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Get Your Flaky Friends to Commit on a Vacation

Get Your Flaky Friends to Commit on a Vacation

You’re so ready for that next adventure. You’ve been working so hard and deserve a much-needed break in your life, like Pronto! It’s time to have some fun and unforgettable memories with your friends!


Your only slight problem is how to get Flaky Fred fully on board. You know, that one friend who gets really excited about going on a vacation in the beginning then fizzled out at the home stretch of planning? You both talked about it for hours over coffee, phone, even during bathroom breaks. And it seemed like it was a sure thing. But when it comes down to making the final plans, all of a sudden your friend realizes they have another event to go to; doesn’t have the money, or has gone MIA and won’t return your texts every time you mention “the trip”.  


Here are 7 tips to help your friends to commit to making vacation dreams come true this year!

1. Plan The Trip

Maybe your friend gets overwhelmed with all the details of planning a vacation or just flat out unreliable. Help them envision all the magical things they could experience by sharing exciting details of what you have planned so far including a ballpark figure of how much the trip will cost. Discuss mode of transportation, possible dates, and where you might stay.

  • Make a video of all the details. How many times you have sent out an email with all the details and you still get a million text and calls forcing you to repeat the information? Try to put together a short video of you explaining the important details of the trip. People are more likely to remember a visual and audio than a lengthy email.  You can easily shoot the video on your cell phone and then use Windows built-in program Movie Maker (Photos for Windows 10 users) to edit it.
  • Share the itinerary. Give them an easy to print itinerary with the most important information even if you have to print it out for them. Make sure it’s not longer than 1 page. Keep it exciting, simple and straightforward. This will keep them on the hook and get them to say YES.
  • Create a travel forum via travel app or website. Filtering through group chats full of emoji’s and bad jokes for important information is the worst. You may already be great at putting an itinerary together but there are several websites and apps that can make the process easier to create and share.


Travel Webs and Apps

Travefy website/app focuses on group travel. It allows you to keep all your documents in one place, create an itinerary, collaborate with friends, manage payments, and chat.   

Facebook Events is still my go to when all the travelers have Facebook accounts. Plus, who doesn’t want to be nosey and learn more about everyone that’s going before you commit.


No matter which platform you use, be sure to set some rules for chats. Request that everyone only comment with important trip details and contact the organizer directly with questions.

2. Get Them Excited

  • Share videos and pictures. If they need more convincing then they may need a visual presentation to get the creative juices flowing. You can help by sending them pictures of the last time you went or pictures you found online. Search Youtube for a video of the location or event. You can send a link of the promotional videos directly from the hotels’ or resorts’ websites or use guests home videos that may include helpful tips.
  • Invite the right friends. Make sure you’re inviting a friend that would truly enjoy the destination and activities. Don’t take someone that doesn’t drink alcohol on a wine tasting tour to Napa Valley. Same goes for those who want to lounge around sipping frozen drinks by the pool to an adventure hike through the jungles of Brazil. Once they know you have similar visions of your dream trip, BOOM, they’ll be gushing to all their other friends and family about it.

3. Get Them Involved

Sometimes your friend needs a buy-in and to be pro-active about decisions before they’ll commit.

  • Delegate the task. Discuss and decide who is going to do what. Which one is better at finding deals on hotels or housing options on Airbnb, HomeAway, Flipkey, etc? If you need additional friends to keep the costs down, ask who has other friends at the ready to help defray costs? Which one of you knows how to put together a mutually fun itinerary of activities in the area? Who’s the foodie and thinks it’s fun to plan your meals, snacks or grocery list. Teamwork makes the dream work, right?

4. Stay Focused – Together

  • Go shopping together. Go clothes shopping together for the big trip or better yet, to save some money to spend during your trip, see who in your circle of friends will let you borrow or swap articles of clothing for your trip. Fun, right?
  • Get in shape together. Take long walks or runs. Download a class or do online workouts at the same time if you can’t meet in person. You can be each other’s accountability buddy. You’ll both look fab and level up on your friendship!

5. Budget Together

When you’re in the early planning stages, you want to figure out what your budget is for lodging, food, activities. Talking about financial details are boring when you’re planning a fun getaway or adventure, so it’s tempting to skip this discussion altogether. But these financial details might be the ones that ultimately ruin your best intentions! It’s hard to enjoy a vacation when the person joining you is budget conscious, wanting to keep things on the cheap when you have saved up all year and expected to go to the finest restaurants or do almost EVERYTHING! Make sure you talk about the budget at the beginning of your planning. It might just save your friendship.

  • Book your accommodations, tickets, and reservations early. Everyone knows the earlier you book the cheaper it will be so don’t put it off.
  • Payment Plans. There are several websites that will let you book now and pay later. If money burns a hole in your pocket and saving isn’t really an option then making small payments is the best option. Try websites like
    • Pay Delay through allows you to book vacation packages with hotel and flight for just $1 down and then make 3 equal payments within 60 days of booking. The great thing is that it is not a credit based program so there’s no worries about accruing interest or completing a credit check. To find this option check for “PayDelay” on the payment screen during your booking. They do charge a non-refundable transaction fee of $5.00 to take advantage of this service.
    • Book Now Pay Later through Expedia. Book vacation packages with hotel and flight and make monthly payments. Reserve hotels and car rentals with no money up front.  
    •  Make a deposit on your reservation at the time of booking and the remaining amount is due 21 days before your date of departure. They do charge a non-refundable deposit fee of $29 to take advantage of this service.
  • Cover more of the cost. If your friends’ budget will not allow the luxury suite but you refuse to live amongst the common folks then offer to pay more. Another idea is to strike a deal. How about paying a percentage of their hotel cost if they agree to drive most the trip.  Better yet, just use our website Haydash to find a long-distance rideshare to save everyone money. 

6. Schedule Activities You Both Love

There’s a certain amount of planning that takes place before a trip. You want to make it easy and enjoyable for everyone involved. Make sure that you are not planning too much on your vacation and that you do things that both of you can enjoy. Sure, as a friend, you should be willing to do a couple things on the list that don’t exactly appeal to you…but if you’re spending that much time with someone, you should be compatible with most of the activities you do. Even if it’s hanging out on the beach doing nothing.  

7. Discuss Your Travel Styles

Are you an A-type personality who is always on the go and checks everything off your to-do list? Is your friend a book worm who hangs out all day on the couch, sipping tea, without a care in the world? This combination can surely work. But you both need to be clear about some things.


Talk about how a dream day on this vacation might look for each of you. Be truthful. If you’re the kind of person who likes to cram in as much as possible each day, while your friend enjoys a “fly by the seat of your pants” style of adventuring, you may have to decide on some ground rules first. Are you a morning person while she’s a grump until after breakfast? Figure out some strategies so that you both feel better moving forward with planning and committing. Maybe this was just the thing that was holding your friend back from this vacation?

Bonus TipShare your location when you travel

Traveling in groups can get tricky and frustrating. Have you experienced a time where you were on your way to meet up with a group and by the time you got there they already moved on to another place or even worse came looking for you even though you told them to stay put. To avoid this headache, try to talk everyone into sharing their location on their phone.

  • Find Friends (iPhone app) if everyone has an iPhone, you can easily use this built-in app to share everyone’s location with each other. When you share your location, your friends can start following your location immediately and easily share their locations back to you.
  • Glympse can let groups share their location and put in a destination to show everyone the estimated arrival time.
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