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A sprawling island, Cuba is a destination with the best of all experiences: cities, beaches, and the countryside. The wide range of destinations throughout Cuba made for a different packing style than most trips taken this year. The heat was also a big factor in deciding what to pack.



I traveled in a carry-on in order to keep things as easy as possible and to avoid having to worry about any lost luggage on the way there. I took my favorite hard-case from Away as it has a locking mechanism, doubling as a place to stash valuables while out during the day. I was able to fit enough clothes for the trip, with some outfits being worn a few times.

Here’s what I recommend packing for a trip to Cuba:


1. Bottoms

I’d recommend one good pair of denim shorts, 1 pair of loose linen shorts, 1 skirt, and 1 pair of loose traveling pants.

2. Tops

Because of the heat, I went through tops faster than I expected and had to do laundry halfway through. I’d recommend at least 3-4 tank tops, 2 t-shirts, and one loose long-sleeve blouse to protect from the sun.

3. Dresses

During the trip, I lived in dresses. I brought 1 maxi, 2 shorter dresses like this and this, and 1 tank dress. If you go out dancing at night, a dress like this is perfect.

4. Shoes

I wore a pair of sneakers on the plane to save space and used them frequently on the trip. I brought 1 pair of rubber flip flops for beach/showers, two sandals for walking (this slide and this red one), and a pair of my favorite espadrilles.

5. Accessories

I packed a light water-proof jacket, though I never wore it. I bought a hat like this once I got to Cuba, and carried it back home with me. I brought two pairs of sunglasses (this and this), as the sun is intense. For out and about, I traveled with my easy to pack Longchamp backpack that is perfect for a camera and essentials. I also brought one swimsuit for the day at the beach.

6. The Essentials

With limited stores, it was crucial to bring things that I wouldn’t find once in Cuba. Here’s what I brought in addition to my normal beauty products:

7. Tech

I left my computer at home and only traveled with my camera and 35 mm lens on this trip. It was great to be off the computer. I’d recommend bringing a Kindle for the long hours on the road, an extra SD card, a camera cleaning kit (<$10) as it can be dusty, an extra battery pack for your phone, and extra batteries for your camera.

8. Travel Insurance

Required by Cuba’s laws, you must have comprehensive insurance to enter Cuba. I advise having two printed copies for your trip.


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These are the sites I use most to book my own trips. Using the links below is a great way to support Bon Traveler’s travel journalism at no extra cost to you. If you need help organizing your itinerary, get my free travel itinerary template here.

1. Book Your Flights

Use Skyscanner to find the best flights. It searches 100s of airlines and websites across the globe to ensure you’re not missing out on any route options or deals.

2. Book Your Accommodations

Use Booking.com for hotels and guest houses. They have the biggest inventory and consistently offer the best rates.

3. Book Your Tours & Experiences

Use Viator or Get Your Guide to find the best tours and experiences. They are my favorite tour search engines. I always check both as their inventory varies depending on the destination.

4. Book Your Car

Use Discover Cars or Rentalcars.com to find the best car rental deals. I recommend comparing rental agency reviews on Google to ensure you are booking with the best company in that destination, as the reviews are often more accurate than the car rental search engines.

5. Don’t Forget Airport Lounge Access

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I never leave the country without travel insurance. It provides comprehensive protection in case anything goes wrong (ie. illness, injury, theft, and cancelations, etc.). I use it frequently for my travels to stay protected.

My favorite companies that offer the best coverage and rates are:


Xx,
Jessica

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