Top 7 Best Florida Keys Sailing Tips

Sailing is a great way to increase your alertness and has many emotional and physical health benefits. Whether you’re new to sailing or are a seasoned sailor, I have gathered some awesome information you need to sail the Florida Keys.  

If you want to know my best sailing books recommendations check this post out!

1. The Off-Peak Season Can Save Lots of Money

From chartering a boat to finding places to eat, everything is more expensive during peak season. While this isn’t surprising as it follows the basic law of supply and demand, it can certainly work in your favor. Knowing the best time to sail the Florida Keys will ensure you get the best deals everywhere you go. 

The off-peak season for the Florida Keys is from March through November. During this time, you can expect to see many deals on places to stay, boats to charter, and fun things you want to do on the trip. 

If you plan to stay in hotels around the Keys, taking the trip during the off-season will save you a lot of money. Budgeting is an important part of any trip, and saving enough money can mean more trips in the future. So, make sure you consider sailing during the off-peak season.

2. Charter a Boat To Reach More Destinations

While sailing the Florida Keys, you may consider stopping along the way to stay at hotels. This is a valid choice, but it can really slow you down. If you want to see as much of the Florida Keys as possible, consider chartering a boat. 

This way, you can have everything you need right there. You can get a boat that comes with lodging, a kitchen, a crew, and even a chef to cook for your group. Without worrying about where to eat and sleep, you can spend a lot more time deciding on the cool places to visit instead. 

While crew members and larger charter boats aren’t cheap, always compare the cost to staying at hotels throughout the Florida Keys. You may save some money by chartering your own boat rather than paying for places to stay. You can also save money by making your own food on the boat rather than consistently eating out. 

Chartering a boat during your visit gives you much more control over all the aspects of your trip. 

3. The Florida Loop Route

One of the most important tips for sailing is to always know where you’re going. This will prevent you from getting lost or running into trouble.

Sailing is a fun and relaxing activity, but it can be dangerous if you don’t know where you are or where you’re going at all times. 

If you’re planning on sailing the Florida Loop, it’s especially crucial to keep your bearings. This route (also known as Smuggler’s Run) travels from the St. Lucie canal, south past Miami, and then loops around Key West.  

From that point, it makes a northward turn, toward Cape Coral and the mouth of the Caloosahatchee River. It then follows the river into the Caloosahatchee Canal and through to Florida’s east coast via the Mayaka Cut.

That said, most folks follow this route in a counter-clockwise direction, as the Gulf Stream current pushing against the bottom portion of Florida (and the Florida Keys) moves eastward. Fighting against this current by starting your journey near the Mayak Cut (instead of traveling south out the Caloosahatchee River) can be challenging.

If you’re not prepared to tackle the Florida Loop, either with navigation tools or an experienced guide, you can quickly end up drifting out to sea while attempting to make your way south to Key West. For that reason, it’s crucial to always stay aware of your current location, vessel direction, and sailing speed.

4. Make Sure You Have Plenty of Provisions

An important part of sailing, no matter where you’re going, is to have plenty of supplies and provisions to ensure your safety and well-being during the trip. 

A good rule of thumb for sailing is to bring 1.5 to 2 times the amount of provisions that you’ll need for the trip to be safe. Whatever the amount you choose, it’s best to at least bring enough food for a few extra days. 

Weather can be unpredictable, and storms can throw your boat off course. There may also need to be times when you could be moving, but you aren’t. When sailing, there are plenty of things that can keep you off schedule. 

That said, don’t worry that you won’t be able to find stops along the way to restock on provisions. The Oceanside Marina in Key West, for example, is a top-notch place to stop and grab some snacks and extra gallons of water. In fact, this marina is part of the brilliantly named Stock Island.

While you might not find many provisions at the marina, Lacurva Groceries is only about a five-minute car ride away. If you’d rather opt out of rideshare services, you can walk there in about 20 minutes! 

Additionally, the Tavernier Creek Marina (in Plantation Key) is only about a mile away from the nearest Winn-Dixie grocery store. So, if you find yourself further up along the Florida Keys in need of snacks or drinks, you can always make a quick stop here and stock up on goodies

 

5. Keep An Eye Out for Debris

Another important rule for sailing is to ensure that you watch out for debris. You can find debris on the water from just about anything, but it’s especially common after a hurricane.

Hurricanes tend to cause a lot of debris from boats, trees, and even homes to be a nuisance when traveling on the water. 

Additionally, the Florida Keys are home to some of the state’s oldest fisheries and fishing ports. As such, decades’ worth of washed-away fishing gear may be floating around near the shorelines, potentially causing problems for you and your vessel.

Debris may seem like it’s not a big deal, but it can be dangerous when sailing. Your propellers can get entangled in fishing net and become hard to get free of. Hard debris can also damage the hull, props, or rudders costing you a lot of money or even impairing the boat enough to make it unsafe. For that reason, you’ll want to watch out for it and avoid it if you can. 

6. Avoid Hurricane Season

We already discussed how beneficial the off-peak season could be for your bank account, but there’s another factor to consider.

In the Florida Keys, hurricane season is between June and November. You can save even more money visiting during this time, but that’s because there’s a greater risk of hurricanes. 

Hurricane season slows down visitors, but it certainly doesn’t stop everyone. From destination weddings to brave sailors, the Florida Keys is never empty. But hurricanes are dangerous, especially for sailors. So, let’s talk about why it’s best to avoid hurricane season as a sailor. 

There’s never a guarantee that your boat will survive the high winds and rough waters that a hurricane can bring. So, it’s best to avoid them altogether if possible. Unfortunately, they’re difficult to track accurately. So, an area that may seem safe now could be in danger if the hurricane changes course. 

So, when sailing the Florida Keys, avoid hurricane season if possible. While it’s cheaper than other times of the year, it’s also a lot more dangerous. So, keep yourself, your boat, and your loved ones safe by planning your trip around this season. 

7. Stop for Some Key Lime Pie

If it’s your first time visiting the Florida Keys, you’re in for a treat. While the exact origin is unknown, key lime pie is a dessert that has truly taken over the area. Offering some of the best options for dessert, the Florida Keys is the best place to get a key lime pie. 

Key limes are grown only in places that never get below freezing. The tropical temperatures of the Florida Keys help grow the most flavorful key limes. So, it’s no surprise that you can find it all over the place here. 

Try a few different places and see which one has your favorite recipe, or make it a tradition to try a new place every time you go. However you do it, make sure you try some while you’re in the Florida Keys. Whenever you plan your trip, make sure to stop for some fresh, flavorful key lime pie along the way. 

Frequently Asked Questions 

If you still have some unanswered questions about sailing the Florida Keys, then we have just what you need. Read on as we answer some of your most common questions. 

Can You Sail Around the Florida Keys?

You can sail around the Florida Keys. Sailing from Miami to Key West takes around 15 to 26 hours. This is a very popular route and offers plenty of amazing stops.

You may be a little more comfortable if you have your own boat, but you can rent or charter your own without much struggle whenever you plan to visit.

Read this to figure out whether or not you need a sailing license before you rent the boat. 

When you do sail the Florida Keys, you can do so with or without stopping. The choice is yours. If you’d like to sail all the way around, feel free. But there are plenty of interesting places to stop along the way if you want to add some more experiences to your vacation. 

When Can You Sail the Florida Keys?

You can sail the Florida Keys year-round. Just be careful during hurricane season (June 1st to November 30th) as the water can quickly become a dangerous place when a hurricane approaches. 

While it may seem strange to have something available to you all year round, that’s the case with sailing the Florida Keys. It may be best to avoid sailing during hurricane season, but it’s certainly not forbidden during these months. As long as a sailor feels experienced enough and knows when to sail toward safe harbor, they can sail right through hurricane season if they want to. 

How Long Does It Take To Sail From Miami to Key West?

It’ll take you a little over a day to sail from Miami to Key West directly without stopping (15 to 26 hours). There are plenty of places to stop along the way. So, plan for a longer trip for anything you may want to do along the way. 

This day-long trip doesn’t leave much time for sightseeing or stops for food. So, if you want to stop for longer or make some extra stops, plan for a longer trip. If you need some help planning your Miami to Key West sailing itinerary, there are plenty of resources out there to help. 

For your trip to Key West from Miami, try sending me an email here. I have a list of some of the most popular destinations along the way that will allow you to see some popular sights as you make your way to Key West. 

Planning trips like this one are vital because there are many spots between Miami and Key West that can be dangerous or forbidden depending on the time of day or part of the season. Keep an eye out for markers that indicate an area is off-limits, and remember to check with local areas for parts to avoid during low tide. 

Final Thoughts

Sailing the Florida Keys is a popular vacation choice for people all over. Follow my tips to ensure you have a safe and fun trip, whether it’s your first time sailing or you’ve done it before. 

Whatever you’re planning to do during your visit to the Florida Keys, be aware of hurricane season, good food spots, and pay attention to your surroundings at all times. Get the planning out of the way ahead of time, so you can relax and enjoy your trip.