14 Simple Steps for Planning Your Next Trip

I remember my first backpacking trip like it was just yesterday. I was only 12 years old at the time. Through a series of unfortunate events, our entire group of 15 ended up getting lost in the middle of nowhere on a mountain in the rain at night.

Can’t get much worse than this. Since then I still experience major setbacks on most trips, but careful planning helps me be prepared for whatever may come.
You’re probably wondering right now what is the first step to planning a great trip? How do I avoid getting lost in the middle of nowhere in the rain at night? Well, take it from someone who has been there and done that, planning may not seem worth the extra effort. But it will save you loads of time and money.

Through countless outdoor adventures and cross-country road trips I have developed this simple foolproof guide for planning your next trip:

Step 1: Pick your destination

Nothing makes your travel plans come alive like actually picking a place you want to go. This gives you a concrete goal to work towards. Picture in your mind your ideal spot (the beach, the countryside, the mountains) and what it would feel like to block out work for just five minutes.

This should be enough motivation to get you started. Print out a picture of that place and set it somewhere you can see it every day. The problem with most travel plans is that they don’t have a specific place in mind at the start. “I just want to travel” is too general a goal and does not challenge the mind enough to act.

Step 2: Pick the duration of your trip

You don’t need specific dates from the start. But deciding now how much time you have for your trip will help determine how much money you need to save. After you decide “I’m going to Vegas,” add “for 5 days.”

Step 3: Estimate costs

So you now know where you want to go. You also know for how long you want to stay for. It’s time to start looking at the prices for:
  • Transportation
  • Lodging
  • Food
So you want to go to Vegas for 5 days. You snagged a flight for $500. You found a hotel for $60 a night. And you plan to shop local for fantastic food and spend about $150. So you now know that you need to budget around $950 for your trip.

Easy ways to cut costs are to play around with these 3 variables. Maybe you can drive instead of fly. Maybe instead of staying in a hotel, you choose Airbnb or a backpacking hostel instead. Maybe instead of going out for dinner every night, you learn to cook and stay in for a few nights.

Step 4: Save money

Time to start building up your savings! In order to do this accurately, you need to know exactly where your money is going each month. Your total profit each month will always be your income minus expenses. An easy way to save more is to break your goal down into small steps and spend less.

So you want to go to Vegas in 10 months and need $1,000. Let’s break this down into a simple manageable step. That would mean you just need to save roughly $3.30 a day until you leave. You could easily do that by cutting out a cup of coffee per day. Here are 3 simple tips to cut expenses and save:
  • Slash the cable: Cable on average costs $50 per month. That’s $600 per year. In the age of Netflix and Hulu, it’s a no-brainer here. Switch to a cheaper service and save money for travel instead.
  • Get your chef on: A recent study found that the average daily cost of eating out (including fast food) is $15.76 per day, more than double the amount it costs to maintain a healthy diet. (1) In my family my wife is a fantastic cook. But I have picked up enough skills from her to hold my own in the kitchen. No excuses here for travel. Save some big bucks by eating in more frequently on your next trip.
  • Chuck the coffee: This may seem like a huge sacrifice. And I will admit that I never drink coffee so it’s easy for me to tell you to stop. But I promise you that in the end, it will be well worth the effort. Americans spend some $2.70 per day on coffee. (2) That’s $986 per year. What means more to you: that cup of Joe or getting to spend time with your family on a helicopter ride over Vegas.

Step 5: Get a travel rewards credit card

Travel credit cards are a great way to save on flights and hotels. If you don’t have one, go get one as soon as you can.

Focus on the cards that offer the deals that make the most sense for you and your situation. Maybe you don’t like to fly but love to stay in nice hotels. There are hundreds of different rewards cards in existence today. Find the cards that make sense for you and sign up. The quicker you sign up the more time you have to build points and miles at a pace you’re comfortable with.

Step 6: Generate extra income

This one sounds like a no-brainer but you would be amazed at how often this step is overlooked. If you really want to travel you need to think about ways to bring in some extra cash that you can stash away for later. Here are 3 ways you can bring in some extra cash
  • Pick up a side hustle: Sites like Uber and Airbnb allow you to use your car or home to make money. Most people have one or the other, so it’s a great way to earn money outside of your regular 9-5 job. Also, take a good look at your skills/hobbies and see if there is a way you can possibly market them. For example, I had a friend that loved to weightlift. Now instead of paying a gym membership fee, he charges other people to take weightlifting lessons from him.
  • Sell your stuff: This is becoming easier as the years go by. Free apps such as Let Go allow you to upload pictures and post ads for your stuff from your phone. Classic websites like eBay and Craigslist are a great place to list that old car, bike, or tennis racket. You could even go old school and have a weekend garage sale. Every dollar counts.
  • Teach: Maybe you have a musical talent you could share with little Johnny. Maybe you know a foreign language. Maybe you know how to play sports better than the average Joe. Teach your skills to someone else for a small fee. You will feel great and be rewarded for your trip.

Step 7: Search for last minute deals

Maybe your dream vacation is Vegas but at the last minute, you find plane tickets 50% off to Maui. You need to set your budget with a specific location in mind, but if you find an equally great location for less money it’s ok to take B over A. Both are great options in this case, and you may find a better deal for a location you never dreamed of being able to visit.

Step 8: Book a flight

Ideally, you will want to use your miles here to purchase a flight. Leave yourself plenty of time and guarantee a seat by booking months in advance. Here are some of the best sites for booking your flight and getting a great deal:

Step 9: Book your crib

Again it’s best to find accommodation early instead of waiting until the last minute. Once you know where you want to go start searching for hotels that fit your budget and that you would actually enjoy staying at. If this means a luxury hotel then book it. If this means Motel 6, then be proud and book it.

Plenty of great sites exist to help you in your quest for finding a great hotel:
Alternatives: If hotels are not your scene don’t be afraid to broaden your horizons and book with Airbnb or WImdu. People also post their homes on hospitality websites like Be Welcome or Couchsurfing. You can always contact these people in advance and see if they will host you for your trip.

Step 10: Plan activities

Look at the cost of major activities in your vacation area and see which ones might be worth the extra money. Doing this in advance will ensure that you have enough money when you reach your destination to do more than sit in the hotel. Also be sure to look around for free activities or festivals that might be happening during your trip.

Step 11: Set up travel alerts

Worse than not having enough money for a trip is not being able to spend it. Can you imagine getting to your destination and not being able to do anything once you get there? Do yourself a favor and let your card companies know where you are going and for how long you will be gone so you won’t have any accounts frozen.

Step 12: Pack

Don’t forget to pack (preferably sooner than the night before). Every traveler needs at least 4 things: food & water, clothing, and a medical kit. These are the basics.

Always be sure to check the weather so you can pack appropriate clothing. If you're like me and get hungry even thinking about food, then it's a good idea to pack some travel snacks. Most solid foods are allowed on airplanes, so an easy way to save money here is to bring your own sandwich and snacks.

Step 13: Buy travel insurance

Travel insurance is especially important for internatinonal travel. Now, I know you are probably wondering why you would ever need travel insurance. Life is a mystery, and you never know when disaster will strike. A broken arm while surfing, a car accident that results in a broken leg, playing soccer and getting a concussion. These things can and do happen.

But travel insurance covers more than just physical injury. It also covers you if your phone breaks, your flight is canceled, or your camera is broken. World Nomads is a great place to start looking for travel insurance for just a couple bucks a day.

Step 14: Sit back, relax, enjoy

You did it! You put in all the hard work, saved up your money, made reservations, and picked some awesome activities for your trip.

Now it’s time to kick back and enjoy the fruits of your labors. Be sure to follow me on Twitter for more travel tips and guides like this one.

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