Boomers are already out in numbers traveling the world. It’s March and the march is on. Let the travel season begin.

I just got back from touring the island of Cuba for 2 weeks. In December, I was in Colombia for another 2 weeks. Like many women, my travel season started early.

President Obama paid Cuba a visit as well, but I don’t think he’s a Boomer yet. Of course, his travel schedule is dictated by the Oval Office. Every detail is taken care of by staff.

Boomer travelers were all around us in Cuba, especially in the city of Havana. I didn’t see many Boomers in other cities such as Trinidad, Cienfuegos, Camaguey, Santiago or Santa Clara.

Maybe they were staying in Havana to catch the Tampa Bay baseball game and to see the Rolling Stones in concert. I heard people talking about that in the lobby of the Parque Central Hotel lobby. But, staying close to Havana limits the Cuban travel experience.

Cuba - Joan

Picking a Destination is a Personal Choice

It’s also an emotional choice. Sometimes it’s a matter of elimination (the preverbal bucket list). My daughter-in-law’s mother has been to some 147 countries. She has a detailed map of the world in her office with pins on every city she has visited. It’s impressive. She has been to Africa 10 times. As I said, traveling is an emotional experience.

For Better or Worse, the People You Travel with Matter

Do you want to sign on with a group of strangers for a tour? Would you prefer to travel with a friend? Do you prefer to travel solo? There are so many choices!

My boyfriend and I experienced our Cuba travel with a map and Airbnb stays. It worked out beautifully, but you have to have lots of patience. We made hundreds of decisions and sometimes it was exhausting. Fortunately, it was also invigorating.

My Colombia trip, with my daughter-in-law’s mother, was booked with a group package and it was easy, flawless and truly one of the best trips I’ve ever had. She said so, too, and she should know.

Choose a Destination that Will Push You… But, Not Too Hard!

Boomers spend decades working toward retirement and an easier and freer life. Travel for Boomers has always been a ubiquitous rite of passage for their future.

Yet, when you arrive at this most important part of your life, the ability to see the world and experience other cultures is not as easy as we dreamed.

The following are a few questions and observations to consider:

  • Have you thought about the third act of your journey with different sensibilities, more compassion, and a good grasp for opposite ideas?
  • Can you tolerate ambiguity?
  • How do you react to setbacks?
  • What are the dominant motifs in your life and how have your decisions helped shaped them?
  • Can you get out of your own way and not be so judgmental about situations and environments?

Truth be told: you are living longer and are more energetically than all other generations before you. Longevity changes the narrative structures of life.

Travel not only helps you orient your life, but it also has the capacity to integrate differences. Of course, there are always accommodations to be made even when traveling with a husband, a best friend or strangers.

All travel scenarios are come with difficult issues and it’s best to handle these with grace. I truly thought that my boyfriend and I would break up after our Cuban trip. It was only the second time we got on a plane together and the first trip was 4 days to San Diego. What could possibly go wrong?

Before I undertook a 3-week trip with my boyfriend, I knew he had a propensity to hover over maps and had to know the details of every outing. Most of the time, he “drove” the bus or taxi.

When he asked me what I’d like to do, I knew he already had another idea. Most of the time, we did it his way. If I had strong feelings about something, I made them known. Sometimes it didn’t go well.

I’m an old hand at travel and I know what I like: breaks, food, rest stops in 4-star hotels and lots of sleep after an arduous day. But, in order to have a really good times haring the travel experience, I had to make many accommodations for my boyfriend. And as far as I know, we didn’t break up.

Traveling with your husband or boyfriend sounds easy until he gets travel fatigue. “This is the last trip I’m taking! You can do it with your girlfriends from now on! I told you this before we left!” Sound familiar?

On the other hand, if you are both relaxed travelers, accommodations have already been made. You have worked out the kinks, know your dietary needs, understand your sleep requirements and respect your resting patterns. Problem solved.

Is a Male Traveling Companion for You?

If you are a woman who doesn’t need to have a permanent, live-in relationship, a male traveling companion may be in your future. You can be your traveling companion’s sidekick.

Finding this man is what I call a self-selecting process. First, you meet a retired man with lots of free time, let’s say at a sushi bar in Los Angeles, when you are visiting your girlfriend. They, you find out how much you both have in common and how much you both love travel adventures. You live in different cities and are both fine with this. The relationship becomes focused on your shared passion for travel.

What About Group Tours?

I’ve had great luck on group tours. Traveling with Brits, Canadians and New Zealanders is a treat. They all travel frequently and understand the value of tours. Most of the time, they are prepared, cheerful, funny and curious.

I usually try to find those countries represented in a group. Many potential problems are avoided because I am familiar with all my travel companions’ eccentricities before the trip begins. Besides, 2 weeks is plenty enough time to travel together.

A Few Tips to Avoid Driving Your Travel Companion Crazy

Establish a few ground rules. Make sure you hang out with others on the tour and give each other personal space. This helps to give you breaks from constant communication.

If one of you wants a separate room, go with that.

That said, when you do talk, be open and honest. You might have meal issues or other concerns so make sure that you talk freely.

Travel is amazing for older adults. It helps you to gain life experiences. It keeps your curiosity sharp and gives you a greater awareness of the world around you. More importantly, it teaches you about yourself. Just remember that the people you choose to travel with can make or break an experience. So, plan this part of your trip wisely.

Who do you travel with? What rules have you established with the people that you travel with that help to keep everyone happy? Where are you going on your next trip? Please join the conversation.

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