This is part 2 of my annual trip series. After a successful first year of traveling in the Pacific Northwest, my brother and I decided that we'd plan a trip together once a year. The two requirements were that we had to use our passports and visit a country neither of us had been to previously. Jake decided to really up the stakes for our Year 2 trip and suggested Cuba. Here's a recap of the five trips we’ve done to this point and the sixth upcoming trip we have scheduled for December 2021 (Year 6). Year 1 (2016): The Pacific Northwest (Portland, Seattle, Vancouver) Year 2 (2017): Cuba Year 3 (2018): The Balkans — Croatia, Bosnia and Herzegovina, Montenegro (and London!) Year 4 (2019): Luxembourg (and Paris!) Year 5 (2020): Africa (South Africa, Lesotho, Zimbabwe, Zambia, Tanzania) Year 6 (2021): Belize Let's get started! Year 2 Background Following the success of Year 1, we knew that we wanted to make our trips an annual event. When summer 2017 rolled around, it made the most sense to do the trip then. This was when I had a break between my sophomore and junior years at Georgetown and only had a summer job to navigate when it came to taking vacation time. Jake was also able to take paid time off from his job to make it work. I had decided (and Jake agreed) that it would be fun to continue to use our passports during our annual trips. At that point, I hadn’t done a lot of international travel compared to him. He had an entire semester of study abroad travel and a summer of TAing in London under his belt. Needless to say, I was itching to explore beyond U.S. borders, and I wanted to use our annual trips as an opportunity to do so. During our discussions of where to go, Jake said, “Well, you know we could really amp it up and go to Cuba.” I had never once considered Cuba as a destination I would ever go to. However, flights from Florida make it a fairly accessible destination. So, after doing some additional research online and talking to a Georgetown friend who had been in the past couple of months, we decided to move ahead with plans to go from July 5 through July 9. Our Itinerary Due to the nature of how customs and immigration handle individuals traveling to Cuba, we kept detailed notes of our trip (where we went and what we did). While neither of us ended up needing to use these notes when we went through U.S. immigration, it’s neat to look back on this and see what we did each hour we were in Cuba. July 5 12:30-1:30 PM: Arrived in Havana, exited the plane, and continued through customs 1:30-2:00 PM: Currency exchange at the airport 2:00-2:30 PM: Taxi to Viazul bus station to purchase tickets to Trinidad 2:30-2:45 PM: Taxi to old Havana Airbnb location 2:45-4:00 PM: Lunch at a cafe on Malecon near Airbnb location while waiting for a response from our host; asked locals if they knew Maykel and discussed that we were from the United States 4:00-5:30 PM: Travel to the major hotel (Iberostar Parque Central) and organized a group taxi to Trinidad (discussion showed that there were no other buses to Trinidad) 5:30-7:00 PM: Walked through the park, talked with locals, and got water/fruit juice from a local coffee shop 7:00-9:30 PM: Located restaurant in Old Havana and ate dinner; discussed whether ice cream with custard may be a strong Cuban dessert (it is not) 9:30-10:00 PM: Travel to Airbnb after host response once they got back on Wi-Fi and provided the address 10:00-10:30 PM: Prepared for the trip to Trinidad the following day 10:30 PM: Sleep July 6 7:00-7:30 AM: Wake up and get ready 7:30-8:30 AM: Travel to shared taxi location and wait for pick-up 8:30 AM-1:00 PM: Shared taxi ride to Trinidad 1:00-1:30 PM: Reserved spot on Viazul bus from Trinidad to Havana on Friday afternoon 1:30-2:00: Walked through Trinidad to locate Airbnb 2:00-2:30 PM: Met/socialized with Lleana, our Airbnb host, over welcome drinks, settled, and prepared to exit 2:30-2:45 PM: Located lunch recommendation from Lleana 2:45-3:30 PM: Lunch 3:30-5:00 PM: Museo Nacional de Lucha contra Banditos 5:00-6:30 PM: Travel to touch the Caribbean Sea, similar waters to the Bay of Pigs invasion 6:30-7:30 PM: Shower and refresh at La Casa 7:30-9:30 PM: Dinner at restaurants recommended by Cubans we met in the street 9:30-11:00 PM: Casa de la Musica 11:00-11:15 PM: Walk back to Casa 11:15 PM: Sleep July 7 7:00-8:00 AM: Wake up, eat breakfast, and get ready 8:00-12:15 PM: Horseback riding through Old Town Trinidad and into the country to see how sugar cane, coffee, pork, and tobacco are used by the locals with our Cuban guide Julien whom Ileana connected us with 12:15-12:45 PM: Converse with Ileana, freshen up for the bus to Havana 12:15-12:45 PM: Exchange USD for additional CUC at the bank 12:45-1:15 PM: Travel to the bus station, stopping to buy water 1:15-2:30 PM: Secure bus tickets and board the bus 2:30-9:00 PM: Bus from Trinidad to Havana 9:00-9:15 PM: Taxi to next Airbnb 9:15-10:00 PM: Change clothes and get ready to leave 10:00-10:30 PM: La F