When NOT to Book a Trip with Friends or Extended Family

Say you’re thinking about taking a relationship to the next level by booking a trip. Doesn’t matter if it’s a friend, a couple, extended family, or a bunch of people with a shared interest (e.g. club, hobby, etc)

🛑 Stop! Think before you book!

A trip is an entirely different level of money, time, compatibility, and most importantly commitment. All of these elements are required for all to have a good time. A trip isn’t an afternoon hanging out, a day at the beach, or dinner & a show.

On a trip, you’ll be living with others for 1 to 2 weeks that you usually don’t, and frankly, maybe shouldn’t. You’ll have spent buckets of money, you all could be exhausted, dehydrated, sore, or all of the above. On a trip, people can be at their worst, not the polished, controlled version of each other you’ve seen under less strenuous circumstances. 

If you aren’t certain your relationship can take it, you really need to think twice, especially for longer, more complicated, bucket list trips. Travel advisors can help remove a lot of the friction with group travel. We are the go between, coordinating everyones individual needs and designing a custom plan that can meet the groups combined goals. 

We’re travel agents, not magicians! If personality & travel styles are not a good fit then the perfect itinerary will not matter.

Top red flags 🚩 not to book a trip with friends or extended family

  1. Not food compatible. Adventurous foodies vs. basic eaters makes every meal time a fraught conversation.
  2. Not sleep schedule compatible. Early vs. late risers or night owls vs. early birds, is always a source of friction. 
  3. Not budget compatible. Big spenders vs. penny pinchers can make either side uncomfortable or downright unhappy.
  4. Not transit compatible. Some just want to walk, others drive, while others insist on public transit.
  5. Disagree how to get value out of an activity. Do you go to an amusement park from open to close but your traveling companions like a more leisurely pace? Watch out!
  6. Beach, sun, and surf…turns out some people just don’t like sand, it’s coarse and rough and irritating and it gets everywhere.
  7. Not travel style compatible. Some people like a fully scheduled itinerary with every day planned & booked in advance. Others like to leave their schedule open and see where the day takes them. 🙅‍♂️ 
  8. Can’t agree on excursions. Some want to zip line, while others want to lounge by the pool every day. Some want to stay at the all-inclusive every day, while others want to venture out for new experiences. 
  9. Spending time together or apart. No agreement, explicit or implied, about how much time to spend together versus apart. e.g. Some travelers need a lot “me time” while others don’t, then separate schedules and more private accommodations would be necessary.

If bringing children…

Traveling with children adds an extra level of difficulty and more things to consider.

  1. Parenting styles & permissiveness. If some kids can go on riskier activities, like cliff diving, but others can’t, hurt feelings are inevitable.
  2. Pre-trip agreement on child care. Will all parents be on duty the entire trip, will the responsibilities be split. e.g will parents take turns having date nights, will the adults split up and do different activities. Having a plan in place ensures no one assumes they will get time off while other adults watch their kids. 

Your trip, if you should choose to accept it…

Group travel comes with many potential pitfalls but also with the possibility of making amazing memories and tightening the bonds of family and friendship. With careful planning a travel advisor can help you avoid a lot of the friction that sometimes accompanies groups.

Our advice, try a starter trip first. A two to three day extended weekend with your intended travel companions can reveal many, if not most of these issues. If you start seeing these or other red flags, strongly consider waving off on a longer, more expensive trip. Don’t ignore that feeling in your gut. If your spider sense tingles, there’s danger!

Some Benefits of Group Travel

  1. Group travel is often more cost effective, especially for groups over 12. Many vendors offer discounts to groups that meet their minimum requirements. Sometimes this is offered for as few as 5 rooms or cabins. 
  2. Pooling financial resources allows access to higher end bespoke experiences. e.g. A private boat tour of Lake Como for 2 adults can cost between $400 -$2,000 depending on length and amenities on board. But split between 6-9 passengers the per person cost is much lower. 
  3. Bonding and memories that will last a life time. With careful planning, compromise, and some patience traveling with companions is a lot of fun.
  4. Special arrangements, private tours before and after hours, and special access to many top tourist destinations is often available only with a larger number of travelers. 
  5. Peace of Mind when traveling, some of the stress that comes with traveling to new countries is alleviated when you are surrounded by familiar people.
  6. Group travel can bring you closer together or allow you to reconnect after time apart. 
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