Philipsburg, St. Maarten

March 13, 2023

Cheers to 9 years! We celebrated by doing a sailing excursion. It wasn’t just a casual sailing day trip – this was different! This was the America’s Cup Sailing Regatta. We actually had to work during this excursion, which we were pretty excited about. While we were waiting for our water taxi to take us over to our sailboats, the man taking our tickets also assigned us our positions for the day.

Andy and I were both primary grinders – which they kept making the joke that we wouldn’t need to go to the gym that day. Two captains were selected to lead the different teams – and we were broken into the different teams. One team would get the Stars and Stripes (a race winning boat) and the other team would get True North.

The crew was fantastic – not us – the captain, first mate, etc. They made sure that we all understood our positions and if we felt uncomfortable we could switch. Some of the other positions were main grinders, winch whench, bartender, etc.

Ultimately, there were six of us that were primary grinders – and there were only four cranks. We got to enjoy the first leg of the trip and watch our new friends crank like there was no tomorrow. We were in a little pit – while we weren’t grinding. It was a lot of fun! And it was something we haven’t done before. We’ve sailed, but never were a part of the crew.

In our pit

It truly was a race. There were a few times that I thought the boats were going to hit – which was pretty terrifying and cool at the same time. I didn’t see this, but Andy had overhead the captain actually yelling at the other boat. Apparently they almost actually hit us – so I guess we weren’t too far off base thinking we were going to die at one point. 😂

The cranks – and one of the many times we came close to the other team
Our vessel and the beautiful water
Our rivals

We lost the race. But we’re all winners here. It was a blast. After the race they brought us back to their “museum” basically just a gift shop. We decided it might be fun to walk around a bit before heading back to the ship. We stopped and had lunch. One of the restaurants that we walked past had taken drift wood after both Hurricane Irma/Maria to reconstruct. It’s a good reminder that no matter how beautiful these places are – they can also have extreme weather. Those hurricanes hit in 2017 – I wasn’t blogging then, but we were in Cancun and there were three hurricanes in the Gulf of Mexico that September. It was a really rough year for the Caribbean.

After lunch we got back on the ship and got cleaned up. We hung out with Jill and Mario that evening. There was a magic show – and we Mario had some business to wrap up in the casino.

Our illusionist, Gabriel
The cruise gave us a little something to celebrate

It was a great anniversary!

Up Next:

  • Roseau, Dominica
  • Titou Gorge and hot springs

Puerto Rico or bust!

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.

They weren’t joking when they said it’s where the Pina Colada was created
Calle de la Fortaleza
Just one example of the beautiful colors in San Juan
Puerto Rican flag – painted black in 2016 due to the PROMESA act
First Pina Colada on this trip!

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!

Chicken Mofongo – and Andy had salmon in the background

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)

Alaska Cruise Day 6 – Skagway

We docked in Skagway early in the morning – we had to take a tender to shore because there had been a landslide in previous years that had damaged the port. The tenders (life boats) actually reminded me of a Star Wars like vehicle. I’ll let you be the judge of that! 

Once we made it to shore we were on our way to the historic White Pass Railway. This tour took us along the mountain side. It was really stunning – lots of great views. It took us to the Canadian border where we turned around. It was a great way to see how the gold rush left its mark on Alaska.

Once we got back into Skagway we had a choice – the train could drop us off closer to the downtown area or near where we would take the tender to get back on the ship. My parents decided to head back to the ship, but Andy and I decided to get lunch in town.

We had lunch at The Skagway Brewing Company – the food and service were both great. I even tried their Rhubarbita – which was really tasty. We also found that Skagway was home to the Klondike Gold Rush National Historical Park. We didn’t have too much time to explore, but would have liked to if we had more time.

We were also incredibly excited because the entertainment that night was The Boy Band Project. It did not disappoint – the band took us through some of the early boy bands – think Jackson 5! All the way up to my favorite band, Backstreet Boys. It was a ton of fun. They were really interactive and encouraged the crowd to participate in the show and singing. It was definitely one of the highlights of our trip!


We had booked another cruise while on the ship – and had won a speciality dining experience from a drawing that we had been entered in. We booked this at the Tuscan Grille. We had to leave the Boy Band Project show a little early to get to our reservation. As soon as we showed up we realized that they had indeed given us one of the best seats in the house. Our waitress was incredible as well and made sure to provide a great experience for us. 

What we loved about it was the fact that they offered half-entrees. That way we could try more food. We had already been eating pretty well on this trip, but this was over the top. We were so full by the time we were done with dinner.

Up Next:
At Sea