The Ultimate Quick & Easy Guide to Vacation Planning

By Ken Faught













When it comes to our vacations, we want them to be absolutely perfect. We want to travel to places that let us unwind, relax and recharge, plus do a few activities. One of the questions that we are asked all the time is how we go about planning our trips. For Vanessa Doleshal and I, our answer vary because some time there is a lot of advanced notice, and some time we find a great deal and have to be are very spontaneous. But there are a lot of common elements and we put together this quick and easy guide.

I like things to be short and sweet, and as a journalist I like to follow the mini skirt rule. I learned this from a friend when I worked for Dirt Rider magazine and have used it ever since. Simply put, the mini skirt rule for journalism require you to write your story short enough to be interesting but long enough to cover the subject. Go back and reread that, because it is so fitting.

So, it all boils down to time of the year travelling, the amount of time you can travel, where you want to go, price and lots of research. So here are our general guidelines.











Google Images is a great place to get a quick visual of any place you are researching as you plan your ultimate vacation. We use this tool before every trip.


Choosing A Destination

Most people only have a certain amount of time that they can get off work, and a limited amount of days that they can travel. Finding your options and your availability is perhaps the best starting point because it will help you narrow down your choices. Say you only have 3 days. Well, you need to keep it short to have fun, with something that is only a few hour drive or a couple hour flight. If you have 10 days or more, the entire world becomes an option, even with jet lag.

Once you know the time of year, then you can start narrowing down your destination, albeit a winter resort, summer hotspot, or somewhere in between. Throughout this process, it’s important to constantly reevaluate your options. Once you build your first itinerary, go back and look at other options for the same or less money. You may also choose to add time or cut the trip short, based on your personal preference. Some people want to plan a lot of activities while others simply want to relax and chill.

We also recommend that you start planning what activities you want to do on the trip. And if there is a particular outing that is whether sensitive, we recommend booking it at the front of the trip in case it has to get rescheduled. This can happen a lot in places where it’s windy, rainy or can snow. Additionally, book something towards the end of the trip that you will really look forward that will finish your vacation nicely on a high note.

The internet is loaded full of great deals if you have the time to shop around. This is a view from one of our rooms at Grand Solmar in Cabo San Lucas.

Researching Things to Do

Much like photography is all about location, location, location, well, planning the ultimate vacation is all about research, research and research. One of our favorite tools is Google Images. Another is Expedia and their Things To Do tab, and we also use Pinterest, Instagram and Facebook. It’s very important to take your time, make great notes, and bookmark key website links. It’s also very important that you start building a budget to make sure that you are realistic in your search for the ultimate fun.

How to Find the Best Places to Eat

Our favorite place to learn about dining is Open Table. They seem to be very detailed and even handle reservations at a lot of restaurants that are busier than normal. They also have a rewards program, which is something Amy Faught has been addicted to since the company was first founded. And while travelling, ask other travelers where they have experienced good food. They are the ones that have the most unbiased opinion, and that’s important when it comes to getting the best results.













If you can travel on a shoulder period, i.e. when kids are in school, there are steep discounts on hotels on some of the best beaches in the world.



Shopping for Travel Discounts

Knowing all the little tips and tricks will help you save a lot of money when it comes to travel. There are things called error fares or mistake fares and you can learn more about that in our detailed section called Cheap Flights. This is where the airlines accidently charged an incredibly cheap price that they have to honor. We also have an incredible section called Cheap Hotels & Resorts that shows you how to save a lot of money on your accommodations. Of course, there are also travel packages available through Expedia, Orbitz, Travelocity and some of the other travel booking platforms.


Travel Planning Checklist

  • How many days can you travel?

  • What time of the year is your vacation?

  • What is your budget?

  • Who is going with you?

  • Where do you want to go?

  • Research package deals?

  • Create an itinerary

  • Book hotel

  • Book airfare

  • Book car

  • Book activities

  • Make any dinner reservations you desire (if applicable).

  • Arrange pet sitter

  • Put mail and newspaper on hold

  • Pay bills that will come due while you are traveling

  • Arrange for someone to watch your house

  • Let key neighbors know you will be traveling (if you trust them)

  • Order any extra prescriptions/medications that may run out during our trip

  • Have you considered a travel credit card. There are a lot of good options.

  • Make a packing list of specific things you want to take on the trip


Vacation Packing List Suggestions


  • Flight, hotel and rental car info

  • Passport (for international travel)

  • Credit card

  • Valid ID

  • Clothes

  • Sweater, sweatshirt or light jacket

  • Base layers like T-shirts and camisoles

  • Pants shorts

  • Socks

  • Underwear

  • Comfortable Shoes for all activities

  • PJs

  • Jewelry

  • Hat (especially if you’re headed somewhere tropical

  • Swimsuit(s)

  • Sunglasses

  • Wet/dry bag


  • Medication

  • Over-the-counter medication (Advil, Tylenol, Pepto-Bismol, Dramamine, Benadryl)

  • First aid kit (Band-Aids, alcohol pads)

  • Shampoo, conditioner and body wash

  • Q-tips

  • Sunscreen

  • Toothbrush, toothpaste, floss and mouthwash

  • Deodorant

  • Contacts and contact solution

  • Hand sanitizer

  • Cologne/perfume

  • Hair products (dry shampoo, hairspray, gel, air dry spray, etc.)

  • Hair brush/comb, bobby pins and hair elastics

  • Razor and shaving cream

  • Moisturizer

  • Lip balm

  • Glasses

  • For Women

  • CC cream or foundation

  • Concealer

  • Blush

  • Highlighter

  • Bronzer

  • Eyebrow pencil

  • Eyeliner

  • Mascara

  • Lipstick

Carry On

  • Cell phone and charger

  • Laptop, iPad or E-reader and charger(s)

  • International power adapter / converter

  • Portable cell phone charger

  • Headphones

  • Camera or video camera, memory card and chargers

  • Travel pillow, eye mask and ear plugs

  • Pen

  • Books and magazines

  • Hand sanitizer and antibacterial wipes

  • Movies and iPad or tablet

  • Water bottle (fill up after TSA screening)

  • Cash

  • Snacks



Q: How far out should you plan your vacation?

A: That all depends on the location. Some places book up fast and it’s advisable to book a year in advance. Depending on your flexibility, there are a lot of last-minute deals available on Expedia,, Kayak, Travelocity and Hot Wire. Normally, we book about 8-12 weeks out.

Q: Is it cheaper to plan your own vacation?

A: We think so, and the internet makes it so easy to search for deals.

Q: How do I plan an affordable vacation?

A: This all comes down researching as many of your vacation options as possible. The more research you do, the better prices we believe you will find.

Q:How do you plan a first-time trip?

A: We suggest by doing extra research on the internet. Also check out things like Pinterest, Instagram, Facebook, and learn as much as you can about resorts, things to do at your destination.

Q: Where can I vacation for $2000?

A: We suggest checking out our story on Booking Cheap Flights and another blog we did on Booking Cheap Hotels and Resorts. These are loaded with great information and often offer incredible package prices.

Q: How do you pick a good vacation destination?

A: We believe that it’s best to start searching for the ultimate vacation based on your ability (i.e. how much time you are available to travel) and the time of the year. If you are in the United States, and want to travel in winter, then you need to look at places that suit your style. If you have a lot of flexibility, then you have to think about what you want to get out of the vacation. Do you want to hit the beach? If so, then Spring or Summer is ideal. If you want to go camping at a National Park, then Spring or Summer might be your best option there as well. Once you know the time of the year, and the time you have available, you can figure out if it has to be a local driving trip, a flying trip inside the Continental United States, or an International Trip.

Q: What is the best travel camera?

A: We wrote an entire blog to answer that very question list some of the Best Travel Cameras on the market under every budget

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Thanks for Reading!

Hi! We are Ken Faught & Vanessa Doleshal. We love adventure travel, photography & share our journey with YOU! Our goal is help you plan that perfect trip & keep inspiring you to take the next one. 

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“Just go . Go see all the beauty in the World.” - unknown