Cuba trip

Question

So we took the trip thru Our Key West to Cuba last week, and as there isn't much written thought I'd give an overview for others. You leave thru the Private Charters part of the airport (same as Dry Tortugas) and depart at 8, pilot and 8 passengers. Plane not new but in good shape, advanced electronics but there isn't much room to move. Go right thru private customs in Havana (50 minute flight) and met immediately by a guide who loads you on to a large, comfortable bus to take you to Hemingway's house. Spend a hour or so there seeing the house and gardens; our guide was very informative and spoke freely and honestly about Cuba and Hemingway. You then take a bus to downtown Havana and see many squares, a market, have a drink at both the Floridita and La Bodeguita Del Medio as well as lunch at a rooftop bar on a square before being spirited back to the airport. We had time to find a cigar store and smoke a cigar as well as have some shots of rum.

Now the things you don't really know... first, as you have heard, no tobacco, coffee or alcohol can be brought back. Beggars asking for a dollar are all over and aggressive; if someone asks if you want a photo taken, be prepared to tip them a dollar or worry you won't get your phone back. Bring toilet paper or tissues; you won't find them in bathrooms. Bring lots of small bills as you can't get change and trust me, you will need lots of small bills to tip, the smaller the better. Sometimes you are giving someone a dollar to just go away. If you give a dollar to someone expect others to immediately descend on you to ask for one too, tugging on your arm. Both on the way and after going to Hemingway's be prepared to think you are in a third world country; the poverty is all around you. In Havana, although the hotels and squares are beautiful, there are areas where it is almost post apocalyptical with buildings in disrepair falling down. Our guide was very frank about the hopelessness most residents feel with no future for themselves and that vibe is present with most you see.

I'm glad I did it and always felt safe but I probably wouldn't go back.

Answer

Thanks for sharing your detailed experience of the Key West to Cuba trip. Your account gives a realistic overview of what travelers can expect, especially first-timers.

Here’s a summary and additional points for others considering this type of day trip:

Departure: You leave from the Private Charters area at Key West International Airport, which is the same area used for trips to Dry Tortugas. The flight is small, with a pilot and 8 passengers. While the plane isn’t new, it’s in good working order with modern electronics, but space is tight.
Arrival in Havana: You go through private customs at Havana airport. A guide meets you immediately, providing transportation to major attractions like Hemingway’s house. The guide was informative and candid about Cuban culture, history, and current conditions.
Highlights: The trip includes Hemingway’s house and gardens, downtown Havana, city squares, a market, and famous bars like Floridita and La Bodeguita Del Medio. Lunch is typically at a rooftop bar, and there is time for cigar shopping and rum tasting.

Practical considerations and realities of visiting Havana:

No tobacco, coffee, or alcohol can be brought back to the U.S.
Beggars can be aggressive and persistent. Be prepared with small bills for tipping or to politely disengage.
Bathrooms often lack toilet paper or tissues, so carry your own.
Bring plenty of small bills for tipping. Even giving a single dollar can attract attention from others around you.
Expect to see stark contrasts in Havana: well-preserved hotels and squares alongside areas of severe poverty and dilapidated buildings. The social and economic hardships of local residents are highly visible.
Overall safety: You felt safe during the trip, but the environment can feel challenging and may be emotionally intense due to the visible poverty.

Overall impression:

The trip offers a unique and eye-opening experience, combining cultural immersion, historical sites, and Cuban cuisine and drinks.
While it was worthwhile for a once-in-a-lifetime experience, the realities of Havana’s conditions may not make it a place you’d want to visit frequently.
Preparation is key: small bills, toilet paper, and awareness of local customs and tipping practices can make the experience smoother.

Your account is especially helpful for first-time travelers who want to balance the highlights with the practical and social realities of visiting Cuba on a day trip from Key West.

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