Travel Hacks for Taking a Perfect Trip with Family or Friends, Podcast #022

Travel-Hacks-Family-Friends-Intro-PicAs you know if you have listened to my podcasts or read my blogs, I am a planner. My goal is to make sure my valuable travel time and money is spent wisely. When traveling with others, that means spending some time in advance to set realistic expectations for enjoying the trip together. Having traveled a great deal over the years with family and friends of all ages and interests, I have learned a few things that might help you have a perfect trip based on what has (or hasn’t!) worked for me. Here are eight tips that I have learned:

  1. Agree Upon Finances

 You are probably not surprised to know that I make an Excel spreadsheet for every trip with my trip costs spent in advance, estimated charges during the trip, including a small budget for unforeseen expenses that may occur during the trip, and charges to be paid after returning from the trip. I often use frequent flier miles and/or hotel points for free flights and miles, but I may be traveling on a very limited budget if I cannot use free points. So, I have learned after traveling with friends or family who may have different spending expectations than I do, to share my spending plans with them. Often, they have asked for a copy of my spreadsheet.

When sharing costs, for example for a rental car, it is extremely important to show all budgeted costs and to agree on who will be responsible for paying the charges and getting reimbursed by the other travelers.

When traveling with my millennial-aged children, my husband and I will often pay for the accommodations and some meals. We communicate in advance with our daughters what we will pay for and what they will need to plan to spend on their own. For example, we may say that we will pay for dinner on 3 nights of a 7-night trip and that each daughter can either cook for everyone on 2 nights of the trip or they can pay for dinner on their two nights.

The main point is to:

  • Agree to all finances in advance,
  • Help everyone set a budget so there are no surprises,
  • Stick to the budget as much as possible, and
  • Have a small reserve for unexpected expenses that arise during the trip.

As an example, on my website post for this podcast I have pasted a copy of a budget for an 8-day trip to Munich, with several day-trips, that my husband and I took last year with my sister and brother-in-law. We all agreed in advance on expenses, and we were able to budget based on our expectations. For example, we agreed in advance that we would not have any expensive meals. We ate our free buffet breakfast each day at our lovely Marriott Residence Inn. Then, we sampled the street food with snacks for “lunch” and had one sit-down meal in an inexpensive or moderate restaurant for dinner each day. Note that there are subtotals for each couple for (1) amount spent in advance of trip, (2) amount to be spent during the trip, (3) charges to be made during the trip and paid when credit card bills are due.

Sample Travel Budget – Munich with Day Trips
  1. Accommodate Special Needs

Since I have had the pleasure of traveling with all ages of family and friends together, I thought I would share some things I have learned about accommodating special needs of various ages and energy levels. For example, in the past few years my husband has developed an autoimmune disease that has flares. Like so many people dealing with autoimmune disease and/or taking biologics, he must be cautious of preserving his energy levels and taking care not to be exposed to unhealthy environments where he could easily become sick. So, when we schedule long flights we book bulkhead seats that provide more room and more space away from others. Sometimes we have to pay extra for comfort class to get these seats, but if we do have to do this we know we are less likely to get bumped from these seats. We also bring packets of wet-wipes to clean our seats and tray tables as much as possible.

After arriving at our destination, as you can see from our budget spreadsheet for Munich, we now pay the money for a taxi to our hotel. This way we are not dealing with luggage and finding our hotel in a new city while we are tired. Usually we return to the airport via cheaper public transportation, since we are not as tired on the return. We also travel much lighter now than in the past when my husband could lift heavy suitcases overhead in a luggage bin on trains or buses.

Usually I schedule time on this day for my husband to relax in the hotel for the remainder of the day while I take a walking tour, or at least a walk that I have designed from my research, to get an overview of the city. This plan also works well when my mother travels with us, as well as for couples with small children. With small children, one parent can stay with the children and the other can take an overview tour.

Mom-Cindy-Daughter Melly at Parthenon
Cindy with Mom and Daughter Melly at Parthenon (Multi-Generational Travel Fun!)
  1. Allow Everyone to Have Their Own Time to Pursue Individual Interests

Due to various interests, age, and levels of fitness, it is important to make sure everyone has the opportunity to pursue their individual interests. Before you go on a trip, discuss opportunities for different pursuits and schedule these as part of your plan.

For example, when we travel to Hawaii, I like to be able to climb Diamondhead. Usually I would like to climb the amazing volcanic crater in the morning, but on my upcoming trip I am going to schedule this mid-day when my husband wants to take some time to rest on Waikiki Beach. By discussing our plans in advance, we can plan a nice walk along the beach in the morning. Then, he can have some time to rest while I pursue my Diamondhead hike.

  1. Schedule Time for Everyone to Be Together

As important as it is to schedule time for individuals to pursue their own interests, it is just as important to schedule time to be together. For example, we recently traveled with my daughter, Melly, and her husband to Disney World. They wanted to ride every roller coaster in every park! We made arrangements in advance to be with them daily for dinner and to schedule some pool time on a couple of non-park days. We did not try to keep up with them all day in each park. They committed in advance to meet us at the times we agreed upon in advance, and they then had the freedom to be on their own to pursue what they liked at other times.

Another time that is great to plan to be together is “down time” at night and in the morning. This works well if you are able to rent a condo or home together that has a common room where family and friends can gather. I would personally take fewer trips and spend a little more money on this type of accommodation in order to have time together with family and friends in a shared living space.

  1. Prioritize the Needs of Small Children

When traveling with small children, it is important to realize that they will not be able to enjoy a trip that disrupts their sleeping, eating, or comfort. For example, when Melly was a toddler, we took her on a trip to see “Cinderella’s Castle” at Neuschwanstein outside of Munich. We took her there in November, and we arrived late in the day. We actually visited the castle during Melly’s usual naptime, so she was rather cranky even to start the visit. Then, when we were waiting to take the special horse and carriage to the bottom of the hill at the end of a cold November day, she had had enough of it. She started screaming and crying so hard that people waiting to get in the carriage insisted we take their seat in the carriage so she could get in! To this day, when Melly is really cold, she says she is “Neuschwanstein cold”!

From this, and too many other experiences like it, I have learned to try to prioritize the needs and schedules of small children as much as possible. For example, when traveling to Disney World, we always try to stay at a Disney resort when we are traveling with small children. We take the children in for naps during the day, and head back out later without having to travel far to and from the hotel. There are Disney resorts for as little as $100 a night, during the least crowded times of year, that are on-property.

  1. Communicate Plans in Advance

Communication is extremely important when traveling with family and friends. For example, if some travel partners want to stay out late, spend more or less money or meals, or have days away from the larger party, a little communication in advance can go a long way in making sure there are not hurt feelings during the trip. Everyone has different expectations about what makes a perfect trip for him or her. Spend time talking about the trip in advance.

For example, we often travel with my husband’s brother and his wife. We make plans a few months in advance of any special trips to have dinner together to just discuss a draft itinerary and budget. It is fun to discuss ideas, and it also helps set expectations for what we will and will not do.

  1. Use Technology or Written Plans to Communicate During the Trip

A great way to remind everyone of the plan for the trip is to provide everyone with a copy of the itinerary and budget via a pdf file that they can put on their mobile phone or iPad mini. For traveling members that do not like to use electronic versions, provide them a written copy to encourage them to follow the agreed upon plans and budget.

At Disney World, when traveling with family, we all use the same log-in for the “My Disney Experience” app to see where everyone is (if they are using their Fastpasses), to be reminded of agreed-upon reservation times, and to easily make on-line changes as needed.

  1. Be Flexible

Finally, the most important thing is to be flexible. While it is important to plan in advance, to accommodate special needs, to set expectations, and to communicate during the trip, it is even more important to be flexible. Planning, budgeting, and communicating only go so far. When traveling with a number of people there will always be things that don’t go exactly as planned. THAT IS OK! The main thing is to enjoy the times you do have together. Remember, years from now you will not remember what you saw inside Neuschwanstein Castle, but you will remember being able to define “Neuschwanstein cold” with your daughter long after the trip!


I hope you will email me your tips for traveling with family and friends so I can share with listeners in the future. You can reach me at

Until next time, I hope all of your travel days are just perfect!


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