#SoooBoca, Home, Travel

Florida Keys Road Trip | 25 Things To Do and Places to Stay

#SoooBoca and Company Loves Islamorada and the Florida Keys

My husband and I had our first long weekend date away in Key Largo and Tavernier back in 1988 and of course we went fishing and spent time at Holiday Isle and the Tiki Bar. We have loved introducing our daughters Kylie and Alle to the Florida Keys to enjoy all the things we have from fishing, to sunsets to just chillin’ out and hanging with the fam.

1988 Holiday Isle – Islamorada

(Scroll to the bottom for show note links)

In the weeks that followed the storm the #SoooBoca squad helped coordinate a local fundraiser at Tim Finnegans in Delray Beach to raise over $25,000.00 to help those in need in the Florida Keys. In December, the mom of the #SoooBoca squad, that would be me, put together a video of some of our trips down to the Keys and shared it on Facebook, Instagram and YouTube to remind people to visit the Florida Keys, spend money there, charter a boat and support the local businesses.

Cue the fabulous Alina Davis!

Alina is an amazing human and fellow Realtor with Coldwell Banker Schmitt! As my little December video was up and out there Alina, who lives in Islamorada, started commenting on what was open, going to open, still closed and clearly has an amazing finger on the pulse throughout the Keys!

So I said “Alina, would you be game to do a Facebook Live interview with me via #SoooBoca and lets talk about all these places that are open and getting ready to reopen and the state of the charter fishing industry and what not”… and she said YES!

We picked our date and of course Alina being Alina says “Hey…do you want to interview Capt. Skip Bradeen of the Blue Chip Too from Whale Harbor in Islamorada? He can give everyone a great update on the charter boat fishing industry here and what is biting.” And that my friends is how we roll!

PS…Sailfish and yellow tail are biting and so are the sharks!

Disclosure: My husband Captain Andy gave me some great questions to ask Captain Skip!

Alina was beautifully situated with a gorgeous view of Whale Harbor and we just chatted up all things happening including events, updates on musicians, art, restaurants, hotels, motels, real estate, fish recipes and of course a great update from Capt. Skip!

Scroll down to see the big list of links that you can click on for information! 

We hope you will subscribe to the #SoooBoca YouTube Channel share our YouTube video with your friends on Facebook, Twitter, Instagram and your social media channels. We want to encourage people who are making vacation plans to include the Florida Keys in those plans. We do point out that areas of the Florida Keys and down in the lower Keys the recovery is still going on and to please be respectful.

PS…If fishing and diving are not on your agenda but you love to just explore, try new food, enjoy galleries, local artisan work and meet interesting people then just take a drive from Key Largo to Key West and stop along the way for lunch, to feed tarpon, enjoy the water views…casually drive via the Overseas Highway where you will travel over a variety of 42 bridges including the fabulous Seven Mile Bridge. Trust me on this one.


The Florida Keys is a special place and each key has a special place in the hearts of all that live and visit there. The one thing I know is the moment you cross the Dade/Monroe county line you truly become one with the Keys. I remember it distinctively on that very first trip and that I felt something shift when we entered into paradise found. If you have never been to any of the Keys make 2018 your year to vacation and fall in love with the Florida Keys. You can thank us later for this sound and sage advice!

By the way…Alina and I will be reaching out to businesses throughout the Keys for our February broadcast so we can shine some light. If you have a biz, event, opening, update or Valentines Day special please let us know by emailing #SoooBoca through the contact form here on the blog!

Great resources include many of the local Chamber of Commerce websites throughout the Florida Keys

Map of the Florida Keys

Islamorada Chamber of Commerce

Key Largo Chamber of Commerce

Marathon Chamber of Commerce

Key West Chamber of Commerce

Monroe County Tourist Development Council

Florida State Parks

 In our interview we mention:


Lazy Daze (Cook Your Catch)

Lorelei (Cook Your Catch)

Craigs Restaurant

Florida Keys Brewing Company

The OV 



Islamorada Fishing Club 

Mangrove Mikes in Islamorada

Snappers Key Largo 

Hotels and Accomodations

Cheeca Lodge

Amara Cay Resort 

Hilton Key Largo

The Moorings Village and Resort

Caloosa Cove Resort and Marina

The Chesapeake Beach Resort 

The Postcard Inn

Pelican Cove Resort –  Opening in February

The Caribbean Resort (March 2018)

La Siesta (March 2018)

Ocean Point Suites Key Largo (March 2018)

Hawks Cay Resort on Duck Key 

Ocean House 

Harbor Lights Motel / Fisher Inn Resort (March 2018)

(Please note if information is incorrect let us know and we will update immediately)

Music and Art is Happenin’ in the Keys! (January and February)

Second Annual American Legion Riders Coral Head Music Festival 

Pigeon Key Art Festival

Key West Food and Wine Festival

Key West’s Master Chefs Classic

Cocktails in the Stream: Life & Times of Hemingway in Key West and Cuba

Third Thursday Art Walk in Islamorada 

Old Road Gallery

Fishing in Islamorada and The Florida Keys

Captain Andy Bellisari with a huge Mahi

Whale Harbor Marina 

Florida Keys Outfitters

Cheeca Lodge Presidential Sailfish Tournament


Different charities including Coldwell Banker Schmidtt teamed up with The Ocean Reef Charitable Foundation for their “Hand Up” program .

Conch Scramble in Islamorada – Floating greens and golf balls! Coral Shores sports teams and Treasure Village Montessori School are beneficiaries

Charter Boats

Charter Boat – Early Bird ( Will Be Back at Bud N Marys in February 2018)


Information deemed reliable, not guaranteed and subject to change without notice. Please, Please, Please contact any references highlighted in this article directly  for the most current and updated information. Due diligence on the part of the reader, listener and video watcher is required:)

You may also like

Leave a Reply

Shopping cart

Shipping and discount codes are added at checkout.