Cuba has been on our list for a long time, both for its history and mystic as a closed (to us) country.  I’ve heard and read stories about people getting there easily via Canada, Mexico, or the Caribbean but then you’d have to lie on your return immigration forms and it just didn’t feel right.  If you did get to go for charitable reasons, you couldn’t stray far from your mission or spend money freely.  That all changed about a year ago as Obama announced a restoration of diplomatic ties.  You still need an official reason for going but they were expanded and you no longer have to apply with the government for permission to travel — you just have to be prepared to be audited for up to 5 years after your trip.  As soon as this change occurred, we knew we wanted to go asap before the flood of other American tourists or before a new administration had the chance to change the rules of travel.

There were no direct flights from the US when we were searching (there are a few now out of Florida) so we could join a tour group or take a cruise.  The tour groups were all pretty pricey and are difficult with children, so we opted for the cruise.  Most cruise lines didn’t allow small children though, so we really only had one option – Celestyal Cruises, based out of Cyprus.  It was all-inclusive, both drinks and shore excursions!  We could join the boat at Havana or Montego Bay, Jamaica.  The cruise agent said that travel to Havana may be difficult and not guaranteed so she heavily suggested Jamaica, and we decided to play it safe.  We stayed in Montego Bay a day before and a day after the cruise as well.

Jamaica

We stayed at a hotel named El Greco.  It’s located on the ‘high’ road and the popular area, Hip Strip, was on the ‘low’ road.  We didn’t really have an agenda other than strolling Hip Strip.  The hotel provided free tickets to Doctor’s Cave Beach so we checked out towels and took a nearby elevator down to Hip Strip (after some zigzagging and spiral staircases, not easy with a stroller).

I was immediately offered drugs which I politely declined (I didn’t realize the stroller attracted dealers).  We continued down Hip Strip and were disappointed by all of the very pushy salespeople.  Nearly every store had someone outside asking people to come inside or braid your hair.  A few of the hotels along the strip were closed down.  It seems like Montego Bay is past its prime — I’m guessing Ocho Rios is the more popular port these days.  We stopped for dinner at Margaritaville at the end of Hip Strip.  The people there were very nice and the food was delicious.  There’s a multiple story water slide I was tempted to take but ultimately decided against when it started to drizzle.

On the walk back, we stayed on the hotel side of the street and mostly avoided the hawkers.  We arrived at Doctor’s Cave Beach a few minutes after they closed — it was still bright out so it was odd that they didn’t adjust their hours.  We went back to the hotel and swam in their pool, which had a gorgeous water view.  After swimming we enjoyed the sunset on the way back to the room.

The next morning we had breakfast at the hotel, mainly because we didn’t see anything else nearby and weren’t overly excited to revisit Hip Strip.  We checked out towels again and decided to give Doctor’s Cave Beach another try.  We got in and were upsold on an umbrella and chairs.  The beach and swimming was wonderful.  It wasn’t crowded at all.  Someone mentioned later that it’s the 7th best beach in the world (I have not personally confirmed).  The kids had a great time too.  We enjoyed a post-swim drink on the beach before heading back and checking out of the hotel.

We took a taxi down to the cruise port and had an uneventful check-in.  The boat was pretty standard.  It was a bit on the smaller side, indicating it was likely a hand-me-down from the big cruise lines.  It held 1,200 people but only had 400 on board (another 250 or so would board in Havana).  This made it quite nice overall — no major lines, not overly crowded, and we got to see a lot of the same faces at various trivia events we attended.

Santiago de Cuba, Cuba

We were provided tickets to our first tour without selecting one.  It seemed odd but not enough to question it at the time, especially since it was the one we would have picked anyway.  It was a bus tour that hit all of the area highlights.  The city was full of retro looking Soviet-style public art.  Our first big stop was a beautiful castle along the coast, El Morro (official name: Castillo de San Pedro de la Roca).  You can wander anywhere, including the roof with its expansive views of the area, and there were original cannons scattered throughout.

The next stop was a cultural one where we sat and watched locals dance and sing for about 45 minutes.  It was the most heavy-handed ‘cultural’ part of the cruise, which is required to qualify for the ‘people-to-people’ reason for travel to Cuba.  We then went to an older park with some Soviet-looking structures throughout and some statues of local heroes.  Nearby was an aging amusement park that had a great retro Ferris wheel (though not one that I’d personally ride).  Our last attraction of the tour was a massive statue surrounded by large spiked machetes in Antonio Maceo Revolution Square.

Next, we had a day at sea.  Upon inquiring about our options in Havana, we were told that Americans didn’t get to choose their excursions and that they were different than any of the ones listed.  That explains the lack of choice the day before!  It didn’t end up being a problem at all, but it was interesting that they were all designed so you didn’t have to spend a dime in Cuba if you didn’t want to.  The first trip went a bit long without any food options and it all made sense now.  This day at sea was also Christmas!  We had stockings for the kids with small presents to open in the morning and Santa was on the boat throughout the day.  The kids wrote letters to him and he gave all the kids on the boat (about a dozen) gifts.

Havana

Our first impression of Havana was a ruined pier next to the boat.  You can catch small glimpses of rooftops and spires further inland.  The pier is in an amazing location — you exit right into a great plaza surrounded by old buildings and popular restaurants.  We had two full days in Havana, including an overnight, and the excursions were scheduled as two the first day and one on the second morning.

The morning tour was a walking tour throughout the north end of Old Havana.  Havana is made for strolling around — so much amazing architecture from several different centuries and the old classic 50s cars driving everywhere (there are about 150,000 left and a vast majority seemed to be taxis now).  The two biggest stops were Plaza de la Catedral and Plaza de Armas.  In the later one, there is a unique book market and we split up to tackle different areas.  When I ran into Jaime and Edie, Jaime pointed out that a man was following Lydia and I around and appeared to be drawing us.  I was completely oblivious to it!  He showed us the picture and asked if we’d pay for it.  I gave him $2 and he went on to the next group of tourists.  Jaime and I liked it so much, I hunted him down and commissioned him to draw Jaime and Edie for $10.  We later saw many other artists drawing other tourists, so it wasn’t a completely unique experience but I do think we had the best artist.  We swung by a Ernest Hemingway haunt, and creator of the mojito, Le Bodeguita Del Medio.  It was too crowded to get inside.  On the walk back to the boat, we ran into a parade of performers on stilts.  They were surrounded by people collecting tips for them as they performed tricks and dances.  It was more surreal than it sounds in writing.

After lunch on the boat, we took a bus tour in the afternoon.  We stopped by the Capital, which was under construction, and took some great pictures of old cars driving by a row of very colorfully painted houses.  We then stopped at Plaza de la Revolucion, which is essentially a very large empty parking lot with large murals on area buildings and a memorial tower.  There is also a parking strip of old cars and the drivers are all very friendly — you can take whatever pictures you want, including getting in the cars or asking to see the engine!  The tour ended up a market which we wandered for a while, and bought a cigar box, before skipping the bus and walking back to the port.

For the evening, we spent more time walking around.  The streets were filled with others doing the same, but it was not overly crowded.  The city is beautiful at night.  All the plazas and streets were lit up.  We stopped at a chocolate museum for some hot chocolate and toast before going to dinner at a place I found called La Vitrola.  There were quite a few people waiting in front of us.  The nice host said he would get us in earlier because of the kids.  I think we ended up only getting in one table earlier, and that group was not happy about it.  The host took it all in stride though.  The food was good and there was live entertainment throughout dinner.  We ordered a fried cheese curd appetizer and it came with a little American flag.  A nice little reminder of home.

The next morning Lydia woke up with an upset stomach.  While Jaime went to grab breakfast, Lydia and I went to the doctor on board to get some medicine.  Jaime stayed behind with Lydia for the morning tour.  The first bus stop was within a neighborhood where a local artist completely redid his house with spires, twists, and turns with colorful tiles.  He also added similar art throughout the entire neighborhood.  Edie passed out just before arriving so we just enjoyed it from the outside.  Our next stop was the Revolution Museum which is located in the former president’s palace.  It was full of history of the communist revolution and the only anti-US propaganda we saw.  The palace still has bullet holes all over the place from when it was stormed by Fidel’s people.  In the back, there are many vehicles used during the takeover.

We then returned to the boat and switched kids.  Jaime and Edie went out wandering around while I stayed behind with a groggy Lydia.  Jaime and I had plans to meet in the main plaza by the port at a certain time if Lydia was up for it.  She slept most of the day.  Once she got up though, she felt completely better.  We met at the rendezvous point and took two old 50s cars on a tour around the city.  It was great fun, and highly recommended.

The following day was at sea and this time Edie got the upset stomach.  Since Lydia was able to sleep it off, we just let Edie relax and sleep all day and she was fine by the next morning too.

Cienfuegos

Our last stop in Cuba was in Cienfuegos.  We took a bus tour around the city.  The first stop was at an art gallery that featured maybe 8-10 artists and they each had a room or a wall with their work.  One wall in particular blew us away.  We ended up buying a painting from the artist himself (Mario Alexander Cruz Moscoso) and are kicking ourselves that we didn’t get two.  The next stop was a full city block of ornately painted houses, music, and various performance artists.  The street and concepts were founded by a locally famous artist, but no idea if he was there or is still active in the day-to-day.  Lydia had a flower painted on her cheek by a random person walking around.

We then made a quick stop at an old palace and hotel along the coast.  Most rich areas were taken over by the government but it’s not clear what they own or not.  We were told several times that there are no rich people in Cuba anymore but then we’d see very nice large houses scattered around.  There were definitely affluent neighborhoods which were converted into public housing or government offices.  Not sure if that was actively still occurring or if it was mostly just after the revolution.  The tour ended walking down a long pedestrian boulevard lined with shops and ended in a massive plaza surrounded by more shops and museums.  We visited one of the museums and discussed local history before heading back to the boat.

Overall, we thoroughly enjoyed Cuba.  It’s extra special because how different and close it is.  We highly recommend anyone visit before American companies start investing heavily, though it’s not clear how much the Cuban government will let them build (as they are known for nationalizing prolific businesses).  One thing we never fully figured out was how communism works.  It seems to boil down to a minimum amount of food (mainly rice and produce) and maximum amount of salary.  The locals have a separate currency provided by the government to use for those basic goods.  The tourist currency, called cucs, is pinned to the Euro, and it seems like most locals work in service jobs or markets to earn cucs for non-essential items or additional food when the basic items run out (which we heard often happens three weeks into the month).

Montego Bay

Back in Jamaica, we spent another night in Montego Bay, this time at Toby Resort.  Our cab driver from the cruise port offered to give us a tour on the way to the hotel and since Jaime’s parents and sister had to catch a plane in a few hours, we decided to take him up on it.  He drove us through the downtown area, talked about local heroes, then drove us into the mountains to drive by a local witch’s old mansion and stop at a nice hotel with an amazing view of the city and coastline.

After the tour, we parted ways with Jaime’s family at the airport and went back to the hotel.  We had lunch at the hotel and then went for a swim.  They had a couple different pools on site.  We intended to go to the closer one but there was a strange woman they kept staring at us so we walked a bit farther and had the less convenient pool all to ourselves.  Not seeing any nearby restaurants online and not wanting to face the gauntlet of shopkeepers, we ordered Domino’s pizza.

The next morning we decided to go to Doctor’s Cave Beach again.  This hotel was at the end of Hip Strip and it was about a 10 minute walk to the beach.  We spent a few relaxing hours there before heading back to shower, checkout, and head to the airport.  Believe it or not, there’s a premium departure lounge at the airport and it’s the #1 attraction in Montego Bay.  It’s a little expensive but cheaper for departures than arrivals so we decided to give it a shot.  You get fast-tracked through security and then after walking to the lounge itself, you get directed to one of three large rooms.  There you get a free wifi, open bar, and a buffet of good finger foods.  After chugging a few beers and filling up on food, we headed to our gate for the flight home.

Next trip is to Denmark, all three Baltic states, and Poland in a couple weeks!

Categories: Travel