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5 Steps To Planning A Trip

5 Tips for planning your next trip pin

I’m the first to agree that trip planning takes a lot of work and can be overwhelming.  Currently, I’m planning one trip for each month of 2020 and a multi-month trip for 2021. If I didn’t love the process so much, I could see why people travel with tour groups or choose to go to all inclusive resorts in order to keep it simple.  But in keeping it simple, you may miss out of some really cool off-the-beaten-path locations that make travel so fun and rewarding.  After traveling full time for the past five years and spending the previous decade planning road trips and week-long getaways, I’ve narrowed down a system that I go through when planning my trips so that you can have more ease in planning a trip.


The first thing you need to do in planning a trip is to dream.  Dream big and dream “your” dream.  We often are conditioned to follow the masses or be swayed by great marketing tactics.  In my Project Life Course I talk about the importance of aligning your actions with your desires and when it comes to planning your trip this is no different.  Sure, when you are sitting in an office cubicle and see picturesque beaches and yourself lying in a hammock with a tropical drink, it seems to make sense, but the answer to your wanderlust may very well may be a small town you’ve never heard of in the southwest of France, 5 tiny villages in Italy, or at the southern tip of Costa Rica.  

If you look forward to having a foodie experience in a city, then maybe the Basque Country of Spain is for you.  If you like movement and nature, then maybe you should consider one of the amazing national parks the United States has.  If you’ve done the national parks and love them, then maybe a national park abroad would be perfect.  Really, the options are endless, but if you are going to commit the time and money to travel, try to make sure your destination aligns with your passions and desires and isn’t just an escape from the grind.  

Travel should be about adding value to your life and learning more about yourself, not about creating monotony in a new environment.

My favorite places to find travel inspiration are through travel blogs, Pinterest, and talking to people.  Sure, I get a few ideas through magazines and travel guides, but they tend to be more sales-y.  Hotels, restaurants, and excursions often don’t get to the root of what I’m looking to create in my travel experience.   We all want to make our kids (and ourselves) happy, and as fun as it sounds like to stand in long lines and eat crappy food at an overpriced amusement park, there’s a good chance you can have just as much (or more) fun with your kids exploring new roads, new towns, and new trails by creating your own customized itinerary. 

Start a bucket list, make notes, and keep spreadsheets on places you come across.  Even if it’s a destination you won’t be going to for another five or ten years, it’s nice to start organizing your dreams into short-term, mid-term, and long-term goals. If they are written down, they will be more likely to become a reality.  One thing that having travel brochures, magazines, and guidebooks lying around our house (or motorhome) does, is get my kids involved in planning a trip.  

My kids love to travel and are excited to visit new places so they rarely ask for us to buy more ‘stuff’ or eat out because they know the money we save goes to something more important…new adventures and lots of memories..

Step 2: Narrow Down The Where and The When

Once you have an idea of a few places you want to go for your next trip, the next step is to look at the logistics.  

How much time do you have for the trip?  If you only have a week off work, you aren’t going to want to fly halfway around the world, especially if you are traveling with kids.  

What time of year are you looking to travel?  A lot of tropical destinations have a rainy season, make sure you aren’t planning a trip in the middle of it unless you are ready to get wet.  If you can travel in the shoulder season, you can often find really good deals.  Check for the temperature and precipitation averages for the places you are planning a trip to so you make sure it’s what you are looking for.

Related Blog: 50 Things To Know Before Your First Trip To Europe

Step 3: Figure Out If You Can Afford To Get There

Once you’ve narrowed it down to a city, state, country, or region, it’s time to see if you can afford to get there.  My favorite website for finding good deals on plane tickets is through I use this app to find out when the cheapest time to fly is and also to see which airlines are the cheapest for the destinations I am considering.  Then I go to that airline’s website directly to compare the price.  If I’m not ready to book travel yet, I sign up for their emails so I get notifications if they run any sales.  I’ve booked all our trips to Costa Rica by getting email notifications from Volaris and typically pay less than $150 round trip per person to fly there. The same is true for our last one-month trip to Hawaii. My kids keep asking to go to Tahiti and I try to put in perspective that one ticket to Tahiti costs us the same amount as seven tickets to Costa Rica!

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Step 4: Budget For Getting Around

For car rentals, I use Skyscanner and to compare who has the best rates.  I also use the Rome2Rio app to look at train and bus fares if I’m going to an area that I won’t need a car.      

Before I start booking my accommodations, I take a closer look at what exactly I’m wanting to do while I’m there.  I don’t need to plan every detail, but I like to have a general idea of whether we will be spending time in the city or out in nature hiking, climbing, or surfing.  I want to be as close as possible to my activities so I can wake up and do my thing right away.  

Deciding on the exact area where you want to spend your time is important so you aren’t spending your vacation time just driving.  

I think of my hometown of San Diego with this one.  If you come to San Diego you want to be as close to the beach and downtown as possible.  Sure, if you are staying in El Cajon or Chula Vista, you can drive to places, but it’s not going to feel the same having to fight traffic and be in a not so scenic location, nor will you be nearby many great eating options.  Get out a map and scour the internet for blogs with specifics on what you are looking for when you’re planning a trip.  

Related Blog: Local’s Guide to planning a trip to San Diego

Step 5: Input Your Food & Activites Budget

Once I have the flight, transportation and accommodation estimated I finish off planning my trip budget by estimating my food expenses.  If you like to eat out while you travel you will need a lot more in this part of your budget then if you tend to cook your own food while you travel.  In addition, add in other transportation expenses such as gas or toll roads, and excursions and activities you want to do. Again, I’m usually not booking anything quite yet, I’m just getting an idea of how much everything is going to cost so I know how much money I’ll need to save.  This part also helps me create balance in our traveling so that we get a good mix of sightseeing, exercise, rest and relaxation.

By now you should have a good idea of how much money your trip will cost and you’ve done enough research to get yourself excited and motivated to make your dreams a reality.   Make sure you read my blog about ways to  Even if you aren’t trying to go somewhere for six months, it has useful tips for redefining your spending habits and finding ways to cut costs and put more money in your travel fund.  

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Apps For Adventure Travel

Since most of our travel involves outdoor adventure, here are a few apps I use to help me plan our trips:

  • Alltrails- hiking
  • Mountain Project- rock climbing
  • Trailforks- mountain biking
  • The Outbound- all types of adventures
  • Magic Seaweed- surfing
  • Allstays- campgrounds + boon-docking

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5 Tips for planning your next trip pin

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