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The Dos and Don’ts of Traveling with Singles’ Groups
From:
Amy Schoen, MBA, CPCC -- Dating and Relationship Expert Amy Schoen, MBA, CPCC -- Dating and Relationship Expert
For Immediate Release:
Dateline: Washington, DC
Thursday, May 8, 2025

 

Are you excitedly planning your vacations for this year? Taking time off is a great way to recharge, see new places, and break out of your day-to-day routine — and if you’re single, it can also be an opportunity to meet someone special. That’s why traveling singles groups are becoming increasingly popular. Whether you’re eyeing a relaxing beach escape, a high-energy city tour, or a meaningful cultural experience abroad, joining a travel group designed for singles can be a fun and exciting way to explore the world.

But before you hop on a plane, there are a few important Dos and Don’ts to keep in mind to make the most of your trip, both socially and personally.

DO choose a singles travel group that matches your interests and goals.

Not all traveling singles groups are created equal. Some groups may focus on a younger crowd seeking nightlife or adventure. Another might be designed for the more mature singles. They might include early morning tours and evening cultural events such as theatre and concerts. Some are geared towards those interested in culture, history, world service, or even faith-based travel. There are many, many options out there!

So, before deciding on a program, don’t think about where the most eligible guys or gals will be, but think about what kind of experience you are looking for. Are you looking for a group with a specific age range? A theme, like food and wine, hiking, skiing, or wellness? Maybe you want a cruise with structured mixers, or a more independent tour with shared dinners. Matching the group to your personal style and goals can make or break your experience. You’ll enjoy the trip more and be more likely to meet people who are truly compatible with your interests, lifestyle, and values.

DO be friendly with everyone.

You may be on vacation, but remember the purpose of traveling with a singles group is to socialize. Making an effort to smile, say hello, and introduce yourself to others will set the tone for the rest of the trip. You don’t yet know who is friendly with whom, and people talk. If you aren’t friendly, they might assume you don’t like them or that you’re a snob. Then people may not take the time to get to know you.

You don’t have to be a social butterfly, but being warm and approachable goes a long way. Sometimes people bring their own insecurities on these trips, so being friendly helps break the ice and creates a more welcoming environment for everyone, including yourself.  Especially if you’re introverted. You may have to make extra effort to be social beyond your normal comfort zone. 

DO be inclusive and not exclusive.

Do include others in your activities, meals, and excursions. People will think more highly of you for being inclusive instead of excluding people.

Group trips thrive on camaraderie, so even if you’ve found your “vacation bestie” early on, keep the door open for others to join. You never know — that person you invite to dinner might end up being a future friend, business contact, or even a romantic interest. People notice who invites others along and who doesn’t. When you include others, you communicate generosity, kindness, and openness. All attractive qualities in friendship, AND when dating for a life partner. 

DO spend time with someone you are interested in. See a particular site, do an activity, or grab lunch together.

It’s okay to enjoy one-on-one time with someone you’re interested in — in fact, it’s encouraged. Most traveling singles groups create opportunities for singles to meet, connect, and have one-on-one moments. Generally, these events are relationship-building opportunities, and if you’ve met someone special, you should take advantage of them.

Sometimes, though, you might have to create your own opportunity. Just be respectful of the group’s schedule and make sure it doesn’t feel like you’re ditching everyone entirely. These little moments can be golden opportunities to see if there’s real chemistry beyond the group dynamic. And if you’re nervous about making the ask, keep it casual — “Hey, I was thinking of checking out the market after the museum tour. Want to grab a coffee after?” That way, there’s no pressure, just a chance to connect.

DON’T hook up too soon when traveling with singles groups.

Vacation vibes can make everything feel more intense and romantic.  Between sunsets, adventure, stolen glances, and cocktails, it’s easy to get caught up in the excitement. But moving too fast can lead to unnecessary emotional entanglement or regret.  It’s very tempting to jump into a relationship when you like someone, but the goal is for you and your love interest to connect after the trip. 

Not to mention what can happen if you let romance overwhelm you, only to find out the next day you aren’t compatible. I remember a friend who got dumped in the middle of a trip, and it was very awkward for her during the rest of the trip.
It’s best to focus on building a genuine connection and see if the interest carries over once you’re back home. You’ll avoid potential awkwardness and drama during the trip, and it leaves room for something more lasting to develop. If someone is truly interested in you, they’ll be willing to wait and pursue something deeper later.

DON’T leave your best friend out on their own unless you have an understanding.

If you’re traveling with a friend or roommate, make sure to communicate expectations before you go. If you are specifically traveling with a group catered to singles, then you both know why you’re there. However, it’s still good to make sure you are both comfortable before and during. Are you both okay with pursuing separate interests during the trip? Do you want to stick together most of the time? Are you comfortable being a wingman or the third wheel if the other person meets someone and you don’t?

Your friends are there for you, and if your love interest doesn’t work out, you don’t want to lose a friend too! It’s better to establish expectations in the beginning than to risk hurt feelings later. If you do find yourself connecting with someone romantically, be mindful of balancing your time so your friend doesn’t feel abandoned. Loyalty and friendship are still important on a singles trip — especially if you want to come home with both a potential date and a solid friendship intact.

What really matters is what happens when you get home from your trip.

Don’t let the vacation high cloud your judgment. Real relationships are built over time and tested through everyday life, not just sunset walks on the beach. So while it’s exciting to meet someone amazing while traveling, wait and see how they show up once you’re back to reality.

Do they text? Call? Make plans to see you again? Hopefully, your love interest isn’t going back to a significant other at home. Unfortunately, that happened to me once. So, build a good foundation for friendship, trust, and respect on your trip, and it will set the course for a possible beautiful courtship in the months ahead.If they follow through, you might be onto something great. And if not, at least you had a great trip and maybe made a few new lifelong friends.

Don’t forget, I’m always here to help you on your journey to find lasting love. If you are considering a trip and would like some guidance, or maybe you’ve returned from one with a potential relationship and desire some coaching to help it grow, reach out. Finding true love is possible for you at any age, and I have just the plan to help you get there! Go to http://www.talkwithcoachamy.com and let’s connect!

If you’re still looking for that special someone to experience life with, download my “5 Signs You’re Ready for True Love” workbook today and make sure you are prioritizing your life for love!

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Name: Amy Schoen, MBA, CPCC
Group: HeartMmind Connection
Dateline: Rockville, MD United States
Direct Phone: 240-498-7803
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