The sparkling waters and glorious beaches of the Caribbean have been drawing winter-bound, sun-starved Canadians for many years.

While our love affair with the beach is likely to continue, the nations within and bordering the Caribbean also have a rich diversity of offerings just waiting to be discovered. From the area’s rich history and cultures to eco-friendly adventures and culinary extravaganzas, there are countless reasons for visiting the region time and again. Here are just a few suggestions about activities and places to include in your Caribbean travel plans in the coming months—or indeed, at any time of year.

BARBADOS

A haven for history buffs, two of Barbados’s treasures include its UNESCO World Heritage-designated Garrison in the well-preserved town of Bridgetown, and the Nidhe Israel Synagogue, also in Bridgetown, which will be celebrating its 360th anniversary this year (November 10–20). The island has a busy calendar ahead, which includes spectacular surfing to be watched during the Barbados Independence PRO SURF FEST (November 13–16); the Food, Wine and Rum Festival (November 20–24) featuring Canadian Chef Roger Mooking, star of Everyday Exoticand Man Fire Food on The Cooking Channel; and Classical Pops, the first festival of classical music in Barbados (December 11–14). visitbarbados.org

CUBA

One of the newest stars on the Cuban scene is a seven-day circumnavigation cruise offered by Cuba Cruise. Sailings on the luxurious 480-stateroom Louis Cristal depart from either Montego Bay, Jamaica (Fridays) or Havana, Cuba (Mondays). From Havana, ports of call are Antilla (Bahai de Nipe), Santiago de Cuba, Montego Bay, Cienfuegos/Trinidad and Punta Frances, on Cuba’s Isle of Youth. With an emphasis on the “Real Cuba,” options include exploring historic Havana in 1950s-era American cars, nautical adventures around the Bay of Nipe, swimming with dolphins in the Bay of Naranjo, mountain hiking and visiting Cuba’s fabled colonial cities. Cuba Cruises’ second season commences December 22, 2014. yourcubacruise.com

JAMAICA

Chris Blackwell’s Island Outpost—a collection of distinctive hotels and villas—recently launched Inside Outpost. This unique program provides insights into Jamaica’s culture, nature, heritage and musical scene that no one else can offer, by sharing the deep-rooted knowledge from Chris Blackwell’s days of founding Island Records. Guests will have unparalleled access to the hottest experiences, such as delving into reggae’s musical history on a private trip to Kingston that includes a live studio track mixing session, or having the ultimate Bond experience, from an early-morning jet ski safari to sunset cocktails at Noël Coward’s hilltop retreat Firefly, to a late night showing of Dr. No. islandoutpost.com

NEVIS

One of the greenest islands of the Caribbean, Nevis offers intimate hotels, lush vegetation and utter tranquility. In the centre of the small island is jungle-clad Nevis Peak, a 985-metre dormant volcano whose geothermal powers are going to be developed over the next few years. The goal: to earn the title “the greenest place on earth.” Meantime, it is possible for anyone who is fit to hike—or to put it more accurately, climb—to the peak, but hiring a knowledgeable local guide is the very best way to tackle it. nevisisland.com/activities/hiking-walking

ST. LUCIA

An island made for love, Saint Lucia has starred twice in ABC’s program The Bachelor. Its endless beauty, encompassing the iconic peaks of the Pitons, lush jungle, sparkling waterfalls and pristine beaches, makes it one of the world’s dreamiest locations. Inspired by the TV series, Red Rose Trail packages help you recreate some of the show’s most romantic moments. The made-for-two island tours capture the magic and passion of each spot visited by Juan Pablo and his bachelorettes. As you follow in their footsteps, you can count on the memories lasting a lifetime. stlucianow.com/thebachelor

SANDALS

Five-star romance is a certainty at every one of Sandals Resorts’ 15 stunning beachfront settings. One of the newest is Sandals LaSource Grenada, which opened in December 2013. Surrounded by tropical gardens, the resort includes SkyPool Suites (complete with infinity-edge plunge pools) and Butch’s Chophouse (the first steakhouse restaurant in the chain). Sandals Barbados will reopen at the end of January 2015 following a multi-million-dollar refurbishment. Its accommodations include opulent beachfront butler suites and new swim-up river suites, while the resort’s 11 dining choices include Sandals’ first ever Indian restaurant. Also opening early in 2015 is Sandals Royal Caribbean in Montego Bay, Jamaica, which will offer the Caribbean’s first over-the-water suites. sandals.com

TURKS & CAICOS ISLANDS

Eagerly anticipated by foodies local and global, the fourth annual Caribbean Food and Wine Festival takes place November 6–8, spread over seven resorts and restaurants on Providenciales Island. Some highlights of the festival include a five-course Gourmet Safari, designed to show off the innovative talents of the Turks & Caicos’ own celebrity chefs; a Women of Wine Luncheon; and—particularly popular with families—the Island Street Food Fair, which focuses on local talent and dishes. Participating wineries include Oregon’s Duck Pond Cellars, the Benziger Family Winery from Sonoma County, Cuvaison Estate Wines from the Napa Valley, among others. The weekend package, which includes the Welcome Dinner, Gourmet Safari, a Food and Wine Pairing and the Island Street Fair, is US$399. However, reservations can also be made for individual events. caribbeanfoodandwinefestivaltci.com

U.S. VIRGIN ISLANDS

Between St. Croix’s underwater national monument, St. John’s protected underwater reserve and St. Thomas’s wrecks and reefs, the USVI attract divers and snorkellers of all skill levels. Must-do dives include wrecks such as the W.I.T. Shoal near St. Thomas and the spectacular Cane Bay Wall off St. Croix. Indeed, some of the Caribbean’s most spectacular diving and snorkelling can be experienced at St. Croix’s Buck Island Reef National Monument. Many dive operators also offer “Snuba”—a cross between scuba and snorkelling—for those leery of diving, while Coral World in St. Thomas offers “Sea Trekkin,” whereby a special helmet enables you to walk the ocean floor entirely free of any scuba gear! visitusvi.com