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

Looking for singles holidays over 40? 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 a holiday for singles 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.

singles vacations over 40 - woman alone at rainbow river in colombia
Cano Cristales colombia, a great sport for holidays for single travellers over 40

Traveling alone doesn’t need to become the way you always travel – instead, singles vacations for over 40s become 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 the comfort that you are not destined to take 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 travel tours for singles over 40.

If you are annoyingly completely unconcerned about traveling on your own you are probably not reading this post.

Top 3 Organized Tour Companies for Over 40 Solo Travelers


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✔️ Dedicated Offers for Over 50s
✔️ Small Group Tours
✔️ No single supplement


boat trip positano view

G Adventures
✔️ No single supplement
✔️ Free time in itineraries
✔️ Evening Group Meals



Encounters Travel
✔️ Private & Small Group Focus
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Top Tips for Singles Holidays over 40

1. Do Something Organised

One of the best ways to do a singles trip over 40 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.

Singles holidays over 40 that start 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 an organized event to introduce everyone to each other and there will usually be planned activities on the best vacations for singles over 40.

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.

⇒ For Great Vacation Ideas for Singles over 40 check out Explore.

group of people on a walk seen from behind
Joining organized walks is a great way to meet other people when on vacation for singles over 40

My first over 40 singles holidays 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. The majority of people on the trip were traveling alone at 40, 30 and into their 50s.

I met others the first night and knew everyone by the end of the week. I also stayed in contact with three girls from the trip after I left.

This type of holiday is one of the best singles vacations for over 40-year-olds and a great option if you’re after European vacations for singles.

Solo Female Travelers Club is a community of more than 90,000, run by the fantastic travel bloggers Meg and Mar. The heart of the community is their Facebook group which has some great information and is the perfect way to meet other females interested in travelling solo.

Meg and Mar also run female-only small group tours that range from luxury retreats to adventurous expeditions in some awesome locations.

images of solo female travel trips

Another option that I think is one of the best trips for singles over 40 options is to 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. This is a great alternative to typical singles travel groups over 40.

woman taking photo of golden statue in thailand
Snapping away on one of my singles vacations over 40s – this one is in Koh Samui when I stayed at Kamalaya

The way Unsettled does this is that it has about 25-30 people sign up, organizes apartments and 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.

Unsettled choose brilliant vacation spots for singles over 40 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. Head to a spa/fitness/yoga etc retreat

A retreat or spa is fantastic for weekend getaways for singles over 40 as well as for longer singles trips over 40. Most retreats have a purpose – fitness, relaxation, yoga etc which gives a plan to the week that helps visitors to feel less lonely.

Also, you are much more likely to meet other like-minded travel singles over 40 if you are attending a retreat based around something you really enjoy. Again it is ideal to arrive at one of these locations for a set program 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 on holidays for solo travelers over 40.

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?” It is all you need to get going. The large majority of people will be friendly and will reply.

If you are feeling brave it is often good to say that you are traveling on your own for the first time and a bit nervous. I can almost guarantee you there will be other over 40s single traveler types on many of these types of trips.

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.

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.

large group of people at a communal table
Lunch on a F**k It Week, one of the best vacation spots for singles in their 40s

Quite a few places where there are solo vacation packages 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) – one of the best vacation spots for singles over 40 in the world. Most will have this on their website or ask about it when you are booking.

⇒ Read my posts on 30 Fantastic Solo Spa Breaks , the best Singles Ski Holiday options and the best vacations for over 50 singles options.

3. Podcasts

I love a good podcast and there are SO many. However, podcasts are particularly great for the 40 travel solo adventurer 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
That’s Mount everest behind that coffee – Everest Base Camp is another great option for over 40s single holidays

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.

woman in a sitting hammock hanging from a tree
Photogenic Hammock on a F**K It Retreat

4. Create a Blog

This does not need to be a big, full-on, lifelong commitment type 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 traveling 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 glamorous 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. Everyone wants to know more.

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 who might also be 40s singles.

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.

several women sitting on yoga mats on a terrace
Yoga on the terrace at my first every solo holiday in Italy

5. 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. There are some great places to travel alone in the USA.

Vacations for singles over 40 in the USA are a great option. If you would prefer to take a designed singles vacation package over 40 specialists for your USA trip check out

Just You

Intrepid Travel


Heading to vacation spots for singles over 40 in Europe? Check out this great post on 25 Tips for Solo Female Travel in Europe. There are quite a few European tours for singles over 40 in this post.

6. Vacation Packages

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 the over 40s singles vacation. 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 over 45 singles holidays, solo travel-based companies, no single supplement, solo weeks – you name it.

⇒ Check out my post on Singles Travel Groups for 30 different options for singles over 40 vacations packages.

This post has everything from adventure trips for solos over 40 to the best resorts for singles over 40 to food-focused travel groups for singles over 40.

A key tip here is don’t just limit yourself to your own country. Australia has quite a few companies which run single vacation packages over 40 travellers as does the UK.

And there are some great options for travel for singles over 40 Australia. I can tell you as an Australian that it is a very friendly place! For solo travel groups 40s + to Australia check out:

G Adventures

Just You

woman holding hands up with walking poles from behind with mt everest in the background in nepal
My first view of Mount Everest on the way to Base Camp – this was on a solo group trip

Here are four of the most popular trips for solo travelers on Explore

Highlights of the Amalfi Coast

Jordan Discovery

Walking in Northern Cyprus

Sri Lanka in Depth

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 traveling solo! I keep adding to my list – please email me with more suggestions! I keep them all in my Amazon shop.

8. Kamalaya

When it comes to the best vacation spots for singles in their 40’s my absolute favorite, and the place I recommend to all newly single friends who are terrified of traveling solo for the first time, is Kamalaya.

Kamalaya is on Koh Samui in Thailand. It is one of my favorite places in the world.

⇒ Read my super comprehensive guide to Kamalaya

I have been to Kamalaya Koh Samui four times – and three of those were solo. It is an absolutely stunning place and fabulous as a retreat. What elevates it for the solo traveler is the wonderful friendly feel of the place.

Everyone at Kamalaya 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 Koh Samui. Oh and at any given time about 40% of the guests are traveling alone.

There is a range of ages but it skews towards the singles travel over 40 end. There are not many couples so it is also a great post-break-up place as well.

This is one of my favorite places to recommend for singles holidays over 40’s might enjoy.

⇒ Compare Prices and Read More Reviews of Kamalaya

dining area at kamalaya thailand
Ah lovely lovely Kamalaya

Frequently Asked Questions by those traveling solo over 40:

There are a few key questions that commonly pop up for the lone traveler 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.

winnie the pooh quote engraved on a brass plate
Nothing like a bit of Winnie the Pooh! This was at Dhulikhel Resort in Nepal

Generator Hostels is a chain of luxury hostels – all of them are currently in Europe – and I think offers 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 spectrum – 5-star hotels. Whilst I can’t guarantee anything I can tell you it is highly unlikely you will meet other people traveling 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 traveling 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.

woman in panama hat take a photo of a red temple in thailand - taken from behind
Panama hats go with everything! Even red temples in Thailand!

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 fewer and a bit more design-focused than say a Holiday Inn (for mid-range big chain hotels the 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. Yes, luxury singles holidays over 40s are possible in boutique hotels.

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

  1. Choose a boutique hotel with a roof terrace/outdoor area for a drink. Kicking back with a glass of 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 traveling alone

2. Go to breakfast at peak time. Breakfast is another great easy time to meet other people and chat – much easier than asking 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 then to say something more at breakfast/terrace drinks

4. Become friends with the owner/person at 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. I have found that the best holiday destinations for singles over 40 tend to be more exotic – like Morocco, Istanbul or Burma. 

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.

woman in hat in front of colourful door and building in guatape colombia
Exploring guatape in Colombia

Personally, I tend to go to 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 backup plan.

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

Hotel Empress Zoe in Istanbul

The Apsara in Luang Prabang Laos

Dar Roumana in Fes Morocco

6. If you’re a cat lover why not consider traveling with your cat? These days there are great options for cat carriers that can make this a great experience for both you and your cat. And many boutique hotels these days allow pets.

2. Do you get your own room on a Singles vacations over 40s all-inclusive?

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 traveling 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 on holidays for singles over 40 I tend to get a single supplement whenever possible. Or I will share if it is only one or two nights.

person walking up big daddy sand dune in namibia - taken from behind
Climbing Big Daddy Dune in Namibia – an amazing place and great for a solo organised tour

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 traveling 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 traveling 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; honestly, this is possibly your best option. I have a lot of friends or people I have met who met someone when traveling.

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.

I think the best chance – male and female – is to go on a singles adventure holiday over 40 skew. 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 for a single adventure holiday if you’re over 40 – 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 traveling 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. An adventure holiday is a terrific option at this point.

pebbled path trimmed by small logs

4. What do I do about dinner?

Dinner is, without doubt, the toughest meal of the day when you are a lone traveler. 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 more conducive to conversing than formal restaurants.

I always try to eat at pubs and bars vs restaurants if I am traveling alone and feel like a chat

3. If you feel like chatting, 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 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 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 question about solo travel that wasn’t in my post? Drop me an email and let me know and I’ll include them in my next solo travel post.

Want to read more about over 40s Singles Vacations?

Here are some more websites and articles that you might find interesting:

Solo Traveler website

Solo Holidays website

Best Travel Places for Singles Travel Article

Here are five travel companies that specialize in offering guided solo traveller groups 40s +:

Solo Female Travelers Club

Just You Travel

Explore Travel

G Adventures

Who Paid for What with this Post

I paid for everything associated with writing this singles holidays over 40 blog post. This was completely me travelling and not working with any tourism boards or hotels etc. I learned most of the above before I started this blog – well it is probably the thing that got me into writing a blog.

However, this post does contain affiliate links. That means that if you click through on them and make a purchase I may well receive a small commission. I just wanted to make sure that you knew. modern outdoor pool and building

Posts you might enjoy:

Singles Travel Groups

All inclusive vacations for singles over 50

Vacations for over 50s singles

Solo Spa Breaks

Like this Singles holidays over 40 Post? Why Not Pin It?

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
woman with pink hat sitting on kerio crater in iceland
woman in blue dress outside door of colourful house in guatape colombia
woman in pink hat standing in front of waterfall in iceland
images of woman from behind in different hats at different tourist spots
woman with pink hat and blond hair from behind with lake in front

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Friday 14th of May 2021

Love this article!!! You are giving me that courage to go just do it and have a solo travel experience. It’s definitely in my buckets list. Especially now that I just got separate from a 19 yrs marriage. I truly need to do this. Thank you for the info and the tips.

The Boutique Adventurer

Friday 14th of May 2021

thanks Claudia - I highly recommend solo travel - the more you do it the better it gets. I am sorry about the end of your marriage - I have been there. And it is when I started travelling solo and it very much helped my recovery. All the best!

Jared James

Monday 3rd of August 2020

Not above 40 yet but I think I can do some of them, thanks for sharing ;)

Vluchten Zaventem

Tuesday 21st of April 2020

My first solo holiday was a few days in Paris several years ago. I found the days were fine as I was of sightseeing but the evenings where a bit hard to deal with. I did find the advice about going into a restaurant or bar if being followed works well. The waiters went out shouting at some guy who was bothering me. I now tend to spend a few days every few months on a solo holiday and love the freedom.

The Boutique Adventurer

Wednesday 22nd of April 2020

Yes the evenings are more difficult aren't they? Going to a restaurant and sitting at the bar is often a great option - important to keep your travelling freedom!!

jojo vito

Thursday 30th of January 2020

These are great places to visit. I would want to try Namibia soon :)


Tuesday 12th of November 2019

After working too hard the past few months, I am looking forward to my trip in Thailand. Most especially the solitude in my resort. These tips here have helped me put things into perspective and I can't wait to get started on my trip in the coming days. Lovely article.

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