Travel Tips: Start Planning

Planning. Planning a trip can be very difficult but it doesn’t have to be. I like to over-plan my vacations. I plan them really far in advance and to an insane level of detail. That’s my style but it doesn’t have to be yours. Some people don’t plan their trips much at all. They choose a destination last minute, pack hastily, and figure out their itinerary on the fly (they may not even know the word itinerary). If that style works for you, planning will be easy. It just so happens to make me feel ill. I’ve actually had nightmares that I was on vacation and had no idea what was going on (duh, because I was asleep) and that we had missed several things along the way. These are not the nightmares of a normal person. They’re exclusive to the over-planner. It’s a curse but also a benefit. Our vacations are pretty awesome.

So how can you over-plan your trips like a pro? If only there was some kind of handy, yet long-winded list you could consult!

1. Choose destination(s): Where do you want to go? I’ve never been to Vancouver so that’s near the top of my ‘reachable by road’ list. If I was flying and had unlimited resources I could envision Sydney and Auckland in one trip. I would also love to sightsee Europe by rail one day. Of course your ideal destinations might be determined by a particular event like a sporting event or musical festival. Maybe your cousin is getting married in Chattanooga. Whatever the reason you travel, nearly every destination is worthwhile.

2. Mode of travel: You cannot drive to Maui. You can drive to Alaska from Florida but it will take considerable time. A plane will get you to Europe but then you might rent a car or take trains to reach multiple places. How you choose to get around will ultimately determine much about your trip in the planning phase.

3. Schedule: Three days, two weeks, or longer. How much time you have will greatly effect how you plan your vacation. If you’re flying to a big city with a lot to do, you probably won’t have time to add in another place (especially to do that first big city justice). And if it takes you three days to drive to your ultimate destination, that will also affect how you plan as well.

4. Budget: This one should be obvious. Planning a $100 trip is vastly different than when money in not a concern. I, personally, like to save money as much as possible regardless of my financial situation.

5. Determine route: When we plan a trip to Vancouver I’m going to pick some other excellent places to see along the way, namely Seattle and Yellowstone National Park. Choosing interesting waypoints between your starting and ending locations is key to making a memorable trip. Some destinations have many viable route options and the most direct isn’t always the best. On our road trip to Houston and San Francisco in 2011, Beth and I took the slower route to Houston so we could visit my best friend Katie in St. Louis. From there, we detoured to both Memphis and Shreveport on our way to Houston. It definitely wasn’t the fastest route but was worth the extra time for that delicious dry rub barbecue!

From our trip in 2011

6. Select Lodgings: There are many different types of places to stay including hotels, the homes of family and friends, B&Bs, campgrounds, and your car. If the latter is your choice, make sure it’s legal to sleep in your car wherever you are and only do so if the location is safe from crime and weather conditions. Accommodations can have a lot to do with budget. Hotels can be expensive but not always. There are many online tools to price-compare your stays ahead of time so you can save the most money. Review sites like

Malmberg 7

JT and Rayna put us up for a night in Cody, WY

TripAdvisor can also prevent you from having negative experiences but more on that later. It is important to know that price does equal quality. Campgrounds can be excellent places to stay but do require a certain amount of gear be brought along and time spent setting it up. Like hotels, they’re not all equal in cost and amenities. On our most recent road trip, Beth refused to stay anywhere without real toilets. The homes of family friends is a personal favorite. Whenever available based on your route and destinations, staying with a loved one is a fantastic way to save money and add reunions to your trip. At any given time I know Beth and I have a place to stay in St. Louis, MO, Schenectady, NY, Columbia, MD, Cody, WY, and five different places Northeast of San Francisco, CA. Map out your network of family and friends (and family friends) and reach out to these people far in advance. Nobody likes it when you just drop in and not everyone will be willing to put you up either (nor should they feel required). If you do stay with a family member or friend, don’t be afraid to pick up the dinner check and it wouldn’t hurt to bring a gift (perhaps a souvenir from your travels).

7. Create a sightseeing checklist: The Eiffel Tower, the Louvre, the Notre Dame… there is an obvious list of sights to see in Paris but perhaps it’s your second trip to the city of light. It doesn’t hurt to re-visit a particular attraction, of course, but you might need to dig deeper to keep your trip interesting and fresh. Compile a list of places or attractions you know you want to see and then do some additional research. TripAdvisor ranks sights in each place by popularity. Scroll the list for each city/area on your route and note any attractions that pique your interest. Using this technique has allowed me to see things (many of them free) that I never would have known existed otherwise. I always try to find something to see in any big city we visit, even if we only have fifteen minutes before we leave for our next waypoint. I found a cool statue park dedicated to the Land Rush in Oklahoma City that we found to be quite interesting, quick, and free!


Example TripAdvisor Attraction List: Minneapolis


8. Read reviews: TripAdvisor and Yelp are good tools to determine which lodgings, attractions, and restaurants are worth the visit. It’s your vacation! Why leave these things up to chance? These websites also provide tips such as pricing, pertinent parking information, menu suggestions, and when to visit to avoid long lines.

9. Create an itinerary: Now that you have a lot of information about your destination, route, and budget, write it all down! I create documents and spreadsheets to keep notes as I plan. Every attraction has a line on the spreadsheet so I can compare allure, costs, and hours of operation. Every lodging has an address, cost (if any), and contact phone number. Having all this information readily available makes putting the pieces together that much easier. The itinerary itself can be as detailed as you want it to be. Below is an example itinerary page from our East Coast Road Trip in 2012.



The page (uploaded in two images for ease) has a couple of parts. The first is a picture of the route for that day. I include a picture of the map because I love maps! They don’t serve a practical purpose if you have GPS, however, so you could choose to leave them out. Next is a list of each segment of that day’s travel. On that particular day we drove from Maine to Boston, from Boston to Providence, from Providence to New York City, and NYC to our next lodging north of Philadelphia (at a Bed and Breakfast I found on Each point to point lists a mileage and drive time total. The next section summarizes how many states and major cities we would be travelling through and the sights we’d see. The final part lays out the schedule. We ended up leaving New York City late and arrived at our lodgings later than planned but it is always good to create an itinerary.


List of attraction addresses in Philadelphia area


10. When everything is planned, all there is left to do is pack the essentials and go! If you have any questions or need additional help planning your own trip, reach out to me in the comments section.



<– Travel Tips: Packing Essentials

Travel Tips: Budgeting –>


Bryan Signature 2





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