We Are Still Celebrating Down Here…Join US!

Welcome in the New Year with KeysCaribbean Luxury Resort Villas & Marina

Upper Keys


Jan. 4, 2018 – Jan. 14, 2018
Uncorked … the Key Largo and Islamorada Food & Wine Festival
305-522-1300  Website
The 10-day food, wine and spirits showcase features 30-plus savory events to please virtually every palate and budget, spread among numerous Upper Keys venues with fresh, locally sourced seafood and international-style dishes. The festival’s outdoor ‘A Grand Tasting,’ is set for Jan. 14. What better reason to ‘Uncork’ and unwind in the Florida Keys. For a complete events schedule, visit website.
Jan. 12, 2018 – Jan. 14, 2018
Sixth Annual Baygrass Bluegrass Festival
Featuring several great Oldgrass, Newgrass and a blend of next generation Bluegrass as well as some tasteful variations of the genre. Tickets to be available in advance online and at the gate. Monies raised help fund music, dance and art scholarships for local students; main event is located at the ICE Amphitheater, MM 87 bayside at Founders Park. Other weekend musical activities are to be planned. Attendees can bring blankets and lawn chairs, but coolers are not permitted. Food and beverages available for purchase.


Jan. 13, 2018 – Jan. 15, 2018
Island Boat Show & Festival
Bob Phelps 239-691-3290 Website
All the top boat brands will be featured at the Island Boat Show, being held at the Island Christian School campus at MM 83. Come enjoy a great show with loads of boats, auction items, food, vendors featuring a variety of merchandise, great fishing seminars presented by local captains… all at a very reasonable $10 admission. Hours are 10 a.m. to 6 p.m. Sat & Sun., 10 a.m. to 2 p.m. Monday. A silent auction and fishing seminars hosted by Captain Rich Tudor, co-host of Saltwater Experience, and other Keys captains, round out the weekend.

Jan. 13, 2018
35th Annual Art Under The Oaks
305-360-8556  Website
Fine art & original crafts, a variety of entertainment, specialty food booths, children’s arts & crafts, as well as a raffle of items donated by the artists are part of the annual highlights. San Pedro Church Gardens, 9 a.m. – 4 p.m., Mile Marker 89.5 on Plantation Key in Islamorada. Onsite parking is available for a $5 donation. Free parking is available at Coral Shores High School, with shuttle service to the event.


Jan. 16, 2018
Florida Keys Concert Association presents: Throwback
This prize-winning Barbershop Quartet, led by Sean Devine, brings together an infectious energy with a love of yesterday’s music. Based in Florida, they have performed to great acclaim from Alaska to New York. All Islamorada Concerts are at Island Community Church @ 7:30 PM, 83250 Overseas Highway, Islamorada, FL 33036 (MM83). Tickets available online.

Middle Keys

Jan. 13, 2018
2018 Bar Olympics to Benefit the Florida Keys SPCA
305-743-4800 Register  Website
Do you have the best bar tending or service team at your bar or restaurant? Can you make the best original cocktail? This Olympic season, in addition to having fun while helping support a Keys local animal shelter, the winning bar or restaurant team of the Winter Bar Olympics at the Lighthouse Grill at Faro Blanco Resort & Yacht Club will take home gold metals and bragging rights for all of 2018. In addition to the main event, from 11 a.m. to 4 p.m., there will be games and challenges for pets and owners to participate in including a tennis ball lottery, red light green light and kissing contest!. With celebrity judges, shelter dog kissing booth, 50/50 raffle, silent auction and more!

Jan. 15, 2018
Florida Keys Concert Association presents: Throwback
This prize-winning Barbershop Quartet, led by Sean Devine, brings together an infectious energy with a love of yesterday’s music. Based in Florida, they have performed to great acclaim from Alaska to New York. show starts @ 7:30PM at the Marathon High School, 350 Sombrero Road, Marathon, FL 33050 (MM50). Tickets available online.

Lower Keys


Dec. 19, 2017 – Jan. 13, 2018
Red Barn Theater presents: Dancing Lessons
Box Office 305-296-9911 Website
Evers, a man with Asperger’s Syndrome, seeks the instruction of a Broadway dancer to learn enough dancing to survive an awards dinner. The dancer, Senga, is, however, recovering from an injury that may stop her career permanently. As their relationship unfolds, they’re both caught off guard by the discoveries…both hilarious and heartwarming…that they make about each other and about themselves. Featuring Carolyn Cooper and Dave Bootle. Show times and tickets online. Red Barn Theater is located at 319 Duval St.

Dec. 26, 2017 – Jan. 13, 2018
Key West Theater presents: Hedwig and the Angry Inch
305-985-0433 Website
Brilliantly innovative, heartbreaking, and wickedly funny. Hedwig & The Angry Inch is a genre-bending, fourth-wall-smashing musical sensation, with a pulsing score and electrifying performances, telling the story of rock-n-roll lead singer Hedwig, one of the most unique characters to ever hit the stage. Broadway choreographer Andrew Palermo is deep in rehearsal directing and choreographing Hedwig and the Angry Inch at the Key West Theater, which stars Phillip Cole White as Hedwig, Alexandra Zeto as Yitzhak, and members of Patrick and the Swayzees as the band “The Angry Inch.” Showtimes and tickets online.
Jan. 1, 2018 – Aug. 31, 2018
Key West Fishing Tournament
Doris Harris 305-923-5934  Website
More than 40 species of fish are targeted during these months, with divisions for men, women, junior anglers (ages 10 to 14) and Pee Wees (under 10 years old). The Key West Fishing Tournament strongly encourages the release of game fish. All participating anglers receive certificates noting their catches and qualify for a variety of prizes.

Jan. 2, 2018 – Jan. 29, 2018
Christopher Peterson’s EYECONS
Tickets 305-296-6706 ext 4 Website
A master of impersonations, both visually and vocally, with impeccable comic timing. The show is all LIVE, no lip-sync. Thrill to his parodies of Marilyn Monroe, Carol Channing, Madonna, Joan Rivers, Reba McEntire, Bette Midler, Tina Turner, Julie Andrews, Barbra Streisand, Liza Minnelli, Judy Garland, Eartha Kitt, Cher, Bette Davis, Lucille Ball, even Lady GaGa. Show dates are online. Show times 9 p.m., at La te da 1125 Duval St.


Jan. 11, 2018 – Jan. 14, 2018
36th Annual Key West Literary Seminar
888-293-9291 Website
The 2018 topic is “Writers of the Caribbean.” Literary aficionados from around the world are to gather for readings, discussions and lectures led by some of contemporary literature’s most acclaimed writers. The island nations of the Caribbean have produced some of the most powerful and exciting writers of our time. For the 36th annual Key West Literary Seminar, we look across the waves to the vital literature that has emerged from this region.

Jan. 11, 2018 – Jan. 14, 2018
Key West Kingfish Mayhem
Jimmy Wickett 954-605-8284  Website
Big fish, big money! Come fish for some of the largest kingfish in Florida Keys waters in this new tournament. Fishing headquartered at Stock Island Marina. First prize could earn $15,000 cash, based on a 50-boat field.

Jan. 12, 2018 – Jan. 13, 2018
58th Annual Key West House & Garden Tours
305-294-9501  Website
Tour elegant and unique private homes of Key West, ranging from exquisite restorations to creative renovations, and the interior design that complements each. January tours are offered 3 to 7 pm each day. Transportation between homes is available via Conch Train for $40 each, seating is limited. Tickets without transportation are $30 in advance and $35 on tour days. Proceeds benefit the foundation’s Oldest House Museum, grant and scholarship programs.

Jan. 13, 2018
Key West Classic Regatta aboard Schooner America 2.0
646-772-4880 Email Website
The Key West Classic Regatta is designed after the Great Chesapeake Bay Schooner race and is a great way to see some of the most beautiful Key West schooners in their element. It is time to jump aboard and take an adventure on Key West’s most stunning sailboat, the 105-foot Schooner America 2.0 and be a part of this annual festivity! So, all hands on deck! Join us as we push off the dock at 10:30 AM for race start! America 2.0 features beautiful teak decks, mahogany-trimmings, and with 3,600 square feet of canvas, she flys! Sit back and relax while she plies effortlessly through the crystal Green Key West sailing waters towards the finish line!

Jan. 13, 2018 – Jan. 14, 2018
13th Annual Florida Keys Seafood Festival
Caitlin 813-362-9555 Website
A family-friendly event with local fresh Keys seafood, drinks, marine-related crafts, youth activities, and live music. $5 admission per person; hours open from 11 a.m. – 8 p.m. on Saturday; 11 a.m. to 5 p.m. on Sunday, at Bayview Park, Truman Avenue and Jose Marti Drive.


Jan. 13, 2018 – Jan. 14, 2018
14th Annual Nautical Expo
305-872-2411  Website
Admission and parking at this event are free, held at the Lower Keys Chamber of Commerce grounds, MM31, from 8AM to 2PM. Find steals and deals on everything imaginable for boating, fishing, diving and more, from nearly 200 vendors. Crafts, food and beverage, live music and entertainment round out the two-day event.

Jan. 14, 2018
Key West Half Marathon & 5k Run
Barbara Wright 305-240-0727  Website
Recognized by Runners World magazine as one of the 10 great half-marathons of the winter season, the race follows a 13.1-mile course that includes Old Town Key West and the scenic waterfront. Now in its 20th year, the race typically attracts American and international runners to compete in Key West’s balmy January climate. Named as one of the United States’ leading winter half marathons in Runner’s World, February, 2014; the same magazine included in its list of Best Destination Half Marathons; in April, 2015; Bucket List Best Half Marathons, and most recently in December, 2015 was ranked among 13 must-do U.S. half-marathons by Competitor.com.

Stay With Us in the Florida Keys


KEYS CARIBBEAN LUXURY RESORT VILLAS & MARINAS  Whether you contemplate visiting the Keys for vacation or some of the many fishing and cultural activities going on all year around-

Anytime  you are in the Keys: Winter, Spring, Summer or Fall……  STAY WITH KeysCaribbean Luxury Resort Villas & Marinas IN OUR AMAZING PROPERTIES THROUGHOUT THE KEYS-

You will be glad you did…

In The Upper Keys: In Key Largo and Islamorada, where KeysCaribbean Luxury Resort Villas and Marinas has the exclusive location –Mariners Resort Villas & Marinas

In The Middle Keys: In the Middle Keys, KeysCaribbean Luxury Resort Villas and Marinas has the Village at Hawks Cay Villas on Duck Key, Indigo Reef Resort Villas & Marina and the Coral Lagoon Resort Villas & Marina vacation rentals in Marathon

In The Lower Keys: In the Lower Keys, KeysCaribbean Luxury Resort Villas and Marinas has the Coral Hammock Resort Villas and Kings Point Marina & Condominiums vacation rentals


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