I’ve been getting lots of requests lately for information about individual travel in Cuba. As I have pointed out in previous articles, Cuba is an exceptionally good country to travel around on your own. It is one of the safest countries for visitors, and just about anyplace you end up should be interesting, entertaining, and fun. If it is your first visit, however, I suggest you should initially go with a group, then return later on your own (or with a good friend). Another option is to visit with a group for 7-10 days, then stay over on your own. With a General License, you can legally stay up to 30 days total. Many travelers on my past expeditions have done that, and they told me they appreciated learning about Cuba and making local contacts before venturing out on their own.

The reason I am saying this is that there is just too much to see and do. You could spend several weeks just in Havana and not see everything worthwhile. I have talked with Americans in Cuba who traveled there on their own. Typically, they’ve told me about being there for a week or so, yet they weren’t sure what were the “best things to see.” Many were just “winging it”–trying to figure out what to do after they got there. A few told me they “just wanted to say they had been to Cuba,” and wandered around Havana, hoping to stumble upon interesting things to see.

When you go with an experienced group, you should gain the benefits of a well-planned itinerary, so you can spend your time wisely and efficiently. Even regarding your free time, you will be able to ask your guides for recommendations of restaurants and sights to see. You can ride your bus or mini-bus to different local areas, much cheaper than taking a taxi. Your cost for a hotel room per day will be much less than if you just walk into a hotel and pay for a room on the spot.

So in general, if you are visiting Cuba for the first time, I encourage you to go with a group. If you are used to traveling on your own around Latin America, and if you spend some time researching your trip ahead of time, you could make it work.

If you decided to see all the sights and events that travelers on my expedition see, but travel on your own, I believe you would spend more money. You wouldn’t benefit from having your own guide, you wouldn’t have an experienced American guide along, and you wouldn’t be aware of when certain exhibits are open, closed, crowded, or sold-out (seasonally or temporarily).

In summary–I think most first-timers would benefit by traveling with a group. In my opinion, the ideal size is 10-15 travelers—big enough and small enough. After a week or so with your guide and group, you will learn how the country works, and you will discover many different geographical and cultural areas to further explore. Cuba—and its unique situation—will contribute to making your visit a one-of-a-kind and rewarding experience.