Traveling with Friends? Don’t Make These Mistakes!

Tips for traveling with friends

Not every vacation with friends goes smoothly.

Sometimes, shit goes sour.

Now, a perfect vacay for me is just me and my sweet boo, at a romantic all-inclusive resort located on some gorgeous tropical beach.

But occasionally I’ll travel with family or friends (or even work colleagues on our annual retreat), and over the years I’ve learned some very important “DOs” and “DON’Ts” when traveling with other people.

First, the DOs
  • Discuss the trip budget — Not everyone can – or wants to – spend money the same way. Talk about who pays for what and don’t overlook things like when and how much to tip, activities that aren’t included in your all-inclusive vacation (off-site activities and tours, spa treatments, boat rental, etc.) as well as stuff like ordering that a la carte (and expensive!) bottle of wine or champagne at a group dinner……discussing the budget ahead of time means that no one should wind up going home resentful.
  • The bottom line is that a little pre-trip planning with everyone involved should ensure that you STAY friends with everyone after you get back home.

  • Discuss shared/group/individual responsibilities — The larger the group, the more important it is that you designate someone to (at least loosely) coordinate things. When everyone is standing around saying “I though YOU were going to take care of that” then invariably something slips through the cracks, like reconfirming your airport transfers, or making dinner reservations when they’re needed (most restaurants don’t, but some do require them).
  • Recognize and respect personality differences — Sure, we love our family and friends for who they are, even if that’s very different from who we are. You can usually avoid problems if you understand different personality types and how to compromise to make sure everyone has a good time.
  • Schedule some time apart — The extroverts in your group may not need this, but doubtless you’ll have some introverts as well, and they certainly will. An introvert needs to have some ‘down time’ to recharge the batteries and will be much happier during the ‘together’ times if they get it.
  • Consider booking a Villa – Yes they can sometimes be pricier than getting everyone individual rooms, but often they’re not, and can be a great option for large families or small groups of friends. Many feature 3 to 6 bedrooms as well as a large kitchen, elegant shared spaces like a living room and outdoor patio, and a private pool and/or beachfront area. You’ll still have access to all the resort’s restaurants, and many Villas offer the option for a private chef as well.
Tip: Schedule a group meeting (which is a great excuse for a party!) to handle your pre-trip planning sesh….if your friends/family are far-flung, consider using Zoom or something like it. Just be aware that not everyone is comfortable discussing financial matters in a public/group setting.
Next, the DON’Ts
  • Share a room (the kind with two beds) if you’re ‘coupled’ (e.g. to save money, sometimes two couples will share one room with two double-beds, this almost never works out well!) — this leaves you with virtually no ‘intimacy’ time with your partner. Exceptions: If you’re traveling solo and want to room with a close friend or sibling, OR you’re sharing a double-bedroom suite, where each couple has their own bedroom and bathroom, with a nice big living room in between.
  • Room right next door — it’s amaze-balls how thin the walls are! NO one wants to hear friends or family arguing, discussing a member of the group that they dislike, or (gasp!) actually having great vacation sex. And yes, they CAN hear you.
  • Expect to do everything together — Sure it will be fun to share some meals and activities, but don’t put the pressure on your friend to go horseback riding or shopping when all she wants to do is relax at the Spa. A little time apart means you’ll have stories to swap over dinner.
  • Over-imbibe — Now I love my evening cocktails more than as much as anyone but sometimes that one-drink-too-many turns into a truth drug that can bite you. Your BFF’s hubby does NOT need to know that you really think he’s a pompous ass with ‘performance’ issues.
  • Make assumptions about activity levels or dining habits — Plan in advance what activities you’ll share and which meals you’ll enjoy together, even if that’s just an agreement to keep everything flexible and unscheduled. Some may like to have every day full of activities and dinner out each night, others won’t…and some folks like to eat an early dinner, others prefer to eat later.
  • Flirt excessively with your best friend’s wife/sister-in-law/the waitress — This one is just a big no-no unless you’re both single – otherwise those comments or touches that you think are innocent can set off an explosion of hurt feelings (your spouse), discomfort (the object of your flirtation), and anger (your object’s partner). Friendly is okay, flirtatious is not. If you don’t know the difference, discuss it with your partner.

The bottom line is that a little pre-trip planning with everyone involved should ensure that you STAY friends with everyone after you get back home.

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About Trisha Miller - Editor-in-Chief 59 Articles
Trisha is also the Editor-in-Chief at Travel Writers Exchange, a community for travel writers & bloggers. She's also a member of the Society of Professional Journalists, and a former member of the IFWTWA, serving on their Board of Directors from 2009 through 2015. When not traveling the world visiting the many all-inclusive resorts she loves, Trisha spends her time writing, mainly about travel and technology, sometimes both at the same time.
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