Florida Keys for the first time

Question

My wife and I are planning a trip to the Florida Keys sometime within the next year. We're currently deciding between two timeframes:

- February/March, or

- Around our anniversary on June 22nd.

Regardless of when we go, we'll fly into Miami and drive down to the Keys.

I'm a first-timer, and my wife hasn't been in over 20 years, so we're looking for recommendations on where to go and what to see.

We plan to visit Key West, but we've decided that we won’t be staying there. Instead, we're thinking about staying in Marathon and exploring from there. We've liked what we seen on the website for Tranquility Bay Resorts.

Anything you could also recommend would be helpful.

Answer

The Florida Keys are a fantastic destination for a first-time visit, and staying in Marathon gives you a nice central base to explore both the Upper and Lower Keys without the hustle of Key West’s crowds. Both February/March and late June are popular times to visit, but there are some differences to consider.

Weather-wise, February/March is cooler and drier, with average highs around 75–80°F, making it ideal for outdoor activities like snorkeling, kayaking, or biking. June is hotter and more humid, with highs in the upper 80s to low 90s, and it is the beginning of hurricane season, which could bring occasional rain showers and tropical storms.

Staying in Marathon at a resort like Tranquility Bay is a great choice. It’s a peaceful location with beach access, pools, and easy access to local restaurants. From Marathon, you can explore Key West, Islamorada, and the Lower Keys without long drives each day.

Key West day trip: Drive down the Overseas Highway, enjoy the scenic views, and spend the day exploring Duval Street, Mallory Square, and the southernmost point. Even if you don’t stay overnight, you can catch sunset celebrations and visit a few museums or historic homes.
Snorkeling & diving: Marathon has great options for both. Sombrero Reef and the Florida Keys National Marine Sanctuary offer guided snorkeling tours. You can also do a glass-bottom boat tour if you prefer to stay dry.
Wildlife encounters: Visit the Turtle Hospital in Marathon, or stop at the Dolphin Research Center in Grassy Key. These are unique, hands-on experiences.
Islamorada: Only about 30 minutes north of Marathon, known for art galleries, fishing, and the famous Robbie’s Marina where you can feed tarpon.
Beaches & relaxation: Sombrero Beach in Marathon is great for a quiet afternoon swim and sunbathing.

Other tips for your first visit:

Plan Key West for a full day to make the drive worthwhile; leaving early will help you avoid traffic.
Bring sunscreen, hats, and light layers. February/March might be cooler in the evenings, while June will be hot and humid.
Consider booking popular activities like snorkeling, glass-bottom boat tours, or the Turtle Hospital in advance, especially in peak season.
Explore the smaller keys along the way, like Big Pine Key for the Key deer refuge, which is unique and interesting for a short stop.
Dining: Marathon and Islamorada both have excellent seafood restaurants, but also check for casual spots and local Key lime pie!

Overall, February/March is the safer bet for weather and comfortable exploration, while June is more likely to be hot and humid with some risk of storms, but it may be less crowded and more budget-friendly. Either way, Marathon offers a central, relaxing base with easy access to the entire Keys.