How We Roll ~ Frequently Asked Vacation Planning Questions

The purpose of this blog is to answer the many questions I have received over the years regarding my vacation planning and to provide you with all the information you need to plan your own amazing adventures. I have planned escapades ranging from day/weekend trips to 19 day cross-country adventures. It is my hope that this site will suit your needs, whether you are just looking for a bit of inspiration on places to visit or would like to avoid planning entirely and simply replicate my itinerary. I will be sharing detailed vacation plans, pictures to give you a beautiful glimpse into every location, reviews of places we’ve stayed, places we’ve eaten, activities we have participated in, and helpful tips of things I would have done differently. I will also be including photo galleries for each destination plus nature photo galleries, so I can share with you my love for all things beautiful.

Waves crashing against the rocky, jagged shoreline at Onomea Bay, Papaikou, HI

Let’s begin! The most frequently asked questions I receive regarding my vacation planning is ‘How do you find out about all of these places? Where do you get your information on what to do, where to stay? How long did it take you to plan this trip? Why did you pick this location over that one? How did you get that airline price? How can you afford to travel for 19 days?’

First up, ‘How do I find information for my trips?’ I will spare you the details from back in the day when you had to send away for magazines from each state that you wanted to visit (yes, young ones, in the days before the internet you actually had to mail away for information) and focus on what I’ve used for the past few years. The first two things I do when we’ve decided on a location and a budget is start Pinterest hunting and get guidebooks on the destinations from the library. You can look here to see my state by state travel boards on Pinterest. I pin anything that looks interesting that we might want to do or places we might want to stay or eat at. I then scour guidebooks, my favorite is Fodor’s, but I’ve used Frommers as well, first looking for things we would want to do. My first course of action is always finding the things we want to see and do and basing where we will stay on that.  We are an adventuresome bunch so most of our activities have a physical component, most frequently hiking. Our family shares a lot of similar interests, so planning activities that everyone will enjoy is usually easy. I also try to plan at least one activity that we haven’t done before: helicopter ride, monster truck ride, white water rafting, snorkeling, etc. Once I have a list of places to see, I do some more research using TripAdvisor . I used to love TripAdvisor, but they are so heavy on advertising now that I rely on them a little less. I do like using it to check their lists of top things to do, top places to eat and top places to stay to make sure I haven’t missed anything. (We had one instance where a place that was recommended to eat at was dreadful and one instance where there were complaints about the food and prices that were off base, at least we liked it.) Back to my list of things to do; I then check out websites, if they have them, for the activities that I am considering including (hiking, snorkeling, helicopter ride, zip lining, botanic gardens, etc). I like doing this for up to date prices and to get a better idea of what activities will be worth our time. Generally speaking, for big trips I usually start planning a year in advance, for shorter trips, usually a few months. I like to be able to take my time, plus I enjoy the planning part. So, over the course of a month or two, I will have found all the things I would like to see, have checked out their websites, know the cost, days and times of operation and location. If I have more activities than I have time for I prioritize everything based on what I most what to do/see. I then ask each person going on the trip what they most want to do and make sure that each of those things are my top priorities.

Hiking across the Kilauea Iki Crater was a must do for all of us! Want to see more? Click here to visit their website.

Next, I write out our daily itinerary. I don’t like spending any more time than necessary in the car while on vacation, so we do the bunny hop throughout our vacations to keep us close to our next major travel spot. In Hawaii, over the course of 13 days, we switched hotels 5 times. The main reason we did this is because to get across the island is very time consuming, mainly because it is hard to find a road that is not filled with nerve-wracking twists and turns. I would rather spend 15 minutes checking in and out of a new hotel than an extra 3 hours driving in a car every day. A benefit of this travel plan is if you end up at a hotel that you don’t really like, you are only there for a few days. A negative to this type of travel is it is harder to get special deals because they usually involve more extended stays and some places will not let you have a room for less than 3 nights. We pack by day so we know which suitcases we will need at each location. For example, days 1 – 3 clothes are in suitcase 1 and everyone’s personal items are in their backpacks, so we only need one suitcase and our backpacks at each hotel. My philosophy is I may only be in this location once, I want to see as much of it as possible in the time I have and that does not include driving the same route for hours every day. It does entail more planning and research, but I enjoy that, strange as that may seem.

Once I have the itinerary set, I start choosing places to stay. We like to stay in a variety of places. We’ve stayed in cabins, treehouses, chain hotels, resorts, and bed and breakfasts. We like them all. What we have really come to appreciate over time is the view. I used to be of the mindset that we will hardly be in the hotel so just go with the bare necessities. I now realize that having a view is worth the expense. Although, we don’t spend a huge amount of time in the hotels, it does take a while for four people to get ready, and sitting outside with a view of the mountains or the ocean is an amazingly relaxing way to start and finish a day. In fact, my husband’s ‘musts’ for Hawaii were snorkeling and an ocean view.

Our view from our hotel room at the Garden of the Gods Resort in Colorado Springs, Colorado

Location and cost are my priorities when choosing places to stay. I check every accomodation’s website. If they do not have a website, I won’t stay there. I like to see pictures of the rooms so there are no unwelcome surprises; I learned that lesson the hard way when I booked a cabin sight unseen and when we arrived it looked like it was from the set of a horror film. Once I have a place that suits our needs I utilize Google maps to determine how far it is from the various activities we plan to do in the area. If everything looks good, I will add it to the itinerary. I am currently planning a trip to Maui and I plan on using Airbnb for the first time for part of our stay.

At this point, I start booking hotels/activities. We generally like to have as much of the vacation as possible paid for up front. I always check the refund policy at each hotel and activity that requires tickets, most of them are very generous, allowing a full refund as long as you cancel with in a few days to a week. If the policy does not allow a refund, I will either choose a different location or wait to book until we are closer to the departure of the trip. I usually book a hotel or activity every two weeks. This enables us to have longer vacations because we are paying for them over time instead of having a huge expense at the end of the trip. I do always look for specials on their websites and will call and ask if there are any specials not listed on their website, the phone call only worked once, but it only takes a second to do. Again, specials are hard to come by with all of our hotel bunny hopping, but to compensate for this we always travel off-season. Since we homeschooled our children this was a very easy option, now that they are in college, it is much harder to do for family vacations. If at all possible, I strongly encourage you to travel off-season! Much better prices, fewer crowds and many times better weather than the intense heat of the summer or the not quite warm enough spring break.

Well, I am about half way done answering my most frequently asked questions and I am out of time for today, I’m sure you may be running out of time too. So, I will pick up where I am leaving off in my next blog post. If you have any additional questions you would like me answer please leave a comment below. Until we meet again, happy travel planning!