Our Successful Repositioning Cruise from Lisbon to the Caribbean

We began this cruise in Lisbon, Portugal, after a two-week train trip across 3 countries.

We arrived in Lisbon the night before the cruise and chose to stay at the airport. We booked an amazing stay at the Melia Lisboa Aeroporto. We relaxed in a beautiful suite after a long travel day. Our Expedia Status provided a free upgraded room, and it was a great spot to relax after our full day of travel. The airport was a 4-minute walk from the domestic terminal!

Why do we like repositioning cruises?

We have taken a few repositioning cruises as our mode of transport when we travel. A repositioning cruise starts and finishes in different ports. Sometimes they are called crossings, transatlantic or transpacific, depending on where they sail.

Here’s why we like repositioning cruises:

• Great way to avoid jet lag and a long flight
• Often coincide with our travel plans in the shoulder seasons, in the spring and fall
• relaxing way to end a busy trip
• Often cheaper than typical cruises, so we can afford a balcony room for an oceanview cabin rate.
• Interesting itineraries
• Read about our repositioning cruise from Rome to Durban
• Read about our cruise from Rio to Barcelona

A repositioning cruise is a great way to relax, and we loved the 15 days without having to navigate, pack up or find our next meal!

How we booked our cabin

We booked passage on the Star part of Norwegian Cruise Line’s fleet. We booked the cruise in January 2025 with Vacations to Go. In July, we noticed the cabin price had dropped, so we asked our travel agent for assistance. We were able to get an upgrade to a junior suite for the same price as an oceanview cabin. If you notice a price change even after making the final payment, it is worth asking for compensation. It will likely come in the form of a future cruise credit. Its worth asking for a partial refund, onboard credit, or a better cabin. Our new cabin was spacious with a large balcony and a bathtub! We also had a free bag of laundry and some WIFI with our package.

Our Itinerary

We love using the Cruise Globe app to record our cruises. Here’s where we travelled:

Ponta Delgada, the Azores

We had a brief stop on our crossing to Ponta Delgada on the island of São Miguel in the Azores. The last time we visited this island was in April 2024. Read more about our Azores trip here if you are curious. Even though it was November, we experienced a sunny, spring-like day. We saw dolphins from our cabin as we neared the island. We walked the downtown area and stopped for a local beer. It was nice to be back in a familiar place, and we enjoyed seeing the holiday decorations around town.

Sea Days

Half of our days on this cruise were spent at sea. It took 6 days to cross the Atlantic before arriving in the Caribbean. We had smooth sailing and sunny weather every day. It got warmer as we travelled southwest every day! Time zone changes were done one hour at a time across several days. There is no jet lag when cruising!

We enjoy relaxing on our balcony, reading, listening to poolside bands and attending educational lectures. Dr. Dowty, a retired professor, did an excellent job of explaining several historical explorations of Columbus, Magellan, Cook, Blyth, and Franklin. Each night after our delicious 3-course meals, we were entertained by several musical acts, a magician, a comedian, and a juggler. Our interent onboard

If you have wondered if a cruise with sea days is right for you, check out our previous posts about sea days.

Philipsburg, Sint Maarten

Our stop in Sint Maarten was in Philipsburg on the Dutch side of the island.

Sea Trek and Snorkelling Excursion

We waited patiently for our excursion to be called, and we were surprised to find out that there were only 4 of us for the Sea Helmet and snorkelling tour. If you have cruised before, you know that excursions organized by the cruise lines are often crowded, so this was amazing to have a whole boat to ourselves! We also had a crew of 6 divers taking care of us. We had never tried a Sea Helmet before.

After a short safety briefing, we were fitted with water shoes and escorted to a 20-foot ladder. Just before our descent, a 70 lb helmet was placed on our shoulders. We could see out of three sides, and air was pumped into it. I felt like an underwater diver seen in an aquarium! A trained guide was beside us every step of the way down. I found it easy to equalize the pressure in my ears.

When we reached the bottom, we followed a flat path and observed fish, some statues, an old helicopter, a submarine wreck and a cannon from the 19th century. We spent 30-40 min at a depth of 20 feet and enjoyed seeing all the fish. It was a great way to get the feel of scuba without having all of the gear. Our guides were helpful and made the experience fun! Read more about the t Sea Trek Tour for more details. The other half of the time, we donned snorkel gear and enjoyed the corals and fish. I missed seeing the eel and ray, but I did see the barracuda. We returned to the ship by boat.

Island tour with friends

After showering and a quick lunch, we met up with Samantha and Mark, who gave us a private tour of their island. They drove us up to a few viewpoints, answered our questions and then we stopped for food and drinks before returning to the ship. Samantha and I taught together at an international school in Vietnam. When I learned she was teaching in Sint Maarten we made a plan to connect. 

St. Thomas, USA

St. Thomas is a lively port, and the weather was sunny and hot! We took a quick tour of some nearby shops and spent the rest of the day on the ship.

Falmouth, Jamaica

Our next port of call was Falmouth, Jamaica. We took a bus tour of the north-east part of the island. We saw some of the damage left behind from Hurricane Melissa. Hydro crews were working on the lines while we were there. The port had reopened for tours 2 days before our arrival.

Since tourism is their main industry, they were happy to see us. Many resorts won’t be open this season, and many locals still have roof repairs to contend with. Our tour guide was still waiting for electricity and a roof repair in his community.

George Town, Cayman Islands

This was my first visit to the Caymans. It is a very flat island, unlike the mountainous islands of Jamaica or Sint Maarten.

We took a snorkelling trip that included a visit to Stingray City. This famous sandbar is home to hundreds of rays, and they receive thousands of human visitors each week. Unfortunately, more humans were standing on the sandbar than rays. Although the rays are free to come and go, they are attracted by the guides who feed them. I did get the chance to touch a ray and feel how soft they are. I did not feel comfortable invading their home. We would not have participated in this activity had we known it was “zoo” like.

The snorkelling part of the day was quite enjoyable as there were more fish, a ray and lots of coral to see. The Caymans have beautiful, fine white sand, and so we enjoyed snorkelling in the warm water. We also avoided any sunburn!

Disembarking in Tampa, Florida

Disembarkation from a cruise ship is easy if you can carry your own bags. We now travel with carry-on only, and so we were free to disembark at any time.

We walked around the Riverwalk in downtown Tampa and enjoyed the Canalside neighbourhood. We had an early lunch on Harbour Island. The café owner was from Montreal! After lunch, we made our way to the Tampa airport for our flight back to Toronto.

The two-week cruise was a great, relaxing way to adjust to time zones, and it allowed us to take a short flight home. We enjoyed taking a cruise as a way to return home from our European trip. We would definitely cruise again to transit to new places.