Best Sailing Charter Destinations

Best Sailing Charter Destinations | Life of Sailing

Last Updated by

Daniel Wade

June 27, 2023

Key Takeaways

  • The best charter destinations for sailing vary on your desires and expected outcomes
  • Locations with perfect views like the Caribbean Sea and Mediterranean are prime spots
  • Planning ahead is your best bet for booking the desired sailing vacation you want
  • Check out consumer reviews from established charters to get a feel for how they work
  • Many prime locations offer great cruising ground and steady trade winds for easy sailing

Sailing charters are a great way to explore the waterways in tourist hotspots near the water. But what are the best sailing charter destinations?

The best charter destinations for sailing include the Caribbean, Mediterranean, and the British Isles. Many sailors also favor the South Pacific, Florida Keys, and the French Riviera. Your sailing goals may differ based on a variety of influences to your trip.

Based on my previous experience, using a charter in one of those locations is perfect for a sailing vacation. Make sure you do your research beforehand on the charter companies that are in operation.


Table of contents

Top 12 Best Sailing Destinations for Charters

If you are in the mood for a sailing vacation but do not want to bring your boat with you on a long trip then you should consider using charter boats. These can vary from a yacht charter to a catamaran.

Depending on where you plan to take your vacation will vary on what type of charter you are able to get. Below are some of the best charter destinations for sailing.



If you happen to be around Barbados or the Dominican Republic then you should consider a charter vacation. There are a plentiful amount of gorgeous beaches and rich vegetation to compliment the perfect water. It also boasts some of the best sailing conditions to make it a relaxing getaway to places such as the windward islands.



The Mediterranean might be one of the most popular sailing destinations to experience with a charter company. With places like Barcelona and Naples you can explore these locations that have a rich culture in addition to the beautiful scenery. It also provides sailors with perfect sailing conditions all throughout the year.

British Isles

Dublin Bay
Dublin Bay

The British Isles provide sailors with a little more of a tougher environment while enjoying a charter. The conditions are windier and tougher on the water but there is a vast amount of history you have to see. Be sure to check out Dublin Bay in Ireland and Liverpool.

British Virgin Islands

British Virgin Islands
British Virgin Islands

Another key location within the Caribbean is the British Virgin Islands. These islands also boast white beaches and emerald waters with perfect sailing conditions. They also feature plenty of luxury charters to choose from.

Greek Isles

Greek Isles
Greek Isles

The Greek Isles is a once in a lifetime sailing experience in Greece. This is perfect for anyone wanting to check out stunning beaches or island hop around. You cannot go wrong with great sailing conditions and beautiful scenery.

South Pacific

South Pacific
South Pacific

When traveling through Fiji or New Zealand you may want to check out some yacht charters. This is a perfect opportunity for a sailing destination since it has many untouched islands and breathtaking scenery. The weather is usually perfect for any occasion and you can explore the rich culture that awaits.

Florida Keys

Florida Keys
Florida Keys

If you are wanting to stay within the US and see some of the best coastal waters then the Florida Keys are a great option. Florida has the most registered boat owners in the US which means there should be someone willing to take you around the most beautiful regions of the state. This is a great opportunity to check out Key West and potentially Islamorada.

French Riviera

French Riviera
French Riviera

If you are wanting to explore French culture and history but also want exquisite views on the water then you cannot go wrong with the French Riviera. Many people from different parts of the world gather to embrace the location and what it has to offer. Be sure to check out a crewed charter to get the best experience.

The Great Lakes

Lake Superior
Lake Superior

For those that are wanting to check out some freshwater locations in the US you can stop by the Great Lakes. These five lakes each have their own characteristics and options for exploring. This also allows you to embrace the different cities that neighbor close by.

Cape Town

Cape Town
Cape Town

Africa has some excellent sailing locations such as Cape Town. It is recommended that you charter with an experienced crew since the wins can sometimes reach up to 60 knots. The weather is reminiscent of California and offers great sailing opportunities.



Antarctica does not really come up as often when searching for charter companies in various locations in search results. People either love or hate the cold but this provides you some excellent chances to see some of the most iconic parts of the world. Exploring here on a charter would definitely be an unforgettable experience.



South America has more than enough sailing destinations to charter a boat. Chile is one of them that offers excellent views and somewhat good sailing conditions to see rich culture. It also offers you a remote location but not too far away from civilization.

How to Find the Best Sailing Charter Companies

Going on a sailing vacation is a great opportunity to see locations without having to bring your own boat. A charter vacation is a popular idea and many tourists take advantage of the chance of a lifetime to see these remarkable places.

Finding the best sailing charter company will vary by many factors. Below you can see how to find the best sailing charters.

Decide What You Want

One of the first things you need to consider is what you are wanting to experience. You also need to factor in how many people are going on this trip so that you can decide what type of boat you are going to need.

Sailing charters can cater to just about every water experience you can think of. From fishing to kayaking there is likely a charter company to help you find the perfect waterways to explore.

Conduct Research

You will need to research a lot of companies to get a good feel for who does what. You may not want a charter that caters to fishing trips if all you want to do is to cruise.

You will likely see various awards or certifications that set some companies apart from others. Researching companies will be your best bet to get a good idea of what to expect.

Check for Recommendations

You always want to hear good things from other people that have already experienced this charter. This could be from friends or family that have gone on these types of trips.

If you are doing this last minute and are trying to go on a charter in a desired location you can ask the locals. You will likely find someone that either knows the person running it or the best idea of which one to go on.

Narrow Down Your Options

Once you have a list of crewed charters you should call each one and find out their information for what they charge or other amenities they provide. You will need to gather as much information to see which one is best for you.

This will also give you the vibes you need to see if the company takes care of their customers or if you feel like you are going to be disappointed. This will greatly benefit your search and you will likely find several worth your time.

You should also consider if you want to rent from a bareboat charter company or ones that have a crew. Bareboat charters allow you to rent the boat and guide yourself through locations.

Consider the Costs

When you call and request a quote for the charter services you will be able to figure out a price. Setting up a budget is key for any type of sailing vacation so be sure to have that in place.

A lot of charter companies will vary in price based on factors such as the type of boat they have and what other services they offer besides cruising. Be sure you ask about a cancellation policy or any extra fees that you might incur.

Check it out in Advance

Planning ahead is always your best bet for a yacht charter since they typically get reserved fast in prime locations. Some places do not have anything available for quite some time and you will have to move onto another yacht charter company.

Booking in advance gives you the luxury of picking and choosing which ones are best without having to settle for ones that you do not want. It also allows you to find the best price if you are on a strict budget.

Keep in Mind Location

The charter vacation that you are going to encounter in the Spanish Virgin Islands is nowhere near the same as ones in Antarctica. These two offer great experiences but cater to different types of boats and weather gear needed to explore.

The availability of some of these boats may change drastically based on the season. The warmer months in prime locations are usually the busiest but depending on where you intend to go may vary.

See Consumer Reviews

A satisfied customer review is a good indication of a good charter company. But simple five star reviews are not going to cut it for the best charter companies.

Look for both the good and bad when it comes to their services and how they treat the customer. Try to put yourself in the reviewer's shoes to see if there were any concerns with safety or well being on the boat.

Tips for Booking the Best Charter for Sailing

Once you think you have the best sailing charter company it is time to move onto the next step. You will need to consider various possibilities that will affect your time out on the water. Do not immediately book since you want to weigh your options to see which ones are best.

How to Pick the Best Boat

Private charter options versus a company that is more like a mom and pop store will feature way more costs. The type of boat they are using will likely have more luxury options but make sure that it caters to your experience and not be unnecessary.

You need to consider how many people are going to fit on board. You also need to determine how much time you plan to spend on board the vessel and if it is worth paying for luxury comforts.

Consider Eating Options

If you are spending all day on a charter you will need to eat at some point and likely several meal options. You will need to find out if they are going to provide food for you or if you have to bring your own groceries.

You should also consider stopping at various ports and eating out at various restaurants or if you are planning on staying out at sea. Packing food with you could be a good idea anyway if you have smaller children on board.

Plan for a Crew

If you are new to sailing or want the freedom of enjoying the voyage it might be best to have an experienced crew to handle everything. This will give you the peace of mind that you are in good hands but also allows you the opportunity to enjoy the exploration. Keep in mind that this might cost more since you are paying for someone else to navigate for you and plan your trip for the day.

What Plans Do You Have?

Some charter companies have a dedicated route that they follow or an itinerary for the day. You will want to coordinate with the company to get an idea of what you will be doing while on board.

If you are trying to visit a certain location try to see if you can have that added to the travel plans. Keep in mind that some are not negotiable and additional costs may be added if they have to go out of their way.

When is the Best Time of Year?

Most people think that sailing on a charter is best reserved for warmer months. While that might be true depending on the location it is best to explore locations in the off seasons.

Consider months such as April or May or even September and October to avoid peak times. This will usually give you the best prices on these trips and help you avoid the larger crowds.

Various Expenses

Even though you might have a budget in place you should add a safety net somewhere in there for unplanned spending. This could be entry fees to various parks or taxes on various purchases.

You should also factor in tips for the charter company. They might have a gratuity in effect for larger parties but keep in mind the larger tips are usually in North America.

Consider Toys on the Water

Some people want to enjoy various activities on the water. This includes having a jet ski or paddleboards. Some charters will allow you to bring these extra toys but keep in mind that it could cost you depending on how they have to haul it for you.

Best Sailing Charter Destinations
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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