Iconic Attractions in Cuba
CubaThese attractions are cornerstones of the Cuban experience. See an impressive memorial to Che Guevara in Santa Clara, steps from his mausoleum and a museum dedicated to his life. Cuba’s landscape and culture inspired Ernest Hemingway so much that he lived here for over 30 years. You can visit his Havana home-turned-museum and admire his collections of books and hunting trophies. To see the past and present of Cuban culture blended together, visit the neighborhood of Old Havana, where Caribbean music spills into streets lined with grand structures left behind by the Spanish.
Cuba Highlights
A curated look at the best Cuba has to offer. These are the destinations that consistently stand out — places with real character, great experiences, and something worth going out of your way for.
Old Havana
Havana Vieja is a fascinating neighborhood where Cuba’s people, culture, and history all intersect—it’s where you’ll want to spend most of your time in Havana. With its cafés, live music, historical sites, and colorful streets, it’s easy to spend several days wandering through this enchanting area.
Explore DestinationEl Pinar Robaina Tobacco Farm
The El Pinar Robaina Tobacco Farm is Cuba’s most famous tobacco farm. The farm, or finca, has been in continuous operation since 1845, and is a fabulous place to learn about tobacco and Cuban cigars.
Explore DestinationErnest Hemingway Museum
The cult of Hemingway is strong in Cuba—his books are some of the few works of fiction sold here, and there are bars devoted solely to his once-regular patronage. Set in his home of 20 years, the Ernest Hemingway Museum offers travelers a wonderful opportunity to learn about the famous author and his relationship with Cuba.
Explore DestinationLa Comandancia de la Plata
Fidel’s rebel hideout in the Sierra Maestra offers travelers an interesting look into the Revolutionary effort in Cuba. La Comandancia de la Plata is set in eastern Cuba near the small community of Santo Domingo.
Explore DestinationFeatured Cuba Trips
Browse our handpicked selection of Cuba itineraries, each crafted by local experts who know the country inside out. Whether you're after adventure, relaxation, or cultural immersion, we have a trip tailored for you.
Cuba's Culture, Charm, and...Rum
Your guidance, personal touches and attention to detail make these trips to Cuba an experience we will continue to do with Anywhere.com. Thanks for a great experience that has gotten better with each trip to Cuba we have done through you!!!!!
History, Culture, and Exploring Nature
Having Anywhere coordinate our trip to Cuba was amazing! We didn't have to worry about anything and always felt very safe and educated!
Tailored to Our Family
Our family was looking for a balance of beach fun, exotic nature, and experiencing the classical culture of Cuba for our two young adults. Anywhere delivered a tailor-made experience on this trip.
Pure Cuba: An Island Nation Essence
What if you could only visit Cuba for a limited time. What must you do? Why, explore Havana and Varadero Beach, of course. If you can distill an experience, this is it.
Our Cuban Getaway
I like the balance between learning from guides and having free time to explore. Daniel meeting us upon our arrival at Casa Prado Colonial was helpful. Giving us a . phone was a nice touch and made us feel cared for by Anywhere. We didn't feel completely on our won.
Our Journey from Havana to Trinidad
Our hosts in Cuba went out of their way to make us feel welcome, as if we were staying in our own home.
Discovering Cuba Together
It’s time to enjoy some quality time as a family. This vacation, unplug in Cuba — a colorful nation with a history still being written, and where time stood still.
Charming Cuba—History and Nature
The people that hosted us and the transportation was great — always on time. Appreciated the Viñales experience and learning not only about agriculture, but also tobacco and meeting locals along the route.
A Quick Havana Getaway
Havana was wonderful. Our 5-day quick getaway includes a thorough introduction to Cuba’s architecture and culture. We also loved the trip to Varadero to experience the beautiful coastline!
Romance 101: Essentials of Cuba
Need a romantic overview of Cuba? Then this Signature Trip is for you. Assembled by Local Experts, this getaway is guaranteed to give you the ideal Cuban experience.
Feeling the Cuban Vibes
Fit a big vacation into a small time frame when you and your best friend get an authentic Cuban experience in 7 days and 6 nights.
A Delicious Cuban Adventure
Prepare for plenty of food, fun, and adventure as you go on a vibrant tour of the island nation of Cuba. Hit the beach and the town, and sample the nation's flavors as you go.
In Search of The Lost Mojitos
Make the most of your vacation — get the sun, fun, and culture you seek on this amazing Cuban adventure through Havana, Varadero, and more.
Rum, Relaxation, and Adventure
This was our 3rd time using Anywhere.com, and as usual, it was almost completely seemless. We felt taken care of, safe and supported. Having a cell phone was a great idea. We used it a few times to communicate with our tour coordinator, which was really helpful.
Alone But Not Lonely: Cuba
See the world economically with this adventure for one on the island nation of Cuba. Your solo voyage lets you explore the beach and the city.
Insider-led Costa Rica Design & Concierge
Your insider team designs the trip around what you care about, then supports you in-country with private logistics, vetted partners, and concierge help when plans change.
Get StartedPrivate drivers; English-speaking available.
Avoid the crowds in private day tours.
Better stays, better pacing, better reservations.
Insider-only experiences and exclusive local partners.
24/7 in-country support by phone, text, and WhatsApp.
Insider-led Costa Rica Design & Concierge
Your insider team designs the trip around what you care about, then supports you in-country with private logistics, vetted partners, and concierge help when plans change.
Real Voices, Real Benefits
We believe travel is more than ticking destinations off a list – it's about discovering new places deeply, feeling connected wherever you go, and knowing you have a trusted team of local experts behind you every step of the way.
