How do you choose a vacation destination? Maybe choose to cruise

Updated: Aug 11

Imagine yourself planning your next trip. It's supposed to be exciting, but you find yourself instead feeling frustrated. Maybe with some frequency you catch yourself thinking, "I'm just not sure where to go..." and you can't even pick a destination to see if your favourite airline has an available connection.


Sound familiar? You're not alone.


There's no better way to stay comfortable and explore a multitude of destinations on one trip!

Counter-intuitively, the paralysis which accompanies now-overwhelming choice of destinations has featured among the most common difficulties our clients face. If only I could turn that seemingly simple notion into an actionable FAQ question!


Of course, the whole team here understands why these decisions can be difficult. The world is a gigantic place and it all looks so inviting, especially if you spend even a moment of your day on social media.


The larger the group, the harder the choice


How hard is it these days to pick one destination or experience over any other and to then commit our travel budget and our valuable vacation days to the journey?


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I had some of the same issues myself in recommending an experience for my family's recent group vacation. A surprise gift from my parents, we were meant to be celebrating a few milestones such as birthdays and careers, our group being a bit diverse in both age and interest.

Any subsequent search for the perfect destination first elicited a few questions. Which destination had it all, or at least featured a more-than-acceptable combination of what we each might enjoy? Which destination might fit the budget? How much travel time should we expect? Which experience would provide our family the best opportunity to make some really great memories???


How do we know which destination is the best when we plan a trip?


In the instance of my recent family group, our choices centered initially on finding a suitable region of the world, Europe vs Caribbean for example. Balancing which activities might be available or the local weather. Even as we refined a region (Mediterranean) and destination (Greece), it would evolve in detail as to whether we'd enjoy Mykonos or Santorini more...

Spoiler alert. My favourite single experience during our family cruise was in Santorini. We celebrated a birthday at the incredible Venetsanos Winery, just outside the village of Megalochori and with the most incredible view. They were very capable of accommodating my boisterous family and delivering an amazing sunset experience.


I might note that outside of any individual experience, I think I'd return to Mykonos before returning to Santorini. Part of my point about choosing to cruise - I might have never known the subtle practicalities which made Mykonos more appealing in the end if I hadn't visited them both on a cruise.


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Outside my personal preferences, the nuance between some client inquiries has been even more subtle in some instances. For example, how do you choose where to spend your only week of vacation this year if the dream trip options are either Spain or Portugal, but you've never been to Europe?


It's hard to feel good about making a choice if you've not got a baseline experience from which a comparison may be drawn.

On the flip side, I typically caution against planning too much. Too many activities, too much packing & unpacking or too much time spent navigating traffic & transfers to various airports & train stations; it leads to a stressful experience. The focus of your attention is drawn away from time you could spend learning about local people and engaging with your destination's various experiences.


A platter of options, from which you can order a main course!


My father reflected cruising in general during our trip, "I like cruising because I can see a whole bunch of places and then decide which ones I'd like to visit again."


That about sums it up perfectly, in my mind. It's easy to forget that we don't have to see the whole world at once. We can return to those places we really enjoy.


On a cruise you can "try out" a few places over the span of a week or two without making enormous sacrifices to your comfort or level of stress. Then once you're home and have some time to reflect on the whole experience, you can better decide if one spot really interested you and whether it may deserve additional time and attention - not to mention those valuable vacation days!

You may even decide that you've seen enough and that you'd like to explore a whole new region of the world, and that's OK too!


It's never been a better time to cruise


As the cruise industry as a whole is set to enjoy incredible expansion over the coming decade, we are really spoiled for choice in itineraries.


I think cruising is particularly well suited for island destinations of an archipelago or where a coastal region enjoys numerous small towns and local landmarks.


Greece or the Galapagos, Croatia, Southeast Asia, or beautiful Hawaii. I can't imagine getting better value out of a first-time visit than by sea. navigating busy train stations in what is no longer an affordable experience among classic European destinations?


Unintended consequences (it's a plus, don't worry)


Let's not forget about the wild card, that call to port that wasn't even on your travel radar in the first place. For me recently, it was Turkey.

Among my family group, none of us had really ventured further than Istanbul when it came to Turkey. While we were selecting one itinerary over another, the call to port in Kusadasi didn't really feature as a driving force behind any selection so much as a "nice to have" or bonus experience.


I could not have been more surprised.


Turkey just blew me away. A feeling shared by my wife and several others in our family group. How has this giant country spanning the gap between Europe and Asia escaped my attention for so long!?!


The history, the beaches... don't get me started on the food!


But, that's the beauty of cruise life. Unpack once, forget about logistics, and just enjoy the moment - explore at your own pace or enjoy an excursion. Forget about the practical aspects and just enjoy making some memories.


Even though our single call to port in Turkey was somewhat short in duration, it allowed me enough of a glimpse into the culture to know that I'd enjoy another visit of a longer duration. Turkey has officially made it onto my personal travel list and it might not have happened for a long time if not for cruising.



Our Mission


Here at Odyssean Travel, our mission is pretty simple. We want you to make better vacation memories with the people who matter most in your life.


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