Embarkation Day in San Juan, Puerto Rico

Day 3 of our Southern Caribbean cruise was embarkation day, and while the morning started a bit more frenzied than we would have liked, it ultimately turned into a lucky and memorable beginning to our time aboard the Grand Princess.

A Chaotic Morning in San Juan

The day began smoothly enough with coffee and packing up our belongings before heading to the port to board our cruise ship. Dropping off the rental car at the airport was surprisingly easy, and at that point we thought we were right on track.

Then things went sideways.

The San Sebastián Street Festival was in full swing in Old San Juan, including the area around the cruise piers. Our Uber driver managed to navigate the traffic fairly well, but despite clearly telling her we were sailing with Princess Cruises, she dropped us off at the Royal Caribbean terminal instead.

Staff at the Royal Caribbean pier told us we would need to walk—but before we learned that wasn’t possible (the Princess pier was actually across the bay), our Uber driver had already taken off. After a bit of scrambling, we finally found a taxi willing to take us to the correct terminal—at a rather inflated price.

Once again, we crawled through festival traffic, hoping we hadn’t lost too much time. Nearly an hour later, we finally arrived at the Grand Princess. Thankfully, we still had plenty of time to spare, and at that moment our luck officially began to turn around.

Boarding the Grand Princess and a Pleasant Surprise

Once on board, we headed straight to Horizon Court for our customary first cruise lunch. Afterward, we wandered around the ship while waiting for our cabin to be ready—and then came the next big win of the day.

We had learned the week before that we’d been upgraded to a premium balcony cabin, and it exceeded our expectations. The stateroom was much larger than what we’re used to, and the balcony was especially spacious and inviting. We spent most of the afternoon relaxing there, soaking in views of Old San Juan as the harbor buzzed with activity below.

Winning Big Before Dinner

Just before dinner, we attended a presentation about the ports of call on our Southern Caribbean itinerary. To our surprise, the good luck continued—we won a free shore excursion in Barbados and a spa treatment. Not bad for our first day on board!

Pizza, Sail Away, and Spectacular Views

Dinner was at Alfredo’s Pizzeria, one of our favorite specialty restaurants on Princess Cruises. The pizza was so good, and we finished just in time to head up to the top decks for sail away.

Watching Old San Juan and Castillo San Felipe del Morro fade into the distance as we sailed out of the harbor was absolutely spectacular—one of those classic cruise moments that never gets old.

An ABBA-Filled Night at Sea

We wrapped up the evening with a lively performance featuring ABBA’s greatest hits, which had the entire audience singing along. It was a fun, feel‑good way to end embarkation day.

What’s Next: U.S. Virgin Islands

Tomorrow, we arrive in the U.S. Virgin Islands and are especially excited for our first visit to Virgin Islands National Park. After a chaotic but lucky start, we can’t wait to see what the next day brings.