Occasionally, nature throws the islands a challenge with which to reckon. The Caribbean is a resilient region with revelers who give as good as they get. Be sure to check-in with your island’s favorite events – so far, it’s a go, unless they say no – – for in the Caribbean, there’s a saying, for those who know – ”soon come.” So, in the event that events have to be adjusted, then try again next year or head down and lend a helping hand as we face Fall in our piece of paradise that will always persevere.


It’s a show of power and endurance at this “tour of human force,” as Tobago closes September and opens October for international cycling enthusiasts. This scenic tour of just about all areas of the island begins at Tour of Tobago, September 27 – October 1 www.trinbagowheelers.com/

At the top of the month, Bermuda hosts family fun with its cultural and colorful gombey troupes performing just a vibrantly with music, dance and merriment. It’s photo-worthy fun for the whole family at Bermuda Gombey Festival, October 7 http://www.gotobermuda.com/event/bermuda-gombey-festival/205

It’s a “battle with the sexes” in Saint Croix, where it’s all about who can make the best catch, during the U.S. Virgin Islands: 16th Annual Golden Hook Guy/Gal Reel Challenge, October  14 – 15  www.fishstx.com .

A sailing event of world class proportion gets underway, complete with onshore Bahamian festivities and gastronomic feasts at the North Eleuthera Sailing Regatta, October 6 – 9.
Then professional and amateur swimmers of all ages cut through the water for the 5K feat in the Abacos islands for the Abaco Open Water Swim Race, October 14.


Bodies will glide through the clear. Seawater, demonstrating fitness and agility during the exhilarating open water race, followed by a grand celebration on shore for the St. Croix Coral Reef Swim, November 5  www.swimrace.com.

Living up to its reputation as the “culinary capital of the Caribbean”, Barbados presents a feast of epicurean cuisine and it’s a gastronomical, gourmet galivant for the palate at the Food, Wine and Rum Festival, November 16 – 19  www.foodwinerum.com


Races are scheduled to be underway, as sails unfurl for the regatta around Antigua & Barbuda, Jolly Harbour Yacht Club Annual Regatta, November 18 – 19  www.jhycantigua.com

A course to be reckoned with – amateur and professional golfers tee off at Cinnamon Hill Golf course in Montego Bay, Jamaica for the Jamaica Invitational Pro-Am Annie’s Revenge, November 15 – 19  www.jamaicaproam.com

Curaçao is on the run and it’s a scenic one for the Marathon and half Marathon courses. Crossing elevations of 185 feet above sea level – one of the highest bridges in the world – offers a breathtaking, panoramic view from the Juliana Bridge and the excitement continues as athletes pass over the   the  “swinging old lady” Queen Emma Bridge. One thing’s for sure, the views will be a delightful distraction as runners take to the half marathon or full, at the KLM Curaçao Marathon, November 26 klmcuracaomarathon.com/

Get your swashbuckling on with the nation’s celebration of an infamous Caribbean pastime – all in a fun and family-friendly fashion.  For forty years, the Cayman Islands have reenacted those days of mutiny with all the fun and none of the peril. It’s the Cayman Islands’ National Festival – Pirates Week, November 12 – 22 www.piratesweekfestival.com


In Barbados, one milers, 5Kers, half and full marathoners – walk, jog or run, there’s something for everyone. In true Caribbean-style, it’s never just about the event, as their tag line reminds, “Come for the run! Stay for the fun!” The Run Barbados Series takes off December 1 – 3 www.runbarbados.org

Getting in on the running fun, and throwing in a relay and a kid’s fun run, The Cayman Islands hosts its annual Intertrust Cayman Islands Marathon, December 3 www.caymanislandsmarathon.com

Yachtsmen sail through Christmas – literally – with a Boxing Day finale during the Antigua Yacht Club High Tide Series, December 21 – 26 www.antiguayachtclub.com/ayc-high-tide-series .  The country closes the year out at sea – where better to wash away the old and usher In the new. The Nelsons Pursuit Race is underway December 31 www.antiguayachtclub.com/nelsons-pursuit-race




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