Can You Sail from the Great Lakes to the Gulf of Mexico by Boat? 

You have years of boating experience and consider yourself quite an accomplished sailor. Lately, you’ve been interested in challenging yourself and traveling greater distances than ever before. If you were to leave from the Great Lakes, could you reach the Gulf of Mexico by boat?

You can sail from the Great Lakes to the Gulf of Mexico, but the trip is 1,530 miles and can take weeks to a month depending on how often you stop and refuel. Since both bodies of water are downstream, the travel isn’t necessarily arduous.

If you’re interested in sailing to the Gulf of Mexico from one of the Great Lakes, this is the article for you. We’ll recommend efficient routes to get you to your destination, talk further about how long it will take to make the trip, and discuss considerations for your journey so you can be safe. 

Let’s get started! 

What Are the Best Routes to Sail from the Great Lakes to the Gulf of Mexico?

Traveling from the Great Lakes all the way to the Gulf of Mexico by sailboat requires leaving from one of the states in the United States on the northeastern or east coast sides and venturing down to the Florida/Texas/Louisiana area.

The trip, as we mentioned in the intro, is approximately 1,530 miles. Here are some recommended routes for you to take.

Lake Michigan to the Illinois Waterway to the Gulf of Mexico

The Great Lakes Waterway is a series of canals and channels, some of which are natural and others of which are artificial. Through these navigational systems, you can traverse the North American Great Lakes. Further, you can eventually reach the Gulf of Mexico.

That would entail you starting your trip from Lake Michigan, which has a width of 118 miles and a length of 307 miles. From there, you could reach either Grafton’s Illinois River or Chicago’s Calumet River.

That allows you to travel down the Illinois Waterway, which is 336 miles long. This leg of your journey will involve you traversing canals, lakes, and rivers in your sailboat. 

Shipping connections to both the Gulf of Mexico and the Great Lakes from the Illinois Waterway afford you the chance to reach the former. 

Lake Michigan to the Mississippi River to the Gulf of Mexico

Another viable route also requires you to begin by sailing through Lake Michigan. Your goal is to reach the Mississippi River.

It used to be that you could take the Illinois and Michigan Canal, which was a connection point between the Gulf of Mexico, the Mississippi River, and the Great Lakes. However, this canal has been done away with and much of it was filled in over time. 

However, you can still access the Mississippi River from Lake Michigan without the help of the Illinois and Michigan Canal. 

Along the way, you’d pass through the Illinois Waterway again. Since the Mississippi River naturally releases into the Gulf of Mexico if you’re about 100 miles south of North Orleans downstream, it’s a natural path to your destination. 

How Long Does It Take to Sail from the Great Lakes to the Gulf of Mexico?

To reiterate, the trip from any of the Great Lakes to the Gulf of Mexico is not going to be a short one. Since the Great Lakes are in such close proximity to one another (for the most part), it doesn’t matter so much which one you choose to leave from.

It will still take you 1,500 miles to reach the Gulf of Mexico, give or take. Then you’d have to turn around and sail back. Overall, you’re looking at a round trip of more than 3,000 miles. 

How far you can sail in a day varies by many factors. You have to consider the type of boat you have, its engine horsepower, the weather, and whether you’re sailing upwind or downwind.

If you’re using your engine a lot, you can maybe achieve 130 nautical miles of sailing per day. When you’re riding downwind, you might be able to pass 100 nautical miles. 

Short-passage sailing would achieve only about 60 nautical miles per day while long-passage sailing would reach 80 nautical miles.

For the sake of the example, let’s just say you’re sailing 100 nautical miles per day. We’ll also round down the distance between the Great Lakes and the Gulf of Mexico to merely 1,500 miles rather than 1,530 miles.

Then it’s just a matter of simple math. If you travel 100 miles per day and your trip is 1,500 miles overall, then you’d reach the Gulf of Mexico in your sailboat from the Great Lakes in 15 days. That’s only slightly over two weeks, which is not bad at all!

However, the above math assumes that you’re sailing all day every day to make those 100 nautical miles per day. In other words, you never stop to take a break or visit a port. You don’t stay overnight at a hotel, you don’t eat, you just keep going. You’re also not deterred by inclement weather at any point on your trip.

As you can surely imagine with your level of sailing experience, none of the above is very realistic. You cannot sail without taking breaks to refuel, sleep, and shower. Bad weather will hinder your plans too.

Thus, you’re only using that 15-day timeline as a benchmark. It’s not a goal you should aspire to, as it’s not realistic. 

We’d recommend taking that 15-day estimate and doubling it. Now you’re giving yourself 30 days to get from one of the Great Lakes to the Gulf of Mexico. That’s a much more attainable timeline.  

What Are the Best Times of the Year to Sail from the Great Lakes to the Gulf of Mexico?

While you can’t control the weather, you can control when you venture out in your boat to set sail from the Great Lakes. 

Especially when sailing alone, you must be careful about potential hazards. The trip from the Great Lakes to the Gulf of Mexico is mostly downstream and not too difficult, but it’s not a time to be lax.

Here is when you should schedule your adventure based on the weather. 


The Great Lakes are the most navigable in the summertime. You generally don’t have to worry about serious inclement weather events this time of year, and the temperature should be stabilized enough compared to the fluctuations of spring.

As you get further along the east coast, the summertime temperatures can be a bit balmy. Be sure to protect yourself from the sun. You may have some cool water breezes to offset the warm temperatures. 

Late Fall

The Mississippi River, which is usually a part of your trip down to the Gulf of Mexico from the Great Lakes, can become flooded out if the area has experienced a lot of rainfall. 

The floodwaters will raise the water level and send hazards such as sizable logs floating across the river. The current speed increases as well, which can cause you to lose control of your sailboat and possibly crash into the passing debris.

The Mississippi rainy season includes these months: January, February, March, April, May, June, July, August, September, November, and December. Yes, that’s nearly every month of the year.

Thus, October might be your safest bet if you want to avoid floodwaters. A drier November is another good time to venture out.

Here’s an added perk of saving this leg of your sailing journey until the autumn. You get to witness firsthand the gorgeous foliage that decorates the Mississippi River this time of year. 

Throughout the Winter

Although winter might not seem like the most ideal time for a sailing trip, as you get closer to the Gulf of Mexico, you will want to be there in the winter. 

After all, by now, you’re way south around Florida and Texas. It doesn’t get too cold in this part of the United States even in December, January, and February. The temperatures might even be warm enough that you could swim if you wanted to.

Plus, by skipping the summer travel along the Gulf, you’re ensuring that you won’t run into any hurricanes. The only ones that could pass through would be very unseasonable

What to Consider Before Your Journey

To wrap up, we want to share our top tips and best practices for your safety when sailing between the Great Lakes and the Gulf of Mexico.

Buy the Right Boat

Although a lot of your sailing trip is downstream, the Great Lakes and the Gulf of Mexico can be moderately turbulent to slightly more so depending on the season and the weather. It’s mostly the inlets and sounds you pass along the way that creates waves. You need a sailboat that can handle the choppy conditions. 

Further, your boat must be able to squeeze under the 19.7-foot bridge along the Illinois Waterway’s mile marker 300. If you can’t get underneath, then you’ll have gone all this way for nothing. You can’t go any other route and still reach the Gulf of Mexico. 

As you shop around for boats, we’d suggest one with a beam around 23 feet, a draft of around six feet, and a length that’s no more than 40 feet.

Link Up with Loopers

Although sailing by yourself can certainly get lonely, you’re less alone than you think. 

Outside of those who sail from the Great Lakes to the Gulf of Mexico is another subset of sailors and boaters known as Loopers. They’re nicknamed that because they like to sail what’s known as the Great Loop.

The Great Loop takes you through the Atlantic Intercoastal Waterway, the Hudson River, the New York State Canal System, the Rideau Waterway, the Great Lakes, the Illinois River, the Mississippi River, the Ohio River, the Cumberland River, the Tennessee River, the Tennessee-Tombigbee Waterway, the Gulf of Mexico, and the Lake Okeechobee Waterway.

Loopers will go around in a big circle rather than settle in the Gulf of Mexico, but you’re still passing through enough of the same places that you and Loopers can meet up. You might just make new sailing buddies!

Have a Budget and Manage Your Money

Even if you work remotely, you’re not going to get a reliable enough Internet connection from your sailboat to work. Thus, the time you spend sailing to the Gulf of Mexico from the Great Lakes is not going to put any additional money in your pocket.

To manage expenses, you’ll want to set a budget and then do your best to stick to it. The budget you set should be realistic, keeping in mind the costs for food, potential lodging, fuel, and other must-haves when in your boat for upwards of a month.

Study Your Route Before You Go

The most surefire way to reach your destination in a reasonable time is to know a route and try not to get off-course. Watch YouTube videos, review a map, read articles or books, or watch a documentary about the trip so you feel readier for your own boating adventure. 

Have More Than You Think You’ll Need

Although you’ll have plenty of opportunities to port on your way to the Gulf of Mexico, the more time you spend off your boat, the longer it will take you to reach your destination. That will in turn delay you getting home.

Plus, having to buy more supplies could cause you to go over budget.

That’s why we recommend stocking up well. For however much you think you’ll need, bring extra. That includes food, fuel, clothes, anything. Maybe you never need your surplus, but if you do, you’ll be glad you have it! 

Expect Things to Go Wrong

Even if you’re a highly experienced sailor, you can’t control Mother Nature, as we said. Inevitably, things will go wrong. If you go into your sailing trip expecting this to happen, you won’t be as surprised when it does. 


Sailing from the Great Lakes to the Gulf of Mexico is doable in about a month, as the trip is 1,530 miles. Plan your adventure so you can avoid ice and hurricanes, set a budget, and bring a surplus of supplies so you don’t run out. Happy sailing!


I am the owner of sailoradvice. I live in Birmingham, UK and love to sail with my wife and three boys throughout the year.

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