There once was a group of twelve ladies who liked to have fun and drink wine. They called themselves the "Thirsty Thursday Group." Later they created "The Have Wine Will Travel Group," which met once a month in each other's homes.
When one of the ladies suggested a Caribbean cruise, the excitement was contagious — and soon eight friends had signed up for a 7-night Princess cruise from San Juan, Puerto Rico.
Thirsty Thursday Caribbean Cruise
March 8 - March 15, 2026 | 10 min read
There once was a group of twelve ladies who liked to have fun and drink wine. They called themselves the "Thirsty Thursday Group." Later they created "The Have Wine Will Travel Group," which met once a month in each other's homes. When one of the ladies suggested a Caribbean cruise, the excitement was contagious, and soon eight friends had signed up for the adventure of a lifetime.
One of the ladies wanted to see some new things and try lots of new foods. She liked to play bocce and loved her ice cream. She loved to drink Coke and make pottery. She once was a teacher and loves to travel and shop. The next lady to join loved to play Mahjong and golf. She loves to drink rose wine with a glassful of ice on the side. She makes awesome creations of glass and babysits her grandkids.
The two friends asked their Thirsty Thursday group: "Who else wants to go?" Everyone was excited and had lots of questions, so the search for a cruise was on. Where should we go? When should we go? How much will it cost? What cruise line? What size ship? What airline? Should we fly in a day early?
Theresa searched options for everyone and presented some ideas. Cindy started looking and Donna started looking as well. Donna had used Vacations To Go for her cruise to Alaska with her family, and Cindy had used them as well. The group chose some dates and decided they wanted to go on Princess on a smaller ship to the Southern Caribbean.
Six more friends joined the group — Cindy, Sheila, Jeanne, Donna, Stella, and Cindy's daughter Julia. Now there was a group of eight and we needed four balcony cabins. Donna called Vacations To Go and asked them to find us 4 balcony cabins. Unfortunately February was fully booked, but we found a date starting March 8 for a 7-night cruise leaving from San Juan, Puerto Rico.
Our second cabin was made up of an adventurous world traveler who loves wine. She plays Mahjong, other games, and has the most energy of anybody I've ever seen — we call her the energizer bunny. She has a cute dog named Holly. She invited her daughter to join us. Her daughter also loves wine, lives in Arizona, and is quite funny. She is a loan/finance property officer and is very smart.
Cabin number three was made up of another wine drinker who loves to dance, loves music, and found some cute doctors on the cruise. She loves to laugh and enjoys a cup of tea in the morning. Her roommate also loves wine but is now drinking virgin Bloody Marys. She loves gardening, traveling, and shopping. She spends time with her family and grandchildren. She is from Canada and was a nurse.
Cabin number four was made up of a wine drinker who now drinks virgin strawberry margaritas. She loves to travel and spend time with her grandkids. She loves gardening, nature, shopping, and musical theatre. She also loves cats. Her roommate drinks wine, loves art, is creative, and enjoys the beauty of the world. She is curious and a shopper. She also loves cats.
Finally, the day of the cruise arrived. We boarded a redeye on Southwest to Baltimore with a short layover and our next flight to San Juan, Puerto Rico — none of us seemed to sleep on the plane. We had a very tight connection to our second flight and barely made it on time. We all decided: no more redeyes on Southwest.
Our friend Stella speaks great Spanish and found us a ride to our hotel. Six of us stayed in three rooms at the Holiday Inn in San Juan. We had to wait because our rooms weren't ready and we were early, so we went to lunch down the street. Donna tried a local dish made with plantains stuffed with chicken — she liked it. Donna forgot her seasick patches at home and needed them for the cruise. She was able to call Kaiser and a doctor sent in a prescription to the Walgreens down the street. Problem solved!
We found a driver to take us to Walgreens and later went to the downtown area for dinner. We found a cool restaurant and ate outside. We all ordered wine and Donna ordered a virgin drink. It was her birthday, so someone mentioned that to the waiter and he brought her out a shot — probably a rum shot. He poured one for himself and one for Donna, who had ordered a virgin drink earlier. Go figure. We got a laugh out of that one.
The next morning we got a taxi to take us to the ship. Donna and Stella forgot to set their alarm and overslept. Luckily Theresa and Claudia called them and woke them up. Donna and Stella missed out on Starbucks and breakfast, but they were all ready for the taxi when it was time to go to the ship.
The boarding process went well. We met up with Cindy and her daughter Julia the night before at the hotel. Meanwhile, we were on the lookout for Gene and Sheila! They had taken the same redeye flight a day later and were planning on just getting on board the ship. That did not work out well — there was a medical emergency on the flight from Sacramento to Baltimore and they were diverted to Kansas. They were quite concerned they were going to miss their next flight to San Juan. They were in contact with Princess and somehow barely made it before the ship sailed. They were quite stressed out by the time we saw them for dinner that night.
We got together for dinner each night at a table for the eight of us. The cruise took us to five beautiful islands:
St. Thomas, US Virgin Islands (March 10) — The group enjoyed city tours of this beautiful island.
Saint Martin (March 11) — A unique island that is half Dutch and half French. Donna, Cindy, and Julia went snorkeling for four hours while others took city tours to see the whole island.
Antigua (March 12) — Donna did a beach horseback ride with three other couples. Each got a chance to ride one of the horses bareback into the ocean and take pictures. It was a thrill of a lifetime for Donna. Later she went shopping and found some cool stuff.
Dominica (March 13) — Donna went whale and dolphin watching and saw a sperm whale, a humpback whale, and a pod of 120 dolphins. She did not know that there were whales in the Caribbean!
Barbados (March 14) — Cindy, Julia, and Donna took a cave tour on a little railroad. They all liked it.
Saturday was a day at sea. Donna was happy to sleep in that morning. The ship arrived Sunday, March 15, into San Juan at 6 AM.
The journey home on Southwest Airlines turned out to be a very big adventure. The East Coast was hit with storms and our flight to Orlando was delayed and delayed. The gang decided to talk to someone from Southwest. If our flight was going to be a problem, we needed seats for six of us. The only thing available if our Orlando flight was cancelled was a flight out of Orlando the next day at 7:30 in the morning.
We decided that getting out of San Juan was the most important thing and took our flight when it became available. The Southwest crew was very grumpy and older than the average crew member. We had a lot of turbulence on the flight and had to stay in our seats. When we got to Orlando we had to circle in the air because the airport was closed and there were no gates available. Finally they let us land and we sat out on the tarmac for what seemed like at least an hour. Our grumpy flight attendant told us that since it had been 20 minutes they had to give us water while we stayed in our seats. The pilot gave us updates and apologized for the delay.
Our original flight home to Sacramento was finally cancelled and everyone was trying to get rebooked. We were thankful to be on the morning flight, but we had to spend the night in the airport. The Southwest crew got grumpier and older with each new flight segment, and the turbulence increased too. But we made it home — with enough stories to last until the next Thirsty Thursday!
