Western Cuba itinerary

Nature
The wow factor for nature - does it show nature at its best? Doesn't need to be the wildebeest migration or diving with hundreds of hammerheads. Rather make you pause as you realise just how awesome the natural world can be
4
Culture
How much does this experience showcase some of the better and finer things that us humans can offer? Sure, it can be ancient ruins and renaissance churches, but it can also be festivals or soaking up some of the great modern cities of the world
7
Fun factor/activity
Very simple - was it fun? This is usually linked in with doing some kind of activity - i mean, walking along some cliffs is nice, but paragliding from them, now that is fun. Its a vastly underrated factor in a truly great experience
6
Avoid the crowds
Big tour groups and being surrounded by loud fellow tourists can sap the life out of even the greatest of travel experiences. This score is to reflect just how much you can avoid this. But. . . The score also takes into account if the crowds actually add to the experience, such as with a party town or a bustling local market
7
World famous
How world famous is the experience?
9
unique
How hard is it to have a similar experience in other places round the world?
10
Overall TE Score
The overall travel experiences score:  fun factor + avoid the crowds + (best of nature or culture) + (best of world famous or unique). Then convert into a score out of 100
75 *What the scores mean and where do they come from
RANKING
How this travel experience ranks compared to all the other experiences on this site, based on the travel experience (te) score
101st/454
Top 30%
continent
North America
country
Cuba
Length of time
Around a week
Typical daily price
This gives you a rough idea of the daily price based on 2 people travelling where they can split costs like accommodation. It excludes travel there and back, and factors in inflation the numbers in brackets show the price range for the full time of the experience (so not necessarily daily). It is a range to reflect different budget vs higher end
$110 (typically $40 - $180)
Time of year visited
May
Primary Tags
Click on any of the tags to see all travel experiences with the same tag
Beaches Local villages Old town
All Tags
Adventure Big city Bustling restaurants Cycling Driving Isolation Palaces Restaurant recommendations Rooftop Bars Scuba diving Sunsets UNESCO world heritage site
Wow Factor
The wow factor reflects just how much you’re likely to say “wow”. As there’s a lot of experiences in the world, and a lot of wows, i’ve gone with a simple ⭐️ ⭐️ ⭐️ ⭐️ ⭐️ to ⭐️ score, and a separate category for the truly "gash"
⭐⭐

Summary

Western Cuba feels less like a destination and more like stepping into a parallel version of the world – one where time has slowed down and taken a different path altogether.

Havana gives you the first glimpse of this, with its faded grandeur, colonial architecture and lively atmosphere hinting at a much richer past. But it’s when you leave the capital that the experience really becomes distinctive. The countryside opens up into vast, largely untouched landscapes, where life moves at a noticeably slower pace and small towns feel frozen somewhere in the mid-20th century.

Driving through these areas, you see a mix of charming simplicity and underlying oddity – long queues outside basic shops, quiet streets lined with porches, and occasional reminders of centralised planning in the form of half-empty developments.

What ties it all together is the people: welcoming, proud, and very much part of what makes the experience memorable.

This slightly surreal contrast — between beauty, decay, warmth and strangeness — is exactly what makes western Cuba not necessarily wow, but quite compelling. It’s not a polished or easy destination, but it offers something genuinely different, especially if you venture beyond the main tourist routes.

The itinerary I’ve listed here is more for the west of Cuba and the one we enjoyed.  Your other option of course is to head south from Havana to the colonial landscape of Trinidad and then dive in Bahia de Cochinos.  The below itinerary though gets you more off the beaten tourist track and this was in particular something that we enjoyed so much about Cuba – a glimpse into that strange tangent the country has taken.

In a nutshell:

  • Feels like stepping into a parallel world — not just “old”, but genuinely different
  • Havana is the headline, but the real experience starts once you leave it
  • Expect things to feel a bit… odd (queues, empty buildings, slow systems)
  • Havana > cycling in Vinales > scuba diving in Maria la Gorda
  • Best for travellers who enjoy observing and experiencing, not just ticking sights

The route

 

Pretty straightforward. Whilst it is a lot of driving due to the there-and-back,  it is the driving that makes for such a highlight as you see the super unusual and quieter side of Cuba unfold.

 

Highlights

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#1 Getting lost in the truly wonderful Habana Vieja - in my opinion the best Old Town in Latin America

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#2 Watching the lazy world go by from a porch on the main street of one of the small Cuban country towns such as Vinales

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#3 Enjoying the amazing visibility scuba dives from the isolated Maria la Gorda

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#4 Taking in some of the superb restaurants, with their often fantastic architecture that make them a pleasure to visit

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#5 Cycling through the tradition-steeped landscapes of Vinales, with some gorgeous green hills breaking up the area into a nice ride through

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#6 Enjoying the lovely stretch of beach that spans the whole Maria La Gorda resort and having it largely to yourself

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#7 Jumping in one of the old-school Havana cabs and just watching the city go by

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#8 The amazing colours! All seems so much brighter in Cuba

Itinerary

Day 1 / 2 – Havana.  Enjoy the world heritage listed Old Town and siping mojitos as you move from one music filled bar to the next.  The best and most atmospheric Old Town in Latin America and, for more tips, see my entry for Nights out and soaking up Havana

Day 3 / 4 – Vinales for a feel for countryside Cuba and to enjoy the gorgeous landscapes all around the town.  For more tips, see the entry for Cycling around the Vinales area in Cuba

Day 5 / 6 – Scuba diving at Maria la Gorda.  Driving through the more isolated parts of the country makes the trip worth it alone, and you’ll get some great high visibility diving, plus a lovely stretch of beach.  More details – Scuba diving at Maria la Gorda

Day 7 – Drive back to Havana for a final night

Travel Tips for Cuba

Cuba often feels like another world – my suggestion is try to embrace this and enjoy the experience.  Throw out the window the expectations of efficiency and how you think things should be run, and be prepared for things simply not to work.  The idea, for example, of customer service can often be very alien in certain industries and you’ll find yourself often being completely ignored in a shop when the shop attendant has found something more interesting to do.

That being said, the Cuban people are a seriously friendly bunch who, if you engage them with the right level of friendliness and respect, can be the real highlight of your trip.  To be able to have a discussion (languages permitting) with people who look at the world so differently to you and are so proud and enthusiastic for their country, is something you’ll always remember.

Stay in a Casa Particular – from what we saw, some of the international hotels (in particular in Havana) were super expensive.  Way better to stay in a casa particular (private homestay).  Whilst the standard won’t be high, its a better experience as it allows you to meet local Cubans (arguably the highlight of the whole trip for us) and to see more of the real side of Cuba (think living in a tropical 1950s).  To find the right homestay, I’d suggest starting with Airbnb and www.cubacasas.net (booking.com didn’t work at the time in Cuba).

Cash – the money situation is a funny one and one that seems to change quite often.  The best tip is just to do a 10min search on google before you go and check with your bank / credit card company as to whether your card will work for withdrawals and for spending.  Broadly when we went, anything US-aligned (eg cash and cards) didn’t work.  Euros did.

Experiences nearby

The below map shows experiences nearby with a colour that reflect the Overall Score of those experiences

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Score Detail

The scores above are the real point of this site.

Over 20+ years and 100+ countries, I’ve tried to rank the world’s best travel experiences — from genuinely mind-blowing ⭐⭐⭐⭐⭐ to the properly gash.

Every one of the 500+ places on this site has both a Wow Factor rating and a more analytical Travel Experience (TE) score based on the things that actually make travel memorable.

If you're curious about the thinking behind it, head to the About page.

Otherwise, explore the map above or on the Home page and see which places truly deliver maximum wow.

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