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Planning your vacation months in advance is an awesome idea. But what happens if you arrive in your destination only to find that the International Clown Convention is in town? (Yes, it’s a thing. It was in Mexico City recently.) Maybe that event is right up your alley – or maybe you were expecting a nice quiet getaway to relax and unwind.

Never fear, guys. The Funjet Insider has you covered so that the vacation you’ve dreamed about matches the reality when you touch down. One of our top tips for planning a vacation well in advance is to do a bit of research on what events might be in town during your getaway. In fact, you may find that there are some cool activities that you want to check out! But if researching in advance feels overwhelming, we’re here to help you out. We’ve compiled a list of upcoming events in some of our favorite vacation destinations – and because we’re dialed into all the details, we even included some for those of you planning holiday-season getaways. You’re welcome.

Know when you're traveling or where you want to go? Jump to:

  • Events in Fall 2014
  • Events in January 2015
  • Events in February, March and April 2015
  • Events in May-December 2015
  • Events by destination
  • Events in Cancun and the Riviera Maya
  • Events in Cozumel
  • Events in Dominican Republic
  • Events in Hawaii
  • Events in Jamaica
  • Events in Los Cabos
  • Events in Vallarta-Nayarit
  • Events in other Caribbean destinations
  • 2014 - If you’re planning a last-minute vacation this fall or thinking about where to spend the holiday season, these are the events you should keep in mind:

    Now-March 2015: Mahi Mahi are hot in Vallarta-Nayarit so get out your rod and reel and charter yourself a boat

    September 25-30: Hang with Lady Antebellum and Scotty McCreery at the Hard Rock Hotel & Casino Punta Cana for concerts, poolside parties and more all week long

    September-November 2014: Sailfish are biting like crazy in Los Cabos, but only for a couple of months, so get on it!

    September 2014-January 2015: Yellowfin Tuna season is in full swing in Los Cabos

    September 2014-May 2015: Grouper fishing season in Cancun and the Riviera Maya, so get your group together and throw in a line

    October 2014-April 2015: Whale migration season in Los Cabos means you can spot humpback, blue, grey and sperm whales as they cruise past the bay

    November 1: Dia de los Muertos is celebrated throughout Mexico with traditional skull candies and decorations

    November 8-16: Jamaica Restaurant Week features tempting discounts at top restaurants in Montego Bay and Ocho Rios

    November 12-15: The 59th International Marlin & Sailfish Fishing Tournament takes place in the waters off Vallarta-Nayarit

    November 20: The Taste of Playa event is held along 5th Avenue in Playa del Carmen and showcases the creativity of chefs throughout the Riviera Maya November 24-26: The Riviera Maya Jazz Festival at Mamitas Beach is a fun, free event

    November 30: Ironman Cozumel takes competitors through the protected waters of the Reefs of Cozumel National Park and offers 40 qualifying spots for the 2015 championships in Hawaii

    November 30-December 6: The annual Sabor a Cabo culinary festival returns for its 9th year in Los Cabos with events like Beer Fest, Wine & Art Walk, Celebrity Chef Dine Around and more

    November 2014-May 2015: Striped Marlin season is red-hot in Los Cabos, so you can catch the big one during your holiday or spring break vacation

    December 6: International Reggae Marathon / Half Marathon / 10K Run in Negril, Jamaica, where competitors “come for the run, stay for the fun”

    December 22, 2014-January 4, 2015: Guests at Palace Resorts in Cancun and the Riviera Maya can enjoy Broadway on Ice featuring Olympic gold medalist Brian Boitano

    2015: If you’re more of a long-term planner looking ahead six months or even a year – well, kudos to you, planning wizard! These events can help you plan an even more amazing getaway:

    January 9-18: Playa del Carmen, Mexico lights up with The BPM Festival, featuring 250 dance music artists (please note that you may be able to hear the festival while on the beach surrounding Playa del Carmen during this time even if you aren’t attending the festival)

    January 15-March 15: Dominican Republic whale-watching season in Samaná Bay, where thousands of humpback whales calve and breed

    Late-January: Annual Headline Barracuda Tournament in Cancun is a renowned fishing event that raises money for local charities

    Last weekend in January: Ala Wai Challenge in Honolulu, Hawaii, is a fun event featuring traditional Hawaiian games like spear throwing and an outrigger canoe race

    January-February: Whale-watching season in Vallarta-Nayarit is in full swing in Banderas Bay – book your excursion through Funjet and Vallarta Adventures, the only company with a spotter plane to scout sightings

    January-August: Sailfish season in Cancun and the Riviera Maya

    Image courtesy of Dominican Republic Ministry of Tourism Image courtesy of Dominican Republic Ministry of Tourism

    February 1-6: Bob Marley Week in Jamaica, celebrating the life and work of legendary reggae singer and activist Bob Marley during the week leading up to his birthday

    February 11-17: Cozumel goes crazy for Mardis Gras with a week of music, parades and parties culminating on “Fat Tuesday”

    February 15-17: Procigar Festival in La Romana, Dominican Republic, is a unique experience with premium cigars, world-class golf, cigar factory tours and more

    February 16: Trinidad & Tobago Carnival kicks off with the pre-dawn celebration known as J'Ouvert

    February 22-26: OHL Classic at Mayakoba in the Riviera Maya is Mexico’s only PGA Tour event, drawing some of the world’s best golfers

    February 23-28: Known as the triathlon of wave riding, the Master of the Ocean event returns to Cabarete, Dominican Republic with top athletes competing in surfing, kitesurfing and stand up paddleboarding

    Every Sunday in February and early-March: Dominican Republic Carnival celebrations and parades

    Late-February and early-March: Carnival is celebrated on famous 5th Avenue in Playa del Carmen, Mexico

    March 8-19: Los Cabos celebrates Festival of San Jose del Cabo, honoring their patron saint with a week of festivities

    March 20: The spring equinox is a unique day at Chichen Itza in the Riviera Maya, when the angle of the setting sun creates the shadow of a serpent on the Kukulcan pyramid

    March 20-22: Fred Duckett Challenge Golf Tournament in Los Cabos is one of the most anticipated golf events of the year on two world-class courses

    March 30: The Ironman arrives in Los Cabos with 50 available qualifying spots for the finals in Hawaii

    Mid-March: ArtWalk 2015 on the “Hip Strip” in Montego Bay, Jamaica

    March-May: Spanish Mackerel and Snapper are in season off the coast of Puerto Vallarta March-August: Fishing season for Blue Marlin and White Marlin in Cancun and the Riviera Maya

    April 3-6: The Montego Bay Yacht Club Easter Regatta in Jamaica features exciting, fun cruises and races

    April 5: Easter Sunday is celebrated in many countries, including Mexico, Jamaica and Dominican Republic; be advised that some establishments do not sell alcohol during Easter Week and it’s a good idea to check with your all-inclusive resort before you arrive

    April 6: Trelawny Yam Festival in Montego Bay, Jamaica, with a street festival celebrating yummy yam country

    April 12-16: Los Cabos hosts the huge Rolex IGFA Offshore World Championship tournament – which set huge world records in 2014 for most billfish releases in three days

    May 5: Cinco de Mayo is celebrated all over Mexico, usually ending in an awesome fireworks display

    Mid-May: Cancun International Gay Festival is celebrated with special events throughout the area

    May-October: This is the time to fish for Tuna in Vallarta-Nayarit

    Mid-June: Ocho Rios Jazz Festival in Jamaica featuring a week of world-class jazz music

    June 20: The King Kamehameha Hula Competition in Hawaii is one of the most famous hula competitions, with dancers coming from all over the world

    June 21: The Mayan New Year is celebrated at ancient ruins throughout the Riviera Maya

    June-August: Events for the Barbados Crop Over Festival, including calypso music and activities like Cohobblopot and the Grand Kadooment on August 3-4

    July-October/November: Blue Marlin, Mahi Mahi and Black Marlin are biting in Los Cabos

    September: Curacao hosts the Southern Caribbean Gay Pride Week (a.k.a. the biggest pride celebration in the Caribbean!)

    September: During sea turtle nesting season, participate in conservation efforts to protect nests, eggs and offspring in Los Cabos – a truly unforgettable family activity

    Last weekend in September: Na Wahine O Ke Kai is Hawaii’s annual international outrigger canoe race from the island of Molokai to Waikiki beach

    October 10: Ironman World Championships in Kailua-Kona, Hawaii – come to compete or come to watch and sip a piña colada

    Early-October (dates TBA): Port Antonio International Marlin Tournament in Jamaica

    October-December: The best Red Snapper fishing season in Cancun and the Riviera Maya

    November 1, 2015: Dia de los Muertos is celebrated throughout Mexico with traditional skull candies and decorations

    Know where you want to go, but not when? Here are all the events categorized by destination:

    General Events

    November 1 every year: Dia de los Muertos is celebrated throughout Mexico with traditional skull candies and decorations

    April 5: Easter Sunday is celebrated in many countries, including Mexico, Jamaica and Dominican Republic; be advised that some establishments do not sell alcohol during Easter Week and it’s a good idea to check with your all-inclusive resort before you arrive

    May 5: Cinco de Mayo is celebrated all over Mexico, usually ending in an awesome fireworks display

    Cancun and Riviera Maya

    September 2014-May 2015: Grouper fishing season in Cancun and the Riviera Maya, so get your group together and throw in a line

    November 20: The Taste of Playa event is held along 5th Avenue in Playa del Carmen and showcases the creativity of chefs throughout the Riviera Maya

    November 24-26: The Riviera Maya Jazz Festival at Mamitas Beach is a fun, free event

    December 22, 2014-January 4, 2015: Guests at Palace Resorts in Cancun and the Riviera Maya can enjoy Broadway on Ice featuring Olympic gold medalist Brian Boitano

    January 9-18: Playa del Carmen, Mexico lights up with The BPM Festival, featuring 250 dance music artists (please note that you may be able to hear the festival while on the beach surrounding Playa del Carmen during this time even if you aren’t attending the festival)

    Late-January: Annual Headline Barracuda Tournament in Cancun is a renowned fishing event that raises money for local charities

    January-August: Sailfish season in Cancun and the Riviera Maya

    February 22-26: OHL Classic at Mayakoba in the Riviera Maya is Mexico’s only PGA Tour event, drawing some of the world’s best golfers

    Late-February and early-March: Carnival is celebrated on famous 5th Avenue in Playa del Carmen, Mexico

    March 20: The spring equinox is a unique day at Chichen Itza in the Riviera Maya, when the angle of the setting sun creates the shadow of a serpent on the Kukulcan pyramid

    March-August: Fishing season for Blue Marlin and White Marlin in Cancun and the Riviera Maya

    Mid-May: Cancun International Gay Festival is celebrated with special events throughout the area

    June 21: The Mayan New Year is celebrated at ancient ruins throughout the Riviera Maya

    October-December: The best Red Snapper fishing season in Cancun and the Riviera Maya

    Cozumel

    November 30: IRONMAN Cozumel takes competitors through the protected waters of the Reefs of Cozumel National Park and offers 40 qualifying spots for the 2015 championships in Hawaii

    February 11-17: Cozumel goes crazy for Mardis Gras with a week of music, parades and parties culminating on “Fat Tuesday”

    Dominican Republic

    September 25-30: Hang with Lady Antebellum and Scotty McCreery at the Hard Rock Hotel & Casino Punta Cana for concerts, poolside parties and more all week long

    January 15-March 15: Dominican Republic whale-watching season in Samaná Bay, where thousands of humpback whales calve and breed

    February 15-17: Procigar Festival in La Romana, Dominican Republic, is a unique experience with premium cigars, world-class golf, cigar factory tours and more

    February 23-28: Known as the triathlon of wave riding, the Master of the Ocean event returns to Cabarete, Dominican Republic with top athletes competing in surfing, kitesurfing and stand up paddleboarding

    Every Sunday in February and early-March: Dominican Republic Carnival celebrations and parades

    Hawai’i

    Last weekend in January: Ala Wai Challenge in Honolulu, Hawaii, is a fun event featuring traditional Hawaiian games like spear throwing and an outrigger canoe race

    Last weekend in September: Na Wahine O Ke Kai is Hawaii’s annual international outrigger canoe race from the island of Molokai to Waikiki beach

    October 10, 2015: Ironman World Championships in Kailua-Kona, Hawaii – come to compete or come to watch and sip a piña colada

    Jamaica

    November 8-16: Jamaica Restaurant Week features tempting discounts at top restaurants in Montego Bay and Ocho Rios

    December 6: International Reggae Marathon / Half Marathon / 10K Run in Negril, Jamaica, where competitors “come for the run, stay for the fun”

    February 1-6: Bob Marley Week in Jamaica, celebrating the life and work of legendary reggae singer and activist Bob Marley during the week leading up to his birthday

    Mid-March: ArtWalk 2015 on the “Hip Strip” in Montego Bay, Jamaica

    April 3-6: The Montego Bay Yacht Club Easter Regatta in Jamaica features exciting, fun cruises and races

    April 6: Trelawny Yam Festival in Montego Bay, Jamaica, with a street festival celebrating yummy yam country

    Mid-June: Ocho Rios Jazz Festival in Jamaica featuring a week of world-class jazz music

    Early-October (dates TBA): Port Antonio International Marlin Tournament in Jamaica

    Los Cabos

    September-November 2014: Sailfish are biting like crazy in Los Cabos, but only for a couple of months, so get on it!

    September 2014-January 2015: Yellowfin Tuna season is in full swing in Los Cabos

    October 2014-April 2015: Whale migration season in Los Cabos means you can spot humpback, blue, grey and sperm whales as they cruise past the bay

    November 30-December 6: The annual Sabor a Cabo culinary festival returns for its 9th year in Los Cabos with events like Beer Fest, Wine & Art Walk, Celebrity Chef Dine Around and more

    November 2014-May 2015: Striped Marlin season is red-hot in Los Cabos, so you can catch the big one during your holiday or spring break vacation

    March 8-19: Los Cabos celebrates Festival of San Jose del Cabo, honoring their patron saint with a week of festivities

    March 20-22: Fred Duckett Challenge Golf Tournament in Los Cabos is one of the most anticipated golf events of the year on two world-class courses

    March 30: The Ironman arrives in Los Cabos with 50 available qualifying spots for the finals in Hawaii

    April 12-16: Los Cabos hosts the huge Rolex IGFA Offshore World Championship tournament – which set huge world records in 2014 for most billfish releases in three days

    July-October/November: Blue Marlin, Mahi Mahi and Black Marlin are biting in Los Cabos

    September: During sea turtle nesting season, participate in conservation efforts to protect nests, eggs and offspring in Los Cabos – a truly unforgettable family activity

    Vallarta-Nayarit

    Now-March 2015: Mahi Mahi are hot in Vallarta-Nayarit so get out your rod and reel and charter yourself a boat

    November 12-15: The 59th International Marlin & Sailfish Fishing Tournament takes place in the waters off Vallarta-Nayarit

    January-February: Whale-watching season in Vallarta-Nayarit is in full swing in Banderas Bay – book your excursion through Vallarta Adventures, the only company with a spotter plane to scout sightings

    March-May: Spanish Mackerel and Snapper are in season off the coast of Puerto Vallarta

    May-October: This is the time to fish for Tuna in Puerto Vallarta

    Other Caribbean Destinations

    February 16: Trinidad & Tobago Carnival kicks off with the pre-dawn celebration known as J'Ouvert

    June-August: Events for the Barbados Crop Over Festival, including calypso music and activities like Cohobblopot and the Grand Kadooment on August 3-4

    September: Curacao hosts the Southern Caribbean Gay Pride Week (a.k.a. the biggest pride celebration in the Caribbean!)

    TL;DR: There’s lots of cool events all year long in Mexico and the Caribbean. Reference the enormous list above when planning your next trip!

    • Events in Fall 2014
    • Events in January 2015
    • Events in February, March and April 2015
    • Events in May-December 2015
    • Events by destination
    • Events in Cancun and the Riviera Maya
    • Events in Cozumel
    • Events in Dominican Republic
    • Events in Hawaii
    • Events in Jamaica
    • Events in Los Cabos
    • Events in Vallarta-Nayarit
    • Events in other Caribbean destinations
    • *Note: this list is just a sample of all the cool things you could do while on your next vacation in Mexico or the Caribbean. It is by no means exhaustive and if you're looking for something specific, just let us know!