Shoulder Season Travel: The Who, What, & Where of Your Next Trip

Shoulder Season is like Goldilocks. It is not too hot and not too cold in most of the world, with often not too many crowds and not too terrible prices. Kids are in school, so mid-career professionals can often capitalize on their vacation bidding at this time. Some pilots and flight attendants may even be able to take an entire month off, sometime after Labor Day and before Thanksgiving, if they fly until the FAA tells them to rest throughout the summer.

Photo by @dreamchasers_visions

There are some exceptions to shoulder season. These include travels for festivals and holidays, such as the Christmas markets in Europe or the Easter processions, like in the south of Spain. Also, the poles often offer something special in their extremes - winter or summer. Places like Iceland and Norway offer the midnight sun in the summer and the Northern Lights in the winter. On the other side, Antarctica can only be accessed by cruise ships in their summer season of mid/late November through February or perhaps early March.

Let's talk about the who, what, and where for you to optimize your time and money and capitalize on your feelings and memories.


Who is going?

Let's break it down into three categories of trips:

  • Solo
  • Couple
  • Family/Friends

You have to be willing to fly alone before choosing to fly together.

There are costs and benefits to each of the above, which we will discover in a later post. Generally speaking, the more people in the group, the more planning you will want to do.

I arrived, solo, in Nepal, with a one-way ticket and zero reservations. Angel and I traveled together, to Iceland, with a confirmed car rental and return plane ticket, but no hotel reservations. When we went to Argentina, our family party of six confirmed all planes, hotels, and cars in advance, with fully-refundable options because 2/3 of our group is flying standby throughout the country.

Solo trip to Thailand
Couples trip to Peru


This question is actually best preceded by, "How do you want to feel?"

Then follow-up with, "What do you want to do?"

These questions are important because you can have radically different experiences in the same place based on how you want to feel and the decisions that follow. Answering these questions honestly will help you to feel like you are not missing out. We can become overwhelmed so easily because of the wealth of information that is available. 

Many people think of Ibiza as the party island. On both of our trips, we did not visit any of the clubs. The first time (for me; Angel get all of the clubs out of his system in half a dozen trips prior to our meeting), we explored one to two beaches a day, punctuated by long, slow meals and lots of salty kisses and sandy toes. This year, with our girls, we took it even slower. We missed nothing. That's because we choose activities around how we wanted to feel. Missing something is based on a feeling, not an activity.

Your desired feelings will often vary between solo, couple, and family trips. 


Atlas, our mascot at our sister site of  

Use your answers to how you want to feel and what you want to do to determine where you want to go. 

If you have little to no preference in destination, your dates are somewhere flexible, and cost is your prime variable, you can visit to find the cheapest flights from your home airport to a variety of destinations.
In determining where you want to go, consider this:
  • How much time do you have?
  • Do you want to visit multiple cities or countries?
  • What activities do you want to do?
Once you have the big picture on time and activities, research the following, in order:
  1. Flight Schedules
  2. Land Travel Time
  3. Hotels and Excursions
Flight Schedules

​For our trip to Argentina, we knew our international flight arrived early in the morning, allowing for a full day of exploring Buenos Aires, with time for a siesta between slow travel and great dining.​

Land Travel Time

We drove between El Calafate and El Chalten. The drive is 3 hours, but we allowed for photos along the way and our favorite one is blown up over our dining room table. We traveled back to El Calafate the last night so we do not have to rush to the airport in the morning.

Hotels and Excursions

We book these last, as there are often many more options than with flights, so that we can find the most economical combination. We already have an idea of the excursions, if any, that interest us, after having answered, "what we want to do." Sometimes it is worth calling the hotels to get quotes on the excursions. The more remote the area, the fewer options will be available online. Excursions are great if special equipment or vehicles are needed. Otherwise, considering just researching the excursions and using them as templates for do-it-yourself adventures.

Need help with your next trip? Email 

Here are some of the places we've been:


USA, Mexico, Dominican Republic, Bahamas, Cuba, Guatemala, Costa Rica, Colombia, Peru, Argentina, Uruguay, Iceland, United Kingdom, Denmark, Netherlands, Czech Republic, France, Germany, Spain, Portugal, Italy, Malta, Croatia, Bulgaria, Morocco, Tunisia, Egypt, South Africa, Zambia, Zimbabwe, Turkey, United Arab Emirates, Kuwait, Nepal, Japan, South Korea, Philippines, Thailand

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