Real Thoughts on My First Ever Group Trip: Sailing with Intrepid Travel

This post likely contains affiliate links. By booking through these links I may make a small commission (which I am very grateful for!) at no extra cost to you.

Disclaimer: I was a guest of Intrepid Travel for this trip. However, all opinions are, as always, my own!

In June of 2019 I had the opportunity to do something completely new for me. Two things actually. The first thing was to join a group tour with Intrepid Travel and the second, which ties into the group trip aspect, was to spend 10 days sailing through the Greek Islands.

Clearly, I said yes.

However, as excited and eager as I was to live out my Mama Mia dreams in Greece on a sailboat, I had my hesitations as well. I’d been travelling for nearly 8 years through 57 countries, mostly by myself. I was used to doing my own thing on my own time and not having to worry about anyone else. Which, let’s be honest, is a big part of why I love solo travel so much. A group trip though? Well, that would definitely challenge my expectations and add a whole new dimension to the trip. A dimension that I wasn’t sure I’d like.

In fairness, I’ve done a couple of group trips before. Most notably a 3-day tour through Jordan and a 3-day tour through the Sahara Desert in Morocco. Both were fine, with people that I did get along with, but I also didn’t have to spend too long with them and the groups were quite small; in Morocco, there were only 5 of us.

My Greek island sailing tour was small as well, at least in comparison to most group tours, but it still meant spending 10 days on a boat with 11 strangers. Which, let’s be honest, definitely had the potential to go badly. In fact, I got so caught up in everything that could go wrong that I actually made an escape plan. Thankfully, I never had to put that plan into motion.

Instead, my first group tour opened up a whole new way of travel to me and ended up being one of the best travel experiences I’ve had yet. Here’s why I loved my group trip with Intrepid Travel so much.

Intrepid Travellers are, well, Intrepid

I think one of my biggest fears was getting stuck in a group of people who were unfamiliar with travel and needed their hand held the entire time. I know, that sounds kind of selfish and awful, but it’s true. I have nothing against new travellers and I actually love meeting newbies on the road and talking to them about what they have seen or done. Most of the time, I find it really refreshing. But, most of the new travellers I meet on the road are also travelling solo and are a little more adventurous than what I expected to find on a group tour.

Turns out though, that my fears were just a negative stereotype (lesson learned) because my sailing group were actually a very adventurous bunch. There was an older Australian couple who were ending their 9 week trip through Morocco, Spain, and Portugal in Greece. An Indian woman, currently living in London, who convinced me that I need to go to Bolivia. Then two friends, women from Australia and the USA, who actually met on an Intrepid tour through Italy and had some great stories. I also met a middle-aged Australian couple who filled me in on their adventures through Iceland, Vietnam, and Nepal, and a German-New Zealand couple who shared what it was like to travel overland through Africa.

While I was, technically speaking, the most travelled of the bunch thanks to my country count, there was no doubt that I was in very good company and I loved that I had found a diverse group of fellow adventures with so many stories to share.

I Felt like I was on Vacation, but still having an Adventure

Travelling alone is amazing. I love the freedom of it and I love that I get to be in control, but damn it can be exhausting. Sure, finding my own way is rewarding in the end but the actual journey can sometimes be brutal. Google maps hates me, I have zero sense of direction, and I constantly seem to end up in the wrong place. At the end of the day, solo travel is a lot of work and a lot of planning.

However, after this group trip with Intrepid Travel, I have learned that there is actually a balance. By joining a group trip, I didn’t have to worry about the silly things like figuring out transportation, actually getting from point A to point B, or even finding a place to sleep at night. That was all taken care of for me. But, at the same time, I still had a lot of freedom and opportunity to explore and do my own thing if and when I wanted. I could eat where I wanted, go to the beaches or shops or sites, or just sit in a bar and have a glass of wine while watching the sunset.

Being on an Intrepid group tour and having the silly basics taken care of for me allowed me to actually relax more and spend more time doing the thing that I love the most-exploring. That was something entirely new to me and I actually really enjoyed the balance. I actually felt like I was on a proper vacation, without that ‘trapped’ feeling that comes with all-inclusive resorts.  

My Intrepid Tour Gave Me an Experience I Couldn’t Have on My Own

Despite the freedom that is so often associated with solo travel, the truth is that solo travel can also be very limiting. I’ve been in so many situations over the years where the fact that I was alone has prevented me from doing and seeing things. Everything from being able to take a shuttle from one city to another, to being able to go to a tourist site on a tour. I’ve learned to deal with it and find alternatives as much as possible, but there’s no question that it’s frustrating.

As an ocean lover and boat enthusiast, sailing through Greece was a dream for me. However, it’s not something I ever could have done on my own: I don’t have a boat, I can’t sail, and unfortunately I’m not made of money and can’t afford to hire a boat or a skipper for myself (one day!). Joining a group tour was the only way that I would be able to sail through the Greek Islands. It was oh so worth it and, funnily enough, sailing ended up being the most cost-effective way to explore the Greek Islands as well. Who knew?

*psst: this is the Greek island sailing tour I did 

So, Would I Do an Intrepid Group Tour Again?

Hands down, yes. I’ve already looked into some if I’m being honest, especially the sailing tours because I did not want to get off that boat.

On top of considering Intrepid Travel for more sailing adventures, I’m also keeping them in mind for specific destinations. If you read my personal post on Morocco, and how difficult it was or me, you will already know that I wish I had joined an Intrepid Tour for that. India is another destination I’ve been on the fence about for a while in terms of going alone or with a friend. When the time comes, I will go to India with Intrepid Travel. I’ve also been eyeing the female-only tours to Iran; a destination I’d love to explore but, as a Canadian, physically can’t go without being part of a tour. If I go (fingers crossed), it will be with Intrepid Travel.

Perhaps the most exciting part of this experience is the fact that I am actually partnering with Intrepid Travel to start offering group tours through Eat Sleep Breathe Travel. For a couple of years now I’ve had people ask me regularly if I’d be open to a travel buddy or would be interested in maybe going somewhere with them and it’s never really been a possibility until now. I’m excited to announce that I am now working with Intrepid in creating small group trip opportunities for readers and followers to travel with me around the world. First up is Egypt in November of 2019, and I’m pretty sure I’ll be doing a Greek sailing one next spring. You can keep an eye on this page for the latest tours as they become available.

I had a lot of reservations about group trips and I think a huge part of that is because I am so independent. But, I was blown away by the experience and, as I mentioned earlier, sailing through the Greek islands with Intrepid Tour was honestly one of the best experiences of my life.

Is an Intrepid Travel Tour Right for You?

Wondering if Intrepid Travel group trips might be a good option for you? As a solo traveller, I was on the fence too. But, as you’ve read above, my mind has been changed. So, here are my thoughts:

If you’re looking for an adventure and a way to make it a little easier, or meet some like-minded people, then consider Intrepid.

If you are eyeing a destination that you just aren’t sure you want to tackle alone, then consider Intrepid.

Or, if you just want to have a good time and see a new part of the world in a fun way, then consider Intrepid.

Based on my personal experience, I don’t think you will be disappointed.

Interested in booking a tour? Check out the Intrepid tour options here.

You can also read my personal story about this experience on the Intrepid Travel Blog here


  1. […] Not sure you want to travel alone? I recommend taking a look at Intrepid Travel’s small group tours. I went sailing with them in Greece and it was a great mix of organized activities and free time. You can check out Intrepid Tours here or read about my experience with them here. […]

  2. […] Not sure you want to travel alone? I recommend taking a look at Intrepid Travel’s small group tours. I went sailing with them in Greece and it was a great mix of organized activities and free time. You can check out Intrepid Tours here or read about my experience with them here. […]

  3. […] For those wondering, I did my Greek island sailing tour with Intrepid Travel. You can read more on my experience here. […]

  4. […] did a 10 day Cyclades sailing tour with Intrepid Travel and it was honestly one of the best travel experiences of my life. We spent a few hours every […]

  5. […] As many of you know, I was supposed to spend the next 3.5 months travelling through Europe and the Middle East. I was to spend 2.5 weeks in Israel before heading to Turkey with my brother on a 15-day Intrepid Travel adventure. I then had a month to spare before I was going to Greece. I booked an adorable Airbnb on my favourite island, Paros, for 3 weeks before I was to host my first ever group tour: Greek island sailing. […]

  6. […] If you are looking to join a sailing tour in Croatia, check out the options from Intrepid Travel. I sailed with them in Greece and it was one of the best experiences ever. Check out Intrepid Travel tours […]

  7. […] Not sure you want to travel alone? I recommend taking a look at Intrepid Travel’s small group tours. I went sailing with them in Greece and it was a great mix of organized activities and free time. You can check out Intrepid Tours here or read about my experience with them here. […]

  8. […] Not sure you want to travel alone? I recommend taking a look at Intrepid Travel’s small group tours. I went sailing with them in Greece and it was a great mix of organized activities and free time. You can check out Intrepid Tours here or read about my experience with them here. […]

  9. Reid Broom on February 7, 2023 at 11:03 am

    I know this is an older post and I’m not sure you’ll even see this – but what was the food situation like? For the tour you did, it says no meals included so I just wondered where you ate. Was it all restaurants? Were there local places recommended by the crew? Just trying to get an idea of that because I can’t seem to find anywhere that explains the eating situation.

    • Hannah Logan on February 7, 2023 at 1:29 pm

      Of course! There are no meals actually included. At the beginning every puts money into the kitty (about 100 euros) and then go grocery shopping on the island, either as a group or nominate a couple people, for some basics for breakfasts and lunch. There is a full kitchen on board but we did more yogurt and honey and fruit for breakfast and sandwiches for lunch kinda thing. Then in the evenings dinner at a restaurant. Oftentimes we did group dinners and our skipper had a place picked out. You could also do your own thing!

Leave a Comment

Dreaming of Adventure?

Sign up to the Eat Sleep Breathe Travel mail list and stay up to date with all the latest travel tips and stories.