Best Winter Sailing Vacations

Best Winter Sailing Vacations | Life of Sailing

Last Updated by

Daniel Wade

June 15, 2022

Winter sailing in the northern U.S. is challenging, but it isn't the only option. Sailing south can turn the cold season into perfect sailing weather.

The best places to sell during the winter are the Florida Keys, the Bahamas, the Gulf Intracoastal Waterway, Mexico, Hawaii, Cuba, Martinique, Cape Verde, the Virgin Islands, and San Diego. These areas have excellent winter weather and are (usually) friendly to American sailing vessels.

In this article, we'll cover ten of the best winter sailing destinations for American sailboats. We'll also cover some areas to avoid and why, along with what to look for when choosing a winter sailing vacation.

We sourced the information used in this article from sailing travel guides and government weather data. Additionally, we drew from the experiences of sailors who have made winter sailing trips to choose the best destinations.


Table of contents

Finding the Right Conditions for Winter Sailing

In many parts of the country, sailing during the winter can be treacherous. High winds, cold temperatures, and lack of daylight are all hazards to sailors. This covers virtually every location north of the Carolinas on both coasts, though the weather tends to be worse on the East Coast.

Ideal sailing conditions, which are warm, clear, and free of high winds, can be found in the southern hemisphere and even the southern United States. Conditions in these locations are sometimes better during the winter, as the season gives you a chance to escape the blistering summer heat.

Avoiding the Rainy Season

It may seem logical to sail off to any old southern island and spend time in traditionally hotter weather. However, many regions that are warm during the winter also experience their wettest months between December and February.

The rainy season presents a whole new set of hazards to sailors, especially in the South Pacific. However, rainy conditions are less severe in many regions. The majority of destinations on our list avoid the worst of the winter rainy season.

Like Atlantic hurricanes, Pacific typhoons are also a concern during some parts of the year. Winter is typhoon season in many parts of the world, especially the South Pacific. It's best to avoid the South Pacific during this time, especially areas close to Asia.

Top 10 Places to Sail in the Winter

The best winter sailing destinations have pleasant weather and aren't too far from the mainland U.S. We chose the following ten winter sailing destinations based on weather, beauty, safety, and the area's ability to dock and service sailboats.

1. Florida Keys

The Florida Keys are an obvious choice, and they're a popular destination for sailors from all over the world. During the winter, the weather in the Florida Keys is warm and relatively easy to handle. Temperatures really drop below 60 degrees, and you won't suffer through the intense heat of the Florida summer.

The Florida Keys are made up of dozens of small islands which make up the southernmost point of the continental United States. For U.S. sailors, this is especially convenient. After all, the Florida Keys are part of Florida, so you won't have to worry about a passport or visa unless you stray from the territory.

Additionally, much of the Florida Keys are inhabited (or at least frequented) by marine traffic. This means that fuel and food are usually not too far from your location, and there's typically a safe place to anchor. If you plan your trip carefully, you can spend your days island hopping and always have a place to stop for the night.

2. The Bahamas

The Bahamas are one of the most popular sailing destinations for American sailors trying to escape the winter weather. The islands are extremely close to Southeast Florida, and virtually everything you need to know about sailing there is written down somewhere.

The Bahamas are known for their picturesque beaches, palm trees, warm weather, and friendly demeanor. Though an independent nation, the country makes it relatively easy for Americans to sail and stay there for vacation. The trip does not take long from Florida, and there are numerous marinas all over the Bahaman Islands that you can book a stay with.

The country has excellent restaurants, fantastic music, and numerous beautiful resorts. Additionally, staying in the Bahamas is quite affordable, and it's an excellent alternative to Cuba or the Florida Keys. It's tough to beat a vacation to the Bahamas, especially when much of the U.S. is blanketed in snow.

3. Southern Gulf and the ICW

If you're not looking to go international, you can always spend some time sailing around the Southern United States and the Gulf of Mexico. This is a popular option for Sailors who are already in the south, and many ports and launch points can be reached via major American highways.

One popular way to sail the south is through the Intracoastal Waterway. This protected waterway, which borders the Gulf, runs all the way from South Texas to South Florida and around the panhandle. Through the ICW, you can stop in well-known American cities such as New Orleans.

There are hundreds of marinas, restaurants, and destinations along the Intracoastal Waterway, which are frequented by other sailors and commercial traffic. If you don't want to spend time maneuvering around other boats, you can exit the Intracoastal Waterway at almost any point and sail just off the coast in the Gulf.

4. Mexico

Mexico is a particularly attractive option for sailors during the winter, as this Central American country is famous for its glistening beaches and vibrant culture. Well-known sailing destinations in Mexico have all the docking and service infrastructure that you'll need.

Cabo San Lucas is a particularly popular destination in Mexico. The area is famous for its fascinating offshore rock formations, beautiful beaches, and friendly resorts. From the coast, you can sail up to the Western United States or down and through the Panama Canal to the Gulf of Mexico.

Additionally, many of the resort locations are safe and welcoming to Americans. With the right planning, sailing to Mexico is easy and can be a very rewarding experience. Another advantage of sailing to Mexico is that it's accessible on both sides of the country.

Mexico shares a coastline with the western United States, and you can also get to it from the Gulf of Mexico. If you're sailing from the East Coast, simply round the panhandle of Florida and head west. Along the way, you can stop along the Intracoastal Waterway in the Southern United States.

5. Hawaii

When talking about winter sailing vacations, who can forget about Hawaii? From the Big Island to bustling Oahu, the Hawaiian Islands are one of the most beautiful vacation destinations in the world. Additionally, many adventurous mariners make the two thousand-mile sailing journey from the western United States.

Sailing to Hawaii is one of the more advanced sailing trips, but it's doable with preparation and it only takes about 20 days under the right conditions. Sailors who depart from Southern California benefit from reliable trade winds, which take vessels almost right to the islands.

It's important to note that the trade winds often fall short just shy of the coast, as the islands disrupt weather patterns. Additionally, the return trip is more complicated and takes longer, though the best routes through this part of the Pacific are well-documented. Hawaii has some of the best Island resorts in the world, great weather, and plenty of places to dock.

6. Cuba

Once completely inaccessible to American tourists, the famous island nation of Cuba is now opening up. Taking a sailing trip to Cuba is more complicated in the Bahamas, though it's now possible with the right preparation and paperwork.

Cuba is famous for its vibrant culture and fascinating history, and it makes one of the best winter sailing destinations in the world. Like the Bahamas, Cuba is a relatively short trip from Florida, and the route is well-traveled.

Additionally, the weather is generally good during the winter, and sailors are never very far from help and resources. If you want to experience the beautiful terrain, great food, and energizing nightlife, then consider taking a trip to Cuba and staying in Havana.

7. Martinique

The breathtaking Island of Martinique offers a one-of-a-kind winter sailing experience. Surprisingly, the island is a French territory and the outermost region of the European Union. As a result, the island is friendly to American sailors, and the infrastructure is up to modern standards.

Martinique is a great alternative to Cuba, as it's just south of the country and still relatively close to South Florida. The island is famous for its vast and safe anchorages, sandy beaches, and luscious green mountain ranges. Made up of four main administrative divisions, the island of Martinique offers numerous hiking and sailing destinations across its relatively small area.

The Atlantic island of Martinique is also known for its sea turtles and tropical animals. There are vast and well-populated anchorages in many parts of the island, along with easy access to the shore and local restaurants. Sailors from all over the world congregate here during the winter, and the region is often filled with boats and friendly sailors.

8. Cape Verde

Cape Verde is a long distance from the continental United States, but it offers some of the best scenery and most interesting culture of any popular winter sailing destination.

Situated off the coast of Africa, Cape Verde is famous for its warm weather, beautiful hiking, and beaches.

The island is popular with sailors, especially from Europe, though Americans are often found there as well. Cape Verde boasts crystal clear water and good weather throughout the year, especially in January and February. The region takes advantage of the Saharan trade winds, which makes sailing predictable and fast and most areas.

In addition to its beautiful terrain, crime is very low in Cape Verde. This makes it an acceptably safe sailing destination. Though the country lacks some modern infrastructure, most sailors have a good experience exploring the area as long as they take reasonable caution.

9. The British Virgin Islands

Are you looking to spend the winter island-hopping around one of the most beautiful sailing destinations in the world? If you are, consider visiting the British Virgin Islands. The area is famous for picturesque beaches, friendly locals, and some of the best snorkeling destinations in the world.

The area is surrounded by untouched reefs and safe anchorages, which makes it easy for sailors to stop for the night. Additionally, most of the surrounding islands are well-charted, which reduces the risk of running aground close to shore.

The British Virgin Islands are friendly to American sailors, and there are plenty of marinas and anchorages to choose from when arranging your visit. Geographically, there's plenty to do in the area and lots of other destinations to visit.

Just beyond the British Virgin Islands are the American Virgin Islands and the U.S. territory of Puerto Rico. Both destinations are excellent places to sell, and most of the region is friendly and easy to navigate.

10. San Diego

California has a lot to offer in terms of sailing destinations, especially during the winter. San Diego is the Southernmost city in California, and it experiences some of the warmest year-round weather on the coast of the state. San Diego is also home to an enormous sailing community. It also features offshore islands that are popular destinations.

San Diego is considered one of the cleanest cities in California, and the city itself has numerous attractions. While not the cheapest winter sailing vacation, there are numerous benefits to staying in the United States. If you don't want to pay to rent a slip in San Diego, there are plenty of anchorages right off the coast that offer affordable moorings.

San Diego is also very close to Mexico, and it makes a great stopping point if you're taking a trip from the Pacific Northwest. If you're looking for a shorter offshore sailing vacation off the coast of California, consider sailing from San Diego to Los Angeles, Monterey, or San Francisco. The Pacific coastline can be treacherous, but the region has virtually no extreme weather (other than high winds) during any time of year.

Best Winter Sailing Vacations
Daniel Wade

Daniel Wade

I've personally had thousands of questions about sailing and sailboats over the years. As I learn and experience sailing, and the community, I share the answers that work and make sense to me, here on Life of Sailing.

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