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Tourists pose for pictures at the archaeological site of Teotihuacan, one of Mexico's top tourist attractions, during its reopening amid the COVID-19 pandemic on Sept. 10, 2020.CLAUDIO CRUZ/AFP/Getty Images

Fall colours and pumpkin spice lattes signal to Canadians that it’s time to pick apples, embrace sweater weather and, for many of us, begin planning for a winter getaway. But with the global pandemic continuing, should sunseekers consider heading south this winter?

Canadian airlines that offer flights and packages to the Caribbean and Mexico – Air Canada, Air Transat, Sunwing and WestJet – are hoping travellers consider working from a tropical setting instead of home, where after-work plans could be watching sunsets beneath palm trees instead of streaming series from the couch.

All of these airlines are dangling another lure: complimentary COVID-19 insurance with all international flights. And Barbados, Bermuda, Aruba and Antigua and Barbuda have introduced new visas to encourage international visitors extended island stays ranging from six months to two years.

Hamilton, Bermuda, Oct. 20, 2012. Bermuda has introduced new visas to encourage international visitors extended island stays.F. ANN SPURLING/The New York Times News Service

Jennifer Craig, sales manager of Toronto-based Craig Travel, says that a year ago she would have been busy confirming client requests for small group and cruise travel, on trips such as fall colour cruises or multiday trips to Costa Rica and Belize. This year, because of the pandemic, clients are dreaming ahead to 2021 and making vacation plans for the future. “People are needing something to look forward to,” she says. “It’s really needed for their mental health.”

For travellers contemplating a sun escape sooner than 2021, Craig says familiar spots such as Mexico, Jamaica and Cuba are A-list destinations for Canadians.

Mexico welcomes almost two million of us a year, according to Global Affairs Canada. Currently, international visitors do not have additional requirements for entry because of coronavirus, but several regions in the country are upgrading health and safety procedures to achieve certification by the World Travel & Tourism Council.

Cancun, Riviera Nayarit, Baja California Sur and Mexico City are joining Jamaica, Aruba, Grenada, Puerto Rico, Tobago and Bermuda in the international Safe Travels program, a new set of best practices for 11 tourism industries such as tour operators, hospitality and car rental to prevent the spread of coronavirus.

The Palladium Hotel Group, with resorts in Mexico, Dominican Republic and Jamaica, are hoping to attract guests by providing complimentary COVID-19 medical insurance at select properties until July, 2021, including the couples-only TRS Coral Hotel and Grand Palladium Costa Mujeres Resort & Spa in Mexico. All-inclusive Club Med resorts are also offering COVID-19 insurance for guests at their properties in the Caribbean and Mexico.

The Dominican Republic is offering free COVID-19 insurance to all international visitors who stay in a hotel until Dec. 31, 2020, while Jamaica currently requires Canadians to submit a travel authorization questionnaire prior to arrival, which includes information about health, recent travels and accommodation in Jamaica.

On arrival in Cuba, visitors will need to show proof of COVID-19 insurance or purchase it for US$30, undergo temperature screening and a free coronavirus test, with results sent within 24 hours; visitors quarantine at their hotel or resort during this time. “All hotels in Cuba’s tourist areas now include an international clinic with a doctor, nurse and epidemiology specialist to monitor the health of hotel guests and workers,” says Lessner Gomez, director of the Cuba Tourist Board in Toronto.

Private taxi driver Esteban Estrada cleans his 1934 Ford while waiting for customers in Havana on June 13, 2019.YAMIL LAGE/AFP/Getty Images

For those wanting direct flights from Canada, free coronavirus testing on arrival and minimal COVID-19 case counts, Grenada, St. Vincent and the Grenadines and St. Lucia fit the low-risk category (the latter two countries also require presenting negative tests upon arrival); none of these islands have recorded more than 65 cases since March and there have been no deaths. Luxe boutique resorts such as Grenada’s Calabash Hotel, Young Island Resort in St. Vincent and St. Lucia’s Serenity at Coconut Bay offer personalized hospitality such as stocking your private bar with preferred spirits, fresh fruit delivered daily from the resort gardens or having the butler set up your exclusive beach cabana. All these hotels include spacious suites, outdoor fine dining and private beach access – in other words, physically-distanced vacations with all the amenities.

Other popular islands like the Bahamas, Bermuda, Turks and Caicos, Martinique, Sint Maarten/St. Martin and Puerto Rico require negative tests upon arrival, regular temperature monitoring by officials and daily curfews. St. Kitts and Nevis will start welcoming visitors Oct. 31 and British Virgin Islands will open its borders in December, while Trinidad and Tobago and Cayman Islands are currently closed to international travellers.

“The main barrier for clients escaping winter is the Government of Canada’s travel advisory,” Craig says, “and the 14-day quarantine.” And she is quick to remind travellers that COVID-19 insurance covers a traveller if they test positive for coronavirus, but doesn’t include coverage of any other medical issue or cancellation insurance. Short jaunts south may not be worth it this year, but for those who can plan a longer vacation, it still may be possible to indulge in Caribbean sun.

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