The Florida Keys are made up of 5 main keys that start at Key Largo, then 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.
Perfect For: Romantic Getaways | Honeymoons & Anniversaries | Fishermen | Scuba Divers
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.
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.
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.
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).
If you love animals or are traveling with children, you’re 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.
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
I wrote a whole blog on Little Palm Island because it’s just that special of a place. Little Palm Island is the only private island resort in the United States and an adults-only hotel, perfect for a weekend getaway, a honeymoon, or to celebrate an anniversary. With 30 suites that dot the perimeter of the island, every suite has a gorgeous ocean view. The resort just underwent a massive post-hurricane renovation and now features all-new cozy, romantic suites. The impeccable attention to every detail in its design is reminiscent of Ernest Hemingway and his era.
What you get when you book with Diego Travel:
The Islands of Islamorada are in the heart of downtown Islamorada, close to the best restaurants and shops. I toured them prior to completion and let me tell you, these luxury private villas are guaranteed to be the place to stay in the Florida Keys. Each 3-story private villa has 3 spacious king bedrooms with en-suite bathrooms plus a fourth bunk or twin room. 11 of the villas come with an elevator and the open floor plan with full kitchen, dining and living room look out to the ocean. Swoon!
The Palm Beach area owners were thoughtful in not only the interior design, but the exterior design and landscape architecture. Each villa has privacy from the others, while all guests can enjoy communal spaces like an open beach, pool, and the Ocean House bar. Soon to be completed will be a restaurant and a new area of smaller 1-bedroom beach villas. I can also help coordinate docking your boat at their private marina during your stay. You’ll have direct ocean access to get out there fishing early each morning!
This is the perfect chic destination to come with the whole multi-generational family, for an extended family vacation. Each unit has a two car garage and wash machine/dryer, so it’d be easy to stay for a month or longer. Heck, I think I might just move in.
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:
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:
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!
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.
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.
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!
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.