How to Spend 3 Days Sailing in the Florida Keys

Lara Mega

Lara Mega - Head of Content

Last Updated: January 4, 2024

Hey there! I'm Lara, a passionate traveler who has spent several incredible days sailing in the beautiful Florida Keys. In this article, I'll share my top recommendations for making the most of your sailing adventure and ensuring an unforgettable experience in this tropical paradise.

If you've got some vacation time from work and either have your own boat or fancy chartering one, why not sail down to the stunning Florida Keys?

With its many coves and beaches, the Florida Keys is a great place to explore or simply hang out on your vessel and soak up the sun.

Whatever your plan may be, creating a robust itinerary is vital to make the most of your time. This guide will give you a head start on planning the perfect sailing trip!

From Biscayne Bay all the way down to Key West, it's time to prepare your itinerary and sail off into the sunset.

Day 1: Stop In Key Largo For Some Snorkeling And Seafood

Beginning in the Upper Keys, it is worth making a stop in Key Largo. As the name suggests, this is the longest section of the Keys.

Key Largo is well known for its glorious scenery and crystal clear waters, so you should take advantage of these conditions and get your snorkeling gear on.

You will find a wide array of exciting and exotic creatures, fish, and coral reefs below the surface. If you are feeling more adventurous, you can even take scuba lessons from any of the numerous PADI-certified instructors in the area and try a dive.

Then, top it all off by heading ashore and sampling the famous Key Largo seafood! Just try to resist the wine if you intend to sail on before you anchor for the night.

While Key Largo makes a great overnight stay, there's nothing more romantic than spending the night in Marathon, just a bit further south, and watching the sunset. Your island-hopping experience starts now!

Plus, the many sights and activities nearby will enhance this experience if you choose to explore in the morning.

Day 2: A Day of Relaxing On A Private Beach

Now that you have sailed to the middle keys, you can pass some time fishing, sailing and most importantly, relaxing. Explore Duck Key island and try swimming in the bluest water you've ever seen.

The Keys are full of secret beaches and coves just waiting to be discovered by adventurous sailors! You might even find an empty beach on one of the islands where you can while away a day in peace.

Whether you are fishing or just lounging in the shallow areas of the turquoise waters, see how many fish and birds you can spot, and let the beauty of the beaches soak in.

Or, for a more active adventure, hop onboard and sail your boat into the ocean to discover the incredible life further off-shore. The coral reef that mirrors the Florida Keys is the only living coral barrier reef in the continental US.

Day 3: Sail Around the Lower Keys and Visit Key West

South of the Middle Keys, you can cruise by Big Pine Key and Sugarloaf Key, Fl. Enjoy this time cruising and taking in the views. Then, arrive in the stunning Key West.

No Florida Keys sailing trip would be complete without at least a quick stop in Key West. This is the most popular Key island and it's not hard to see why!

At this southern tip of the US, you feel at the edge of the world. Drop anchor and soak in the stunning Lower Keys. If time permits, take this chance to discover the most western point of the Keys, Dry Tortugas.

Dry Tortugas is a national park located about 68 miles west of Key West in the Gulf of Mexico. Here, you will find Fort Jefferson and seven small islands. This is a hidden gem in the ocean and well worth the journey.

Then, when you're ready, let the wind take you home and cruise back to your everyday life.

Hopefully, this suggested sailing itinerary has inspired you to get some sailing instruction and start planning the perfect vacation!

Most Recommended Thing to Do

John Pennekamp Coral Reef State Park

Top Choice Hotel

Playa Largo Resort & Spa

Our Top Choice Restaurant

The Fish House Encore

Our Top Choice Bar for Nightlife

Mariners Club Key Largo

Best Time to Visit

Warm weather, clear skies, and beautiful sunsets prevail.

Average Temperature

The average temperature in Key Largo, USA is warm.

Transportation Options

Car rentals, taxis, shuttles, bicycles for transportation in Key Largo.

Average Cost ($, $$, $$$)


My Top Recommendation

Key Largo, located in the United States of America, is a tropical paradise that offers a multitude of exciting adventures for every traveler. From pristine beaches to vibrant coral reefs, this city promises an unforgettable escape from the mundane.

Indulge in the sparkling turquoise waters and immerse yourself in the captivating underwater world by embarking on a snorkeling excursion to the magnificent John Pennekamp Coral Reef State Park. Alternatively, bask in the sun on the soft sands of Cannon Beach, feeling the warm embrace of the gentle ocean breeze. With breathtaking natural wonders, Key Largo is the perfect destination for those seeking tranquility and adventure all in one place.

What You'll Need to Bring

  1. Valid passport or identification
  2. Comfortable walking shoes
  3. Swimwear and beach accessories
  4. Sunscreen and hat
  5. Camera or smartphone for capturing memories
  6. Personal toiletries and medications
  7. Cash or credit cards for purchases and emergencies
  8. Lightweight and breathable clothing for warm weather
  9. Snorkeling gear, if interested in exploring underwater beauty
  10. Travel guidebook or map for navigation purposes.

What Not to Miss

  1. John Pennekamp Coral Reef State Park
  2. Key Largo Fisheries Backyard Cafe
  3. Florida Keys Wild Bird Rehabilitation Center
  4. Dagny Johnson Key Largo Hammock Botanical State Park
  5. African Queen Canal Cruise

What to Avoid

  1. Crowded tourist spots
  2. Overpriced souvenir shops
  3. Subpar seafood restaurants
  4. Rush hour traffic
  5. Expensive parking fees
  6. Tourist traps
  7. Public transportation during peak hours
  8. Unsafe neighborhoods
  9. Overbooked hotels
  10. Limited dining options for vegetarians/vegans

Get Your Vessel Ready For The Trip

A three-day trip might not sound like a lot, but without the proper preparation, you could find yourself spending more time messing around with your ship than actually enjoying yourself!

If you live outside of Florida but cannot transport it yourself, you can transport your yacht with Cross Chartering, which can move it from one location to another hassle-free. This will save you time and hassle.

Then, there are a few things you need to do to ensure smooth sailing:

Pack adequate clothing:

It will likely be hot and humid regardless of when you set sail (most of all from June to November). So, pack suitable clothing to make your trip comfortable. This includes correct footwear for the boat, hats, light clothing, and a few dressier outfits for when you eat out.

Stock up on essential supplies

Food, water, and fuel are the three main essentials. Ensure you have plenty of all three, so you don't get caught short.

Bring some additional entertainment

Although you will be occupied for most of the journey, you should pack your Kindle or tablet for those times you want to unwind.

Pack a well-stocked first-aid kit:

Accidents can and will happen when cruising on a ship, so keep a well-stocked kit on hand for emergencies.

Ensure your radios and safety devices are working:

Before you push off, you need to be sure your radios work and all the appropriate safety gear is aboard and in good condition.

Things To Add To Your Florida Keys Itinerary

Now you have your boat stoked and ready, it's time to plan what you will do.

Before planning a multiday Florida Keys sailing trip, decide what you want to achieve. If you are going for pure relaxation, you can spend most of your time aboard your ship.

Conversely, if you plan to take in the sights of the main islands, you should plan ahead to book space at a jetty.

Regardless of what you intend to do, you must ensure your ship is in tip-top shape and has everything you need for the adventure.

Now, let's work through a hypothetical 3-day itinerary for the Florida Keys sailing.

Frequently Asked Questions Relating to Sailing in the Florida Keys

Let's take a look at the most frequently asked questions relating to sailing in the Florida Keys.

What are the main national parks in Key Largo?

When sailing to Key Largo, it is worth stopping at the National Marine Sanctuary National Park. John Pennekamp Coral Reef State Park is also located in Key Largo, and Everglades National Park is just a short drive away.

How do you spend a day in Key West?

Key West is the most popular of the Florida Keys. While in Key West, you can visit the southernmost point of the continental US, enjoy the crystal clear water, visit Ernest Hemingway's house across from the lighthouse, and bar crawl along Duval Street.

Is Key Biscayne one of the Florida Keys?

Although it has "Key" in its name, Key Biscayne is not geographically part of the Florida Keys. Rather, it is a barrier island located in Biscayne Bay, north of the Keys. If you stop here on your way to the Keys, jump on land and check out Coconut Grove and Miami.

Should you take sailing classes before you charter a boat?

It is not actually a legal requirement to have a license or complete any sailing courses in Florida. However, it is advisable to take sailing classes at a reputable sailing school before you embark on a sailing vacation in the Florida Keys. Having prior sailing experience will make the experience safer and more fun.

Summing Up: How to Spend 3 Days in the Florida Keys

So, if you're sailing to sunny Florida, why stop at Fort Lauderdale or Miami Beach when you can head on down to the picturesque Florida Keys?

It is undeniable that the Florida Keys is one of the most beautiful spots in the continental United States. From Key Largo, past Duck Key, and all the way down to Key West, Fl, this part of the world is truly spectacular.

So, charter a boat, head over to the sailing school to develop your skills, and hit the ocean! While sailing classes are not mandatory, they will provide tips to keep you safe and well.

Then, it's time to start cruising the Keys. Have a great time in Florida and sail safe!