Planning your vacation can be a daunting task, but by breaking it down into the most basic components it becomes quite manageable and can even be a lot of fun in itself. Here are the basic steps we take each time we plan a trip.

Peruse some guidebooks and websites. At this stage you don’t necessarily need to buy guidebooks, you can simply check out your local library or bookstore just to take a look. Do some web searches on things to do in your desired destination, and check tourism bureau sites. Look for what excites you and what makes your destination unique. What is your destination known for? Are there great hikes? Legendary surf breaks? Unique foods? Historic sites? Begin to compile a list of the things that you are really excited about and wouldn’t want to miss. If there will be multiple people making this trip with you, have each make their own list and rank the items on it.

This is also a good time to look into what type of weather to expect during your intended trip – and to make some schedule changes if it is not what you were hoping for.

This South African hike ranged from cliff tops to beaches and included the opportunity to see hundreds of seals sunbathing and surfing and was high on my priority list for our drive around the country in 2014.

Research primary transportation options. If you will need to fly to get where you are going and your vacation timing is flexible, do a number of price comparison searches using a variety of dates to get a feel for seasonal pricing trends. is a great online resource for these searches.

If your dates are set, use Skyscanner to determine the cheapest airports and airlines for your desired flight path. It can be useful to price your trip as a series of one-way individual flight segments rather than only as a single round-trip package. This isn’t always better, but often provides more and sometimes cheaper options.

Example: We live in the middle of the country and often find that instead of booking a series of connecting flights, say from Denver to Europe, it is better to book a direct New York to Europe flight and then separately find and book a cheap flight from Denver to New York. Sometimes we can even work out the bonus of a long stopover this way. Twenty-four hours in New York can be a blast.

We also frequently fly in and out of different airports with short hops in between so we can see more.

Example: On a recent trip to Hawaii, we flew to Kona on the Big Island, spent a week there, and then took a short flight to Oahu, where we spent our second week, before flying home from Honolulu.

Research other short-distance transportation options such as train, ferry, rental cars or public transportation – both for getting to your destination if it’s not too far, or for exploring once you are there. Overland travel lets you see more of an area’s towns and countryside than skipping over it all by air. Additionally, flying to a nearby, cheaper airport can sometimes be an option as well, if there is an easy secondary form of transport to your final destination.  

Example: My mom and I are planning a trip to Scotland this fall. Our flight arrives in London at 10am and we are ultimately headed to Edinburgh. Rather than spend all day in the airport waiting for an evening flight to Edinburgh, we’ve chosen to take the train. It’s a 4.5-hour journey, instead of the 1.5 hour flight, but we will have a chance to get out to see London for a few hours (assuming our flight is on-time) and to see a lot towns and beautiful countryside along the way. In the end, we’ll arrive at about the same time as if we’d flown. It is always worth looking at all the options before just assuming there is only one way to get somewhere.

Scottish Countryside – The train ride north from London is much more relaxing and enjoyable than another flight.

Research lodging options. I usually start with hotels first, using a site like or This gives me an idea of what price range we’ll be looking at. Particularly if the prices are prohibitively high, I also check Airbnb. In some locations hotels and Airbnb prices are comparable and in others, dramatically different. You can read more about our comparison of these and more lodging options here.

Example: On a recent trip to Miami, we found the hotels very expensive, but our own entire apartment through Airbnb very affordable – the Airbnb price was less than half the price of an average hotel. Plus we got to live in a quiet neighborhood, have our own small kitchen, patio for relaxing outside and free parking for our rental car – a huge additional cost saver compared to downtown hotels.

Our Little Havana Airbnb included a small kitchen, comfy bed and every amenity we could think of from snacks to spare toothbrushes for less than half the cost of an area hotel.

Plot a basic itinerary. With all this basic research done, you should feel good about picking some dates and starting to rough out an itinerary. I usually draw out a calendar and I always use pencil, as it’s a bit of a puzzle working out the best way to fit everything in.

Based on the lists of things each person in your group wants most to experience, start to fill in the calendar, allowing more time than you think you need for each one and including an extra day in each location if possible to allow for bad weather or unexpected cool additional things you discover once you arrive.

This initial plotting should give you the information you need to decide if you want to visit multiple locations and if so, how many days you’ll want to stay in each place.

Example: On our trip to Miami, we were also planning to visit the Florida Keys, but it wasn’t until we started mapping out the activities and locations we wanted to include that we realized we needed more time in the Keys and less in Miami than we’d originally thought, and that we wanted to split our time in the Keys between the town of Marathon, mid-way down the Keys, and Key West.

This is an example of one of my rough itineraries. From a trip to Hawaii last year where we stayed in 5 different towns, it was a bit more complicated and involved a lot more erasing and rearranging than some.

Outline a basic budget. With this proposed itinerary completed, you know how long you’d like your trip to last. Now, based on all the information you’ve gathered on transportation, lodging and specific activities or attractions you’d like to experience you should be able to put together a basic estimate of what your trip will cost. Make sure to also add in a daily estimate of food costs based on whether you will be eating at restaurants, cooking your own food, or a combination of the two.

Do not stop here!

This step is where sometimes you have to get creative or make a few concessions. I always start off with my ideal trip and then have to start prioritizing and arranging things to make it work. Maybe that means I don’t get to go snorkeling with dolphins AND manta rays, maybe we commit to making a certain number of meals at “home”, or maybe we decide we’re not willing to compromise on much and the trip just needs to be shorter instead. There are endless negotiations at this step – just believe that you can make it work, because you can.

And example of a rough budget for the same Hawaii trip as the previous itinerary photo. We ended up dropping a number of these things to make it fit our budget, but we had an unforgettable trip.

Whenever I start to get discouraged in this phase, I find it helpful to ask myself, “Would you rather have half of these experiences than none at all?” Since the answer is always yes, this lets me carry on excitedly with planning, even as I cut amazing things from the plan.

Inevitably there will always be more that you want to do than time or money allows. That is why you will never be done traveling. Instead of allowing yourself to get overwhelmed or sad about this, remember that every new experience you have on this trip is one you wouldn’t have had if you had stayed home. Every new experience is the direct result of your being brave enough to take time out and to plan and take this trip.

Start booking! Once you have your basic itinerary and a budget you feel is feasible, you can start actually booking some things. I usually start with airfare because it’s generally the most expensive and can vary quite a bit depending on day of the week. Then we fill in with intermediate transportation and lodging.  However, it’s important to start with whatever is most important to you. If there is something you absolutely must do, book that first and build the rest of your trip around that. You don’t want to get non-refundable plane tickets and hotel reservations in place and then find out the show you just had to see is sold out the day you’ll be in town.

I hope this little bit of guidance is enough to get you excited about planning your next trip and to give you an outline that makes it easy to get started. If you take things one step at time you’ll be counting down the days until your dream trip before you know it.