12 Steps to Successfully Planning a Family Trip

Planning a family trip can be stressful, but with some guidance you may start to enjoy it. I’ve been traveling with my kids for almost 12 years, since they were less than a year old, and I’ve learned some things along the way. I really enjoy planning our vacations and I want to share what I know with you to help you plan your next vacation.

planning a family trip
St. Mark’s Square, Venice, Italy

Related: Tips for a Multigenerational Family Vacation, Tips for Flying with Kids, and Tips for Traveling with Kids.

Disclosure: I only recommend sites I would use myself and all opinions expressed here are my own. This post may contain affiliate links that, at no additional cost to you, I may earn a small commission. 

There have been studies that say that the most enjoyable part of vacations are before, when planning, and afterwards while reminiscing. But, I think with some careful preparation, you can also enjoy the actual trip.

Here’s how…

1. Plan in advance:

The more time you have to plan your trip, the better. I suggest planning between 6–12 months in advance. First, this will give you time to organize your work schedule and work around the kids schedules. Second, you will have time to research your destination and make all necessary arrangements, such as booking flights, accommodations, and activities. Moreover, it will give you more time to save money and get better deals.

Personally, I’m always thinking of what I want to do next. I enjoy planning so much that I’m typically planning my next vacation and researching the following one that is more than a year away!

How to Stay Organized When Planning a Family Trip?

Use travel apps to help keep track of your itinerary. Once you start making reservations and booking activities, Tripit.com helps keeps it all organized for you. Just create an account and send your plans to their email from your account email and it’ll organize it by day and time and gives a nice snapshot of your vacation. You can also share the itinerary. 

Traveling with a multigenerational family? I have some helpful tips to make it easier. Tips for a Multigenerational Family Vacation

2. Determine your budget:

What is your budget? How much can you spend? Expenses to consider:

  • Flights
  • Taxis / ride sharing
  • Car rental & gas
  • Lodging
  • Food
  • Activities

You may be able to space out your travel expenses over a few months. Some expenses like airfare will be paid ahead of time. Most airlines allow bookings up to 10 months before your return date. Others, such as hotels, will be paid at check-in/check-out. However, if you are renting a house, most require a deposit and payment ahead of time.

Knowing how much you can afford will determine where you can go. Which leads to the next step:

4. Choose your destination, travel time, and dates:

At the airport in Miami before our trip to London

What kind of vacation do you want? Do you want it to be relaxing, adventurous, cruise, cultural, etc.? Make a list of the top 3 places you want to go.

Then research the places on your list. Find out the best times to travel, activities that are available, and how much it will cost to get there and stay there. Also, take any time zone changes and weather into consideration. Here’s why that’s important:

You don’t want to plan a beach vacation during rainy season.

And, you don’t want to go to a location with a 12 hour time difference for only a few days.

Travel dates

When can you travel and for how long? How much time can you take off from work? Think about your schedule and that of your travel companions.

Documentation

Consider your destination’s passport and visa requirements. Most countries require you to have a valid passport at least 6 months after your return flight. Will you have enough time to get these documents before your trip?

5. Consider travel insurance:

Once you know when and where you are going, consider whether or not you want / should get travel insurance. It’s not something people normally think about, but it can provide peace of mind when traveling, especially if you are traveling with kids or older people.

Look for policies that cover unexpected expenses, such as medical emergencies or trip cancellations. Most travel insurance companies will require you to purchase the insurance within 14 days of your first deposit to cover pre-existing conditions.

6. Book your transportation:

Obligatory kid pic in the cockpit of the airplane

Book your flights or other transportation. Research options at your destination, such as public transportation or rental cars.

Flights

vacation with kids
My son sleeping in his car seat on our flight to Greece

As I mentioned earlier, airlines typically don’t let you book more than 10 months in advance. But, the closer you get to your travel dates the more expensive flights become. When booking your ticket, think about how much you want to spend and whether or not you want to pay extra for seat selection and baggage check. Kids under 2 usually fly free if they sit on your lap. But, consider getting them their own seat. This will make everyone much more comfortable and it’s safer.

Car rental

Book rental cars in advance. If traveling to an island, rental cars are limited, so book those ahead of time. Check their cancellation policies. Some car rental companies don’t allow you to cross into certain countries. If traveling with kids, consider car seats or boosters. You’ll have to pay extra, but it would prevent having to take your own. Also take the size of the car into consideration. Many older towns aren’t conducive to large cars on their streets.

Rail tickets

vacation with kids
London “tube” train

Book train tickets in advance if you are traveling long distances. If you are traveling to multiple destinations, consider a multi-day or multi-leg rail pass. They are usually less expensive.

Road trip

If you are doing a road trip, plan to do a maintenance of your car before you leave. Have them check the tires as well. Plan where you will stop to eat, rest, get gas or EV charge on your way to your final destination. Think about whether or not you want to drive all the way through or stop overnight somewhere.

Airport transfer

Taking a much needed nap in a car with a hired driver from London Heathrow airport to Dover, England

If you aren’t renting a car how will you get from the airport to your lodging? Some hotels offer free shuttles. Check with your hotel ahead of time. If traveling light, you may prefer public transportation. A taxi might be convenient if you have a lot of luggage. Many places also have ride share companies, like Uber or Lyft. Some countries have their own version and it would be worthwhile to research this ahead of time. Alternatively, you can hire a private driver.

Consider distance, cost, and convenience when deciding how you will get around. On one trip we flew into London Heathrow and were going to Dover in Southern England to get a cruise from there. It was less expensive to hire a private driver than it was to take public transportation. It would have required taking the Tube, the train, and then a taxi in Dover to get to our hotel.

Combined for the 4 of us, it was more expensive than hiring a private driver to pick us up at the airport and drive us directly there. And I’m glad we did, because we didn’t have a great flight (I fainted on the plane) and it took a really long time to get through immigration. We were so exhausted when we arrived that I don’t think we would have been able to do the 3 legs of transportation. We slept in the car the entire way to our hotel in Dover.

7. Book your accommodations:

Research and book your accommodation, whether it’s a hotel, rental, or another type of lodging. When booking accommodations, make sure to choose options that might be helpful for the type of vacation you want.

If you are going skiing, a ski valet might be useful.

A beach vacation? Chairs and umbrellas would be convenient.

Do you like biking? Are there free bikes or bike rentals available?

If you have young children, you may want to look for hotels that offer cribs or childcare services.

Also consider whether or not you want lodgings with a kitchen or free breakfast, so you don’t have to worry about that. I like searching for accommodations at Booking.com. They have great options and are very thorough with their descriptions.

8. Plan your activities:

Make a list of activities you want to do at your destination and research any tours, excursions, or tickets you may need to book in advance.

We don’t always plan our vacations around the kids, but we do try and incorporate things that they will also enjoy. I like to plan a morning activity with lunch options nearby and then an afternoon activity. Also, I try and balance them between indoors and outdoors and activity level. If the morning is outside hiking, then the afternoon is spent indoors doing something less active.

Will you be traveling over the holidays? If so, will things be open while you are there? What will you do when things are closed?

Schedule tours

I like to schedule at least 1 tour that gives a good historical and/or cultural background to get a sense of the people and place that I’m visiting. There are usually group and private tour options. Of course, private tours are more expensive. If really tight on cash, there might be self-guided tours that you can find online. It will take a little more work on your part, but they’re usually free or for a very small fee.

If you are hiring a tour guide, it’s always helpful to find one that understands the needs of kids. Tours by Locals let’s you search for a guide that suits your family and you can contact them and let them know what you want to do or ask for suggestions. They are usually pretty accommodating and will tailor a tour.

11. Pack your bags:

Pack your bags according to the weather and activities you have planned. Remember to pack any necessary documents, such as your passport, visas, or travel insurance information.

Pack smart

Packing can be stressful, but try to pack smart and minimize the amount of luggage you take. Make a checklist of essential items and prioritize what you really need. Also think about whether or not you will need to pay for checked bags or not, depending on the type of airline ticket you purchased. Keep in mind that most airlines have a weight restriction of 50 pounds.

See 12 Handy Travel Essentials for Kids to help you pack for your next family vacation.

12. Enjoy your vacation:

Remember to relax, have fun, and enjoy your vacation experience!

Get a FREE printable travel planning checklist!