Chartering a Sailing Yacht
An Exciting Alternative for your Annual Vacation

Chartering a sailing yacht is a great way to enjoy a vacation that combines adventure, relaxation, and exploration. Whether you are an experienced sailor or a beginner, you can find a sailing holiday that suits your needs and preferences.

You can choose from different types of charters, such as bareboat charters, where you sail the yacht yourself, or skippered sailing charters, where you hire a professional captain to take care of the navigation and safety.

You can also decide on the size and style of the yacht, the duration and itinerary of your trip, and the destinations you want to visit.

Five Islands, AntiguaFive Islands Bay in Antigua. It might be tempting to linger here for a while...

One of the main attractions of chartering a sailing yacht is that you can explore some of the most beautiful and diverse places in the world by sea.

You can sail to secluded coves, sandy beaches, historic towns, and natural wonders.

You can also experience different cultures, cuisines, and activities along the way.

You can enjoy the freedom and flexibility of sailing at your own pace, stopping where and when you want, and changing your plans as you go.


Booking Agency or Direct?

One of the first things to decide is whether to plan your sailing vacation with the help of a Yacht Charter Agency such as PlainSailing.com or do the footwork yourself and go direct to one of the many Yacht Charter Companys such as Sunsail, Moorings or Dream Yacht Charter etc.

  • A Yacht Charter Agency is a company that acts as an intermediary between the yacht owner or charter company and the potential charterer.
  • A Yacht Charter Company is a company that owns or manages a fleet of yachts for charter.

Like most of life's choices there are both benefits and disadvantages of using a yacht charter agency as an alternative to dealing with the yacht charter company direct.

Some of the benefits are:

  • A yacht charter agency can offer you a wider selection of yachts, locations, and prices, as they have access to multiple charter companies and independent owners. They can also help you find the best match for your preferences, budget, and itinerary.
  • A yacht charter agency can provide you with professional advice, guidance, and support throughout the booking process and the charter itself. They can handle the contracts, payments, insurance, and other paperwork for you. They can also assist you with any issues or requests that may arise during your charter, such as itinerary changes, special arrangements, or emergencies.
  • A yacht charter agency can negotiate better deals and discounts for you, as they have established relationships and leverage with the charter companies and owners. They can also save you time and hassle by doing the research and comparison for you.

Some of the disadvantages are:

  • A yacht charter agency may charge a commission or fee for their services, which can increase the overall cost of your charter. However, this fee is usually included in the quoted price and is paid by the owner or charter company, not by the charterer.
  • A yacht charter agency may not have direct control or influence over the quality and condition of the yachts, as they are not the owners or operators. They may rely on the information and feedback provided by the charter companies and owners, which may not always be accurate or up-to-date.
  • A yacht charter agency may have limited availability or flexibility for certain yachts, dates, or destinations, as they are subject to the availability and policies of the charter companies and owners. They may also have less influence over the terms and conditions of the charter contract, such as cancellation policies, deposits, or liability clauses.

The Top Five Worldwide Charter Locations

The Caribbean

The Caribbean is a dream destination for many sailors, and for good reasons. The region offers warm weather, steady trade winds, clear blue water, and stunning scenery.

You can sail among hundreds of islands, each with its own charm and character.

You can visit famous spots like the British Virgin Islands, St. Martin, Antigua, Grenada, or St. Lucia, or discover less crowded places like Belize, Martinique, or the Bahamas.

You can also enjoy a variety of activities on land and sea, such as snorkeling, diving, hiking, shopping, or dining.

The Caribbean sailing season runs from November to July, with the peak season being from December to April. The weather is generally sunny and dry during this time, with average temperatures ranging from 24°C to 30°C (75°F to 86°F). The wind speed is usually between 10 and 20 knots (11 to 23 mph), making for pleasant sailing conditions.

However, there are some factors to consider when planning your trip, such as hurricane season (from June to November), high season prices and crowds (especially around Christmas and Easter), and local regulations and fees (which vary by country).


The Mediterranean

The Mediterranean is another popular destination for chartering a sailing yacht. The region boasts a rich history, culture, and cuisine, as well as diverse landscapes and climates.

You can sail along the coastlines of countries like Greece, Croatia, Italy, Spain, or France, or explore the islands of Corsica, Sardinia, Sicily, Malta, or Cyprus.

You can also visit iconic places like Monaco, Venice, Dubrovnik, or Santorini.

You can also enjoy a range of activities on land and sea, such as sightseeing, wine tasting, fishing, or kayaking.

The Mediterranean sailing season runs from April to October, with the peak season being from June to August. The weather is generally sunny and warm during this time, with average temperatures ranging from 20°C to 30°C (68°F to 86°F).
The wind speed is usually between 5 and 15 knots (6 to 17 mph), making for easy sailing conditions.

However, there are some factors to consider when planning your trip, such as seasonal winds (such as the Meltemi in Greece or the Mistral in France), high season prices and crowds (especially in July and August), and local regulations and fees (which vary by country).


Southeast Asia

Southeast Asia is a destination that offers exotic and diverse sailing experiences. The region has a tropical climate, lush vegetation, and rich wildlife.

You can sail among thousands of islands, some of which are uninhabited or have indigenous communities.

You can visit places like Thailand, Malaysia, Indonesia, or the Philippines, or explore the Andaman Sea, the Gulf of Thailand, or the Java Sea.

You can also enjoy a variety of activities on land and sea, such as diving, surfing, trekking, or spa.

The Southeast Asia sailing season runs from November to April, with the peak season being from December to February. The weather is generally hot and humid during this time, with average temperatures ranging from 25°C to 35°C (77°F to 95°F). The wind speed is usually between 10 and 20 knots (11 to 23 mph), making for moderate sailing conditions.

However, there are some factors to consider when planning your trip, such as monsoon season (from May to October), low season prices and availability (especially from June to September), and local regulations and fees (which vary by country).


South Pacific

The South Pacific is a destination that offers a paradise-like sailing experience. The region has a warm climate, turquoise water, and coral reefs.

You can sail among hundreds of islands, some of which are volcanic, atoll, or lagoon.

You can visit places like French Polynesia, Tonga, Fiji, or the Whitsundays.

You can also enjoy a variety of activities on land and sea, such as snorkeling, whale watching, hiking, or golfing.

The South Pacific sailing season runs from May to October, with the peak season being from June to August. The weather is generally sunny and dry during this time, with average temperatures ranging from 22°C to 28°C (72°F to 82°F). The wind speed is usually between 15 and 25 knots (17 to 29 mph), making for challenging sailing conditions.

However, there are some factors to consider when planning your trip, such as cyclone season (from November to April), high season prices and crowds (especially in July and August), and local regulations and fees (which vary by country).


North America

North America is a destination that offers a diverse and exciting sailing experience. The region has a temperate climate, varied landscapes, and cultural attractions.

You can sail along the coastlines of countries like Canada, the USA, or Mexico, or explore the lakes, rivers, or bays.

You can visit places like Vancouver, San Francisco, Los Angeles, Miami, or Cancun.

The North America sailing season runs from April to October, with the peak season being from June to September. The weather is generally mild and sunny during this time, with average temperatures ranging from 15°C to 25°C (59°F to 77°F). The wind speed is usually between 5 and 15 knots (6 to 17 mph), making for easy sailing conditions.

However, there are some factors to consider when planning your trip, such as winter season (from November to March), high season prices and crowds (especially in July and August), and local regulations and fees (which vary by State).



Planning your Trip

  • Decide on your destination. The first thing you need to do is to decide where you want to go for your sailing holiday. You can use the information above to help you narrow down your options, or you can do some more research online or offline. You can also consult with a travel agent or a charter company to get some advice and recommendations.
  • Decide on your charter type. The next thing you need to do is to decide what type of charter you want to book. You can choose between bareboat charters, where you sail the yacht yourself, or skippered sailing charters, where you hire a captain to sail the yacht for you. The choice depends on your sailing experience, confidence, and preference. If you choose a bareboat charter, you will need to have a valid sailing license and some proof of sailing competence. If you choose a skippered sailing charter, you will have more peace of mind and guidance, but less freedom and privacy.
  • Decide on your yacht type. The third thing you need to do is to decide what type of yacht you want to charter. You can choose between monohulls and catamarans, which are the most common types of yachts available for chartering. Monohulls are single-hulled boats that are more traditional and agile, but less spacious and stable. Catamarans are double-hulled boats that are more modern and comfortable, but less maneuverable and authentic.
  • Decide on your budget. The fourth thing you need to do is to decide how much money you want to spend on your sailing holiday. Your budget will depend on several factors, such as the destination, the charter type, the yacht type, the duration, the season, and the extras. You can use online tools or calculators to get an estimate of how much your trip will cost, or you can contact a charter company or a travel agent to get a quote.
  • Decide on your dates. The fifth thing you need to do is to decide when you want to go for your sailing holiday. Your dates will depend on several factors, such as the destination, the season, the availability, and your personal schedule. You can use online tools or calendars to check the best time to visit your chosen destination, or you can contact a charter company or a travel agent to check the availability of yachts.
  • Book your trip. The final thing you need to do is to book your trip. You can book your trip online or offline, depending on your preference and convenience. You can use online platforms or websites to compare prices and options from different charter companies or travel agents, or you can contact them directly by phone or email. You will need to provide some information and documents, such as your personal details, passport number, sailing license (if applicable), credit card number, etc., and pay a deposit or a full amount.

Once you have booked your trip, you can start preparing for your sailing holiday. You can pack your bags, buy travel insurance, arrange transportation, etc., and get ready for an amazing adventure.


Chartering a Sailing Yacht: A Few FAQs...

What are the different types of sailboat charter holidays that are available?

There are different types of sailboat charter holidays that you can choose from, depending on your sailing experience, preferences and budget. Some of the most common types are:

  • Bareboat charter holidays: This is when you rent a sailboat and sail it yourself, without any crew or skipper. You have full control over your itinerary and destinations, as well as the responsibility for the boat's maintenance and safety. This type of charter requires a valid sailing license and some sailing experience.
  • Skippered charter holidays: This is when you rent a sailboat with a professional skipper, who will take care of the navigation, sailing and boat handling. You can still decide where you want to go and what you want to do, but you don't have to worry about the technical aspects of sailing. This type of charter is suitable for beginners or those who want to relax and enjoy the scenery.
  • Flotilla sailing holidays: This is when you join a group of other sailboats, led by a lead boat with a skipper and a host. You can sail your own boat or hire a skipper, but you will follow a pre-planned route and itinerary, with daily briefings and social events. This type of charter is ideal for families, friends or solo travellers who want to meet new people and have fun.
  • Sail by the cabin holidays: This is when you rent a cabin on a shared sailboat, with a skipper and sometimes a cook or host. You will share the boat with other guests, who may have different backgrounds and interests. You will follow a fixed route and schedule, with stops at various ports and attractions. This type of charter is perfect for those who want to experience sailing without having to rent a whole boat or learn how to sail.

What qualification and level of experience do I need to be captain of a bareboat sailing charter?

To be captain of a bareboat sailing charter, you need to have sufficient sailing experience and qualifications that match the requirements of your chosen destination. Different countries may have different regulations and expectations for bareboat charterers, so it is important to do your research before you book your trip.

One of the most common and widely accepted qualifications for a bareboat sailing charter is the International Certificate of Competence (ICC), which is issued by the Royal Yachting Association (RYA) in the UK. The ICC proves that you have the necessary skills and knowledge to operate a pleasure craft in coastal or inland waters. To obtain an ICC, you need to pass an assessment at a recognized RYA training center, or have a specific national boating license that is equivalent to the ICC standards. You also need to have a valid passport and pay a fee. The ICC is valid for 5 years.

Another qualification that may be accepted in some destinations is the International Proficiency Certificate (IPC), which is issued by the American Sailing Association (ASA) in the US. The IPC is similar to the ICC, but it is based on the ASA sailing courses and certifications. To obtain an IPC, you need to have completed ASA 104 (Bareboat Cruising) or higher, and have a valid US passport. You also need to fill out an application form and pay a fee. The IPC is valid for 5 years.

Some other qualifications that may be recognized in certain destinations are the International Sailing License and Credentials (SLC) from NauticEd, or the RYA Day Skipper Course from the UK. These qualifications also demonstrate your competence and ability to charter a yacht in various conditions and locations.
However, having a sailing qualification does not guarantee that you are qualified for a bareboat sailing charter in every destination. Some places may have additional requirements or restrictions, such as minimum age, boat size, insurance, crew composition, etc. Therefore, it is advisable to check with your charter company or local authorities before you plan your trip. You can also contact us for more information and guidance on choosing the right destination for your sailing experience.

Can I sail a bareboat without any qualification or experience?

No, you cannot sail a bareboat without any qualification or experience. Sailing a bareboat is a serious responsibility that requires adequate skills and knowledge to ensure the safety of yourself, your crew, and other boaters. You also need to comply with the laws and regulations of the destination you are sailing to, which may vary depending on the country, region, or waterway.

As we mentioned in our previous answer, there are different sailing qualifications that are accepted in different destinations for bareboat sailing charter. Some of the most common and widely accepted ones are the ICC, the IPC, the SLC, and the RYA Day Skipper Course. These qualifications prove that you have the necessary competence and ability to charter a yacht in various conditions and locations. You can obtain these qualifications by taking sailing courses and assessments at recognized training centers or online platforms.

If you do not have any qualification or experience in sailing, we strongly recommend that you take some sailing courses before you attempt to charter a bareboat. This will help you gain confidence and competence in handling a yacht, as well as learn the essential rules and regulations of sailing. You can find many sailing schools and courses online or near your location that offer different levels and types of sailing instruction. You can also contact us for more information and guidance on choosing the right sailing course for your needs.

Alternatively, if you do not want to take any sailing courses or obtain any qualification, you can still enjoy a sailing holiday by hiring a skipper or joining a flotilla. A skipper is a professional sailor who will take care of all the aspects of sailing the yacht for you, while you can relax and enjoy the scenery. A flotilla is a group of yachts that sail together under the guidance of a lead boat with an experienced skipper and crew. Both options are great ways to experience sailing without any stress or hassle.

We hope this answer has clarified your doubts and helped you understand the importance of having a qualification and experience for bareboat sailing charter.

Can I take a sailing course and gain a qualification while taking a holiday on a chartered sailboat?

Yes, you can take a sailing course and gain a qualification while taking a holiday on a chartered sailboat. There are many options available for you to choose from, depending on your location, budget, and level of experience. Here are some of the web search results that might interest you:

  • RYA Sailing Courses | Sailing Holidays: This website offers a range of RYA sailing courses in the Greek islands, from beginner to intermediate level. You can book a berth on a school yacht, or book a whole boat and a private instructor. You can also pair your course with a flotilla holiday, where you sail in a group of other yachts with support from a lead boat.
  • Learn to Sail | Sailing Holidays: This website also offers RYA sailing courses in the Greek islands, with a similar approach as the previous one. You can learn to sail in the sunshine, with instructors who are passionate and experienced. You can also sign up for a VHF course, which is required by law in some countries to charter a yacht.
  • Sailing Package Holidays 2023 - Mark Warner: This website offers sailing package holidays in various destinations, such as Greece, Turkey, Italy, and France. You can learn to sail on holiday by taking part in a relevant course for your age group and skill level. You can also enjoy other activities such as windsurfing, kayaking, cycling, and tennis.
  • Learn to Sail Holidays | Beginner & Intermediate Sailing Courses: This website offers learn to sail holidays in Florida and the British Virgin Islands. You can take a beginner sailing course with no prior experience, or an intermediate sailing course to improve your skills. You can also explore the beautiful scenery and wildlife of these locations.

Where can I charter a sailing yacht?

You can charter a sailing yacht in many destinations around the world, depending on your preferences, budget, and season. Some of the most popular destinations are the Caribbean, the Mediterranean, Southeast Asia, the South Pacific, and North America. You can find more information about these destinations in this article.

How much does it cost to charter a sailing yacht?

The cost of chartering a sailing yacht depends on several factors, such as the destination, the charter type, the yacht type, the duration, the season, and the extras. The cost can range from a few hundred to a few thousand dollars per day. You can use online tools or calculators to get an estimate of how much your trip will cost, or you can contact a charter company or agent to get a quote.

How do I book a sailing yacht charter?

You can book a sailing yacht charter online or offline, depending on your preference and convenience. You can use online platforms or websites to compare prices and options from different charter companies or travel agents, or you can contact them directly by phone or email. You will need to provide some information and documents, such as your personal details, passport number, sailing license (if applicable), credit card number, etc., and pay a deposit or a full amount.

What do I need to bring for my sailing yacht charter?

You will need to bring some essential items for your sailing yacht charter, such as clothing, footwear, toiletries, sunscreen sunglasses, hat, swimwear, towel, camera, phone, charger, adapter, passport, visa (if required), travel insurance, sailing license (if applicable), and cash. You should also bring some optional items, such as books, games, music, snacks, drinks, fishing gear, snorkelling gear, or diving gear. You should pack lightly and use soft bags that can be easily stored on board.

What are some safety tips for my sailing yacht charter?

Some safety tips for your sailing yacht charter are:

  • Check the weather and tides before you set sail and avoid sailing in extreme conditions.
  • Wear a life jacket and appropriate clothing when on deck or in the water.
  • Follow the instructions and advice of your skipper or instructor and respect the rules of the boat and the road.
  • Learn how to use the safety equipment and emergency procedures on board and have a contingency plan in case of trouble.
  • Stay hydrated and avoid alcohol or drugs when sailing.
  • Be aware of your surroundings and potential hazards such as rocks, reefs, or other boats.
  • Have fun but know your limits and don't take unnecessary risks.

What are some etiquette tips for my sailing yacht charter?

Some etiquette tips for your sailing yacht charter are:

  • Be respectful and courteous to your skipper, crew, and fellow sailors.
  • Communicate clearly and honestly with your skipper and crew about your expectations, preferences, and feedback.
  • Share the chores and responsibilities on board such as cooking, cleaning, or keeping watch.
  • Respect the privacy and personal space of others on board.
  • Keep the boat clean and tidy and don't leave any trash behind.

The above text was drafted by sailboat-cruising.com using GPT-4 (OpenAI’s large-scale language-generation model) as a research assistant to develop source material; we believe it to be accurate to the best of our knowledge.

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