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10 Helpful Tips for Traveling With Friends ... and Remaining Friends

As you might expect, we're HUGE fans of travelling. It should come as no surprise that we do it quite a bit here at Vacation Home Rentals, Worldwide (VHR, WORLDWIDE) ... for business (to check out the properties we represent and update our information on the various destinations where our properties are located) and leisure (with family and friends). There's a great, big, wonderful planet out there just waiting to be discovered. And exploring it with friends can result in memories that will last a lifetime.

Here's our list of guidelines and recommendations to make them good memories based on our 30+ years of personal experience planning vacations for groups of friends (including our own):

1. Choose appropriate traveling companions

Girls' Trip to Barbados 2017

You're going to be with these people for several days or a week or more, and if they are driving you nuts now (they're always late, they're cheap, they're slobs ... for starters), the situation will only get exponentially worse on the road. Be aware of their habits. Leave the drama queens at home. Choose like-minded travel companions who are laid back, flexible, kind, generous, easy-going, and respectful of others.

2. Have "The Meeting"

This is where you all get together, in person and/or via Skype, and figure out where everyone wants to go and what they want to do. As a part of arriving at that conclusion, be honest about your expectations. Keep in mind the cost of airfare and frequency of flights out of each person's nearest airport as some destinations (such as Punta Cana in the Dominican Republic) can be inexpensive due to the number of flights from numerous hubs, and others are not as affordable and have limited flights to their island. Our Villa Specialists can help you with your airline reservations if you do not have a travel agent.

Just because you all want to go to Jamaica doesn't mean that everyone wants to run around naked in Negril (not that we have any problem with that, but ...). Really get a good feel for what individual members of the group envision the ideal vacation experience to be. Have each person make a list of five things that are important to them, in priority order, and discuss it.

3. Set up a budget

After you all agree on the destination, the next step will be to determine the type of atmosphere everyone will enjoy - whether it be a cozy beach bungalow, modern high-rise condo, or luxurious estate - and how much each person can afford for their share of the accommodation and other expenses. Keep in mind that some of the larger, fully-staffed villas with multiple bedrooms may be higher in rental price overall but are a better value because the per person cost is less. Here are some excellent examples: is a fully-staffed, 4 bedroom, luxury villa on Jamaica starting at $81 per person/night. boasts 4 bedrooms on the beach in Barbados , with a full staff, for $51 per person/night. has 7 bedrooms and overlooks La Cana Golf Course in Punta Cana, priced from $125 per person/night.

VHR, WORLDWIDE lists the per person rate with its pricing to make it easier to understand what each individual in the group would pay for the villa.

4. Put one person in charge of the arrangements

You will need a 'lead person' to collect the money for the villa or condominium rental from everyone and forward the funds to our office. The person you choose for this important role should be a responsible individual who will ensure that payments are made on time, and that any information about the villa is shared among the group prior to leaving on your trip.

Asking for money is never fun, so this can be a crappy job. Don't be the kind of friend who is last to pay because holding up your portion of the deposit or final payment can result in losing the property which will make your friends very unhappy.

As a show of appreciation for handling this task, we have always allowed the person who assumes this important role to have first choice of the bedrooms. Seems fair and works for us.

5. Consider the roommate situation

Generally speaking, when renting a villa, there are two people to a bedroom. If everyone going is a couple, then it really doesn't matter. But if you have some single folks traveling together who will be sharing a bedroom, be aware of things like snoring which can ruin the trip for the person who has to put up with the noise and possible lack of sleep. Let's be honest, if your snoring will wake the dead, then it's only fair that you take (and pay for) a single room.

6. Assign one person to manage the 'kitty'

This is, perhaps, the most profound advice I can give you, something I know from personal experience. My girlfriends and I always put Wendy in charge of the money that is used to pay for group expenses - such as groceries and other food, beverages (except alcohol which we buy individually), restaurants, entrance fees, tips and anything that involves all of us - once we arrive. Wendy manages the kitty, and lets us know when we need to contribute. Works like a charm!

7. Appreciate that you don't have to hang out together all the time

As you consider the many options for sightseeing and entertainment, you will come to realize that not everyone has the same interests as you do. Part of the group may want to go river rafting on the Rio Grande and the others are hell-bent on strolling through the straw market for handmade crafts and bargains. On my last trip to Barbados with my college pals and other friends, I sent them off on a tour of the rum factory and Harrison's Cave (which I have done a gazillion times) while I did site inspections of the villas we represent. Worked out perfectly.

8. Understand what everyone wants to get out of the trip

Start a Google spreadsheet listing the various sightseeing and other activities available at your group's chosen destination, and share it with the people with whom you are traveling. This allows everyone to add sights and activities that they would like to do; and your travel companions can include their name next to the individual entries of interest. By independently researching, collectively listing, and planning ahead like this, everyone will feel that they are involved in the process and will get the most out of the trip.

Also, if you are the type of person who appreciates some 'alone time', choose a villa that has a library, den, multiple decks/patios, hammock or other 'quiet space' to chill by yourself for awhile.

9. Download WhatsApp on your cellphone

An amazing free program, WhatsApp allows you to communicate with others who have the app - for free - as long as you have access to WiFi - with which most of our villas and condominiums are equipped. You can call, text or send photos for FREE. Terrific way of staying in touch if your group splits up. One of the best travel cost-saving measures we have found to date!

10. Savor the time you're together

Oh how tempting it is to post your fabulous trip photos on Facebook as they happen but your friends want to spend time with you and not have you distracted by your social media prowess. You'll have plenty of time to share your great adventures with your peeps later. Plus, it's never advisable to let people know that your house or apartment is empty while you're away. Wait to share your precious moments until you return home.


With more than three decades of experience under our belts, your friends at VHR, WORLDWIDE are very knowledgeable when it comes to planning vacations with friends. Give us a call or drop us an e-mail to get the ball rolling. We look forward to hearing from you!

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