The Backstory

Italy has always called to me. Not only because of ancestral ties but the gravitas of history, art, and architecture that have defined Western civilization from early Rome to the Renaissance, and continue to exert their influence today. As art history was a substantial component of my college coursework, Florence would naturally be at the heart of any journey, regardless of how the details took shape.

While I have wanted to visit Italy for a very long time, planning for this trip began in earnest as our “real honeymoon” almost a decade ago. After a lovely resort staycation, I started looking into actual costs. Rome, Florence, and Venice were perhaps the obvious trifecta, but many other places a little further off the beaten path also called—Padua, Ravenna, and Siena. With so much to see only in Florence, I knew I could spend weeks there. And let’s be honest. I could happily spend the rest of my life in Italy, exploring every aspect of its art, cuisine, and culture from hillside villages to bustling metropolises.

The first step was to make a list of pros and cons for joining a tour versus traveling solo. I knew I didn’t want to go on a cruise. Of course there are myriad options and I’m sure many people have a wonderful time. What came to mind was a lot of time spent shuffling off, then back onto the boat, while being time bound at each port. It didn’t sound ideal.

Many land tours felt similar. A whirlwind of selfie stops to check “been there, done that” boxes wasn’t the experience I was after. Much more appealing was the idea of getting lost winding through narrow medieval streets, finding local spots away from the tourist areas, speaking Italian, remaining open and spontaneous as unanticipated opportunities unfolded. Even if that unanticipated opportunity was sitting at a cafe for an hour or two to enjoy a coffee or spritz while watching the city swirl around me.

Being the first time traveling abroad, these are some of the key pros and cons that were top of mind:

Going solo:

• Pro – traveling by oneself can be an exhilarating and empowering experience.
• Pro – the entire agenda is up to me, and I have the flexibility to do what I want, when I want.
• Con – the entire agenda is up to me.
• Con – potentially missing out on hidden gems and getting recommendations from someone who knows the city well.
• Con – wanting the freedom to wander without being alone the entire time.
• Con – not being fluent in the language, what would I do if there was an issue?

With a tour:

• Pro – the agenda is arranged and managed by professional and knowledgeable guides.
• Pro – a tour director can help tailor your experience based on personal interests and desired level of activity.
• Pro – some meals are likely to be included in the cost of the tour.
• Pro – skip the line access to popular sights and museums where lines often wrap around the building during peak seasons.
• Pro – most tours allow you to participate in group activities or explore on your own as much as you want.
• Pro – should something happen, you have a point of contact who is ready to help.
• Con – group activities at sites with a guide may be more limited than desired.
• Con – personal dynamics within the group could be a detractor.

Clearly, the pros of joining a tour outweighed going solo. Now it was a matter of finding the right tour.

Costco Travel

Early in the process, Costco was mentioned as a great option. At the time, I was looking for independent travel rather than tours. So I started my search there and found a perfect two-week trip to Florence and Venice. Costco provided pleasant surprises in both flexibility and customization from package and hotel options, length of stay in each city, to booking activities in and around each destination. 

Ground transportation to and from airports and between cities was also pre-arranged, greatly simplifying any travel by rail which can be somewhat complex and overwhelming for newbies. All at discounted member rates with additional perks such as meal credits. One of the best features was having airfare included because that gave me a set target to save for.

Costco also offers a multitude of packages for those who may prefer a cruise experience. While I didn’t see much in the way of guided group tours, that wasn’t the focus of my search and may very well be offered.

Smithsonian Journeys

Not surprisingly, a Smithsonian Journeys catalog made its way into my home. It didn’t come as a surprise because I had been telling friends, family, and coworkers about this epic, years-in-planning trip every chance I got. Some offerings felt a bit short or spanned the entire country in a matter of days. And then I saw it – Living in Italy: A Three-Week Stay in Florence. Perfetto!

For me, it was the exact balance of group activities to key sights and museums, day trips to smaller towns in the surrounding area, while also providing ample time to explore on my own. Enrichment tracks in Art & Architecture, Language, and Cuisine were also offered at an additional cost.

This was the ultimate way to travel abroad by myself for the first time. I had the freedom to do as much or as little as I wanted with the group, as well as the reassurance of support once I arrived. It was an absolutely amazing experience, highly recommended whether you are a new or seasoned traveler!

Okay, well, the pandemic certainly put a damper on international travel for the better part of two years. Even as things started to open up, varied requirements for masking and testing across countries and regions as well as the potential of getting stuck in quarantine was not worth the risk. Putting that whole thing aside, ten years is an awfully long time for a trip you’ve been dreaming about for most of your adult life to linger in planning.

I had to stop making excuses about why it wasn’t possible.

Not enough time or money

These are huge factors and I completely get it. Before such a trip was financially feasible, it took quite a while to bank both time and money. Everyone’s situation is different and I was very fortunate to have a job that allowed me to set aside funds and accrue enough paid vacation. However, after those barriers had been overcome, I found other things continuing to hold me back.

What about the kids?

I’m a single dad. Three weeks would be the longest I had ever been away from my boys. Despite being 11 and 14 at the time, so not real little, I worried they would be upset with me. Perhaps resentful that I was going without them, or even feel abandoned. It may sound silly, but it weighed on me.

Sometimes it can become easy to get stuck in the same old day to day routines. Day to day becomes week over week. In some ways it’s comfortable in the sense of knowing what to expect. It’s also boring AF.

In preparation, my kids saw Dad practicing Italian, watching videos, talking about some of the places he was going to visit, sharing his passion for history and art, being excited for a trip he spent years dreaming of and working towards.

And when I got back, they were absolutely fine!

I don’t want to go by myself

Italy is well known as one of—if not the most—romantic countries in the world. When I envisioned what it would be like, there was always a component of sharing this amazing place with an amazing person. A mutual passion for art and culture, having experiences that would create memories to last a lifetime. While on dates, dreaming about the Italian lifestyle and this trip was one of my go to litmus tests for gauging potential longevity. It wasn’t a super long time, but I certainly put off booking with the hope of romance being an integral component.

In hindsight, I’m glad I decided to go alone.

I don’t know the language

Language was less of a barrier and fluency certainly wasn’t going to happen through books and videos. That said, I did want to learn some basic verbs and phrases, how to be polite, as well as cultural dos and don’ts. Honestly, I think it’s rude to visit a foreign country and not know how to at least say please, thank you, excuse me, and sorry. While Italians are known for their openness and warmth, it goes a very long way to show some effort no matter where you go.

Fortunately, there are a ton of online resources and YouTube channels, along with well-known apps like Duolingo and Babbel that can get you well on your way in no time.

In 2023, I decided this was the year it was going to happen. No more worrying the money would be better saved or spent elsewhere, no more waiting for someone to go with, no more excuses.

Confidently striding to the Smithsonian Journeys website months ahead of an intended October departure, I filled out the online form to book a reservation. To my dismay, October was booked solid for single travelers, as well as the following April. The agent was quite helpful answering questions and put me on the waiting list. Being eighth in line, I knew my chances were slim, so I snapped up an open spot for August—2024.

Booking well in advance reserves a spot at a time that is ideal for you. It also allows ample time to plan and save up for expenses and final payment. There was availability for double occupancy, so you may have better luck booking on shorter notice if traveling with a companion.

At this point, we’re talking a year out from the time I was making the reservation. Well, 2023, I did my best…

Carpe diem

If you’re wanting to travel and see the world like I am, don’t wait! Yes, it takes time and money. Time is the only resource we cannot make more of and there is no way to check the balance on that account. While I would not recommend going into massive debt by putting an entire trip on credit cards, I would suggest that if you come up a little short, in the long run, you’ll regret not going more than paying off a small balance.
Carpe diem—seize the day, the opportunities that lay before you. Seek adventure, get lost, amaze at the beauty which surrounds us, be uncomfortable for a moment, only to discover and experience the common threads that make us all human.