San Juan, Puerto Rico

Every year I take a trip for my birthday in October. This year I chose Puerto Rico to celebrate turning 33.

Here's my itinerary and some photos to help plan your trip there:

Flight: I flew Delta from IAD - SJU roundtrip for 27,000 points. That's cheap because October is off-peak for Puerto Rico. (The weather was fantastic with infrequent rain.)

Island Transportation: RENT A CAR! You will want to drive around the island. I have corporate discounts which vary but it made financial sense to rent the car. We did utilize Uber on one night when we went drinking.

Lodging:

Airbnb of course. Rented a guest house for about $200 for 3 nights total.

Activities:

Old San Juan walking tour - This gave us a chance to explore the city with a guide the first evening we arrived. We learned some history, current political facts, and where to find the best bars (including the one from the Despacito video).

Snorkel Day Tour - Neither one of us can swim. And motion sickness loves me but I just had to go snorkeling. The water and sea life is so beautiful. And we got to meet some wonderful people.

Afro-Caribbean/Art & Culture Tour - My favorite part of the trip because we left the touristy area of San Juan and went further in the country. Our host Derek was very knowledgeable about the people of Loiza. Loiza is where many Afro Puerto Ricans live. He was also take you to Samuel Lind's place where you can see the most beautiful art and give back to the community.