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Best deals during Caribbean shoulder season

Best deals during Caribbean shoulder season

Posted by Shanelle Weir on September 17, 2014

Apart from the Caribbean curse of the hurricane season, which officially ends on November 30, days are reliably sunny, nights are always starry and local festivals are way more fun than staking out a sun lounger on a crowded beach. Take your pick from our hot list and enjoy a sunny vacay without a big bill and hordes of tourists.


With a shopping bag of bargains through December 15, 'Fall in Jamaica' is too good to miss. More than 30 hotels, attractions and eateries are slashing prices up to 50% with bookings made on the island's website ( From all-inclusives to ritzy hotels with butlers and chefs, a stay in Montego BayNegrilOcho Rios and Kingston is affordably appealing without the throngs of tourists who come only for the high-season holidays. Get happy on October 18 when the Reggae Wine Festival — the first of its kind in the Caribbean to marry vino with reggae — is a thirst-quencher in Montego Bay. For golfers, "Annie's Revenge" from October 29 to November 2 is played on The White Witch and Cinnamon Hill fairways in Montego Bay; and for lovebirds on a budget, Holiday Inn SunSpree in Montego Bay is slicing room rates for newlyweds who can prove they've been married for one month or less (bring the marriage license).

St. Lucia

Nirvana for choco-philes, "Discover Chocolate" at the sister resorts Jade Mountain and Anse Chastanet from October 10 to 14 serves a sweet array of activities. Guests can tour the Emerald Estate to see more than 1,000 cocoa trees and take chocolate-making lessons at the resort's own Chocolate Lab. Massages at the swishy spa are cocoa-inspired (think: great for smooth skin); chefs are delighted to introduce the local brew called "cocoa tea" to curious tourists, and for those with an unforgiving sweet tooth, the resort's organic line of chocolate bars are a treat to savor.

Puerto Rico

The Caribe Hilton in San Juan is celebrating the 60th anniversary of the Piña Colada, which was first mixed and blended at the hotel in 1954 by bartender Ramón "Monchito" Marrero. For fans of the fruity concoction, "Piña Colada Fest" includes room rates as low as $60 per night through the middle of December, breakfast for two and welcome drinks. To sweeten the pot, mixology classes at the Oasis Bar aim to make ace bartenders out of any tourist.


Below the hurricane belt and with convenient TSA pre-clearance at the airport on your way home, Aruba is a good bet from September 15 — December 21, when the Radisson Aruba Resort, Casino & Spa drops room rates up to 35% and throws in resort credits of $150 for an eight-day stay. As part of "Discover Your Playtime" and under the watchful eye of the general manager who is also a personal trainer, the seaside resort is adding fitness to the beach mix with gratis mountain biking on desert trails, stand-up paddleboard lessons, 5K runs and yoga on the rooftop. For the ultimate indulgence, Salt & Oil Scrub in the Larimar Spa will do the trick.


A slew of shoulder-season fun kicks off with a tennis clinic hosted by champ Venus Williams from November 1–2 at the uber-chic Sandy Lane. For surfers, Barbados Independent Surf Fest 2014 hits the waves from November 13–16 and for gastronomes, Food, Wine & Rum Festivalcooks up a storm from November 20 to 23, with a star-studded cast of culinary masters and samples galore. Taste the real deal with the "Re-Discover" program that dishes up three-course menus at USD$50 and a gratis bottle of vino per couple through December 15. Top-notch eateries jumping on the bandwagon include L'Attitude Beach Bar & Grill in Speightstown, where Chef Gregory's vegetarian specialties are delectable and Lanterns by the Sea is coveted for Barbecue Buffet on Mondays and ocean views every night.

St. Kitts

Book before the end of October for stays through the middle of December and enjoy free nights at a host of hotels, including Ottley's Plantation Inn with its exotic Mango Orchard Spa, and St. Kitts Marriott Resort & The Royal Beach Casino. Aimed at wooing travelers during shoulder season, "Fall for St. Kitts" ups the ante with a "value card" that's good for discounts at attractions, stores and restaurants. For inexpensive inter-island travel, a one-way flight from San Juan to St. Kitts aboard Seaborne Airlines is as low as USD$119 through November 19.

St. Barths

A guaranteed palate-pleaser, Taste of St. Barth Gourmet Festival opens on October 30 with a party on Shell Beach, a short stroll from the capital city of Gustavia, and continues for four days with creative cooking from around the world. Chefs from seven of the island's best restaurants will show off menus perfected by visiting chefs from France, Japan, Brazil, Sweden and the USA. Jean-Georges Vongerichten, the New York restaurant guru with three Michelin stars, is the Patron Chef of the inaugural festival. Gratis on the otherwise pricey isle are cooking lessons from the masters, cocktail-shaking demonstrations from France's top bartenders and tastings of traditional island fare.

Trinidad & Tobago

The root vegetable called dasheen that turns blue when it's cooked is the star attraction at Tobago's Blue Food Festival on October 19. Twenty-five chefs compete with their dasheen-inspired dishes, from pizza and ice cream to a national treasure called "oil down" — a scrumptious medley of coconut milk, dumplings, pigtails and the blue root. Across the pond in Trinidad, October 23 is the Hindu Festival of Lights or "Divali" that invites with Indian movie screenings, concerts and plenty of Trini food. Bring your camera at night when lamps made of bamboo arches and plantain trees are lit across the country.


The tiny island northwest of Martinique is a musical powerhouse from October 24–26 whenWorld Creole Music Festival plays to standing room-only crowds in the stadiums in the capital city of Roseau. Book a few extra days and check out the spectacular natural attractions, from waterfalls and rivers to untouched rainforests and unrivalled diving.

Turks & Caicos Islands

The big ticket for gourmands, Caribbean Food & Wine Festival hosted by Grace Bay Resorts and the Turks and Caicos Tourist Board is on the calendar from November 6 – 8. Guest chefs include Leah Cohen of New York's Pig & Khao, David Lefevre of Manhattan Beach Post in California and Hans Peter Haider of Austria's Hotel12. Generous pours from vintners like Benziger Family Winery in the Sonoma mountains of California, Napa Valley's Cuvaison Estate and Oregon's Duck Pond Cellars will wow the crowd at the annual celebration that raises funds for the 'Little Chefs' program, encouraging kids to pursue careers in hospitality.

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Monthly newsletter featuring articles hand picked by our country managers from the best content across the Caribbean Region on PanamericanWorld.