Every November, hundreds of "pirates" invade the beautiful Cayman Islands to celebrate its buccaneering history with an array of fun-filled, family-friendly festivals and events. In its 39th year, Pirates Week is now a month-long event with activities ranging from a swim meet and a 5K race to several street parties, fireworks displays, parades, a Children's Fun Day and Heritage Festivals. So pack up the kids and your family's best pirate costumes, and prepare to have a swashbuckling good time.
While the celebration is jammed packed with things to do, there are several not-to-miss items for families on the Grand Cayman itinerary. The first Friday night of the festival, throngs of island residents and tourists, many of whom are dressed in head-to-toe pirate costume, head to Harbour Drive for a spectacular fireworks show that lights up the Bay. Afterwards, Harbour Drive turns into a family-friendly Street Dance Party with live entertainment. I highly recommend reserving a table in advance to watch the fireworks during dinner. A couple of great options right on the bay are the Lobster Pot, for more upscale family-friendly fare, or get a little closer to the action and reserve a spot at one of the picnic style tables at Cayman Cabana.
The highlight of the festival is the annual mock pirate invasion; full of "spectacle and pageantry," the theatrics take place on the first Saturday. This year, the overall theme of the festival was "The Age of Romance" and throngs of onlookers gathered along the bay to watch as a huge pirate ship sailed to shore and dozens of pirates invaded the island. The story is told as follows: a young pirate and the governor's daughter are in love and he is here to rescue her. A skirmish with the Red Coats ensues, and the fun-loving pirates kidnap the daughter, and proceed to take over the island for the week.
Photo credit: Shankar EbanksThe pirates celebrate by leading a parade of festive floats and participants in brightly colored costumes in a procession down the main drag. Great views of the landing and parade can be found at Breezes By the Bay, a local spot for pizza, which offers a special menu with drinks for those wishing to watch the festivities from overhead.
Although most of the events during Pirates Week are family-friendly, they do not forget about the kids. Children's Fun Day is a wonderful event complete with pirates, games, a costume contest, bounce houses, face painting and more. And there couldn't be a more beautiful and historic location for an event. Set right on the ocean at the historic Pedro St. James, the location is a destination in and of itself and provided a brilliant backdrop for this fun-filled event.
The Pirates Week activities are just the "icing on the cake," so to speak, in this gorgeous setting. A trip to the Caribbean would not be complete without some time spent on and near the water. If you only have time for a couple of excursions, I highly recommend horseback riding on the beach and a sail to snorkel and visit Stingray City.
The highly rated Pampered Ponies offers relaxing and beautiful two-hour rides on uninhabited shores. You may even choose to swim with the horses. Riding horses on the beach was one of those bucket list items for my daughter and me.
While there, we were asked over and over "have you been to Stingray City yet?" And there is a reason for that. Stingray City is not an area on the island, it is a sandbar a mile or so from shore, a spot where, according to a local guide, fisherman used to anchor to clean their fish while huge stingrays would gather to feed. The fishermen have been gone for decades, but the stingrays still gather and allow human visitors to get up close and personal with them. Several companies provide snorkeling sails with a stop at the barrier reef and Stingray City. We recommend Red Sail Sports which offers a variety of Stingray City Sandbar and reef catamaran sails.
There are plenty of fantastic options for accommodations on Grand Cayman, but look no further than the Caribbean Club for ultra luxurious and modern, over-sized three bedroom units with a view, perfect for families. While the units are spacious, the property is just the right size - this is one of those places where you can get to know fellow travelers during your stay. And, dining on-site does not disappoint; the upscale Luca, offers alfresco pool/beach-side dining or room service dining.
The Island of Grand Cayman is teeming with incredible restaurants. Don't miss upscale seafood at the Lobster Pot, which offers incredible food with views to match. Be sure to go around 7:30 when they feed the dozens of large tarpon hanging out in the water below the outdoor dining area - this was a big hit with the kids. Agua is another great upscale but family-friendly option. They have an extensive wine list and serve exceptional contemporary Mexican and Caribbean cuisine.Brooklyn Pizza and Pasta, located in a walkable newer shopping center, is a great casual option with fantastic pasta and pizza. Brooklyn Pizza and Pasta was ideal for the kids, as well as the adults.
As if gorgeous warm weather, beautiful beaches, water sports and fascinating sea life were not enough of a reason to visit one of most spectacular islands in the world, throw some pirates into the mix and you're in for a swashbuckling adventure of a lifetime.
The "Pirates Week" festival typically runs through the month of November. Check www.piratesweekfestival.com for dates and activities. Visit www.caymanislands.ky for more information about the Cayman Islands, activities and accomodations. Check out more photos of Grand Cayman and Pirates Week on Instagram.
The writer and her children were guests of The Cayman Islands Department of Tourism. Meals, activities and accommodations were included to facilitate this review. All opinions are those of the writer.
The "Pirates Week" festival typically runs through the month of November. Check www.piratesweekfestival.com for dates and activities. Visit www.caymanislands.ky for more information about the Cayman Islands, activities and accomodations. Check out more photos of Grand Cayman and Pirates Week on Instagram.
The writer and her children were guests of The Cayman Islands Department of Tourism. Meals, activities and accommodations were included to facilitate this review. All opinions are those of the writer.
