This was my first trip to the Florida Keys...my husband wanted to go diving and I decided to join him. The dive sites are close to land so it is easy to combine scuba with one of the many other activities the Keys have to offer. Depending on what part of the Keys you want to visit, you can fly into Key West or Miami. I wanted the full Keys experience, so we flew into Key West and out of Miami and rented a car.
The Key West airport is small and even during COVID, there were 2 flights landing at the same time. That overwhelmed the system, so flying into Key West requires some patience. The line to pick up a rental car was long and the agents were on "island time" so it can take a awhile. Masks are required in the airport, but the small space made social distancing difficult. Somehow in that small space, they found room for a bar (in between the door and the baggage claim carousel). Key West begins the party as soon as you are off the plane.
Key West is known for being the Southernmost point in the U.S. and Key West is closer to Havana, Cuba than it is to Miami. Key West has a lot of history and you see lots of beautiful old buildings driving into town. As you get closer to Mallory Square and Duval Street, you also see a lot of bars and clubs :) I would say most people who visit Key West go for the party scene. There are lots of hotels and bed and breakfasts within walking distance from the main areas of Key West. It is nice to not have to drive...or pay for parking which can be very pricy. Many people think there are great beaches in Key West---a few hotel properties have private beaches and there are a few public ones, but they do not compare to the beaches of other parts of Florida like Miami, Ft. Lauderdale, Naples or St. Petersburg. If you are looking for a beautiful beach, Key West is not the best fit (public beach photo below).
There is only main road in all of the Keys, so it is easy to find your way. As we headed north, the crowds thinned considerably. The scenery is beautiful in between towns. There are lots of bridges, including one that is 7 miles long....called 7 mile bridge (so creative!). It is also possible to bike up and down the Overseas Highway (US Route 1), although some points just have a small bike lane next to car traffic (other places have a dedicated bike trail off the main road).
We stopped at Isla Bella Resort in Marathon for a quick tour. This resort opened in 2019 and brings luxury to an area of the Keys that hasn't had it before (at least without having to take a boat to the resort). Isla Bella sits on 24 acres of land and offers beautiful rooms and 1 to 5 bedroom suite options. They are also pet friendly and have their own (small) dog park on-site. There are lots of options for spending time outdoors and the resort grounds feel like a botanical garden...super relaxing.
About 45 minutes further north is Islamorada, a town known for sport fishing. There are lots of options for restaurants, shopping and places to stay in Islamorada (along with a Publix grocery store). As you drive into town (which is actually quite large), you can only see the ocean as you go over bridges....the rest of the road is built up. Turning onto a small street, brought us to our stop at Cheeca Lodge. Cheeca has been around for decades and they have a history of welcoming many very important guests, including presidents. The vibe is luxury, but also has sort of a camp feel. There are several pools, a golf course (9 hole), tennis, pickleball, volleyball and basketball courts, tons of watersports, the longest pier in the Keys for fishing (or admiring the scenery) and bikes for exploring. We saw lots of families and the resort is very kid-friendly. Checca Lodge also has one of the larger beaches in the Keys. The sand is coarse (no powder soft sand here) but there are beautiful sunrise views.
Key Largo is the Northernmost Key and is about 30 minutes from Islamorada (depending on traffic). Key Largo is also well developed so you can't see any of the beautiful scenery from the road, but just a minute off the road on either side give you views. Key Largo's most famous spot is probably John Pennekamp State Park...the country's first underwater park. You can snorkel, dive or take a glass bottom boat. There are also a few walking paths through the mangroves on a boardwalk. The sunset views are great at several restaurants in Key Largo (many have lots of outdoor seating). We chose to charter a boat with a some friends so we could see the mangroves and see the sunset from the open water. We were 6 people in total and the price of chartering our own small boat was about the same price as paying for 6 people to join a larger sunset sailing. Having a private experience was so much better...there are lots of boats offering this option (or options to go out snorkeling during the day).
Key Largo has lots of options for lodging, including The Bungalows. They are one of the few all inclusive resorts in the United States. They are an adult only property and have several options for dining and drinks. Key Largo also has several larger resorts, like the Marriott Key Largo, where you can snorkel right from the hotel beach. Plenty of options and Key Largo is only about 1.5 hours from Miami.
I am happy to plan your next trip to the Keys. Please message me to get started.
Tracey is the owner of Unraveled Travel and has traveled to every continent except Antarctica.