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Travel to Cuba with Dave!

(See photos at bottom of page)


If you choose to travel with me, you WILL experience the widest variety and range of natural, historical, cultural, architectural and urban locations that Cuba has to offer, and you WILL get to know real Cubans, and many who are my friends.  If this all sounds good to you ... read on! 

- Dave Anderson


Our trips can vary according to what you want to see and where you want to go, but here are some of the highlights of my upcoming 5-10 day trips:


  • Overview: 

       Dates for 2024 will be determined soon!

  • Cuba was awarded the Excellence Prize as the safest country in the world for tourism, at the 38th annual International Tourism Trade Fair, in Madrid, Spain.

  • All of my trips visit the lively city of Havana and then travel on to the gorgeous Viñales Valley. The New York Times named the Viñales Valley as one of the “52 Best Places to Go” in the world, and for good reason.  It’s the most rural, and most picturesque area in all of Cuba.  (Usually 6 days/5 nights.) 

  • On the way to Viñales we'll also stop by the eco-village of Las Terrazas where you'll have the opportunity to swim in a crystal clear mountain stream, and eat at a locally-sourced organic restaurant.

  • If you have a couple of extra days, we can also go to the southern coast to the "best preserved Colonial city in the Caribbean", Trinidad (and other points along the way). All of these locations have been named as UNESCO World Heritage sites.  (The Havana and Viñales trips are 7 days/6 nights. Add 3 days to make the trip 10 days/9 nights to include Trinidad.)

  • During your entire trip, we’ll stay in bed and breakfasts (casa particulares) with my friends in these locations.  We’ll also eat in private restaurants (paladars). This type of travel is the absolute best way to get to know Cuba, its people, and its culture – plus it keeps us legal (Authorized by the general OFAC license.§ 515.574 Support for the Cuban People.).  Cuba is a very safe country, and Cubans truly are some of the friendliest people you’ll ever meet.  To help satisfy our legal requirements, I'll also ask you to bring a few supplies that our friends in Cuba need (baby supplies, etc.). 

  • Keeping it Legal:

    • In order to travel to Cuba legally, we travel with a general OFAC "Support for the Cuban People" license. [U.S. Code: Title 31 → Subtitle B → Chapter V → Part 515 → Subpart E → §515.574]  If you're interested in traveling with me, I'll tell you more about how we support Cuban families later. 


  • Havana:  

    • Experience the urban life of “la Habana”.

    • A walking tour of the four historic plazas.

    • Eat and drink just like Hemingway did (well, he was a pretty hard drinker, so maybe not that so much!).  Eat at some of the city's best restaurants (yet, all very affordable).

    • Meet local artists who I know and have the chance to buy some of their works (all very affordable!).

    • See many of the colorful characters of Havana and have the opportunity to explore some of the many museums and galleries, both large and small (if you wish to do that). Many venues are free, or are very low cost. 

    • After showing you a few of the highlights of Old Havana, you can either stick with me or I’ll give you an easy to follow map so that you can explore on your own, and meet me afterward at a designated location.

    • Experience the fabulous cabaret show at the world famous Tropicana (extra fee, but well worth it).

  • Viñales and Western Cuba:  

    • After Havana, you'll travel west to the provinces of Artemisa and Pinar del Rio and the lush, rural countryside of western Cuba.  This is my favorite part of the entire island.

    • We'll make a stop at Las Terrazas, an eco-village located in a UNESCO-designated biosphere reserve. Here you will visit with artists, swim in a crystal clear river under the waterfalls, and have lunch in an organic restaurant. 

    • We'll then travel on to Viñales with its unique and spectacular magotes (mountains that rise straight up from the valley floor). You'll love the people of Viñales, as they are some of the friendliest you'll ever meet.

    • Explore Cueva del Indio, a cave in one of the magotes.  you'll walk through part of it, and then ride a boat for the remaining quarter mile.  

    • Take a tour of the small, but very interesting botanical garden.  You'll learn about many of the trees, flowers, and fruits found in Cuba. 

    • Take an exhilarating horseback ride to meet tobacco, coffee, and fruit farmers, and sample some of the products of their work. Of course, you'll get the chance to take some of their unique guava rum, honey, and hand-rolled cigars home with you.

    • Viñales also has several very good paladars (restaurants), and I only take you to ones that have at least a 4 out of 5 rating on TripAdvisor.  

  • Trinidad (south central Cuba):

    • Walk the cobblestone streets while admiring the brightly-colored buildings of this wonderfully preserved Colonial City.

    • Climb to the top of a bell tower to get a spectacular 360 view of the whole city.

    • We'll stay in a renovated Colonial mansion.

    • You can take a walking photo tour of all the highlights in the beautiful afternoon sunlight. 

    • The white sandy beaches of Playa Ancon on the Caribbean are only a 15 minute taxi ride from town.

    • Spend an evening listening and dancing to the music at “La Casa de la Musica” in the heart of town.  

  • Cost: The fees can vary depending on our dates of travel and itinerary, but usually range from $1800 for a 7 day trip, to $2500 for a 10 day trip that includes Trinidad (Cuba).  This fee includes accommodations, partial airfare, breakfasts, ground transportation, most entry fees, and more.  (You'll know the exact cost before committing.) 


    •  Dates for 2024 will be determined soon!


NOTE:  Travel to Cuba is NOT for everyone!  Although you will have clean and comfortable accommodations and a private bath in your room, it won't be the Ritz. If you expect or need that type of luxury, then this venture is not for you.  You also need to be in good enough shape to walk a couple of miles or more each day, traverse some stairs, and make your way across cobblestone streets (in some places).  There's also not a bathroom available on every corner. The weather can be hot and humid most anytime of the year, but is especially humid in the summer months.  (Your room will have AC, though!) Winter months can be very pleasant and may even have slightly chilly evenings.     

The People, Places, and Things of Cuba

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