Sailing to the Old World

This is part one of a five part round the world trip.

• Sailing to the Old World
• Istanbul not Constantinople
• Better in Bangkok
• Killing Time in Kuantan
• Sunny in Sydney

Since beginning with points and miles, I've always wanted to tackle an around the world trip. To me, it was a challenge that felt like a capstone project or like defending a thesis, the culmination and application of all the tools and tricks I'd picked up over the years.

Little did I know, my carefully laid plans would all soon go out the window before I even arrived on my first continent.

The trip started with an extraordinarily cheap 14-day transatlantic cruise on Carnival Dream.

• Galveston
• Bermuda
• Gibraltar
• Málaga
• Alicante
• Barcelona

Carnival has a new "SEA" offering which stands for "Sailings Exclusively for Adults." To promote these new cruises, and because this was a repositioning cruises, the offers for this cruise were the best I've ever had. 

• $200
• X onboard credit
• Y gratuities
• Z fees

When I got the offer in late Summer of 2025 it was just too good to resist so I booked it and decided I'd figure out the rest later. Even though I would have preferred to travel West (for jet-lag), the cruise quickly became the seed for my Around-the-World trip dream.

With the cruise booked, I needed to figure out the flight to Houston, transit to Galveston, and a hotel for the night before.

I flew into IAH which is about 70 miles from Galveston. For context, that is about 8 miles further away than the legal definition of outer space. Despite being 30 miles further than HOU, my IAH flight was direct and booked completely using cash like credits. Flying into HOU in business would have meant perhaps 25k miles and a layover.

To get to Galveston, I could have booked a shuttle for around $60, but I wasn't seeing very good reviews and there seemed to be confusion around pickup. Instead, I managed to get a Lyft all the way there for around $105 after factoring in a 15% discounted gift card.

Despite being the most expensive ride share I've ever taken, it felt like a reasonable cost of doing business given the cruise itself was around the same price.

The Amex Business Platinum card comes with a $50 quarterly Hilton credit and I was able to book the hotel through the Capital One Shopping portal with 15% cash back. Between that and regular points earning, the effective room out of pocket was arguably around $35.

With just one evening in Galveston, I found an interesting Doc Holliday themed restaurant nearby. The food was a bit expensive, but it had a fun theme. There were boots and things hanging from the ceiling and they seemed to be playing the movie Tombstone on virtually every screen.

This is the view from my balcony at the Spark hotel. Not bad. 

Embarkation in Galveston was among the easiest I've ever experienced. Repositioning cruises often sail under capacity, but lines to get aboard were virtually non-existent. We did end up getting delayed leaving while waiting for some of our supplies to get loaded, but this just gave us more time to enjoy the dolphins and the sunset.

I loved the artwork in Carnival Dream's stairwells. It had a very dogs playing poker aesthetic.

In Bermuda, I spent the day walking to Sea Glass Beach, stopping at interesting looking places along the way. This used to be a place where they dumped old glass and now the sea has worn it all away leaving everything smooth and rounded and very pretty.

On the way back to the cruise ship, I stopped at the Frog and Onion Pub for a Rum Swizzle and a traditional Bermuda Fish Sandwich, which is served on toasted raisin bread.

The sandwich was fine, the raisin bread was neither offensive nor particularly good. The swizzle, however, was outstanding. Frog and Onion seemed a little overpriced but it was a nice place with good ambience near the port so it made a good place to stop after an afternoon on the island.

Gibraltar was both a highlight of the trip and a turning point. 

I distinctly remember waking up that morning, with the Rock just coming into sight on the horizon and seeing the news that the US alongside Israel had just launched an all out war on Iran. Being in Europe, getting up early for a shore day while everyone back home was still asleep, we were among the first US citizens to learn of the war.

My plan for Gibraltar was to hike to the top of the Rock, visit some of the sights up there, and then head back to the boat. These pics cover some of the territory getting up to the start of the paths and roads that actually lead up the rock. There are sooooo many steps to even get this far and it's barely even the start.

I thought the homes along these winding streets and stairs were really pretty cool, lots of quirky places, maybe some without any direct road access.

Tunnels

Walking to the top of the Rock was grueling, but I was rewarded with lots and lots of macaques. They are wild animals and there were lots of warnings about how they could become aggressive but this didn't stop people from feeding them from tourist vans or even holding them.

There is a long set of extremely steep stairs going down. I took these down and here the macaques revealed their dark side as they'd clearly been chipping away at the steps, loosened the hand rails, pooped on the stone wall, and strategically placed literal banana peels on precarious steps. Sometimes they would walk right past you on the narrow stairs.

This was my second visit to Málaga. In my first, I walked up through the gardens to the Alcazaba. This time, I walked into town to see a museum. On the way, I bought some toffee grapes which might be the best thing I've ever eaten on a stick.

The museum I picked to visit was Museo Carmen Thyssen Málaga. This is a collection of mostly 19th and 20th century Andalusian art, much of which focused on coastal scenes, gatherings, countryside and animals. It had a really up beat feel to it and I liked the style.

This was also my second visit to Alicante. The time I spent most of the day walking down the beach and back around the hillside. My original plan was to loop around it, but I was still very, very sore from Gibraltar and Màlaga the day before. So I didn't quite make the full loop.

The cruise ended in Barcelona and I would have really loved to stay in the city, but our arrival coincided with Festa de Sant Medir and virtually all hotels were completely sold out a month in advance. Certainly there was no award availability.

So my plan was always to continue on by flying to Istanbul that very day. As a result, I went straight from the cruise terminal to the airport.

This is part one of a five part round the world trip.

• Sailing to the Old World
• Istanbul not Constantinople
• Better in Bangkok
• Killing Time in Kuantan
• Sunny in Sydney

Continue the story in Istanbul.