Read Wanderlust

Trip Planning: Havana, Cuba

July 25, 2015

I have to laugh at myself a little (or a lot) writing a post on trip planning because, in all honesty, much of my past ‘planning’ has taken place mid-flight before touching down at my destination (or googling stuff in the car, if it’s a road trip). And that wing it mentality can be awesome, don’t get me wrong. Some of my favourite trips I’ve had no clue where we were headed after landing. But I’ve learned that a little pre-departure research means you won’t get home and find you’ve missed something you didn’t even know existed (*face palm*). I think the key is to not plan too much. My favourite thing to do in a new place is set out on foot and simply explore. Be sure to leave ample wander time. But part of the fun of a trip is the anticipation, right? Just thinking about it. And, in that way, doing a bit of pre-planning whets the appetite. Here are some ideas to get you started.

1. Lonely Planet Is Your Friend

Suggesting you get your hands on a Lonely Planet is far from fresh advice, but it really is a great jumping off point. It’s perfect to get an overview of what the main ‘touristy’ things are to see and do. I’ve bought guides in the past (depending on the trip), but that often doesn’t make sense because a) they can be pricey, b) it’s a heavy thing to tote around with you and c) it will soon be out of date. I prefer to get it from the library. If there’s information you want to remember just snap a photo or write it down. If your trip is short enough, you can even bring the library copy along with you. I know you can download onto your e-reader and phone, but I personally prefer the experience of leafing through a physical book. In Lonely Planet, I like to first get a sense of cost so I know how much I can expect to pay and for what. Lonely Planet also has a section for ‘Women Travelers’ so I look to see if there’s anything to know ahead in terms of safety, dressing, or finding tampons (learned this lesson the hard way in Morocco!), etc. You can also see whether any vaccines or medications are recommended or required for wherever you’re going. The ‘Month by Month’ section is great to see if your trip coincides with any festivals or holidays. While this can be really cool to be part of, it can also mean that a lot of places are closed (or crowded!). I also like to get the policy on tipping and haggling (I find the latter awkward no matter where I am [plus I suck at it]). And I personally enjoy reading the history section because a) I like history and b) it obviously gives you a more complete picture of place and people.

2. Read City Guides From Your Favourite Blogs, Websites, & Magazines

I love the guides on Design*Sponge so they’re my first stop. There are a lot to choose from with lists of guides for various cities, countries, and US states. Without their Cleveland guide, I would’ve missed out on a memory-making cup of coffee and some of the best ice cream I’ve ever had. One of my favourite magazines is Anthology (and it’s ending soon! Boo!) and I like to see what they suggest as well (either in my complete-but-for-one set of back issues or on their blog). I hit almost all the points on a California road trip piece they did and it was amazing (this trailer park being a serious highlight)! Local Wanderer also looks good, however, I haven’t yet a chance to visit any of their recommendations – but their Instagram makes me want to!

3. Make Some Lists

Full disclosure: I love lists. I love writing lists, reading lists, finding old lists. If you can’t relate, well, you’re probably in the majority. Anyway, grab a pen and paper (so much more satisfying than on your phone!) and make a list of ‘really want to see/do/eat’ and ‘would be nice to see/do/eat.’ This helps prioritize your time and, if you’re traveling with another person/people, you can see if your wish lists overlap or not. Be as general or specific as you like, ie. I want to explore the downtown or I want to explore this neighbourhood by bike.

For Havana, I’m still poking around the Lonely Planet, but so far I’d like to walk around the city a lot, maybe do a bike tour (or just rent bikes), people watch, eat guava, and visit Hotel Ambos Mundos (a Hemingway hangout). We leave in two weeks and booked it less time ago than that. When I flipped my desk calendar to May and saw Havana was the picture I took it as a good sign.

Do you plan for trips or play it by ear? Have you been to Cuba? I’d love to hear your suggestions and advice!

You Might Also Like


  • Reply Marty July 10, 2015 at 12:01 am

    So…I hope you’re gonna write about your trip when you get back!
    Was Lonely Planet accurate…??
    How timely was the info…Cuba is a hard place to visit if you’re an American.

    • Reply eileen July 13, 2015 at 5:24 pm

      Hello! Yes, I will definitely be writing a follow up post about my Cuba trip and will keep your questions in mind to answer! Look for it soon with lots and lots of photos 🙂

  • Reply Cari July 26, 2015 at 10:46 am

    Love the new website Eileen!!

    • Reply eileen July 28, 2015 at 6:43 pm

      Thank you so much, Cari!! 🙂 xx

  • Reply Laura July 29, 2015 at 4:24 pm

    Our favourite is obviously food/restaurant planning and I can highly recommend watching Anthony Bourdain’s city-specific shows to get THE BEST ideas. YUMMY!

    • Reply eileen August 18, 2015 at 12:49 pm

      Awesome idea! I love his shows! I went to one of his recommendations in Lisbon and most definitely ate lobster poo kind of (???) by accident.

  • Reply Davin March 15, 2016 at 4:06 pm

    this was zero help on actually planning a trip to Cuba

    • Reply eileen March 15, 2016 at 4:58 pm

      Hi Davin! Thanks for your comment. This post was meant to be about trip planning in general and what I personally do before visiting a place. I can see how the title could be a bit misleading. At the time of writing I was planning a trip to Havana so that’s what I had in mind (and why the photos reflect that too). I did another blog post since returning from Cuba where I get more specific about my favourite experiences and what I’d recommend for a trip to Havana (that blog post is here, if you’re interested:

    Leave a Reply