. Having said that you absolutely can use apps like tinder and happn when travelling alone and they work – but this is definitely shall we say more in the fling territory as a general rule. However, there is no reason you couldn’t specify what you were after and to be honest this is possibly your best option.

I have a lot of friends or people I have met who met someone when travelling. Personally, it has only ever happened to me once and it happened after the trip! But I think I must be a bit of a jinx – so don’t go on a trip with me!

The best chance – male and female – I think is to go on an activity-based organized trip. If you are a female and like being on a bike then a cycling trip is a great way to meet men in lycra – although some may come with their wives! Locations like Cuba and Vietnam after often good ones for solo travel – as I said that touch more exotic has a lot of appeal for those travelling alone. Climbing a mountain is always a good option – when I did Kilimanjaro I think of the 18 of us there were only 2 couples. Anything where it is more difficult to find someone who would want to do the same activity at the same time is good for travelling alone.

Of course, a lot of “older” single people are coming out of potentially long-term relationships so are often re-examining their lives and thus are taking more risks and having more adventures – or looking for something physical to succeed at to buck up vulnerable self-esteem!

holidays for singles over 40

4. What do I do about dinner?

Dinner is, without doubt, the toughest meal of the day when you are a lone traveller. Who wants to face the host saying Really – just 1 of you? It can break you!  So here are some of my tips:

  1. Always try to stay somewhere that allows you to eat dinner at the hotel. You may well be exhausted or  just not up to dinner on your own so the hotel is a  great option

2. Try somewhere more casual where you can go in for a drink and then grab something to eat – no awkward just one moments. Also, pubs and bars are so much more conducive to striking up a conversation than a formal restaurant. I always try to eat at pubs and bars vs restaurants if I am travelling alone and feel like a chat

3. If you do feel like chatting definitely definitely sit at the bar. Strike up a conversation with the bartender. This is often easier a bit earlier in the night when they are not so busy. They are of course someone to chat with and may have some fab local suggestions. However, I also think it is much easier to join a conversation or include someone in a conversation when you have a neutral third party like a bartender. And you can always ask the bartender to help you meet other people!

4. I would encourage you NOT to go somewhere too upmarket – to me, this always highlights being on your own. Of course, go if you are dying to try somewhere and don’t mind – I tend to do the restaurants I really want to try at lunchtime when I am doing solo travel as I feel way less self-conscious and then go somewhere more casual for dinner

5. One of the toughest things is do you sit there staring out into the abyss or do you bring a book/magazine. The book/mag is great but it can put people off speaking to you. Personally, I think a laptop is better – it can be open but you can sit back “in thought” and scan the room and look to make eye contact with a safe place to retreat. I am also a big fan of podcasts – as long as you have sports type small headphones in this scenario. You can easily have these it but it will not be clear to others – so you are entertained but still approachable. If you have giant Beats headphones obviously you may as well be buried in your kindle.

Got any burning questions about solo travel that weren’t in my post? Drop me an email and let me know and I’ll include them in my next solo travel post!

And if you’re looking for a new laptop to entertain yourself with Netflix, Prime etc check out this great post

Want to read more about travelling solo?

And check out the Solo Traveler website – if has great info for solo travelers and some great deals

Click here for Travel Insurance

And Check out Solo Holidays Here

The Best Travel Places for Singles Travel

Here are four travel companies that specialize in offering solo travel group tours:

Just You Travel

Exodus Travel

Explore Travel

G Adventures

trips for singles over 40

I traveled solo for the first time when I was 35. What if I didn’t speak to a single person the whole time? What if something went wrong? What would I do in the evening? The whole notion of singles holidays over 40 was daunting! It is now 10 years later and I have done quite a few vacations for singles over 40, a lot more trips with people I have met along the way, organized trips, partners at the time, trips with friends and family – you name it. #solotravel #femalesolotravel
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Also published on Medium.

Vacations for Singles over 40
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Vacations for Singles over 40
Singles Vacations over 40s can be tricky to find - and particularly intimidating when it is your first time. Here is your solo travel guide
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The Boutique Adventurer
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