Stories by CheapCaribbean

The Ultimate Caribbean Holiday Bucket List

November 22, 2019 0 Comments

The holidays are a magical time of the year for many reasons. One, it brings so much joy and energy to people everywhere; two, unique and cultural traditions begin all around the world; it also gives you the chance to stop for a moment and reflect on the year that has flown by and prepare for the new one ahead. Spending the holidays on the beach this year? Check these items off your Caribbean bucket list before the year is over!

1. Attend the Junkanoo Festival in the Bahamas

Each year on December 26 (Boxing Day) and New Year’s Day, the streets of Nassau are filled with vibrant décor, cultural dancing and traditional costumes. Want to truly experience the culture of the stunning Bahamian islands? Join in on the Junkanoo celebrations–it’ll be a holiday for the books, for sure!

Festive dancers in traditional costumes at the Junkanoo Festival in Nassau on New Year’s Day.

2. Get Cultured during the National Carnival in St. Kitts

Dedicated to the island’s rich cultural traditions and folklore, St. Kitts’ National Carnival festivities begin in late November and last through New Year’s Day. Traveling to this Caribbean island during this magical time means getting to experience colorful processions, poetry, dancing and lively street performances–look for the “Moko-Jumbies” (dancers on stilts), they’re hard to miss! And if you’re staying until January 1, you won’t want to miss the annual Grand Parade that takes place in the island’s capital, Bassaterre.

3. Shop around the holiday-themed Grand Market in Jamaica

Calling all shopaholics! You don’t want to miss Jamaica’s annual shopping extravaganza, the Grand Market, on December 24. Featuring an island-wide street vendor set-up, local vendors typically sell tons of handmade items, toys, sweet treats and much more. Experiencing the lively atmosphere of the market, soft tunes of reggae and sips of seasonal sorrel cocktails is something every traveler should check off their Caribbean holiday bucket list!

Jamaican sorrel (Hibiscus flavor) is a must-try when in Jamaica during the holidays!

4. Experience Muskanoo celebrations in Turks & Caicos

While there’s never a bad time to visit the dreamy archipelago of Turks and Caicos, the holidays are especially the perfect time to visit. Each year, December 26 kicks off the cultural Muskanoo Festival, rooted from African traditions, which features a masquerade parade with bright costumes, masks, delicious food and rhythmic drums. Not only can you spend your beach vacay lounging on what’s considered the World’s Best Beach, Grace Bay, but you’ll get to see a unique side of Turks and Caicos you only get to experience during this time of year.

5. Channel your inner holiday foodie in Puerto Rico

Let’s be honest, Puerto Rican food is delicious all-year-round. But, during the holidays, the food is at an all-time high with all the traditional dishes in demand like mofongo, lechon asado (the traditional pig roast), pasteles, tembleque (coconut pudding) and, of course, their famous coquito cocktail. Between the food, the rum, the parades and charming holiday décor twinkling throughout this magical island, a Puerto Rico vacay during the holidays is a must!

Fish tacos and maduros (sweet plantains). Um, yes please! (Photo by: @jujitsupanda)

With the Caribbean islands being so incredibly diverse and rich in culture, there’s no better place to spend the holidays or better time to visit. Between the traditional cultural celebrations, festive décor and delicious seasonal food, it’s time to cross a few of these bucket list-worthy items off your list! Take a look at these awesome beach vacation deals happening now.

Rachel Tellez

Storyteller and grammar nerd by day, traveler and adventure seeker by long weekend.




Limited time and availability. To be eligible for this promotion you must 1) be an approved ER&R Club member by 11:59 p.m. CST on November 4, 2019 2) be within the first 25 ER&R Club members to sign up for the promotion 3) make a double or single occupancy booking for 5 or more nights. Bookings must be made and payment must be collected through a designated CheapCaribbean agent between November 11-20, 2019. Travel must be completed between January,1 and June 30, 2020. Blackout dates include but are not limited to April 3-19 and May 20-27, 2020.


Flight accommodations will be booked in economy class or lower on United Airlines. Flight requests will be taken into account but are not guaranteed. In areas that are serviced by more than one airport (for example New York, Chicago, San Francisco), clients are expected to use the airport that provides the lowest fare available.


CheapCaribbean’s travel protection and cancellation policies for the hotel portion of the booking will apply. Travel protection will only be valid on the hotel-portion of the booking. Cancellation or a rebooking of your hotel stay outside of the allowed travel period will result in forfeiture of the free flight(s). Any changes to flights will be subject to the airline’s policies.


Offer not valid on previous bookings. Offer may not be combined with other special offers, discounts or promotions (including promotional codes). This promotion is not available to employees, or family members of employees, of CheapCaribbean or affiliated companies of the Apple Leisure Group.