Book the Right Trip to Cuba

Designing stellar trip experiences for travelers since 2007, you can count on us to plan and book the perfect vacation. From arranging travel logistics to finding the right accommodation, you can customize an existing trip or build one from scratch!
Filter and browse trips that match your preference. View Trip to see the day by day itinerary. Favorite entire trips or individual experiences that catch your eye. Plan My Trip is a shortcut to creating your own personalized trip!

Showing 12 results of 21

Cuba's Culture, Charm, and...Rum

Customer Reviewed 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!!!!!


Best
Cave Exploration
City Tour
Guided Tours
Hiking
Museum
Walking
Zip Lines
9 days $$$View Trip
History, Culture, and Exploring Nature

Customer Reviewed Having Anywhere coordinate our trip to Cuba was amazing! We didn't have to worry about anything and always felt very safe and educated!


Architecture
Best
City Tour
Cultural
Guided Tours
Historic
Train
Walking
6 days $$$View Trip
Tailored to Our Family

Customer Reviewed 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.


Architecture
Best
City Tour
Guided Tours
Historic
Museum
Train
Walking
7 days $$$View Trip
Pure Cuba: An Island Nation Essence

Expert Choice 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.


Best
Cave Exploration
City Tour
Cultural
Guided Tours
Historic
Walking
4 days $View Trip
Our Cuban Getaway

Customer Reviewed 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.


Best
Cigar Tour
City Tour
Guided Tours
Historic
Train
Walking
7 days $$$View Trip
Our Journey from Havana to Trinidad

Customer Reviewed Our hosts in Cuba went out of their way to make us feel welcome, as if we were staying in our own home.


Architecture
Best
City Tour
Guided Tours
Historic
Museum
Train
Walking
7 days $$View Trip
Discovering Cuba Together

Expert Choice 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.


Best
Cave Exploration
Cigar Tour
City Tour
Cultural
Guided Tours
Historic
Walking
6 days $$$View Trip
Charming Cuba—History and Nature

Customer Reviewed 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.


Architecture
Beach Trip
Best
City
City Tour
Guided Tours
Historic
Leisure
Museum
Night Tour
Walking
5 days $$View Trip
A Quick Havana Getaway

Customer Reviewed 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!


Architecture
Beach Trip
Best
City Tour
Dance Lessons
Guided Tours
Historic
Leisure
4 days $$View Trip
Romance 101: Essentials of Cuba

Expert Choice 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.


Best
Catamaran Tour
Cigar Tour
City Tour
Guided Tours
Historic
Museum
Snorkeling
Train
Walking
8 days $$$View Trip
Feeling the Cuban Vibes

Expert Choice  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.


Best
Cave Exploration
Cigar Tour
City Tour
Guided Tours
Historic
Museum
Walking
6 days $$$View Trip
A Delicious Cuban Adventure

Expert Choice 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.


Best
Cave Exploration
City Tour
Guided Tours
Historic
Museum
Walking
4 days $$$View Trip

Showing 12 results of 21

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"Booking with Anywhere was the best decision we made. Our trip was absolutely amazing, everything we wanted, plus everything we didn't know we wanted!"

- Stephanie M.

Trustpilot 5-star rated