The Small Details That Make a Trip Memorable
Still, there are some new experiences on the front end, and on the back end, well, another kuksa is to be made, and this time perhaps with Rosa’s name on it. For those who may not know, a kuksa is a traditional hand-carved wooden cup from Lapland, often used throughout the Nordic region. It is one of those practical, beautiful things that feel very connected to the place where it comes from. After all, the first one I made featured a puffin, what else! It is those little personal details that make a trip memorable, even when part of the itinerary feels familiar.

Shared Accommodations and Speaking Up
The only other issue I have with the organization of this program is that we were told there would be shared accommodations for the first two nights, something that was not mentioned at the beginning. It was mentioned less than a week ago. If I had known, I would not have opted for the program at all, and perhaps I would not have taken this return visit to the Arctic and Lapland so soon after the first one. But when I expressed my concerns, they made an accommodation for me with a single room and private facilities. My days of youth hosteling and shared accommodations are behind me, so I am glad they took my concerns seriously.

Cooler Air Above the Arctic Circle
Overall, getting out of the Roman sunshine for a week will be good for me. The temperatures here in Rome have already been in the 90s F, or around 32 to 34 C, and even though I remember last May being extremely hot and forcing myself not to use the AC at home, the past few days have had it on and off as I have been in and out quite a bit. So, the cooler air and fresh air above the Arctic Circle will be a welcome change.

Expecting the Unexpected
It also reminds me that travel is never just about the destination. It is about timing, flexibility, surprises, and knowing how to adjust when plans change. That is true whether you are traveling for business, for leisure, or because life simply decides to send you in a different direction.
I suppose what I will take from this upcoming week is that you have to expect the unexpected. Having been a teacher as long as I have and a professional travel planner for as long as I have, I know that anything is possible — from the extremely positive to the extremely negative, and everything in between. I am grateful that I had teachers growing up who taught me to think outside the box and not have a narrow view of the world. I do not think I would be here if that had not been the case. Remember, there are always going to be bumps in the road, no matter what, and they are not always going to cobblestones, so being prepared professionally or personally. 

​Travel, Planning, and the Space Between
Ultimately, whether it is spontaneity, pinpoint planning, or something in between, it is important to be prepared for anything that life or business throws your way. Sometimes that means a last-minute trip to Assisi. Sometimes it means a familiar destination with a few unexpected twists. And sometimes it simply means being ready for whatever comes next or a cancelled trip, or a misunderstanding in the travel planning. 

What do you think matters more in travel and in life: spontaneity, careful planning, or the ability to handle the unexpected when it shows up?    

What About You?
Have you ever taken a spontaneous trip that turned out to be better than expected? Or is Assisi one of those places you have been meaning to visit someday?
If Assisi has been on your list, maybe this is your sign to move it a little higher. And if you are planning an Italy itinerary and want help shaping a trip that includes places like Assisi, I would be happy to help you make it something meaningful.

Last week, if you didn’t catch it, I explored the whirlwind onset of high season—the grind between calm and chaos—and how, once that busy period settles in, things most often smooth out. One of the ongoing challenges in our industry, on many levels, is balancing business demands with personal balance. This naturally brings the idea of shoulder season, and even low (or off) season, to the forefront—not just in conversations with my clients but across the travel industry as a whole.

Many destinations around the world have pushed back against the overwhelming surge of tourism. This pushback isn’t just about protecting economies or cities; it’s about preserving the lives of local people. We’ve seen it in places like Venice, Barcelona, and Dubrovnik—cities overwhelmed by cruise ship passengers, where locals have found themselves struggling to live in their own homes. Protests have erupted, cruise lines have been ousted, and restrictions have been put in place because ultimately, the impact falls hardest on communities, and not in a good way.

The travel industry—guilty as charged—has had to find ways to balance sharing the world with visitors while being mindful of these pressures. Some solutions have come proactively; others have been imposed by necessity. For example, no cruise ships are allowed to dock directly in Venice anymore. Instead, they unload in towns outside the city, and visitors are bussed in. Venice even started charging an entry fee a year or two ago during high season to help regulate tourist numbers and spread out visits. That high season, which used to be a compact June, July, and August, has stretched longer over recent years.

Focusing on American travelers, who historically have flocked to the summer months, airlines and the industry itself have tried to expand the shoulder season. What once was simply May and September became a longer window—sometimes from May through September—because demand never waned. Prices reflected that, effectively stretching high season to five months. The hope was to diversify travel over a longer period, easing congestion, but post-pandemic demand actually intensified.

So, what do we do? How are destinations evolving to welcome travelers without becoming overwhelmed?

Generally, the answer has been to extend the travel season—especially when weather remains pleasant, like here in Italy during April and October. In my view, even March falls into shoulder season, offering fewer crowds, better value, and often a richer experience. I recognize this isn’t possible for everyone, but it’s a worthy option.

This topic is gaining serious attention in the travel industry. In fact, I’ll be attending an event this June in London called SHOP—short for Shoulder & Off Peak. It focuses on how destinations can stand out during these less-traveled times, highlighting experiences designed to attract visitors year-round. I’m impressed by how hard destinations, tour companies, and hotels have worked to develop enticing activities in these off-season months.

It's crucial we understand the value in spreading the travel “wealth” throughout the year, rather than packing it all into a few summer months. Again, I’m speaking mainly about the American market, as the summer months have traditionally defined high season. While that tradition is loosening—due to changing work habits, remote jobs, social media influence, and shifting family structures—the summer core remains strong.

I firmly believe destinations offer incredible opportunities in the off and shoulder seasons—even places like Iceland where winter days are short still have magic to share. Expanding travel possibilities beyond peak months isn’t just smart; it’s necessary. Sure, not everyone can be flexible with timing, but I’ve always been someone who thinks outside the box—traveling off the beaten path, challenging traditional 9-to-5 thinking, and encouraging learning through experience, even if that means taking kids out of school for a week during quieter times.

For the good of our planet and its people, we must consider new ideas. Destinations increasingly focus on what they can offer in the low seasons, and I’m genuinely excited to bring those ideas back from the SHOP event.

What do you think? From a business perspective, having more steady streams of travel is attractive. And yes, as I mentioned last week, I still thrive on the chaos of travel’s busy peaks. But at this stage of my professional life, I’ve grown accustomed to the ebb and flow.

More importantly, for the benefit of local communities and travelers alike, it’s worth seriously considering what travel during less busy months can offer—for everyone’s long-term good.

As travel professionals and travelers, embracing shoulder and off-peak seasons isn’t just about beating the crowds or scoring better deals. It’s about respecting destinations and communities, spreading the joy—and impact—of travel more thoughtfully throughout the year.

I’d love to hear your thoughts:

Have you ever traveled in the shoulder or off season? What was that experience like?
How do you feel about restrictions on cruise ships in historic destinations?
How can we, as travelers, balance our wanderlust with respect for the places we visit?
Let’s keep the conversation going—and together, help create travel that benefits the planet, the people, and ourselves.

If you want to explore travel beyond traditional seasons, or find new ways to experience your favorite destinations more sustainably, 

\Last week, I opened up about some of the serious challenges behind the scenes in travel planning—unexpected disruptions, Force Majeure situations, and the constant need to adapt on the fly. This week, I want to share what it’s really like living the daily reality of a travel professional—where chaos and calm collide with every sunrise, and a cup of coffee is never quite enough. Whether you’re a fellow traveler or industry friend, I hope this gives you a better peek into the passion and grit that keep Wandering Puffin moving forward.

The Never-Ending Dance of Chaos and Calm
Nearly 30 years in this vital, ever-changing industry have taught me that the balance between chaos and calm is a daily battle. When one fire is put out, another flame often springs up—usually when you think you finally have things under control. The calm moments? Rare and sometimes just a deceptive lull before the next challenge.

I won’t say I don’t thrive on chaos—I do. When clients admire the glamorous side of travel, visiting amazing destinations, I remind them it’s a choice that comes with trade-offs. Many hours—8 to 10 daily—go into hotel inspections, partner meetings, detailed planning, and resolving unexpected issues. Unlike large agencies that can spread tasks among many team members, as a one-person operation I wear both the owner and employee hats. That’s both the challenge and the joy of running Wandering Puffin.

Wearing All the Hats: Owner, Advisor, and More
Despite the hectic pace, I love what I do—especially when meeting clients in person. Those moments add meaning to an already fulfilling profession. I’m supported by accountants, lawyers, social media experts, and partners who share about 35% of my bookings, but the ultimate responsibility for client concerns rests with me.

People often say, “You have such an amazing life.” And yes, it’s special—but I believe in sharing the realities too. Travel planning isn’t all fun and games; the value of experience often makes the difference between a smooth journey and frustration.

Changing Seasons and Shifting Trends
Historically, May has been a quieter shoulder season, but the world has changed. Travel demand has exploded, even in turbulent times, and May is shaping up to be one of the busiest months I’ve seen lately. Clients this month are heading to Germany, northern Italy, Switzerland, France, Spain, the Arctic, and beyond. For those who think I only focus on Europe, I’m also arranging trips to St. Croix and a South African safari later this year.

Planning and preparing itineraries for such a variety of destinations means long days and tight deadlines. Thankfully, electronic documents help save time, reduce waste, and keep things organized. Still, balancing personal and professional demands, plus seasonal shifts and new trends, keeps me on my toes.

Passion Beyond a 9-to-5 Job
This isn’t a typical 9-to-5 “job”; it’s a passion that doesn’t respect bankers’ hours. Ideas and solutions come at all hours—for instance, I’m writing this at 3:00 a.m. when inspiration struck. Some nights, it’s about organizing e-portfolios; others, it means catching a quick nap before a full day of client work.

Over time, I’ve learned to streamline processes—moving from paper to paperless, adapting to new technology while still accommodating clients who need printed materials. It’s a balancing act, especially as high season creeps earlier each year.

Embracing the Challenge and Reward
The ebb and flow of client bookings, external disruptions, and shifting travel trends mean that travel professionals must be ready for anything. While the “chaotic heartbeat” of the industry can be exhausting, it’s also what keeps it interesting—and rewarding.

When I’m out on the road (my “working holidays”), I recharge both personally and professionally, gaining fresh perspectives that fuel the work ahead. My systems aren’t perfect, but the drive to improve never fades.

At the end of the day, this industry is about trust and relationships—not a commodity to be bought or sold cheaply. And that’s why I push through the chaos and calm every single day.

Let’s Keep the Conversation Going
What’s your experience with the ups and downs of travel—or managing chaos in your own line of work? How do you find calm in unpredictable times? If you’re a traveler wondering about the realities of working with a travel professional, or a fellow advisor navigating this ever-changing business, I’d love to hear your thoughts.

Thank you as always for supporting my little crazy world across the pond. If you’d like help turning your travel plans into memorable adventures amidst whatever challenges come your way, reach out anytime at [email protected].

Here’s to embracing the journey—chaos, calm, and all!