How to Plan the Perfect Trip to Cuba in 2024: A Step-by-Step Guide

Want to plan the perfect trip to Cuba in 2024 but don’t know where to start?

A trip to Cuba can be a dream come true – BUT it’s complicated!

With its beautiful beaches, vibrant cities, rich cultural heritage, and friendly locals, Cuba offers an unforgettable experience. But you really need to know what you’re doing.

This step-by-step guide will help first-time visitors plan the perfect Cuban getaway for 2024, from visas and flights to packing and choosing activities.

P.S. Step 6 and 10 are my two most important steps. Thank me later.

Step 1: Choose the Best Time to Visit Cuba

When planning your trip to Cuba, timing can make a huge difference.

High Season (December to March): Ideal weather for beach days, sightseeing, and festivals like the Havana Jazz Festival. This season offers the most lively atmosphere.
Low Season (May to October): Expect fewer tourists, lower prices, and a warmer climate. This is also hurricane season (July–November), so keep that in mind when booking.
Shoulder Seasons (April and November): A great balance between pleasant weather and moderate crowds, perfect for travelers seeking good deals and fewer tourists.

Tip: While hurricane season doesn’t guarantee a storm, it’s still something to consider when booking your trip to Cuba.

Step 2: Get Your Cuba Tourist Visa and Travel Documents

An imperative part when starting to plan your perfect trip to Cuba in 2024 is the visa – and the process has been updated!

All foreign visitors need a Cuban tourist visa (or “tourist card”). Up until now (Oct 2024) this has always been a physical paper visa. Whilst these are still valid until June 2025, you can now get an online-visa.

The process is straightforward and depends on your nationality. If you are in the US, you can get the e-visa in the US via your airline.

You can still get a paper visa through:

Cuban Consulates or Embassies
Your airline or travel agency
An online visa service

Tip: U.S. travelers should check current regulations, as authorized travel to Cuba requires meeting specific criteria.

Step 3: Book Flights to Cuba

Direct flights to Cuba are available from major cities like Mexico City, Miami, Toronto, and Madrid. Book flights well in advance, especially for high-demand periods like Christmas and New Year, to get the best prices.

Tip: Arrive early at Cuban airports for your return flight, as long lines and delays are common. Take USD in small denominations – you’ll get CUP back as change which will be worthless to you.

Step 4: Plan Your Cuban Itinerary

Cuba is full of incredible destinations but logistics aren’t straightforward.

You need to consider travel time between cities, modes of (reliable) transport, how much time you’ll be spending on the road versus in the location, cost, etc. All of these factors are the difference between a great Cuba trip and a disaster one.

Here are the main destinations with reliable (ish) tourism infrastructure:

Havana: The heart of Cuba, known for its colorful streets, classic cars, and historical sites like Old Havana (a UNESCO World Heritage Site) and the Malecón. There are many amazing restaurants, museums and independent shops and galleries to explore.
Viñales: A lush valley with tobacco farms, scenic hiking trails, and iconic limestone mogotes—a great destination for nature lovers (and cigar lovers!)
Trinidad: A beautifully preserved colonial town with cobblestone streets, pastel-colored buildings, and nearby beaches. A triple threat, with city + nature + beach.
Las Terrazas & Soroa: often overlooked but two of my favourite places. Less tourists, beautiful countryside, rivers to swim in, waterfalls to bathe under, wonderful local hosts. A perfect time to switch off in the mountains.

Tip: To travel between cities, hire a classic car with a driver for comfort and flexibility. Trust me when I say your driver in Cuba can make ALL the difference to your trip!

Step 5: Book Accommodation in Cuba

If you want a truly authentic and high quality stay in Cuba, choose ‘casa particulares’ or boutique hotels over resorts or chain hotels.

Staying with the locals is far superior to staying in a faceless hotel. Don’t be fooled by an ‘Iberostar’ and think it’s good – it won’t be. You’re in Cuba.

In the casa particulars, the quality is better, you’re supporting the local economy, attention to detail is better, and you’ll receive a much more authentic experience.

There are some wonderful, high quality ‘casa particulares’ which actually feel more like boutique small hotels. In Viñales you’ll have more of an ‘authentic’ experience, staying in small ‘casas’ where the family usually live too, but you’ll almost always have your own independent quarters so won’t feel like you’re in someone else’s house.

Tip: Book early during peak season, especially through platforms like Airbnb or Cuban-specific booking sites to secure your spot. Watch out for scams – they’re common.

Step 6: Currency and Budgeting for Your Trip to Cuba

Cuba uses the CUP (Cuban Peso), USD and Euro. It can be complicated knowing when to use which currency, and you need to ensure you’re exchanging your money with reputable sources. Click here for more help with this to make sure you don’t lose all your money!

Here are some essential budgeting tips:

Bring Cash: ATMs can be unreliable, and U.S. bank cards don’t work due to embargoes.
Exchange locally: Exchange on the informal market with trusted locals – NOT at the CADECAS or government run establishments like hotels, airports or banks.
Budget for Casas Particulares and Meals: Casas cost around $20–$100 per night depending on location and quality; meals from $10–$50, and activities can vary widely.
Be really careful of scams: once you are scammed out of your money, it’s incredibly difficult to get your hands on more cash. I see SO MANY horror stories, even from seasoned travellers, who lose all their money to a silly scam on the first day, and they’re screwed for the rest of their trip. Don’t let that be you.

Step 7: Pack Smart for Your Cuban Adventure

To plan your perfect trip to Cuba in 2024 is to plan your perfect suitcase.

Due to embargoes and intense political reasons, most of your usual items are hard to find in Cuba, so you need to pack everything you need.

Toiletries and Medications: Bring all personal care items and medications, as they can be incredibly difficult to find locally.
Reusable Water Bottle: Tap water isn’t drinkable; bring a filtered bottle or buy bottled water.
Power bank: power cuts are common so bring a couple of these & donate them to a local who *genuinely* needs it when you leave.

Step 8: Learn Basic Spanish Phrases

While English is spoken in tourist areas, knowing a few Spanish phrases can help you connect with locals. Use language apps like Duolingo or a simple phrasebook. Don’t rely on the locals to always speak English – remember, you’re in THEIR country!

Tip: Get a local Cuban SIM card to have access to internet when you’re out & about, and then you can rely on Google Translate!

Step 9: Plan for Limited Internet Access

Wi-Fi is available mainly in public parks and hotels, but you’ll need to buy ETECSA Wi-Fi cards.

You can now buy a local physical SIM card. Make sure your phone is unlocked, and that you purchase the SIM card in advance of your trip.

Step 10: Plan Your Tours and Activities in Cuba

If you really want to plan your perfect trip to Cuba in 2024, you need to plan your tours & activities in advance. This is how you guarantee an amazing time, and also save bringing a whole ton of cash with you because you can often pay online in advance.

This is the exciting bit when you see all your dreams and bucket-list ideas come to life!

Booking tours in advance is the best way to experience authentic Cuban culture. Connect with locals, enjoy one-of-a-kind experiences, and explore hidden spots that showcase the real Cuba. Make the most of your time on the island with personalised tours that offer a unique, immersive adventure.

My personal favourite is my Cuban family’s AirBnB Experience – visit their tobacco farm in Viñales! It’s a once-in-a-lifetime experience that you won’t regret, trust me.

•Hire local guides: Supporting local guides gives you a unique perspective on Cuban culture, history, and daily life. Even if you’re not usually a ‘guide’ person (like me!), I highly recommend branching out in Cuba and hiring a local – thank me later.

NEED MORE HELP?

Planning a trip to Cuba is overwhelming, there’s no doubt about that. But don’t fret – that’s why I’m here!

I am an epic trip planner, there’s no doubt about it and I will toot my own horn. I bring you authentic, unforgettable experiences that you can only get if you know someone on the inside – hello it’s me! From personalised itineraries to all my local connections (friends & family!) and hidden gems, I’ll make sure your journey is seamless and rich with Cuban culture.

When you choose me to help you plan your Cuba trip, you’ll not only have fun, but also immerse yourself in the local culture. You’ll experience the real Cuba through authentic interactions with locals, gain insights from their stories, and navigate your visa requirements with ease.

Let’s turn your travel vision into reality—reach out and let’s start planning your perfect Cuban adventure!

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