Whether you’re dreaming of the turquoise waters of the Ionian or the or Island hopping in the BVI’s, a sailing charter holiday is the ultimate way to reclaim your sense of adventure and experience the thrill of sailing. But for a first-timer, the transition from “landlubber” to “charter skipper” often comes with a lot of questions. In this post I share my top tips and answer the most common questions that I get asked by RYA Day Skipper and ICC students who are planning or looking ahead to their first sailing holiday charter.
Here is everything you need to know to plan, pack, and set sail on your first charter holiday. First I explain the key differences and options for your charter, if you already know which option you want to go for just scroll down for my Q & A’s – to help get you ready for your charter holiday.
Choosing the right charter holiday for you…
Not all charters are created equal. Depending on your confidence and experience level, there are 3 types of sailing charter holiday available to you:
1. Bareboat Charter Sailing Holiday
- What is a bareboat charter holiday? You rent the boat and nothing else. You are responsible for navigation, mooring, and safety.
- What experience do you need for a bareboat charter? Depending where you’re chartering you might need a recognised qualification (like an RYA Day Skipper or an ICC) and a resume showing you’ve handled similar vessels. Greece is the most popular place to charter in Europe, for Greece the standard requirement for a bareboat charter is that the skipper must hold an ICC qualification. In the Caribbean, charter companies are more relaxed and instead of formal qualifications are often satisfied with a run through of your sailing resume.
- Best for: Independent, experienced and confident sailors who want to wake up whenever they want and sail wherever the wind takes them.
- Pro’s and Con’s of a bareboat charter: Pro’s – You get to experience the freedom that sailing can bring, planning your own itinerary and spending time where you want to. You can choose who’s onboard and don’t have any strangers with you. Want to stay another night on your fave anchorage? Then you can stay. Want to jump in the sea? You can. Want to eat ashore? You can. I think you get my jist! A bareboat charter puts you in charge of your holiday and brings a freedom that you don’t get on other sailing charter holidays. Con’s – You need to have a solid amount of experience at skippering a boat. You’ll need to do the passage planning and weather planning yourself. If marinas, mooring balls or quays require booking in advance, then you’ll need to do this task each day. You’ll need to provision the boat, cook and plan your meals as needed.
2. Flotilla Charter Holiday
- What is a flotilla sailing charter holiday? You skipper your own boat, but you sail as part of a fleet (usually 5–12 boats) led by a professional “Lead Crew” on a separate yacht. This is an ‘in-between’ option (in between Bareboat and Skipper charters) – you get the benefit of just having your friends and family onboard, but the stress of passage planning is taken away from you, and you have a ‘safety net’ with a lead boat on-hand if needed.
- What experience do I need to go on a Flotilla sailing charter holiday? A moderate level of experience is needed. Most charter companies require a Day Skipper or ICC, but the Lead Crew handles the morning weather briefings and helps you park (often the most stressful part for inexperience sailors!) every evening.
- Best for: Families and first-time skippers who want independence during the day and to experience a sailing holiday, but want to de-risk it, take some of the pressure off and have support on hand and close by (including when it comes to berthing)
- Pro’s and Con’s of a bareboat charter: Pro’s – Skippers often feel reassured by having other boats and a lead crew nearby and on-hand. The lead crew carry lots of spares, so if you have an issue they’ll jump on board and help you, they’re also on hand to help with mooring. They do all the planning and give a full weather briefing each morning. Con’s – It removes the freedom of sailing, as you’ll be sailing to a pre determined itinerary, you’ll also have other boats in the flotilla so won’t get to experience the isolation and peace and quiet that a bareboat charter might bring.
3. Skippered Charter
- What is a Skipper charter: You rent the boat and hire a professional captain/skipper to live on board. The skipper will be in charge of the boat, they’ll do the safety checks and will be responsible for the sailing – planning the passage and keeping an eye on the weather.
- What experience do I need for a skipper charter sailing holiday? Zero experience is needed. You can be as “hands-on” or “hands-off” as you like, as the professional skipper will be responsible for the boat, the sailing and passage planning, removing and pressure and stress from you.
- Best for: Complete beginners, those without any qualification, or groups who just want to relax and be shown the “secret spots” by a local expert.
- Pro’s and Con’s of a skipper yacht charter holiday – Pro’s – This is the zero pressure, ultimate de-stress option for a charter holiday, you don’t need any experience as your professional skipper will take care of everything. Often the boat is provisioned for you (but always check just in case!). If you’re learning to sail your skipper may help you with your learning and some companies may even be able to award you a qualification as part of the holiday (combining a course with a holiday). Con’s – You rarely get to choose your skipper and they may not be a personality fit. The skipper will be with you for the duration of your charter which some people don’t like (no privacy), although if you get someone with experience, they’ll often be good at reading the cues and make themselves scarce when needed. It is an expensive option, because you’re now paying for a professional for the duration of your trip, as well as the cost of the charter.
Your questions answered – Everything you need to know about chartering a boat on a sailing charter holiday….
Q. What experience do I actually need to charter a boat on holiday?
A. If you want to go Bareboat, most Mediterranean countries (Greece, Croatia, Italy) legally require an ICC (International Certificate of Competence) or an RYA Day Skipper license. In Croatia, at least one person must also have a VHF Radio License. If you have zero experience, don’t worry—a Skippered Charter requires no experience at all!
Q: How expensive is a sailing charter holiday?
A: The cost of a sailing charter could be more affordable than you might think—often comparable to a high-end villa stay. For 2026, expect:
- Monohull Sailing yacht: £2,500 – £4,000 per week.
- Mid-range Catamaran: £5,000 – £8,000 per week.
- Extras: You will need to pay a deposit (which will be refunded at the end of your charter (this will vary depending on the boat think £1000 for a 40ft monohull, up to £5000 for a 50ft catamaran). You’ll need to budget for fuel (this will depend on how much you sail vs motor) I’ve chartered before and spent just £15 on fuel, but it’s not uncommon for catamaran charterers who have relied more on engine that sail to spend £400+ on fuel for a week. Marina fees will set you back£50–£150 per night in hotspots, but can be avoided or significantly reduced if you anchor or opt for a mooring ball instead. Provisioning will also need to be considered and will vary depending on your diet and requirements! Finally, it will be possible for you to hire extras (a BBQ, kayaks, paddle boards, inflatables, hammocks etc) – these ‘toys’ will vary by charter company. We often hire a paddle board or kayak and these typically cost between £30 – £50/week.
- Tip: Split the cost by 6 or 8 people, and the price per head becomes much more reasonable.
Q: Where is the best place for a first-time sailing charter holiday?
A: Some sailing grounds are more suitable for a first-time charter. I personally recommend:
The Ionian, Greece: Think island hopping and Greek tavernas, known as the “nursery” of the sailing world. You can expect calm winds, short distances, and crystal-clear water. A popular sailing holiday destination, there are size main island clusters in Greece – the Cyclades, Ionian, Dodecanese, Sporades, Saronic, and North Aegean Islands, and charter companies often grade island clusters by recommended experience. The Greek sailing season runs from May – Sept.
The British Virgin Islands (BVI): The BVI’s is undoubtedly one of the top sailing charter destinations in the world offering “Line of sight” navigation, picture perfect tropical islands, beach bars and the perfect chilled Caribbean vibe. With hundreds of ‘mooring balls’ located throughout the BVI, there’s no anchoring or marinas to contend with, removing stress for the first-time charterer. The best time to go is Nov – April (great for some winter sun).
Q: What should I take on a sailing charter holiday? Here’s a complete list for you…
- Quick drying towel – charter companies often provide towels for fresh water only
- Snorkelling gear – if you own it it will save on hire charges
- Soft luggage – newbies often make the mistake of bringing a hard suitcase, but storing that can be a nightmare. I recommend bringing a soft duffel type bag so it can be squashed down
- 12v car charger – to help with phone charging when you’re not on shorepower
- Battery power bank for charging devices when power is low
- Reef safe sun cream – do your bit and don’t damage the marine life
- Playing cards – nothing beats a game of cards, with a rum punch as the sun goes down
- Inspect repellent – where there’s water, there’s mosquitos!
- Lib balm with SPF – trust me on this one
- Beach shoes/aqua shoes – great for wading ashore when you have to leap out of the tender (protecting your feet from stings/shells etc)
- Drybag – essential for trips ashore
- Reading book – for chilling in your hammock
- Clothes – pack light, you’ll always wear less than you think. Think sarongs, swimwear, light t shirts and shorts
- Pegs – handy for pegging your wet swim wear and towels to the guard rail so they don’t disappear
- Sunglasses – take polarised glasses – helpful for seeing the seabed/anchor and rocks underwater
- Sun hat – ideally with a strap and clip to clip to your top so it doesn’t end up overboard
What are your top tips for a sailing charter holiday to help it go smoothly?
- One Hand for the Boat: Always keep one hand on a solid part of the boat (a “handrail” or “stay”) while moving. Even in calm water, a passing wake can unbalance you.
- Protect your feet: Nothing beats that feeling of bare feet both onboard and in the sand – but to keep your feet from injury if you’re going to go bare feet onboard tread carefully and don’t rush, it’s easy to stub toes on blocks when moving about (especially going forward). Take aqua shoes for tendering ashore – you’ll often have to leap out for the last few metres and it’s easy to jump on an unsuspecting ‘stinger’ of some sort or a shell – you can always whip them off once you’ve dragged the tender up above the tide line.
- Respect the head! – Never put anything down the toilet that hasn’t been through your body (yes, that includes toilet paper—it goes in the small bin provided). Ignore this tip at your own peril, and only if you want to spend your holiday unblocking the toilet!
- Feeling a little rusty? – It’s often to hire a skipper for the 1st 24 hours to help you ease your way in to your holiday, even if you don’t want to have a skipper onboard for the whole holiday
- Keep an eye on the power – If you’re not going to be ‘on shore power’ each night, then you’ll need to keep a close eye on your battery level. Your boat will have both house batteries and a starter battery (which helps get your engine started). If you’ve got the fridge running 24/7, leave cabins lights on and are charging phones regularly, then your batteries will run down fairly frequently and will require monitoring and charging. A healthy 12-volt boat battery should read between 12.6V – 12.8V when charged and at rest. A reading below 12.2V indicates the battery is 50% or less charged, and it should not fall below 12.0V, as this can damage the battery and threaten starting reliability. Thankfully charging is simple, you just need to run the engine (ideally at 1,500 RPM or more) for an hour or two each day. Some high-end charters may have solar panels which will make battery management much more simple.
- Provisioning – Don’t buy everything at the marina supermarket—it’s always more expensive, instead walk inland to the local market for better produce and lower prices.
- Island time – Sailing is dictated by the wind. If the wind is against you, don’t fight it for six hours. Change your plan, find a closer cove, and open a bottle of local wine. The best memories are often the ones you didn’t plan. In the Caribbean all locals will also operate on Island time, so chill get into the Island vibe and go with the flow.
Should charter a monohull or a catamaran?
Monohull – Classic Sailboat: This is for the purists. When the wind catches the sails, the boat heels/leans over. It feels like real sailing. They are generally more affordable, easier to find space for in crowded Mediterranean marinas, and more sporty and fun to handle.
Catamaran – The Floating Villa/Caravan: With two hulls, these boats don’t lean—they stay level, which is a lifesaver for those prone to seasickness. They offer massive ‘trampolines’ at the front for sunbathing and a huge social cockpit area. However, they are much more expensive to charter and often cost double in marina mooring fees because they take up two spots.
Got some sailing charter holiday tips that you’d like to share? Leave them in the comments below!