• Carrie Mitchell

How To Plan The Perfect Group Trip

Updated: Jan 28

While I am prone to solo travel, I have been asked to lead a few group excursions and while it can indeed be a hair-pulling experiment in frustration, I have learned a thing or two. It’s like an art form – done well, it can be the most glorious of times, done poorly, it can get bad in a hurry. So consider this your guide to traveling with a big group of people—headache avoided.

1 – Let someone lead

Anyone who has ever traveled in a large group knows that someone inevitably ends up stepping up to the plate and acts as leader. Do not try to resist this! Having a leader or two will make things much easier for everyone, and likely keep a million emails/text messages from flying around randomly with no direction or solutions. It streamlines everything. Also, use Google Drive and apps to keep things organized.

2 – Assess your group dynamics

A couple of questions to ask so you can better design an itinerary that addresses everyone’s needs:

  • Are all your group members on the same page about how you like to spend your time?

  • Do most people in the group prefer to chill out at home or go hit the clubs?

  • Are people more fearful or more adventurous?

  • What about introverts and extroverts?

3 – Group Rate Discounts and Perks

Whenever possible, go for group rates and deals – always ask, people/companies want your business!  If you have a larger number of people, look for group airfare rates, ability to waive a change fee, or even swap passenger names. You can also score sweet group deals on your accommodation as most hotels will offer a complimentary suite upgrade if you book more than 10 rooms, and flag you for VIP treatment.

Personally, whenever I travel with more than two people, I skip the hotels and rent houses, which can be more fun and affordable as a group. If you want to go super luxe, check out some upscale home rental sites, like onefinestay,Sonder, and Oasis, in addition to your usual suspects (Airbnb, VRBO, etc.)

4 – Handy Apps

There are (free) apps to help both the planner and the group. Consider:

  • Travefy. It lets you gather everyone’s flight and hotel info into one single, shareable itinerary, and you can chat with everyone on your trip in the app. You can also create group polls, enabling you to easily take a crowd vote.

  • Prava. Similarly, you can share a group itinerary and talk to your friends within this app, but Prava has an additional feature that lets you share your location while doing so.

  • Doodle. If you only want to create group polls, go for this one. It’s also available in desktop form, which allows you to send a Doodle poll in an email.

  • Venmo to help you with the dreaded money issue, and can send cash to one main payer asap

  • Splitwise (free). Everyone enters the amount they paid, and Splitwise tells you who owes what. Thanks to a partnership with Venmo, you can settle your bill directly in the app. One problem: Splitwise doesn’t factor in international currencies, so if you’re traveling abroad, consider downloading Splitwise Pro, which costs $2.99 per month but has currency conversion capabilities, as well as other features, like the ability to scan your receipts.

  • Splittr ($1.99). It does convert your currency, but it does not incorporate Venmo or payment abilities, so you’ll have to pay your friends back outside of the app.

5 – Get the Food & Beverage Planned

A lot of your money goes toward food and drinks, so go into your trip thinking about food and drinks – don’t forget to book restaurant reservations in advance (I always use Open Table within the US)! And if you’re taking the rental route, you can cook up big, fun group meals OR hire a local chef.  Obviously make one grocery run at the beginning of the trip for basic stuff—think eggs,bread & jam, wine, chips, wine, good cheese…did I say wine?

Hope some of these tips helps you plan a low-stress trip, you’ll be able to enjoy that quality time together even more. In today’s all-too-hectic, digital world, those rare uninterrupted moments of togetherness are precious. And that’s really what traveling with your friends & family is all about.

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About Me

Travel Oracles founder Carrie A. Mitchell is an entrepreneur, strategist, podcaster, writer & author. Inspired by global culture and history, this project was born to spread knowledge, connection and creativity 


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