Thursday & Friday, March 9-10

We’re setting sail on our second cruise together – and with Celebrity Cruises for our 9 year wedding anniversary. We had found an incredible deal for a 7 night Caribbean cruise last year – and decided that it made sense to head back to the waters of where it all began!

Unfortunately, this cruise doesn’t stop in the Dominican Republic, where we actually got married. It had a really interesting itinerary with a lot of different island stops.

Itinerary as follows:

• Tortola, British Virgin Islands
• Philipsburg, St. Maarten
• Roseau, Dominica
• Bridgetown, Barbados
• St. George’s Grenada

The cruise starts and ends in San Juan, Puerto Rico. Thursday after work we caught a red eye flight with JetBlue to JFK, New York. There was a small delay, but nothing too significant. We had a good experience and were left wondering why we never fly with them.

JFK is a bustling airport – even for 6:00 AM! We got a quick bite to eat and then we were on our way to San Juan! Puerto Rico has always been really high on my list, but we just haven’t been able to make it there prior to this trip. There’s something about the fact that it’s a USA territory – and that it’s in Caribbean.

Once we landed, we got our bags pretty quickly and requested an Uber. There were plenty of taxis available, so both options are there and seem safe.

Since we only had the one night in Puerto Rico, I had looked up best areas to stay and landed on Old San Juan. It was close to the cruise ship port – and had a lot of history.

We stayed at Sheraton Old Town San Juan. The hotel had a great walkable location – and we were able to check in a little early. We had initially booked a free walking tour at 4:00 PM, but after the red eye and the fact we were starving – we decided to skip it.

We made our way to Barrachina, a famous restaurant in the area known for creating the Pina Colada! There was a 20 minute wait – so we just walked around that area. The colors of San Juan are just so captivating! We got to see a few fun sights and made our way back to the restaurant.

Once we got seated we ordered our first Pina Coladas of the trip – we did ours with Captain Morgan, but the most popular (at least at the restaurant) were made with Don Q rum.

The menu had a lot of fun options, but I chose to do a more traditional Puerto Rican meal – Mofongo. It is a fried plantain dish – and it was super tasty! You could order it with different proteins – but I went with chicken and it was great!

We walked around a little bit more – taking in the sights before turning in for the night. We were exhausted, and wanted to be able to do some more sightseeing in the morning before boarding the cruise ship.

Up Next

Our own walking tour of Old San Juan, which included:

• Callejon de la Puerta Bandera
• Plazuela de la Rogativa
• Puerta de San Juan
• Castillo San Cristobal
• Cayo Caribe (lunch spot)