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How to Plan a Trip with Friends
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How to Plan a Trip with Friends

Posted on Thursday, April 15th, 2021

Story by: Ken Lovering | Travel Writer

It’s been said that life is a lot like riding a bike: It’s all about balance.

The same can be said about traveling with friends. The ideal trip does not require that everyone stick together 24/7. Far from it. It’s all about balance, communication, and respecting each other’s different styles and preferences.

Indeed, achieving that balance goes a long way in creating lifelong memories of your time together… and in deepening relationships. By trip’s end, you want all your friends to feel like they enjoyed traveling together as a group and appreciated having the freedom to do their own thing.

Our Group Travel Program helps you bring balance to your adventure while enjoying special savings and extras—but that’s not all we have to offer your cohort. We created our bicycling vacations to maximize the sociable pleasures of traveling with a group. So we know a few things about making the most of a vacation with friends. Here are a few of our top tips:

Be Crystal-Clear Upfront.

Surprises and moments of serendipity can bring a lot of joy to travel. But some surprises should be avoided when traveling with friends. Obviously, you want to make sure everyone agrees to the destination and daily itinerary before you make reservations. You might also check that all travelers know what to pack—whether their preferred riding shoes or protective glasses. Most important, agree on how money will be handled, including how you’ll split the check during shared dinners. Of course, reserving a VBT Bicycling Vacation will help you with all of these things—we provide detailed itineraries and packing lists; plus, with many meals included on many tours, you won’t have to worry as often about making sure everyone chips in on a bill.

Agree to a Schedule.

Some like to keep to a strict schedule, even when traveling. Others dance to their own rhythms. Surely everyone will want to enjoy their vacation in their own way. But setting a rough schedule for each day will help keep people’s differing tendencies in sync. The structure of a VBT Bicycling Vacation does some heavy lifting here: since the day’s agenda is set, you don’t have to worry about negotiating different styles. Even better, because we’ve fully vetted and planned the itinerary, you’ll never have too much crammed into one day.

Build in Downtime.

There’s no question that traveling with friends is hugely rewarding and can enhance relationships in immeasurable ways. But some in your tribe might not want to spend every waking moment together. In fact, some in your group might see your trip as two vacations in one: First, it’s an opportunity to explore and discover the world with people who mean a lot to them. Second, it’s a chance to indulge in individual experiences. Each experience is equally rewarding. Be sure to create opportunities for everyone, including yourself, to set out on their own. VBT Bicycling Vacations are structured so that there’s downtime most every day, so we have you covered.

Designate a Photographer.

Most groups include at least one shutterbug who’s always searching for that perfect shot. If the group agrees to play to his or her strengths as a photographer, you can all focus on enjoying the travel experience and spending time together. That way, you won’t end the trip with six versions of the same photo for every vista and every landmark. It will also streamline the photo-sharing process when you get home. No shutterbug in your group? See if anyone is willing to play the role.

Choose a Group Leader.

Ideally, every moment of a trip goes silky smooth, everyone gels together, and decisions magically align. But every journey has its occasions when the group must make a decision. You can avoid the phenomenon of “group decision paralysis” – when no one wants to impose their preferences and no one wants to take charge – by selecting a leader who can focus decision-making and drum up enthusiasm for the day’s activities. VBT Bicycling Vacation guides come to the rescue when it comes to indecision: They keep your day moving forward, routinely manage group dynamics, facilitate conversations and ensure no one is left out.


Some travelers say it’s not really a vacation if your phone is on. One of the joys of travel is its tendency to heighten our senses … to open our eyes to the details that make a place so authentic … to open our ears to the sounds of a new morning in a new place … and, when you travel with friends, to listen and engage with them in meaningful ways. You’ll miss all these things, and so much more, if you treat your phone with more urgency than you treat a sunset over the ocean. Try keeping your phone on airplane mode for the duration of the trip—you can still take advantage of our voice-activated turn-by-turn directions on GPS.

Plan on Some Meals Apart.

To enjoy the best times together, travelers sometimes need a few moments apart. Maybe you’re traveling with your spouse and you’d like some time alone. Or maybe you want to reconnect with a friend on your trip who you haven’t seen in a long time. That’s why we’ve intentionally built independent lunches and/or dinners into every tour—so our guests can enjoy private time, alone or in smaller groups, before coming back together.

Share the Memories.

The fun doesn’t have to end when you arrive home! Schedule an informal “reunion” for a month or two after your trip ends. Maybe one of you hosts a party, or you meet at a restaurant or on Skype or Zoom. There’s nothing like reminiscing about your shared experience, sharing pictures...and planning your next adventure!

Are you interested in putting together a trip with family or friends? Learn more about our Group Travel Program today.

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