Published on October 25th, 2015


Prepping for Cuba: Part II

O.k. kiddies, when last we left off, we’d covered the two most pressing issues for USofA brats like me contemplating a dip into “The Forbidden Land”.

And I should probably add here, that while recently there’s been a political thaw between Cuba and my native land (including the reinstatement of a U.S. Embassy in Havana – yay!), technically the (did I mention 53 years old?) “embargo” remains solidly in place. And while we now can apparently visit via each our own independent “license” – such requires fitting the raison d’être of your visit into a decidedly narrow set of 12 “authorized categories”.

Opinions vary widely as to if/how one might, or might not technically fit into say… the “educational” or the “journalistic” activities category, but suffice merely sipping mojitos whilst lying on a beach just ain’t gonna cut it. That said, as I mentioned in Part I – U.S. immigration doesn’t seem to care who’s dropped into Cuba and who hasn’t. So what it all boils down to is this: YMMV and it’s up to you to do your own due diligence research and make up your own mind.

Ah but enough of the Cuba embargo nonsense – let’s now take a look at the more usual trip research chores. You know, the standard homework for any trip:

How cheap of an airfare can I get?
How many days shall I visit?
Where shall I go once I’m there?
Where shall I sleep?
How will I get around?
Oh and btw…

What shall I pack?

Nabbing a Cheapo Airfare:

I started looking at airfares long before I had even a window of when I might head to Cuba (for often it is a matter of stumbling upon a sweet fare – to most any country I’ve yet to explore – that rules what my next travel adventure will be).  As time wore on though, I decided that yep – Cuba would be my next trip and began trolling for airfares in earnest.  At first I thought it would be epic to spend New Year’s Eve in Havana, but then… I remembered last NYE here in Cuenca.  In a word: AMAZING!  So no way did I want to miss it. Besides, the fares were higher the later in the year I searched, so I narrowed the hunt down to a window of about 2-3 weeks in October/November.

Btw cheapo fare tip: as I have the sublime benefit of being retired and thus can come and go most any time I please, I always search via “Cheapest Month” or at least “Full Month” to find the combination of dates that have the very lowest fares.

In short, I ended up with a rather sweet roundtrip fare of $563 from Guayaquil to Havana – via Panama (with short layovers both to-ing and fro-ing).  Booked (after much perusing of sites like Skyscanner, Kayak, Adioso, Hopper, Momondo, et al) directly on the Copa Airline site.

The days with the lowest fares determined my travel dates: a 16 day window (27 October – 11 November). Thus the next order of business, was…

Itinerary Planning:

The most time-consuming (and fun) part of any trip prep. Wading endlessly ’round the www to glean both an overview of Cuba, as well as get an idea of the highlights I might fancy. Integral to the the latter, was the most serious question of just how much I could reasonably squeeze into a 15 night itinerary (without racing to so many different corners that it all would blur together and I’d miss the very reason I travel: to hang out with the locals, and get a true feel for the culture.) For this, I find sites offering tours (which I otherwise rarely seek out) most helpful. And here Cuba was no exception.

Perusing the itineraries of such tours gave me a good idea of just what all I might include in a 16 day itinerary – and what I couldn’t. Suffice it swiftly became clear that but 3 or 4 locales was all I could reasonably manage given the Cuba terrain (ruling out domestic flights which proved pricey, not to mention superseded the pleasure of gawking at the Cuban countryside), and thus pretty much eliminated the possibility of exploring the far eastern reaches of the island on this trip (besides, did I really want to see… Guantanomo? I think not.)

This research drudgery (NOT) also entailed reading most every blog on Cuba I could find, along with Lonely Planet and TripAdvisor “Best of” recommendations. The more I read, the more I wished I had a MONTH or more to amble around the smallish island of Cuba. But slowly I began to narrow it down to a loop of 4 locales:

  • Havana
  • The western province of Pinar del Río (specifically Viñales)
  • Playa Larga (I mean, snorkeling in the infamous “Bay of Pigs” has a kinda nice ring to it, dontchathink?)
  • and the World Heritage site of Trinidad.


Such a conservative loop seemed easily doable by local transport (bus and taxis) yet offered plenty of diversity (i.e. the legendary color and vivacity of Havana, Viñales’ tobacco fields and stunning “mogotes” landscapes, Trinidad’s colonial town, and plenty of beach options along the way.)

Then again… while I generally much prefer getting off-the-beaten path in the countryside rather than big cities, as my researched progressed I kept finding more and more great things to do in Havana, so I’m now thinking I may well devote a generous third of my itinerary there.  But of course nothing is in stone. I’ve pre-booked only accommodations for the first 2 nights in Havana, so the rest remains open to my whim once I’m on the ground.  Which neatly segues us to…



“Casa Luly”, my sweet “casa particular” – right in the heart of “Habana Vieja”

Among the unique attributes that sets Cuba apart from the many other countries I’ve traveled is their lovely system of “casa particulars” – staying in a spare bedroom in a Cuban family’s home. Oh, there are hotels as well in Cuba, but apparently casa particulars are happily ubiquitous throughout the country. I’ve always favored homestays no matter where I’ve roamed (indeed, I was among the first tour operators to offer homestays in Belize for my small group trips – way back in the 80’s), so needless to say, I’m thrilled to be able to sit at the kitchen table for breakfast (even in Havana) in a Cuban’s home.

Even better, the “casa particular” system is regulated by the Cuban government, so prices are relatively uniform (though you can always negotiate of course), and more importantly – apparently the amenities (e.g. private hot water bath, air conditioning, etc.) too are strictly regulated, so one can count on a most economical and comfy stay no matter where you go. The only downside to the system (though only to we “solteros”) is that all casa p’s charge by the room, not the number of people. Thus while the prices range from about $25 – $40 per night (meals additional), alas couples can split that (i.e. $12.50 – $20 pp.) while we solo’s pay the full amount. In short, ’tis a 100% “single supplement”, but nonetheless still a bargain for the opportunity to connect with Cuban families.

btw, you won’t find any of these “casa particulars” on the usual hotel booking sites like agoda and While there are a few on airbnb, I found them to be higher priced there than on specifically Cuban sites like cuba-junky, bbinvinales (with casa p’s for all of Cuba, not just Vinales), casaparticularcuba, casahavanaparticular, etc.

Also, apparently there’s quite a little “underground-railroad-like” system among the many casa p’s all over Cuba. Your initial casa particular host will be happy to call ahead (to their cousin/friend, natch) to reserve a room for you in your next locale. There’s a small “commission” involved of course (generally $5 additional), and you miss the opportunity to negotiate a more favorable rate. But given that wifi is apparently rare as hen’s teeth in Cuba, and even a sim card for an unlocked phone, quite pricey – it’s a convenient system to ensure an advance reservation, and a perfect example of: “Welcome to how things are done in Cuba!” 😉

Getting Around:

Antique Chevrolet

Zoom, zoom, zoom…

More kudos for Cuba. Not only are there a myriad of local transport options in Havana including cute little 3-wheeled, yellow ball-shaped “coco taxis” and “bicitaxis” (much like Asian pedaled rickshaws), but of course those legendary jalopies of old – all (amazingly) restored in glorious living color. Often used as taxis, apparently you can reenact your favorite “Happy Days” fantasy as you sail down the Malacon in one of these honeys for $30 per hour.

CheGuavaraIcon450There’s also a 5 buck “HOHO” (Hop On, Hop Off) double-decker bus that I’ll likely “hop on” my first morning in Havana – to get an overview of the city. Apparently one of the stops is at Plaza de la Revolución (guarded over by the infamous Che Guevara icon emblazoned on the side of the Ministerio del Interior building. It also stops by the Colón Cemetery (renowned for its striking religious iconography and elaborate marble statues) but I dare say – more importantly to this geocacher – there are several caches hidden nearby, including an Earthcache right in the middle of it!

For land transport further afield, there’s both trains and swift, comfy buses. The former are said to be unreliable and uncomfortable for long-distance travel, but I hope to jump aboard the electric “Hershey” train for a couple of hours while in Havana, as well as possibly the antique stream train that is said to run (irregularly) out to the” Valle de Los Ingenios” (Valley of the Sugar Mills) near Trinidad.

And the latter (economical a/c buses) shall be my transport mainstay (unless I happen to hook up with a few other intrepid DIYers and share a private taxi) to head to Vinales, Playa Larga, Trinidad, and/or… wherever else catches my fancy along the way.


Over the years, I must have posted near a dozen different photos here at TL of what my ever light, carry-on-only packing caboodle looks like, so I shan’t go into details here. Indeed, only to say that… (as I so often preach: No matter a week, or a month…) if I can manage an entire month in the frigid wilds of MONGOLIA with but carry-on – I can most certainly travel ever so lightly amid the (one thing I’m NOT looking forward to) sweltering heat and humidity of Cuba.

Inside Cuba: The History, Culture, and Politics of an Outlaw Nation

A kindly lend from a chum here in Cuenca – can’t wait to crack a wood-pulp book for a change!


Furthermore, for this foray into the back-roads of Cuba where wifi is certain to be seriously scarce (see above “hen’s teeth”) – I’ve decided to leave even my little netbook at home, and travel with only my Kindle (and a single wood-pulp BOOK!), plus my smartphone should I happen to find a little digital juice for a Facebook check-in along the way. Indeed, while the prospect of cold-turkey digital withdrawal for more than 2 full weeks looms a tad daunting, I’m rather looking forward to traveling (once again) as in blissful (sans technos) Neanderthal days of yore.

Leather-bound travel journal - from days of yore

No keyboards for me this round…


Shoot, I’ve even dug out my old leather-bound paper travel journal (last used whilst backpacking ’round South Africa and Mozambique in 2004) and I have every intention of scribbling in it – as I rock to and fro in a rocking chair on the porch of my cozy casa particular in view of the bucolic tobacco fields and mogotes of rural Cuba.

Hospitality Gifts

Hospitality gifts


The only extra I’m packing for this trip, is a stash of little “hospitality gifts” for the hosts of my casa particulars and their kiddies – hair ribbons, scented soaps, tea, and pot holders for the kitchen. Just small tokens of thanks for sharing their homes with me.

Oh and… nope – I’m NOT packing my cat Dulce on this trip! 😀



And finally – surely no “Prepping for [fill in your most lusted-after exotic destination here] treatise would be complete without a stern reminder of my ever trusty travel mantra:

Yes, yes, researching your trip is good. Great fun and highly recommended to save you both time and money once you hit the ground. Likewise such research can greatly enhance your trip, avoid costly (in time and money) errors, and guide you to spectacular locales and attractions you might otherwise miss as you roam about your destination. Heck, solid, up-to-date research might well avoid a serious travel disaster.


After all is said and done. After those 6 colorful Google letters have become a blur, and all the dogged digital research has come to an end. When it’s time to slide on through security, hand-over your boarding pass, hop on that great big silver cigar tube, and rise up towards the heavens…

At that precise and singular moment, it’s time to take all the nitty-gritty trip research minutia and…


Yes, you heard me right: TOSS.IT.ALL.OUT.THE.WINDOW. in favor of letting traveling serendipity have its merry way with you.

For in my mind dear readers, THAT is the very BEST way to travel!

About the Author

Off-the-beaten-path travel is my passion,and I’ve always lived life “like-a-kid-in-a-candy-store” – eager to sample as many flavors as I can. Indeed, my life motto has long been: This ain’t a dress rehearsal, folks!

6 Responses to Prepping for Cuba: Part II

  1. Ted says:

    Hey Dyanne, didn’t take you long to start grabbing a bit of Cuba. Hell, you might even get to ride in an Edsel….
    Ted kindly contributed to world literature by posting…Merignac and street kidsMy Profile

    • Dyanne says:

      Nope, I don’t recall seeing any Edsels while skipping around Cuba Ted, but I did see boatloads of every other make and model from the days of my childhood and have LOTS of great pics to share, stay tuned!

  2. Burt says:

    As I’ve mentioned, my experience is 10 y/o, so it is possible things have changed. However, we took an overnight bus from Havana to Santiago de Cuba (extreme East end of island), and a train from there to Trinidad. Both had seats that were quite comfortable, but…

    They LOVE their air conditioning in Cuba. On both routes, we had every jacket we brought on, plus extra clothes, and were still too cold. I caught a cold on the bus East, but fortunately, got over it in a day. Evelyn caught a much more serious cold on the train, and remained sick the rest of the trip.

    We spent NYE in Trinidad. It was interesting, but rather low key. Certainly nothing like Cuenca NYE!
    Burt kindly contributed to world literature by posting…Random Walk After Two Years, Part 2My Profile

    • Dyanne says:

      Sorry to hear it, Burt. But yes, frigid buses are the norm pretty much all over the globe. That’s why I always keep a pair of wool socks plus a fleece jacket and plenty of layers ever handy – even in the tropics. I also tuck in earplugs and an eye mask for those overnight buses. In every country I’ve traveled, I can pretty much count on *loud* music and middle-of-the-night sudden bright lights at every stop.

      Ah, ’tis the bitter-sweet life of the traveler! 😉

  3. cathy says:

    Thank you for sharing. I, too have been looking at Cuba but several sites said a single woman should not travel alone. Thank you for pushing me in the direction I want to go!

    • Dyanne says:

      Oh my Cathy – a woman *should not* travel alone? Seriously – that’s just nonsense.

      I’ve traveled to 40 countries (including Egypt, Morocco, Mongolia, Myanmar, Borneo, Nepal, younameit) utterly SOLO. Indeed, at the ripe (young) age of 6-oh! I backpacked solo across South Africa and Mozambique. I’ve been traveling solo all over the globe for nearly 40 years!

      Glad I could give you a little nudge. I’ve felt perfectly safe all over the world, and I understand that Cubans are especially kind and friendly. Don’t put off a visit just because you’re a solo lass – it’s a great big wonderful world out there – go for it!

Back to Top ↑

Show Buttons
Hide me