Caribbean is a great place to calm down and relax!

Over the last 25+ years of travel, we’ve been lucky enough to enjoy some great vacations in the Caribbean. But to be honest, I started basking in its beauty when I was much younger! Read this travel review: Caribbean for more details.

Early years

Early on, my dad wanted to get away in the summer to a place with lots of water for swimming, and lots of warmth. This made the winters we had in Canada more bearable. A California-boy, he was interested in either Hawaii or the Caribbean, and we enjoyed both as I grew up. Our first trip to the islands was via a Windjammer Barefoot Cruises, on the S/V Polynesia. It was a storybook vacation, and I still have vivid memories of some of my experiences on this sloop.

Our experience included:

Helping to hoist the sails on our first evening leaving port;
Walking up to the bar of the tall ship to order my first drink! (a shirley temple!)
Swinging from the mast ropes to plunge into the deep water off the ship and swim under the boat;
Sleeping under the stars on the top deck;
Singing in front of my first audience; and,
Being on vacation with my parents but enjoying myself with other new friends!

Although only 8 kids onboard, the crew made it feel like we ruled the world! We were looked after and catered to, and it was so much fun! On this cruise we visited some real treasures: St. Kitts, Martinique, Saba, and Saint Martin. The week after the cruise we spent idyllically on Antigua, exploring the beaches (there are 365 of them!). One of just a handful of times in my life that I recall absolutely relaxing and falling asleep on the beach.

First big-ship cruise

My first big-ship cruise was with my parents as well – in the Caribbean on Sitmar Cruises, later purchased by P&O. That 11-day cruise was my first introduction to cruising as it exists now (or at least did pre-COVID). Antigua, Martinique and Sint Maarten stand out in my memory, but, there were a few more stops that I don’t recall.

Cruising in the last 20 years

My husband and I went on our first cruise together with friends in 2000. This Caribbean cruise was memorable for the fun we had with our friends, as well as all the beautiful islands along the way. This was our first introduction to Celebrity Cruises, on a now retired ship, the Zenith. (Check out our post on planning and booking a fantastic cruise! ) Troy remembers there being no balconies! I remember lots of good food, and way too much alcohol! Our itinerary included Venezuela, Aruba, Curacao, Martinique, Barbados, and St. Thomas. Another great exposure to different islands, and cultures, and we soaked it up! (want an itinerary that suits you? Check out our post on selecting itineraries that meet your wants and needs!)

Over the last 20 years, we have ventured to the Caribbean a couple more times via cruises, in 2009 and 2014. These have been relaxing and energizing and definitely check the boxes for shopping, food, drink, and all around fun in the sun!

Highlights for us in Caribbean include:

Snorkeling in Martinique: lots of fun memories with our friends, but also some great boat tours from the locals. Check TripAdvisor for the current best companies.

Catamaran in Barbados: one of the best days on the water we have ever had! Four snorkeling stops, great food, a wonderful captain, and amazing sites to enjoy. Check out Silver Moon for your adventure!

Island exploring on St. Kitts: It is so much more fun when you can tour with the locals and get to know the island the way they do! Rose & Jim are locals, and can fill you in on everything from politics to food to farming – we had a great day with them!

Jewelry shopping in St. Thomas: Once was enough. However, it was a wonderful experience, and I recommend it as it really is a great way to cap off your visit to the Caribbean! There are alot of stores, so, check them out ahead of time online to see which one may be of interest to your tastes!

Shopping in Philipsburg, St. Maarten: Not necessarily the most picturesque of stops, but, definitely worthwhile for the shopping! At least twice we have thought of skipping town and exploring, but, we always end up shopping and picking up some hard-to-find liquor and clothes.

Learning about Dominica with Bumpiing Tours: This outfit was well organized and lots of fun! We explored all over the island, went for a swim, jumped in puddles, and 4 x 4’d to our hearts content!