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Diego Travel

The Florida Keys

Why Your Next Vacation Should Be in The Florida Keys
MARIA DIEGO

The Florida Keys are made up of 5 main keys that start at Key Largo, followed by Islamorada, then Marathon, then the Lower Keys and finally Key West. To drive from Miami to Key West takes about 3 hours, so all the Keys can be covered in one trip. The Florida Keys have had recent renovations to Little Palm Island and Cheeca Lodge & Spa and notable additions to the luxury hotel lineup over the last five years including Isla Bella Beach Resort, Tranquility Bay Beachfront Resort and The Islands of Islamorada.

Perfect For: Romantic Getaways | Honeymoons & Anniversaries | Fishermen | Scuba Divers

The Florida Keys Family Travel Guide

Getting There

SS Truman

Fly: From 1.5-3 hours by car from Miami International Airport MIA) or fly into Key West International (EYW). Alternatively all of the keys are accesible by private yacht or sailboat..

Recommended Stay: Weekend getaway to one week.

Elevation: 0 feet

Best Time of Year to Visit: March to November

The Florida Keys

What to do

The biggest misconception about the Florida Keys is that there are plenty of sandy beaches. I hate to break it to you, but there’s not! The Keys are all about getting out on a boat for fishing, snorkeling, cruises and exploring marine and wildlife. The nightlife can be pretty great too, if you visit at the right times of the year.

Snorkeling

From Key Largo to Key West, the dive spots in the Florida Keys are numerous and plentiful with fish and protected sea life. With dive spots like Hens and Chickens or Looe Key, your best bet is to go with a guide that can take you to a spot where you will see the most fish while snorkeling. Also, there are spots better suited for children if you’re traveling as a family. We also like taking stand up paddle boards with a few masks and snorkels and swimming in shallow areas in the bayside.

Fishing

There are seasons for catching lobster and certain types of fish, and they have to meet size criteria prior to catching them. The local Coast Guard will pull you over and check your cooler, measuring each and every fish – it’s happened to us on more than one occasion – so unless you’re an experienced fisherman with a boat in the Keys, it’s best to leave it to the professionals and hire a company that specializes in fishing while you visit. An expert fishing captain will be able to take you to the right spot whether bottom fishing or trolling, and the Keys is a whole lot of water to take a shot in the dark.

Sunset Cruises and Sailing

Another option if you’re not a huge fan of fishing is sailing or a sunset cruise. I am the black sheep in my family because I am the only one who isn’t a huge fan of spear fishing, free diving and line fishing. I usually stick to the boat, unless the water is over 80 degrees or I’m getting too sea sick from rough seas to stay on the boat. Then I go in for a swim. What I love most about boats is riding at sunset, especially on a calm day. If there’s one thing you shouldn’t miss while in the Florida Keys, is catching a sunset from either a boat or the view at Pierre’s or Morada Bay (more on that later).

Marine & Wildlife Sanctuaries

If you love animals or are traveling with children, youre not going to want to miss a visit to a Wildlife Sanctuary.  While there are too many to count, the Florida Keys Wildlife and Environmental Area offers a hammock forest, coastal rock and mangroves with hiking, cycling and paddling trails.  The Florida Keys National Marine Sanctuary in Key Largo and the Turtle Hospital in Marathon are two other must-sees and personal favorites.  Plus, each time you visit one of these places, the entry fee goes toward their maintenance costs so that you can help continue their mission.

Where to Stay in The Florida Keys

Isla Bella

Isla Bella Resort

Isla Bella Resort is a new property featuring 199 oceanfront suites. It’s very rare to find a resort with all ocean views, but Isla Bella did it beautifully. With a name meaning Beautiful Island, what more would you expect? The rooms and suites are spacious and airy, decorated bright white with accents of coastal blue. They come in a variety of options, from one and two-bedroom guest rooms to suites with a kitchenette, making an extended stay very practical. What I love most are the first floor rooms that have direct access to the oceanfront sand and pools. You have your own oceanfront porch where you can sit outside, read a book, and watch guests ride back and forth on the property bicycles. These ground floor options also allow for social-distancing, as you wouldn’t need to enter through common areas like the hallways or elevators.

Isla Bella’s property is large, with a “town square” area that consists of a large marketplace with a cafe, the spa, conference space, and retail shopping with the cutest beach and resort wear and any pool toys and floaties your kids might need. One of the coolest things about Isla Bella is its Watersports Activity Center. Like I mentioned earlier in the blog, if you haven’t gotten out on the water, then you haven’t experienced the Keys. Isla Bella offers all the water sports right there for your convenience with brand new boats, fishing equipment and even jet ski and kayak rentals. They are top-notch professionals and I highly recommend a stay here just to make use of this amazing water sports center.

What you get when you book with Diego Travel:

  • Priority upgrade to next room category at check in, subject to availability
  • Daily Full breakfast for up to two guests per bedroom, served in the restaurant
  • $100 Resort Credit, Per Stay
  • Priority early check In & late check out, subject to availability
  • Complimentary Wi-Fi

4th Night Free on Premium Rooms in the Florida Keys

Isla Bella Beach Resort & Spa is excited to extend Diego Travel clients a 4th Night Free Promotion, on select premium guestrooms & suites, valid for stays through December 19, 2024!

Ocean residences

Cheeca Lodge & Spa

Cheeca Lodge & Spa is one of the better known resorts in the Florida Keys and with good reason.  With an expansive ocean view, a 9-hole golf course, tennis courts, spa and now 5 pools, they make it easy and convenient.  The rooms vary widely from golf course view rooms to ocean-front suites, so tread with care and definitely use a travel advisor (that’s me!).  The in-the-know professionals know which rooms to ask for, with one suite in particular that stands out from the rest.  And no, I’ll never tell!  I reserve that suite for Diego Travel clients.  It’s also important to know that only the golf course view rooms are pet-friendly, so if you are planning on traveling with your furry family member, be sure to book this room. 

Cheeca Lodge & Spa recently purchased oceanfront casitas and bungalows, formerly part of The Moorings property.  These exclusive villas have their own pool, tennis court and beach (yes, actual beach!  On of the few real beaches in The Florida Keys and private too).  Two of these two-bedroom villas are beachfront, while the others are set back further on the property.  The great thing about these casitas is that guests have access to all of the amenities and restaurants at Cheeca, but guests at Cheeca do not have access to this area.  So, think of it as your semi-private VIP area but with additional resort amenities to enjoy like more pool options, golf, restaurants and of course the spa.

What you get when you book with Diego Travel:

  • Upgrade upon arrival if available
  • Daily complimentary breakfast for 2
  • $100 resort credit
  • Early check-in/late check-out
The Georgian Room

Where to eat?

Key Lime Pie

Let’s not beat around the bush and get straight to the good stuff – what the Florida Keys is best known for – key lime pie!  You may even want to taste-test your way down the Keys.  My kids and I are gluten-free, so I’d start my list with Key West Key Lime Pie Co.  They ship too!  Other Key West notables are Pepe’s Cafe and Old Town Bakery. 

Further up the Keys is a locals’ favorite at the Green Turtle Inn, and whether you’re getting the key lime pie on the menu or anything else, you just can’t go wrong.  They are the same owners of the nearby Kayo Grill and SushiKayo Grill and Sushi, that has The best sushi I have had in the Florida.  Back to key lime pie though…A final mention is either of Mrs. Mac’s Kitchen’s two locations near Key Largo.  The key lime pie is to die for!

Fresh Fish and Seafood

When you’re not eating dessert first, you may want to choose the catch of the day off of every menu.  Atlantic’s Edge at Cheeca for a fancier dinner with killer views or Islamorada Fish Company are two favorites for a fresh catch.  Some more casual, only-the-locals-go spots can be found at the Cuban restaurant Habano’s on the Creek (when you’re starving and coming back in from a fishing trip), Made 2 Order Cafe (another pull-up-in-your-boat for a quick lunch), or the Galley Grill between Key West and Little Palm Island. 

Restaurants With a View

If the view is what you’re after, which you should be in the Keys, then you can’t miss these spots.  Hit Morada Bay or Pierre’s for their monthly Full Moon party – it falls on the Saturday nearest to the full moon of each month.  With a sunset view and an area of sand to party post-dinner, you can’t miss this monthly event.  Latitudes at the Westin in Key West has beautiful sunset views as well.

A Few of My Favorite Things

The Florida Keys

The Florida Keys is different for everyone. Depending on if you want a resort that you land at and never leave, or your prefer to venture out and spend little time at your hotel, will determine the area that is right for you. My family has had a home in the Florida Keys for 15+ years, so the amount of time I’ve spend exploring each Key gives me an advantage while planning travel that is perfect for you.

Islamorada of The Florida Keys

My family’s home is located just north of Islamorada, in Tavernier. Islamorada happens to be my favorite spot in the Keys, just because I like the combination of bayside and oceanside boating there, and the array of top-notch restaurants and fun little shops. I’ll never forget bumping into Martha Stewart at Ocean Gardens where you can find Hemingway-era nautical antiques and a vast collection of hard-to-find shells. My dad wasn’t shy and struck up a conversation with her about the Florida Keys and what she loves about visiting. She told us that Ocean Gardens is always a must-see, so there you go!

Location

Key Largo is about one hour south of the southern most part of Miami, while Key West takes a full 3 hours to reach. So to drive from the northern-most key to the southern-most key takes about 2-2.5 hours, depending on traffic. The roadway is a 2-way lane, so holiday weekends can see traffic back up for hours. Locations are described by the locals as being at Mile Marker “__”, with the Key West starting at Mile Marker 0 and working its way up. So when you stop to ask for directions and you’re told, it’s at MM 87, you’ll know in which direction you need to head. It’s only North or South in the Keys!

Activities

Aside from the daytime activities I already listed, you can’t miss watching a sunset with a live band playing in the background. The Keys food is known for being fried, unhealthy, and yummy, and the drink menu plentiful. So plop yourself down at a bayside restaurant somewhere along the strip (my favorite is Pierre’s, at MM 82), order a drink, and relax. It’s also the perfect spot for a small destination wedding, which I can help you plan! Other activities I love to do with the kids is feeding the tarpon at Robbie’s, visiting the Turtle Hospital in Marathon  and Theater of the Sea for swimming with the dolphins and educating them about marine biology.

Beyond The Keys

Because of our network, Diego Travel clients get added amenities to many of the Florida Keys hotels and resorts. Depending on whether it’s your first time or tenth time to the Keys, we’ll make sure to plan your stay based on your needs. We love to combine a trip to the Florida Keys with Miami, the west coast of Florida with stops at places like Marco Island, Naples, or Captiva, or even a visit to the Happiest Place on Earth at Disney World in Orlando. Contact us to help plan your next Florida vacation to elevate your experience, VIP your travel, and make the most of your time at each destination.
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Related Posts

Hotel Review: Little Palm Island

Hotel Review: Isla Bella Beach Resort