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Chartering a sailing boat: how to plan a trip under sail, wherever you want to go

There is a particular kind of freedom that only comes on a sailing boat. You wake up in a quiet bay, swim before breakfast, raise the sails and spend the day moving with the wind to a new island, a harbour town or a beach you can only reach from the water. At night the boat becomes your home, rocking gently at anchor under the stars.

You do not need to own a yacht to live like this for a week or two. Around the world, charter companies and private owners rent out sailing boats of every size, with or without crew. This guide explains the main ways to charter, how to choose a boat and a destination, and what to check before you sign.

Four ways to spend time on a sailing boat

Sailing holidays come in several forms, and the right one depends mostly on your experience and how much responsibility you want to take on.

• Bareboat charter. You rent the boat without crew and act as skipper yourself. This gives the most freedom, but it also means you are responsible for navigation, safety and the boat. Charter companies usually ask for proof of sailing experience, and licence or qualification requirements differ per country and per company, so always check exactly what is needed for the area and boat you have in mind.
• Skippered charter. A professional skipper comes with the boat and takes charge of sailing and navigation. You can help as much or as little as you like. This is a good choice for beginners, for groups where no one wants to be in command, and for anyone who wants local knowledge of the best anchorages.
• Crewed or cabin charter. On a fully crewed boat, a skipper and often a cook or host look after everything. On a cabin charter you book a single cabin on a shared boat and sail with other guests, which suits solo travellers and couples who want the experience without renting a whole yacht.
• Sleeping aboard in a marina. Some owners rent their boat as a floating room that stays in port. You get the feeling of life on the water, the sound of halyards and gulls, and a waterfront location, without leaving the dock.

Catamaran or monohull?

One of the first choices you will make is the type of boat. A catamaran has two hulls, so it sails fairly flat, has lots of deck space and a large living area, and often gives each cabin more privacy. It can reach shallow anchorages and feels stable at anchor, which many people prone to seasickness appreciate. On the other hand, it is wider, which can make finding a marina berth harder, and it usually costs more to rent.

A monohull is the classic sailing yacht with a single hull and a keel. It heels over when sailing, which many sailors love because it feels more responsive and more like "real" sailing. Monohulls are often easier to fit into busy harbours and are generally more affordable to charter. Interiors are narrower, but a well-designed monohull can still be very comfortable for a family or a group of friends.

Where in the world to sail

Popular charter grounds exist on almost every continent, each with its own character:

• The Caribbean, with the British Virgin Islands known for short, easy hops between islands, and the Grenadines for their reefs, turquoise water and small, laid-back islands.
• The Mediterranean, including Croatia's island-studded coast, the many island groups of Greece, and the Turkish coast with its sheltered bays and ancient ruins close to the shore.
• Thailand, where the waters around Phuket and the Andaman Sea offer limestone islands and warm water.
• Australia's Whitsundays, a group of islands close to the Great Barrier Reef, and New Zealand's Bay of Islands, with many protected coves.
• French Polynesia and the Seychelles, for remote tropical sailing among lagoons and granite islands.
• The Pacific Northwest, where the San Juan Islands and nearby waters combine forests, wildlife and cool summer sailing.
• The Baltic and Scandinavian archipelagos, with thousands of rocky islands, long summer evenings and a strong tradition of sailing.

Timing matters. Tropical regions have hurricane or cyclone seasons when many charter companies reduce their fleet or recommend other destinations, so check the local calendar before choosing dates. Remember that seasons are reversed in the Southern Hemisphere: the best months for New Zealand or southern Australia are very different from those in the Mediterranean or the Baltic. Wind patterns also vary; some areas have strong seasonal winds that are exciting for experienced crews but tiring for beginners.

Life on board: food, nights and weather

Provisioning. Unless you book a crewed charter with meals, you will buy your own food and drinks. Some companies offer a provisioning service that stocks the boat before you arrive, which saves time on the first day. Otherwise, plan simple meals, remember that fridge space is limited, and bring enough drinking water. Eating ashore in harbour towns is part of the fun in many regions.

Anchoring or marinas. Nights at anchor are peaceful and often free, with swimming straight off the boat. Marinas and mooring buoys offer showers, electricity, fresh water and shops, and can be easier in strong winds. Most charters mix both. In busy seasons, popular marinas can fill up early in the day, so plan ahead.

Weather and seasickness. Check the forecast every day and let it shape your route rather than the other way round. If you or your crew are prone to seasickness, choose sheltered waters, a stable boat and shorter passages, stay on deck with your eyes on the horizon, and talk to a pharmacist or doctor about remedies before you travel.

Safety comes first

Every good charter starts with a safety briefing. Expect to be shown the life jackets, lifelines, fire extinguishers, first aid kit, radio, bilge pumps and how to handle a person overboard. Make sure there is a properly fitting life jacket for every person on board, including children, and agree on when they must be worn. Tell someone ashore your rough plans, and never be afraid to stay in port when conditions look doubtful.

Questions to ask before you book

• What licence, qualification or sailing experience do you require for a bareboat charter in this area?
• Is a skipper, host or cook available, and what are their arrangements for meals and sleeping on board?
• How many cabins, berths and bathrooms does the boat have, and how old is it?
• Which safety equipment is on board, and are there life jackets in the right sizes for children?
• What is included, such as fuel, bed linen, towels, dinghy, outboard and snorkelling gear?
• How large is the security deposit, and is damage waiver insurance available?
• Are there areas we may not sail to, or rules about sailing at night?
• Do you offer provisioning, and how early can we board on the first day?
• What happens if bad weather stops us from returning to base on time?

Find your boat in the listings above

The sailing boats on this page are grouped by continent, country and region, so you can start with the waters you dream of and compare options nearby. Each link goes to the owner's own website, where you can see the boat, check availability and book directly. Do you rent out a sailing boat or run a charter fleet? Add your link for free with the button above and help sailors find their next adventure.