1.  Decide on a Destination.

Using Pinterest is a great place to start. Social media like Instagram is another, and so are travel websites, like this one.

2.  Look at Historical Weather Patterns.

Look at the weather to decide when you should go. Make sure you look at historical weather patterns from previous years to get an idea of when the best times to travel to your location are. If your trip is coming up shortly, look at future weather forecasts too. It’s never a guarantee, but does help.

You never want travel plans ruined by historically bad weather seasons.  

3.  Budgeting.

Look at your budget. You want to enjoy the most you can, so always look for coupons, deals, and discounts. You don’t want to miss out on that important activity, but you also want the most for your money. Things you may want to consider are: Military or Veteran discounts, memberships like AARP, AAA, Costco, professional or bank memberships (like Credit Unions), Viator, and even the main website of the attraction you are going to. Sometimes local magazines, Groupon, or businesses in the area you are visiting have coupons and deals too. Be sure to look at lots of online resources and even ask the locals when you arrive. This is in no way meant to be an inclusive list of resources, there are many others out there, so do your research. The same goes for flights, car rentals, and hotels. Many credit cards offer travel deals, points and rewards for travel. Some of my favorites are Barclays Aviator Advantage, the Alaskan Airlines Visa Signature Card, and Chase Sapphire. For hotels, I tend to use Hotels.com for deals, ideas of where to stay, and to read the reviews on the different locations.  I compare them to the main hotel website price and any discounts they may have for memberships, AAA, AARP, etc. Again, there are so many others out there, so do your research and see what you can find. Whatever you use, keep a good list of your reservations in case you need to make changes later. I like to include this information in my Detailed Itinerary. Other things to consider are peak travel times, as this can be more expensive, and crowded. 

4.  Developing a Basic Plan.

It’s extremely important to have an idea of what you want to see and do when you arrive. You don’t want to get there and need to try to find things to do, or miss out on seeing something to only find out later when you get back home that you missed it. Keep your plans simple and give yourself time to be flexible.  I tend to use TripAdvisor. This is a great tool for picking the top activities in the area, along with restaurants, hotels, etc. I will also go to the local city website and see what they may say for ideas. Viator, Pinterest, blogs, and other internet searches can give some great ideas. There are also many great apps out there for local attractions and activities. Be sure to check out lots of different resources.

Never pack too much in one day.  Add a few alternate activities that you can enjoy on any one day if you have time. 

5.  It’s in the Details.

Check out the details for each item you need during your travel prior to booking. Things to consider are: car rentals along with any rules they may have for that location (like traveling out of the country or extra mileage fees), hotels available in the area, and even restaurants to eat at. You’d hate to stay in an area that has limited places to eat, too expensive to stay, or no rooms available because they book out a year in advance. The same goes for car rental locations with limited open pickup hours. You don’t want to arrive on your early morning flight and need to wait for a car. Be sure to look at the operating hours for any attractions you are considering.  Any details you can gather prior to booking will help you make a successful trip and get the most out of your days. 

Bucket lists can be ruined if you arrive and find out that attraction has seasonal operating hours and they are closed when you visit.

I like to look at the driving distance between locations and the roads you may use (as some may be closed during certain seasons). It is best not to spend more than 3 – 4 hours driving in any one day (if possible). Try to put attractions and stops along the way to break up the driving.  Stay a minimum of 2 nights so you can really get a feel for the area and enjoy your time in a relaxing way.  If there’s nothing in the area, then it’s ok to spend one night along your route, but again, try not to put too much driving distance on the road before resting for the evening. You are on vacation! I love packing food for the road trip too. It’s horrible feeling hungry and not finding a place to eat.  Be sure to give yourself some comforts of home and pack some food, snacks, and lots of water to take along with you. Picnics always make me feel relaxed, so try to put one in on your trip too. You might just enjoy it.

There is nothing worse than rushing through a trip and not feeling like you were actually on vacation.

6.  Detailed Itinerary.

Now that you know where you are going, when to go, what your budget is and deals available, what to see and do, when they are open, and the driving distance between locations, you can now pull it all together in a Detailed Itinerary. I like to list as much detail as I can so I can enjoy my day by just following my plan. Again, make it flexible and leave plenty of time for activities and rest periods. Be sure to download offline maps and print out your Itinerary and any tickets you may need (including attractions, trains, etc.) prior to leaving home, just in case internet connectivity is limited in the area. I like to save them as PDF files and put them in my Notes section on my iPhone. You can also put them in Books or my absolute favorite way to keep my travel organized is through the app TripIt. You can email them your tickets, tours, flights, etc and they will automatically put it in a calendar style itinerary for you. Be sure to check it out. It’s super easy and simple and I love the calendar style schedule.

As you are putting in your details and looking at the distance between attractions and locations, operating hours, and estimated time frames you need for each activity, you will be able to see it more clearly and be able to lump activities together in a more productive way. I like to include rest and meal breaks in my day and even give myself some choices for food options in the area so I’m not looking for a place to eat.

Itineraries should include whatever you feel is important.

Things you may want to consider are:

– Flight information, car rental location with confirmation information and price, or any other transportation you may need. If I am traveling overseas I like to look up how to use the public transportation system, like the kiosk, prices, payment methods, and hours of operation. There are some great apps you can download too to help you with this. There is nothing worse than being overseas and your train is late or cancelled and you have no idea how to assess the schedule, rebook your ticket, or find another way to get there. 

– Hotel Info with breakfast hours, time of check-in/check-out, address, phone number, type of room with amenities (i.e. refrigerator, laundry room, pool, parking, wifi, A/C, etc.), confirmation number, price and who you booked through in case you need to make changes.  Apps are great for holding this information too, as long as you have internet or it holds this information offline.

–  A map with driving directions listed out, travel times, and the distance between each. Remember, if you are driving in the mountains, you need extra time. I like to mark on my map each attraction that I am stopping at for the day so I can see my day very clearly.

– Brief notes on each attraction, what you might see, coupons you found, operating hours, and maybe even a website if you need it again. 

It’s usually the unknown that makes people feel uncomfortable. So be sure to give yourself the tools to lower your stress level and make it enjoyable for you. Here is a table you can download and use to make your trip planning a cinch. Use it for note taking and covering your baes until you for a calendar for your trip with all your details.

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Do you have any other tips to add? Are there any websites you like to use for deals, hotels, flights, or favorite apps?

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This article is dedicated to:
My dear friend Jason.