How Safe Is Sailing In The Caribbean?

Most Caribbean islands are safe if you avoid sailing in severe weather during hurricane season. However, certain areas are prime targets for bandits. And violent crimes like armed robberies and murders are not uncommon. 

Sailing in the idyllic Caribbean with its aqua-colored waters and sun-kissed beaches is a dream vacation. Although, it can quickly become a nightmare if you are in the wrong place at the wrong time! 

So, if you want to know when the best time is to sail weather-wise in the Caribbean, read on! I’ll tell you more about which islands are the safest based on current US travel advisories.

I have personally been to all the windward islands and most of the leeward islands in my 10-year career working in yachting, and I never had an issue.

So, How safe is sailing in the Caribbean? Read on to find out!

📝 Sailing In The Caribbean: What You Should Know

According to the Caribbean Safety and Security Net (CSSN), most reported crimes in the Caribbean are comprised of petty thefts or pickpocketing (which happen across the globe). 

And most experienced Caribbean cruising sailors and yachtsmen will tell you that there has been a lot of unnecessary gloominess about the overall levels of crime in the region, especially in the media. 

So, while there have been cases of stolen dinghies, boat engines, or expensive items like mobile phones and laptops, they mainly were opportunistic crimes in many cases. And those items were mostly stolen because the owners did not take safety precautions. 

There have been worrying media reports about the explosive crime level on some Caribbean islands. This forced the US State Department to create travel advisories for all the Caribbean islands. 

Some Caribbean islands have become no-go zones due to high crime levels, including gang activities, drug trafficking, and high murder rates. Despite this, it is essential to maintain perspective and understand that their murder rates are still far lower compared to some crime-ridden US states. 

Furthermore, the 2020 CSSN safety and security report showed a significant decline in reported crimes in the Caribbean. Although COVID-19 restrictions could have played a part, most logged crimes were petty thefts (not violent crimes). 

Although most Caribbean islands are relatively safe, it’s essential to be on your guard, aware of your surroundings, and watch your valuables. These basic safety precautions will greatly reduce the risk of petty theft and security incidents. 

🧷 The Safest Time To Sail In The Caribbean

There’s no doubt that sailing in the Caribbean is a great experience. However, choosing the right season for your journey is essential, as this tropical region is prone to nasty tropical storms and hurricanes. 

Ideally, plan your sailing trip for May or June when most Caribbean islands are sunny, and there are warm temperatures. This is also when the weather is ideal. There are only a few heavy downpours, and encountering dangerous storms is unlikely. 

However, as we all know, tropical weather conditions can sometimes be unpredictable. So, installing a good weather app on your smartphone is helpful and keeping an eye on weather forecasts before you depart. While they are not always accurate, at least you will be prepared for all weather conditions. 

☀️ The Best And Safest Caribbean Islands

So, now that we have covered general safety issues in the Caribbean region. Let’s look at the most popular islands, ranked from the safest to the least secure. You can make a wise decision before you go on your Caribbean adventure. 

Please note – this list of the safest Caribbean Islands is based on current US Department of State travel advisories. These consist of level 1 (exercise usual caution), level 2 (be more careful), level 3 (reconsider your travel plans), and level 4 (cancel your trip) classifications. 

Most importantly, check out the Global Disaster and Coordination System (GDACS) for up-to-date weather forecasts and potentially life-saving travel alerts.

St. Barts

Beautiful Saint-Barthélemy, or St. Barts, as this French tropical paradise is better known, is one of the safest islands in the Caribbean. It has below-average crime statistics for petty thefts. There are also no violent crimes. 

The island’s people are not as poor compared to other Caribbean islands. This is mainly because St. Barts is a popular travel destination for wealthy visitors who only have to worry about irritating mosquitoes and sunburn. And not being victims of violent crime.

The stunning Gustavia harbor, St Barts

Leeward Islands

The stunning Leeward Islands region includes several popular tourist destinations like Anguilla, Antigua and Barbuda, Montserrat, Saint Kitts, Nevis, Saint Martin, and the Virgin Islands. 

One of the safest Leeward Islands is Anguilla which the US Department of State has classified as a level-one travel destination with the lowest number. Although petty thefts occur, they are easy to avoid if you take some precautions. 

Montserrat, a British territory, is better known as the spectacular Emerald Isle due to its unique terrain and rich heritage. 

Like Anguilla, Montserrat has a low crime rate. The only potential risks on the island include an active volcano (on Soufrière Hills), including hurricanes from June until November. 

In stark contrast, be careful when you visit St. Kitts and Nevis islands. The US Department of State has classified them as minimally risky destinations. Nevertheless, there are a lot of petty thefts. 

Other famous Leeward Islands include Antigua and Barbuda. The island is home to stunning beachfront and rainbow-colored buildings with buzzing ports. They are not classified as dangerous islands, but petty thefts are rising. It’s best to constantly watch your possessions and avoid certain areas.

Sunset at Shirley Heights lookout (Photo credit: Unsplash)

The Cayman Islands

Although petty thefts are not uncommon, violent crimes are rare in the beautiful Cayman Islands. This is because they have the strictest gun laws that limit the number of weapons on the island. 

However, visitors are currently advised to avoid visiting the Cayman Islands due to Level 3

Covid restrictions. It’s recommended to keep an eye on the US Department of State’s travel advisories if you want to travel to the islands.

The Caymans are a boating paradise (Photo credit: Unsplash)

Windward Islands

The Windward Islands are a network of islands roughly 200 miles from north to south. These include the famous islands Martinique, St Lucia, Saint Vincent, and the Grenadines. 

If you plan to sail to Martinique, be careful. Petty thefts are common, especially in the Fort-de-France area. So, take precautions by avoiding large crowds and keeping your possessions safe. You should also not travel at night or withdraw cash at an ATM where tourists usually are targeted. 

Saint Lucia is far safer if you take safety precautions like not showing off your expensive stuff or walking alone at night. 

However, it would be wise to avoid sailing to Saint Lucia towards the end of summer and fall. During the island’s terrible hurricane season, between August and November, nasty thunderstorms are common. Therefore, it’s best to avoid the island. 

It’s also important to point out that Saint Lucia, like several other Caribbean countries, has made same-sex relationships illegal. So, it’s risky for LGBTQ+ travelers to visit the island. 

There are few reports of petty thefts in Saint Vincent and the Grenadines port areas like Bequia, Union, including the Blue Lagoon or Young Island Cut regions. However, they are mainly safe, and violent crimes are uncommon.

The imposing Pitons in St. Lucia (Photo credit: Unsplash)


Barbados is a relatively safe travel destination. But petty theft and being harassed by drug dealers are not uncommon. These occur primarily in tourist areas like Wellington Street, Nelson Street, and Crab Hill. 

However, avoiding traveling at night and exploring the island with friends makes it far easier to prevent petty thefts.


With only 200,000 visitors each year, there are few opportunistic criminals in Grenada compared to more popular Caribbean islands that attract vast crowds. 

However, petty thefts are not uncommon. So stay on your guard and explore the island in a group, especially at night when solo tourists are robbed. If you do visit Grenada, be sure to check out the underwater sculpture museum.

Grand Anse beach in Grenada (Photo credit: Unsplash)

The Dominican Republic

The Dominican Republic attracts millions of visitors yearly to enjoy the region’s fantastic beaches and waterfalls. But unfortunately, this attracts violent crime and makes the country less safe for tourists. 

Resort areas are relatively safe. However, the country’s most densely populated areas, like Santo Domingo, have a lot of violent crimes, rapes, murders, and armed robberies. This is not a country where you can let your guard down. So hide valuables!

Due to the US Department of State’s level 2 travel advisory, the Dominican Republic is more dangerous than other Caribbean islands.

The US Virgin Islands

The US Virgin Islands is like its neighboring British island regarding its culture and crime statistics. 

Most crimes in the US Virgin Islands are classed as petty thefts. It would be wise to monitor your valuables and avoid crowded areas where pickpocketing typically happens. 

It’s important to point out that sexual assaults are common, and women are often harassed. So, if you are female, don’t explore the US Virgin Islands alone.

The Bahamas

With more than 700 spectacular islands, it’s easy to see why the Bahamas is such a popular sailing destination. It has a fantastic climate. Between December and April, the weather is warm. Hurricanes are also uncommon, unlike June to November during their hurricane season. 

However, due to the incredible number of tourists who visit the islands each year, the Bahamas hides a dark underbelly. This has forced the US Department of State to create a Level 2 travel warning. 

Petty thefts are common in touristy areas with vast crowds like Nassau. Unfortunately, there is also a lot of violent crime in the Over-the-Hill neighborhood, so you can’t let down your guard for a moment!

Like the US Virgin Islands, sexual assaults are commonplace in the Bahamas. These attacks on women take place in broad daylight, so even female daytime joggers are not safe. 

Although they occur primarily at night when women may be drunk and mainly happen near casinos, hotels, and beaches.

The famous swimming pigs of the Exumas (Photo credit: Unsplash)


If you are considering sailing to Jamaica, it would be wise to reconsider your travel plans. This country has a lot of violent crimes like armed robberies, murders, and rapes. In addition, the local police do not have enough resources to keep visitors safe. 

The most dangerous communities in Jamaica are Spanish Town, Montego Bay, and Kingston, where gang wars and gun crimes are common. So, it would be a good idea not to travel to Jamaica as it is risky. 

🏴‍☠️ Potentially Dangerous Caribbean Sailing Routes

Now you know which islands are relatively safe to visit (if you are careful). However, it’s important to point out that some sailing routes are dangerous. They should be avoided, even if it means taking alternative passages that may take longer. 

The Venezuelan region is top of that list of areas that should be avoided. Here, opportunistic robbers tend to board yachts and steal valuables. 

Another sailing route that should ideally stay away from is Grenada’s southern coast towards Trinidad and Tobago’s northeastern area. This is a popular drug smuggling route for criminals who travel in that area on canoes. 

Trinidad and Tobago also has the reputation of being the sixth most dangerous country in the world. Additionally, the government has the highest crime rate in the entire Caribbean, with Jamaica in a close second, followed by the Bahamas and Puerto Rico. 

As mentioned above, most violent burglaries and crimes in the regions can be attributed to government corruption, drugs, gangs, and high levels of unemployment. 

It is also important to mention that criminals tend to work in areas with gas drilling rigs. This is because they are often used as landmarks for boats that do not have working navigational equipment on board. 

Criminals in open fishing boats also travel between Nicaragua and Honduras, so there have been several attempted piracy reports in that area.

Caribbean Island Safety Tips And Tricks

So, now you know which sailing routes and islands should best be avoided. Here are a few helpful Caribbean safety tips and tricks to remember. Even if your travel destination is relatively peaceful, take a common sense approach.  

ATMs: if you need to withdraw cash, ask a fellow passenger to stay with you to act as a lookout for potential robbers who often target tourists and, most importantly, cover your PIN.

Harassment:  chances are high that you will have to deal with harassment, especially in poor areas where small local businesses rely on the tourist trade. So, avoid eye contact, and if necessary, say “no thanks” loudly.

Passport: avoid traveling with your passport if it is not necessary. However, should you need to do so, hide it in a waterproof secure pocket and keep a copy of your passport in a safe place.

Drink-spiking: spiking with Rohypnol and other date-rape drugs is sadly common in bars, and nightclubs, especially in the Bahamas, and most visitors are attacked, robbed, and abandoned afterward. So, always keep an eye on your drinks.

Clothing: try as much as possible to blend in, and avoid dressing in touristy T-shirts and other clothing items that might make you look like a foreigner. This includes camouflage clothing and illegal accessories on several islands like St. Vincent.

Small Change: where possible, exchange your US dollars for local currencies, as visitors are often short-changed when they pay for goods or meals with foreign notes.

Getting around: While renting a car might sound like a great idea, it’s risky, especially in countries like the Dominican Republic. So, instead, use clearly marked, registered taxis, and agree on a price upfront before you drive off. 

Frequently Asked Questions

The Caribbean is famous for having severe thunderstorms and devastating hurricanes. Hopefully, the following information will answer any questions you might still have about the safest time to sail in the Caribbean.

When Should You Avoid Sailing In The Caribbean?

Even though the Caribbean climate is warm, October through to December are the worst months to sail in the Caribbean as its hurricane season, and there are severe thunderstorms. 

Summertime thunderstorms are typically short but intense, with high waves, strong winds, lighting, and hail, so it’s best to avoid them or sail around them if needs be. 

And most importantly, make sure that your life jacket is on during thunderstorms or easily accessible as unexpected waves have swept many experienced sailors overboard.

Is It Safe To Sail The Caribbean During Hurricane Season?

Sailing in the Caribbean during the hurricane season is not recommended. This is because they are far more dangerous than typical thunderstorms, with winds over 100 knots hundreds of miles wide.

High seas, flooding, mudslides, and tsunamis are expected during the hurricane season, and the weather is highly unpredictable and dangerous. Fortunately, weather predictions regarding hurricanes are usually accurate. 

Although having said that, it’s essential to stay clear of any Caribbean islands during hurricane seasons. 

🗣️ Final Words

When the weather is ideal between May and June, you can have a dream vacation sailing to safe islands like St. Barts, Anguilla, including the Cayman Islands.

Other regions like Jamaica, including Trinidad and Tobago, should be avoided due to their high levels of violent crime. And before you set sail for your Caribbean adventure, keep an eye on the latest US travel advisories and the weather forecast. Safe travels!

I’m the founder and chief editor here at Sailing Savvy. I spent a decade working as a professional mariner and currently, I mix those experiences with digital publishing. Welcome, and I hope that we can be the hub you need for safe passage.