Should You Travel Solo or With Friends? How to Decide What’s Right for You

Ever told friends about a dream getaway and watched them invite themselves along? We’ve been there. Today we walk through the real tradeoffs between solo travel and trips with friends, and we get honest about freedom, safety, budget, and the hard truth about compromise. Cheryl shares why traveling alone can unlock spontaneity, deeper cultural immersion, and personal growth, while also acknowledging the joy of shared memories and the relief of splitting costs on rooms, rides, and groceries.

We break down the key compatibility questions to ask before you book with someone: travel style (budget vs. luxury), pace (early riser or night owl), food preferences and allergies, and how each of you handles stress and change. You’ll hear practical ways to protect the friendship and the itinerary, like agreeing on must-do lists for each person, setting a realistic budget, planning intentional alone time, and using clear meet-up points so everyone gets space without derailing the day. If you’re drawn to culture and connection, we talk about how comfort zones can quietly shrink your experience—and how going solo or simply splitting up for a few hours opens doors to local conversation and serendipity.

Most importantly, we anchor every choice to purpose. If you need decompression and reflection, solo may serve you best; if you’re celebrating or easing into travel, a friend or group can be perfect. We also cover graceful ways to say no when someone invites themselves, how to align expectations, and how to avoid resentment by being upfront about intentions. By the end, you’ll have a simple framework to choose your mode, design a trip that fits your season, and return with more than photos—return with clarity. If this helped you plan smarter, follow the show, share it with a friend, and leave a quick review to tell us your travel style.

Chapters

• 0:00 The Travel Dilemma
• 0:21 Solo Travel Foundations
• 2:44 The Joys Of Shared Memories
• 4:36 Comfort, Culture, And Safety Tradeoffs
• 4:57 The Cost Of Compromise
• 6:05 Are We Travel-Compatible
• 10:31 Intentions, Honesty, And Boundaries
• 12:36 Must-Do Lists And Fair Itineraries
• 13:15 Which Is Better

Transcript

SPEAKER_00: 0:00

Have you ever started to plan a trip and suddenly all your friends are interested in joining you? Or maybe you have actually planned a trip with a friend and then maybe last minute they could not go. What do you do in these cases? How do you handle this predicament? Welcome to Solo Travel Adventures. I'm Cheryl Esh, your host. Well, this has happened to me, uh, the first scenario, basically, uh, where I, you know, I talk about my travels and they know I love to travel and suddenly want to come with me, or they've kind of invited themselves. And it's kind of awkward, uh, especially if you have been planning that trip and you have all these ideas and you wanted to do it solo. Well, how do you handle that? Well, I just want to address that solo travel is not the only way to travel, although it is my favorite way to travel. So I may be biased and I may also be difficult to travel with because I am also so very accustomed to solo travel and having my own ideas and being able to fulfill those is just so freeing. And there are, of course, pros to having someone join you. But solo really, it just fills my heart. Now, I don't say I do solo all the time, I have gone with other people, but solo travel does offer you the freedom to do whatever you want, meaning you can pick your destination, you can pick the activities you want to do, you could plan your itinerary or don't plan your itinerary, and then how you spend your time on the trip is all up to you. And so you don't have to worry about other people accommodating other people or worrying about how they might respond, getting along, um, all that stuff. And there's actually, if you solo travel, you are more likely to meet more people because you're almost forced to, instead of staying kind of uh cliquish with your person or group that you might be traveling with. Solo travel also gives you the opportunity to get to know yourself better. And I don't know, there's just this sense of freedom, and you do learn a lot about yourself when you solo travel. Now, there are some pros about taking a friend. You can share these experiences with this friend, and you have shared memories, which are incredible. I have some shared memories with some friends, and some are from 35 years ago, and we still tell the same tell the stories and we laugh about it. And all these stories, these memories, are for a lifetime. And so, yes, there is that, and that you can actually share the experience with someone is it's a beautiful thing. And maybe you get closer with that friend because you are traveling together. That also could be a plus. You can share the expenses in certain things. For example, you share expenses in accommodations, in taxis or Ubers, maybe even share in food, if you're especially if you're going to, you know, maybe cook in and and you know, you don't like go to the grocery store. And, you know, traveling with friends is familiar, it's comfortable, so it's less scary than going solo. But there could be a downfall to that too. When we stay in our comfort zone, whether we're traveling to another country, this really prevents us from really experiencing the culture because we're staying in our comfortable zone with our friend or friends or significant other, even, right? You're having just conversations with them or you're doing things just with them and not really truly experiencing um things that are outside of that comfort zone of your own language, your own culture. It truly can feel safer when you do travel with somebody. That is true. So, say you're hesitant about solo travel, going with somebody else could really soften that. That could make it a whole lot more comfortable when you travel in pairs or more. There is a safety about that versus by yourself. Now, the downside to maybe traveling with a friend or a group is that you will have to compromise. I hate to tell you that, but we have people coming in with their own ideas of what they want to do on a trip. And everybody might throw in their ideas and you can't do them all, right? So you have to compromise. Maybe you compromise on where you even stay or what you do or where you go, because not everybody can decide on the same place. So there is that, unfortunately. And if you go into a situation like that and knowing that you have to compromise, just be gracious and don't be bitter about it. Um you know that you're sad that you missed something that you really wanted to do. Um, if that's the case, then stay an extra day or go a day early from your group trip or your friend trip so that you can experience that on your own. Now, if you are traveling with a friend, I really highly recommend that you ask these questions. Do you enjoy similar things or activities? So do they share that similarity with you? Do you share similar travel styles? For example, are you a budget traveler, but your friend is a luxury traveler? That might not work out because the luxury luxury traveler is not gonna want to stay in cheap hotels or hostels. And then if they get their way and you know they get a really expensive hotel, then the budget traveler person is might be resentful or feeling um because they're having to put out more money than they maybe expected or even had in their budget. So then there could be some tension or animosity there. So you want to make sure that you share similar travel styles and the activities that you do, of course, that um they are similar in that you are gonna both maybe enjoy museums, or maybe you both enjoy being in the outdoors. So making sure that that is the same, so that when you pick activities, they are gonna you're gonna both want to do similar things. A third question you can ask is, are you compatible in temperament? This also may include their sleeping patterns. And so if they're a morning person and you're a night person, that could cause a little issue, especially if you're planning to share a room, you're gonna be scheduling maybe tours or something, um, that you know, if they're a morning person, they're gonna want to get up and do it in the morning. Whereas you would rather wait till afternoon. Are you compatible in your temperament as far as your attitudes and how you approach things? Maybe even down to do you share the same um values, right? As far as you know where you might go, uh, what you might spend your money and time on. So making sure you're compatible. I have only found a handful of people that I have found compatible in traveling with. And I do love that about finding people that I travel well with. Because when you find that you are traveling, maybe you are dear, dear friends and you've done tons of things together, and you're good friends in short periods of time, meaning, you know, you can handle each other a few hours a week. And then you get into the situation where you are around that person 247, and suddenly you realize, yeah, we're not good travel buddies, and that can happen. And unfortunately, that could make your travel experience not such a positive one. So if you're asking these questions beforehand, also I would add in there, what are their expectations for this trip? Um, do they need some alone time? Are they an introvert? Are they an extrovert? How will you balance that um time? Especially for introverts, they do need some alone time to recharge. Um, otherwise, like me, you might get cranky, right? So considering that, considering the maybe even the types of foods that you both enjoy, making sure because, you know, maybe one likes a certain type of food and the other would prefer, you know, not to eat that kind of food, um, or has allergies like myself. So it makes it a little more challenging to find restaurants that could be um compatible for both parties. Well, whether you travel solo or with someone else, it may also come down to what your purpose or intention of your trip is. If it's just to really experience um another culture, to see new places, um, and to, you know, enjoy some different cuisine, different activities, then you know, going with someone else or with a group, even a group is great because then they they will plan all that for you, would be good. But if your intention is to, you know, be alone, then obviously if someone does invite themselves or is interested in joining you on the trip that you're planning, please be honest and tell them what your intentions are for that trip. And that could be, you know, just being honest. Uh we'll keep that friendship. Because if you decide to give in unwillingly and they do come, um, it's your expectations of what you had originally wanted for your trip has changed. If you've invited a friend, you said, okay, yes, you can come. You're, you know, you've compromised, um, because you don't want to hurt your friend's feeling, right? And you do love your friend. But then you get on that trip and suddenly you're resentful because it's not turning out as you had in originally intended it to be. So respect yourself and what your purpose is or intention for your trip, and but also be honest and respectful to your friend or significant other about the trip. Even if you both need to sit down and set expectations, um, set a budget, uh, decide together where you're going. I like to, when I'm planning with somebody, I often we will often say, okay, what are your must do's? Like, I am not giving in to this. Um then we will do those. And the other person might have one or two of theirs, like they must do. And so that could also just be a great way to create an itinerary that is satisfying for both parties and gives both parties a chance to really experience what they desire to see when they go. So, which is better? Solo travel or travel with friends? There's no right or wrong answer to that. And as I mentioned earlier, it may depend on the purpose and the intention. Now, granted, you are planning a girls' trip, man, you invite as many girls as you want for that trip. A birthday trip, you want to invite all your friends, invite all your friends. They know the purpose of that trip is to celebrate your birthday. Go for it. But if your intention is to find some like decompress time away from maybe a stressful job, then maybe a solo trip is better suited for you. I love solo travel. It is my preferred way of traveling. So don't shoot the messenger. But I do like to uh share my travels with other people as well. Which do you prefer, solo or with somebody? And if you've never solo traveled, I truly encourage you to take that chance this year. Go and take that first solo trip for yourself. And maybe you'll get the bug like I did, and you'll understand what I'm talking about.