Cruising South? 11 Tips for Smooth Sailing.

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When the fall colors emerge, some are taking out rakes, while others are stowing away lines. Cruisers prepare to sail south.

We have taken that route ourselves, and I wish we were better prepared. But, what we know now can help you and get you to warm sunshine faster.

Here are a few tips for a smoother cruising south.

Our Favorite Boating Resources:
BoatUS – Piece of mind, if towing is needed. We were always members.
Predict Wind – We always used it to check the weather.
West Marine – We were members, earned points and enjoyed discounts.
Booking.com – For stays when traveling away from the boat.

1. Review Your Boat Insurance Policy.

Before you head towards the manatees and pelicans, make sure you are not sailing outside of your insurance window. Your insurance policy will specify when and where you will be covered.

sails up on a cruising monohull

The hurricane season lasts from June 1st until November 30th (National Hurricane Center). That does not mean you have to freeze yours and your boat’s bottoms in the cold bay waters too long.

Start heading south, it is a longer journey than you might imagine. By the time you reach Florida (the Georgia-Florida border is the start of the hurricane zone for many insurance companies), it might be well into December.

If planning to stop at marinas, keep the insurance coverage page handy – every marina will ask for it (yes, even if the state does not require it).

Still shopping for boat insurance?

We have used State Farm for many years, and we found the premiums were a lot lower, if you insure your boat while still north. We insured in Virginia.

Boat insurance can significantly add to the cost of living on a boat, so explore options. I also have a very useful post on other costs associated with living on a boat:

The cost of living on a boat for a family

2. Be Prepared, Just in Case.

From running aground in the muddy ICW bottom, to occasional engine fails – you never know what trouble might happen along the way.

engine being taken out a boat for a rebuilt
That’s our broken engine; it locked us in the cold Chesapeake for the entire cruising season.

We have run aground a couple of times. Thankfully, we were able to wait a bit free ourselves. But we have seen more boats than I can count stuck along the way.

Experienced boaters and novices alike may find themselves in need of towing, or help. I called BoatUS to rescue our dinghy once, when I was alone with the kids, and the dinghy floated away at night (we had not learned our knots that well yet).

Help on the water is very expensive. We had worked so hard to make our sailing dream come true, we did not want to lose it by losing our cruising savings.

Do some research and see what towing service might work best for you.

While cruising the US, we kept our BoatUS membership active.

3. Join a Rally.

Join the Salty Dawg Caribbean Rally. They leave from Hampton, VA around the beginning of November, weather dependent.

a sailboat and three more in the distance sailing together

Once you join, they provide training and many additional tips and resources.

You do not have to be with the rally the entire time, it is not a race. You can leave on a different day. You can be a lot slower, or a lot faster.

The Salty Dawg starts from Hampton, VA and continues to Antigua, but many cruisers veer off to the Bahamas as well.

Headed to the Bahamas? Do you have a plan for provisioning? I do – here it is:

Provisioning for Bahamas in (With Free Meal Plans – Totally Doable!)

If you are planning to sail to Florida, and want a slower cruise, with occasional stops (like we did), the rally won’t be a good option. But you can always join and take advantage of the resources offered.

4. Reserve the Transient Slips Early.

While cruising south, make sure you reserve your planned marina stops in advance.

a marina full of boats

I wish we had. It was a struggle to find a slip along the way. And back then, we sailed on our small monohull. Catamarans have a harder time finding a slip without a prior reservation.

You will also like:
Catamaran vs Monohull: Let’s Solve This (we Lived on Both).
Buying a Catamaran in 10 Steps – Complete 2024 Guide.

There are quite a few snow birds headed south, the ICW (Intracoastal Waterway), as well as the coastal waters can be quite a busy place to cruise in the fall.

Call ahead of your cruising journey and reserve slips. Marina managers know all too well how cruising works and that much depends on the weather.

It is better to have a reservation and call to change it, rather than search the internet for marinas with availability while on the way.

5. Keep Your Warm Clothes on.

Sailing in cold rain, wind, or both is a given, if you cruise in the fall.

a man and two small boys on a sailboat in cold weather
That’s us, somewhere on the ICW, headed south, in the freezing November of 2018.

Keep your foul weather gear ready.

If you are still shopping around, buy jackets and boots that are waterproof, not water repellent. When something becomes wet aboard, it stays wet for a long time. Drying without the tropical breeze outside is a pain, and a recipe for mold.

We were fortunate to inherit great quality foul weather gear from Joe’s grandparents, who had sailed a lot in their younger years.

6. Watch for Occasional Frost on Deck.

We had snowy decks in St. Augustine, Florida. It was such a strange site to see, when headed towards the Bahamas.

snow at marina docks

The bathing suits were lined up, I was preparing to donate all the winter gear.

For the occasional frosty morning, be very careful stepping out on deck. It will be slippery.

We heated the boat with a small space heater, while aboard, but there was still frost on deck, some mornings.

While on the topic of not slipping, check out my long and useful post about boating and sailing shoes.

Comfortable Sailing Shoes for Every Boating Need

7. Plan Your Route

I love the ICW. Joe does not.

The ICW offers protected waters, slow travel and a myriad of adorable small towns along the way. On the flip side, there is almost zero sailing. It is all engine cruising.

a boat traveling into the sunset with a child on the bow, on the ICW

The ocean is what the boats are made for, I agree. It is faster too. But when you are new to this whole liveaboard adventure, an overnight sailing trip is a scary idea.

If, like us, you and your crew agree to disagree – do a bit of both.

It is how we ended on living on a monohull and a catamaran.

And we loved both:
Pros and Cons of Living on a Boat. By Experienced Boaters.
Catamaran vs Monohull: Let’s Solve This Thing!

Take the ICW in Virginia and North Carolina, where it is a lot better maintained. Avoid the swampy marshes of Georgia and hop outside for an ocean cruise from the Carolinas.

Besides, around Georgia is when the color of the water really changes into that postcard blue.

8. Choose Your Weather Carefully

Let your experience and comfort level guide you. What one sailor considers excellent sailing weather, might ruin the journey for another.

Sunset on the water while sailing the Mona Passage

Not to mention the damage to the boat and crew.

We almost ripped a sail in a small gust of wind, during an unsuccessful tack. And screamed in unison, while exiting an inlet with an out-going tide and an in-coming wind.

We have made plenty of mistakes.

Which is why the most important part of choosing your weather carefully, is you.

We love PridictWind and Passage Weather. We compared both, while planning a passages. The ECMWF model on PredictWind is more accurate.

9. Find Cruising Buddies

Cruising is not a lonely endeavor. It can be, but I recommend against it.

three boats lined up to go through a bridge

Some of our greatest friendships started on our journey south. We bid “goodbye”, only to run into each other a few weeks later. Most cruisers with kids tend to follow similar routes.

Wondering where to find cruising friends? Attending a boat show is a great place to meet like-minded dreamers and boaters. And I do have a great post to help:

Want to Live on a Boat? Attend a Boat Show.

Here is another neat post about ways to find friends for the kids, on the water:

Sailing and Socializing Kids – 8 Ways to Find Friends on the High Seas.

It is so fun to chat over sailing and weather, while the kids do what boat-kids do best – run around barefoot and play boatkid games.

10. Double-Check the Boat Systems

When preparing to sail south, make sure your tropical cruising won’t be interrupted by a ripped sail, a broken engine, or another system aboard, which you ignored, while in a rush to head off.

a monohull hauled out for maintenance

Boat repairs are expensive, and prices tend to go up the further south you go, where yachting is a thriving industry.

Boat repairs in the islands are sometimes impossible, or will set you back weeks, or more.

Our old electric panel caught fire from a faulty voltage regulator, while we were in the middle of the Chesapeake, with kids aboard. Thankfully we have fire extinguishers aboard and within quick reach.

Not all future repairs can be anticipated and predicted. Repairing something aboard is a daily hobby.

Purchase spare parts, while still cruising in the US (if planning to sail away). Cost of labor in cheaper destinations is low, but finding the right part is hard.

Don’t ignore the galley, properly storing and organizing food aboard will help you avoid bug infestations and food waste (something we are quite passionate about):

Storing and Organizing Food Aboard – You Can Beat Heat, Moisture and Motion!

11. Be Patient

Keep the calendar for the pretty pictures and do not look at the dates much.

an anchorage full of boats

There are too many variables, which determine the cruising course. It is great to have a general direction – like, heading south. Stop there.

We headed to Guatemala, but found amazing cruising buddies with kids, and ended up in the Dominican Republic.

Be prepared to change plans, marinas, passages and deadlines.

A Tip for Those by the Fireplace

A quick tip for friends and loved ones, who are fortunate to know you well enough and would love to visit.

Dear boat guests, who cannot wait to hop aboard during winter break. Please, pick either a time, or a place to visit your cruising loved ones, not both.

Oh, and leave large hard-case luggage behind.

And bring maple syrup.

More Posts About Boating Life

Visit our page dedicated to boat life – tons of useful and fun tips and stories:

Boat Life @ No Texting & Tacking

Cruising the US – You will Like These:

We called these marinas home. And so can you.

7 Cruiser-Friendly Towns, on the East Coast, to Escape the Winter Blues with Your Loved One.

Cruising the ICW – the Magical Waterway in our Backyard.