Tripping – Part I

One thing I will never have false modesty over is my ability to plan a trip. What can I say? I’m just really good at it. This skill is one that I never would have anticipated developing back in the days when I relied upon a travel agent to book my simple flight from NYC to California, a journey that I’ve since taken more times than I can possibly remember. 

Of course, forty years ago booking flights and accommodations and rental cars was a much more challenging endeavor. Without a computer, or the internet, accessing airline schedules and other travel industry information was a difficult and intimidating task. 

But, no more.

At this point, I’ve lost count of the number of times I’ve flown across the Atlantic for a European adventure. Somehow, this kind of trip has become my speciality and, in the past 5 years or so, my comfort level with vacations abroad has grown and resulted in lengthier, broader excursions. When I share my travel plans with friends and social media acquaintances, I’m regularly asked if I book my own itineraries. Often, when I respond in the affirmative to that question, the next thing they want to know is “How do you arrange, book and pay for a 3 – 4 week vacation?” 

Well, I’m about to tell you…

Let’s look at next summer’s trip as an example – and, yes, I’ve already booked my 2024 summer vacation. So, my first suggestion is this: once you’ve decided upon an area or destination to visit, book early. My process for going to Italy (yes, again) involved determining what sort of vacation we wanted to have (beachy & relaxed) and what we wanted to see (new to us locations).

This time around, we primarily wanted to explore and experience places we’d never before visited in Italy. While we TOTALLY loved our Summer ‘23 trip, we were interested in getting to a new, to us, region. To help us to figure out the answer to this broad question we watched some television shows focused upon Italy (thanks, Stanley Tucci and RIP Anthony Bourdain), read some books (ibid), spoke with well traveled friends and consulted with an online travel board (Fodor’s) for tips.

Our ultimate decision: Puglia a.k.a “the heel” of Italy.

Now that we had something to focus on, I began virtually exploring specific towns and villages in the Puglia region. I appreciate the sense that I’m staying somewhere rather than just passing through and my preference is to stay in a specific location for 3-4 nights, rather than bouncing every day or two to a new place. I honed in on 3 separate towns which interested me – Polignano, Santa Maria de Leuce and Lecce, two of which are coastal with Lecce being inland but easily within reach of beaches.

I started looking at airfares and airport options. Bari provides the best access to the Puglia region, but fares when I initially looked were $1200+ r/t, kind of steep for a girl who likes to keep plane tickets below $1000. I explored different departure (NYC, Boston, Hartford, Montreal) cities as well as arrival destinations (Naples, Rome and Florence) with the thought that we could spend a couple of days revisiting a particular area we had enjoyed this year. One Saturday morning I hit what I thought to be paydirt – an open jaw ticket departing from Logan airport which would get us to Bari and home via Naples for $900+ and on a European carrier.

Honestly, those flights could not have been better for our vacation. Arriving in the area where we would be spending the majority of our time and departing from a city that we both love, is the ideal situation for us. We get to explore Puglia and return to Naples where we can once again wander the wildly crowded streets eating pizza and gelato. That would count as a win in my book.

There are two additional details about these tickets which you should be aware of – and this is important: 

1. We’re flying a European airline which means that if there are issues with our flights (ie, delays beyond a couple of hours or cancellations) the airline is obligated to compensate passengers and

2. Although I found these particular tickets using a travel search engine, I booked them directly online with the carrier. Nobody at Expedia or Cheapoair is going to be available if we run into a problem when we’re thousands of miles away from home. Always purchase tickets from the airline – and, while you’re at it, you may as well download their App and sign up for mileage rewards.

So, we had tickets and a general outline of the length of the trip. Time to start filling in some details…

(To be continued.)