Start Planning that Summer Vacation!

By Kevin Gibbons

With the extreme weather hitting much of the country, many of us are dreaming about getting away to someplace warm and fun. While this may be a natural time for us to fantasize about laying on a beach or hiking through green fields, it is also the ideal time to actually plan for our summer vacations.

June will be here before you know it. As I write this article, the start of summer is four and a half months away. That may seem like a long time, but you will be amazed at how quickly the weeks start disappearing. You want to give yourself enough time to set aside the money for the venture. Also, many prime destinations like Yosemite National Park are already filling up with reservations. So grab a cup of coffee or hot chocolate and let’s start planning!

Where to Begin?

We offer an entire one-hour seminar on Savvy Travel. I’ll cover some of the highlights of that seminar here, as well as some non-travel related topics.

Where and When

For many of us vacations are determined by either “where” or “when.” Some of us have a destination already in mind, be that visiting family, going to the dream location we have always wanted, or having access provided by friends and family (like a vacation home or time-share). For others, we are guided by our schedules. Due to work, school or other commitments, we know that our vacation window is set to a specific time of the year. In either case, identify your guiding constraint so you can narrow down your options to what will work. There is no reason to get excited about a great May travel opportunity if you know the kids will still be in school until the middle of June. If you are free in both respects, then great!


An important part of planning your vacation is to understand why you want to go to a particular location at a particular time. Understanding why may open opportunities for you. We had a client who wanted to go to the Galapagos Islands. The trip to South America was pretty expensive. We did a little digging and determined that the reason she wanted to go there was to see the bioluminescent organisms living there. Melissa did some research and found Bioluminescent Bay in Puerto Rico. The client was able to see what she wanted at a much lower cost. I mentioned above that reservations for Yosemite National Park fill up quickly. If you want to experience the splendor of  California’s Western Sierra Nevada , look to nearby Sequoia, Stanislaus and Sierra National Forests. Places like June Lake, Mammoth and Montecito-Sequoia Lodge offer much of the same attributes with less crowd and cost. If, on the other hand, you have your heart set on dining at the famous Ahwahnee Hotel, then you know you have to visit Yosemite.

Plan, Plan, Plan

Even if you are a free spirit traveler, there is some planning you need to do. The first thing to do when deciding on where and when to travel is to determine what else is going on there and then. Not only can that have a significant impact on the price and availability of travel and lodging, it can seriously affect your enjoyment of the vacation. Think New Orleans during Mardi Gras versus the Jazz Festival versus a comparatively “quiet” time of the year. One of my travel destinations is the Isle of Man twice. The Isle of Man is between Ireland and England and is famous for a very exciting motorcycle race one the streets that circumnavigate the island. It is also an amazingly beautiful place, rich in history. I want to go see that famous race, but I know the entire island is a madhouse during that time (they actually let visitors drive the race route in something of a free-for—all.) So I want to go again when I can actually ride a motorcycle around the island a bit more safely and take in the beauty.

Other things to consider in your planning are the types and availability of lodging, transportation, food and activities. Make a checklist. This is the stage to write things down so you don’t forget them. It is also the important first step in determining your Spending Plan. Include what needs to be done at home while you’re gone (pet-sitting, plant watering, mail pickup, etc.) Some people like to plan everything to the last detail so they do not have to think when they are on vacation. Others want to be more adventurous. Wherever you fall on that continuum, doing the research ahead of time to understand your options will make your vacation safer and more enjoyable.


For many of us, the two biggest aspects and expenses of a summer vacation are airfare and lodging. Predicting airfares in the future is extremely challenging. Generally, prices are best around 21 days before departure. However, if you are planning a significant vacation, you may not be able to run the risk of flights not being available that close to your travel dates, especially in the height of travel season, and if you want your entire family to be able to sit near each other on the plane. Some of our favorite resources for purchasing airline tickets are:

  • – Get fare and deal alerts sent to you for when is the best time to buy.
  • – Allows searching for multiple airports and air carriers. Be aware that some low-cost carriers do not list their prices on Kayak, so you may have to visit their home sites to get all the information.
  • – An airfare aggregate site for international travel
  • Travel Agent – For more complicated trips, with multiple connections or foreign travel, or if you are very busy, travel agents are great resources. They are professionals who can find the good deals and can be your advocate if things ever get rocky.

For lodging, if you know where you want to stay, contact the business directly. Here’s a tip that we’ve seen used successfully many times: Go on the hotel’s website and check the room rate. Check it through an aggregate site such as, or Call the toll-free reservations number if it is a chain. Then call the hotel directly. Be sure to ask for any membership discounts you may qualify for (many auto clubs, employers and insurers offer discounts for members – almost every place in the United States offers a military member discount). You may get significantly different quotes from each site. This takes a little time, but it can be well worth your effort. Again, even if you are the adventurous type who doesn’t make reservations ahead of time, this is worth doing so you have an idea on what to expect for availability and pricing when you do arrive at your destination and find your impromptu lodgings.

Package Deals

Some people like packaged tours while others avoid them at all costs. To borrow a favorite expression of The Savvy Life founder Melissa Tosetti, “I’d rather stick a fork in my eye” than go on a guided tour. I’m just more independent-minded, and do not particularly like being around a lot of people. But there are many different kinds of vacation packages out there. Sure, there are the all-inclusive tours, but there are also individual vacations that companies have put together to take care of a lot of the planning. Several years ago, my wife and I spent two weeks riding motorcycles around Ireland. We found a great company (Celtic Rider) that provided motorcycles, lodging, and GPS routes all for one price. It was an unguided package, so we were on our own. All we had to do was show up, get the motorcycles and then make sure we made it to each inn or B&B on the scheduled day. They provided detailed interesting routes for us to take each day, but we were free to follow them or not. We just had to key in the lodging destinations at the end of the day to make sure we found our way home.

Groupon is a fantastic resource for many purchases. We have many friends and family who have used this for vacations to Italy and Iceland, among other adventures. The deals can be quite extraordinary. However, these are packaged deals, that are fairly rigidly structured (that is how they are able to get such good prices). So, make sure that the package is exactly what you want.

So, whatever your vacations plans are for this year, start laying the groundwork now! Not only will it provide a welcome break from the mid-winter routine, it will get you well set to being sure you can enjoy your vacation when the time comes, knowing that you have made your plans and arrangement. This will let you concentrate on enjoying that time instead of worrying about logistics.


Kevin Gibbons is the Vice President of The Savvy Life and co-author of the international bestseller Living The Savvy Life. For the past eight years, Kevin and Savvy Life Founder Melissa Tosetti have worked with over 600 individuals and families to create Spending Plans.

They also work with financial advisors and their clients doing cash flow planning as well as giving Savvy Living presentations via webinar and in-person to audiences across the U.S.

If you’d like to learn more about how Kevin and Melissa work with clients, visit The Savvy Life’s Programs page.

If you’d like to learn more about how they work with financial advisors and their clients visit: The Savvy Life Advisor’s Page