Grand Cayman!

Without a doubt, it would be our first trip to St. Thomas in 1991. My wife and I were married in the Gazebo on the hill at Frenchmans Reef. It was the perfect setting to a perfect day. The wedding coordinator (Norma Kennedy-RIP) had us moved from the main hotel to a beachfront condo on Morningstar Beach. We have visited many beautiful islands in the Caribbean since then, but the memory of that special day will last forever!

we were travelling with our three children and another family with kids as well. we booked the southampton princess sixth floor concierge and when we arrived, the hotel was entirely booked, not a room to be had......orlando, who still works the concierge ten years later today, gave us the penthouse which had a kitchen, dining room, living room three bedrooms, three bathrooms, a changing room and a pantry completely surrounded by glass sliding doors with a continuous balcony......a once in a lifetime experience...probably never to happen again.....needless to say we tacked three more days onto this vacation...wouldnt you? we witnessed the most amazing thunderstorm from that penthouse, something my kids still talk about today....memorable? you bet.

oops, forgot to mention this was on the beautiful island of bermuda....

Good thread.
I was thinking back to some of the places I have been in the Caribbean.

Memorable ones are: The first trip my family took to the Caribbean, Bermuda in 1976 :) I was amazed. We went from cabin vacations in NH( I loved those memories too) to the luxurious brand new Sonesta on a tropical island. I wore a sundress that had stripes. I remember that.
The Deep had just been filmed there and our cab driver, Winky was in the movie.
My trip to Puerto Rico at 19 with my Mom. Just her and I for a week. We had so many laughs. I have decided my girls will need to take a trip like that with me when they get older. I can still see my mom counting her money every night. She was so nervous about traveling without my Dad. We had so much fun.
My brother was marrried on Puerto Rico and his wedding was a blast. Everyone who attended the wedding was married the following year, including me! :)

My honeymoon on Paradise Island (pre Atlantis days)

We have had many fun trips to the Caribbean and some are more memmorable than others, but most were good. :)
We are taking two next year-PR and GCayman. So, we are looking forward to them.
My fave is still Bermuda. We just keep going back!

It's easier for me to say which trips weren't memorable, as all of my travels to the Caribbean have been wonderful and I loved each island as I was experiencing it. St. Lucia is memorable because it was my first visit down there. Antigua is special because I was married there. Guana Island is special because I honeymooned there. Nevis and Jamaica were wonderful because we really got out and about for those visits. Tortola and Vieques are special because we traveled there with our granddaughters. Grenada, Bequia & St. Vincent are all very fresh in my memory right now. The only one that doesn't stand out was my trip to Barbados--I loved it while there, but there was no one thing about that trip that makes me long to return.

So many memories. :-) Here are a few:
Our first trip to an island was Nassau and I still remember feeling wowed upon my first glimpse of the turquoise water.
Then came our 1st trip to Jamaica. I was delighted with the hospitality and the ubiquitous "no problem" answer for everything. :D :D I still use it. :-)
Another neat memory comes from our 2nd trip to JA. It was June 21st, the first day of summer and the longest day of the yr. As I lain on the beach just watching the sun slowly set in perfect weather for at least a few moments in time I had no cares in the world. :-) Yah mon. :D :D

This is an easy one for me ;-)

I had come to know and respect Tiverton through his posts here. He took a chance on me, reading between the lines I think...and I took a chance with him, just because I had also come to trust him.

My first Jamaican experience was back in 1970 at Half Moon...when Montego Bay was in the throes of many changes. For those who post here about their fear of leaving the resort, I try to recall my fear, when I went into town back then. I try to assure people that the Jamaica of today is very different than it was then...but many readers here were not even born in 1970...but I digress ;-)

When I ventured to Jamaica again in 2004, it was to stay at the Jamaica Inn...followed by several trips to villas managed by Linda Smith. All lovely, but far away from any real interaction with Jamaicans who would love to talk about many things :-)

So...I took myself to one of the properties that Tiverton represents in Great Bay (Treasure Beach area ).

I still remember my feeling of ooooh and aaah as I approached the area...just as Tiverton had described.

Once I had established with the Parchment sisters that I was not a fancy lady ;-) the fun began. A nicely balnced duo are these sisters. One who loves to cook and one who knows everything about the trees, the flowers, the birds, the butterflies, the weather as predicted by the ocean, and the life of a fisherman.

Yes, that first glimpse of the ocean and the mountains, lives, vividly, in my heart and mind.

Marion

My first trip on a sailing ship. I had NO idea what to expect. Traveled alone first time out of the country on an adventure that was once a wish I had as a teenager fresh out of high school or close to it. Cosmo featured an article about Windjammer cruises back in '70 or '71. The pictures and description made me want to leave the next day. I didn't leave for 20 years but certainly worth it. I remember looking out the window on the plane and seeing the prettiest color of blue/green water I had ever seen, then the blast of heat as I walked down the steps from the plane in St.Maarten. As you entered the airport terminal a small band of old men were playing the song Yellow Bird. The ride to Phillipsburg, what a view from the hills overlooking the sea. Front Street and all the congestion of people and cars. This was long before they fixed up the area around Captain Hodge's. Then my ride in the launch and crossing Great Bay and catching my first glimpse of the tall ship Polynesia. Breathtaking is an understatement. It only got better. The the sails were raised the next day to the strains of Amazing Grace, such majesty. I can't describe the emotion. Tears, butterflies in my stomach, a sense of peace and awe as the sails climbed higher. Tranquility as we sailed, leaving St. Maarten in the distance. The breeze, and gentle rocking really seemed like a dream. Pinch me. Is this for real? Yes, it finally began to sink in. I truly was sailing the Caribbean on a tall ship.

I have sailed 10 times so far. Even so I continue to remain in awe of the majesty and grace of the ships always being swept up in the emotion of that first sail. Amazing Grace always brings a tear. No matter where I hear the hymn it always provides me with that sense of peace and tranquility, as well as wonderful memories of my
first time.

My most memorable trip was my first trip to Negril (2nd to Jamaica) in 1987. It was a two week trip I took with my family during my sophomore year in college. Negril cast a spell on me that trip and is resposible for the affliction I have for Negril and Jamaica in general. That trip was also responsible for my desire to give island life a try as I moved to St. Croix after graduating college and went to work for a CPA firm in Christiansted. While my wife and I were engaged, I took her to St. John and we honeymooned in Negril later that year. She has been bitten as I have and we enjoy annual trips to the Caribbean. It is our preferred destination with Jamaica referred to as our second home.