The Ultimate Islamorada Experience Giveaway

The Ultimate Islamorada Experience Giveaway

Islamorada Times is 100K strong on Instagram! To celebrate our awesome followers and the online community we’ve created together, Islamorada Times is giving one lucky winner and their family or group the chance to experience the absolute best Islamorada and the surrounding Keys has to offer. Our Ultimate Islamorada Experience Giveaway includes a one-week stay complete with complimentary dining and activities. Total package value is 4200.00.

Islamorada and Key Largo are the island gems of the Florida Keys. Equidistant between Miami and Key West, our fishing towns boasts some of the best restaurants and outdoor/water sport activities. From fishing to paddle boarding to happy hours, beach-goers, families, adventures and everyone in between will be thrilled with Islamorada and Upper Keys offerings.

We’ve teamed up with the best of the best in Islamorada and Key Largo to offer what we believe to truly be The Ultimate Islamorada Experience. Thanks to our partners, the package includes:


One-week stay at a single family home in the beautiful, gated Angler’s Reef community. Amenities include: 2 bedrooms, 2 ½ baths, resort style swimming pool, private beach and marina. Provided by Islamorada Waterfront Rentals.

Anglers reef 1


Day passes and a dining experience at Baker’s Cay Resort Key Largo. The Resort offers a prime location that’s just the right amount of being-away-from-it-all, this luxury resort lends itself to unforgettable beach experiences. Provided by Baker’s Cay Resort Key Largo.

Breakfast or lunch at the Hungry Tarpon waterfront restaurant. One of the coolest waterfront restaurants to enjoy a great meal. Provided by Robbie’s Marina.

Robbies 7

Enjoy a dining experience at one of the following restaurants: Mia Cucina, Nikia Sushi Lounge, Tiki Bar, or Atlantic’s Edge – all located at the legendary Cheeca Lodge. See the History of Islamorada through the iconic pictures that line the walls of the lobby and take a stroll on the famous Cheeca Fishing Pier. Provided by Cheeca Lodge & Spa.


A dining experience at Sundowners to enjoy an amazing waterfront lunch or dinner. Sundowners Key Largo features one of the most impressive dining and entertainment experiences in The Florida Keys. Provided by Sundowners.

Enjoy a dining experience at the Postcard Inn’s Ciao Hound Italian Kitchen featuring authentic Tuscan flavors with fresh Keys sourced ingredients. Provided by The Postcard Inn.


Half Day Fishing. Captain Regina specializes in Reef Fishing. She is a top notch Captain and is fun to be with and always goes the extra mile to make sure your experience is unforgettable. Enjoy great company and fantastic fishing with Size Matters Fishing Charters. Two shirts, two hats and two koozies included as well. Provided by Size Matters Fishing Charters.

Snorkeling trip on boat Blue. Jump into the water and into some fun with a snorkel tour in the Florida Keys! Come aboard our boat Blue for one of our two daily snorkel excursions, 10 a.m. or 1:30 p.m., or a sunset cruise on Wednesday, Friday, or Saturday. Don’t forget to feed the tarpon while you’re there! This famous attraction is a must-see while visiting Islamorada. Provided by Robbie’s Marina.

Paddleboard Tour. Stand up paddling in the Florida Keys is some of the best paddling in the world offering calm conditions, crystal clear warm waters, and an incredibly rich ecosystem above and below the surface. Provided by Otherside Boardsports.

One tandem kayak for you to use during your week stay in Islamorada. Kayak can be conveniently launched and stored at the private beach just steps away from your house in Angler’s Reef. Provided by Paddle The Florida Keys.


How to Enter:

Contest entry is super simple! Follow these easy steps for your chance to win:

  1. Follow Islamorada Times on Instagram
  2. Follow Islamorada Times on Facebook
  3. Tag 3 friends in the comment section on our contest post on either Instagram or Facebook

Rules and Requirements:

Accommodations & Travel:

Ultimate Islamorada Experience is valid for up to 4 people. Winner must be over 25 years of age and supply Proof of ID, per Islamorada Waterfront Rentals rental agreement. Winner will be required to sign a rental agreement that includes a fully refundable $1000.00 deposit. Stay must be used from September 1 to November 15 in 2020 and based on availability; week stay will be Saturday – Saturday. Winner will work with Islamorada Times staff to coordinate booking. Airfare, rental cars, or travel expenses to and from Islamorada are not included.


Dining experiences at Robbie’s Marina, Sundowners, Ciao Hound, Cheeca Lodge, and Baker’s Cay are limited to the amounts provided on the gift certificates that will be given to the winner. Tip is not included – please be sure to tip your servers!


Winners will agree to and abide by all rules, regulations, waivers and safety requirements set forth by participating companies. Tip is not included – please be sure to tip your captains & tour guides!

Social Media:

All entrants must be 25 years of age or older to enter due to rental agreement requirements. This contest is no way affiliated with or sponsored by Instagram or Facebook. Entrants release Instagram, Facebook and Islamorada Times from any and all liability related to contest, travel, accommodations or activities included in the prize. All rules must be followed for an entry to be considered complete and valid. Only one entry per person will be counted. Winner will be randomly selected from entrants. Prize is non transferable, only redeemable by chosen winner. proof of ID required.

Winner will be chosen randomly on February 14, 2020, Valentine’s Day.