What does it take to become a sailing cruiser? I remember that initial deluge of questions when Simon and I first started dreaming of casting off the lines. It feels like a lifetime ago, yet the same core curiosities and anxieties bubble up for every new cruiser we meet.
I’ve been looking over the Internet – looking at forums, Facebook groups, and Reddit threads – and it’s clear that no matter how much the world changes, the fundamental queries of the aspiring sailing cruiser remain remarkably consistent. So, if you’re sitting there, perhaps staring at a boat listing or a chart, wondering where on earth to begin, you’re in excellent company!
I’ve compiled the 20 most popular questions new sailing cruisers are asking, and more importantly, I’m going to give you some valuable takeaways that I wish someone had told me years ago.
Become A Sailing Cruiser – Top 20 Questions
1. What is the best boat for cruising/liveaboard, and what size should I get?
There is no “best” boat, only the best boat for you. It’s like asking what’s the best car – depends on your needs, budget, and desired lifestyle. Don’t fall into the trap of thinking bigger is always better. Smaller boats are often easier to maintain, cheaper to run, and can get into more anchorages. We started with a 56-foot Oyster, and while we loved her, she came with a very high price tag concerning maintenance and marina fees. For many, something in the 35-45 foot range offers a fantastic balance of space, comfort, and manageability. Focus on condition and suitability for your cruising grounds over brand name.
2. How much does it really cost to buy and outfit a cruising sailboat?
Double your budget, then add 20%. Seriously. The purchase price is just the down payment on your new lifestyle. Surveys, unforeseen repairs (there will be unforeseen repairs), safety gear, dinghy, outboard, spares, electronics upgrades… it adds up faster than you can say “fenders.” Get a comprehensive survey and factor in at least 20-30% of the purchase price for immediate necessary upgrades/repairs.
3. What are the ongoing costs of cruising/liveaboard?
This is a chameleon! It changes dramatically based on your cruising style. Are you always in marinas? Are you a DIY wizard or do you hire out everything? Do you eat out frequently or cook on board? As a rough guide, plan on 10% of your boat’s value annually for maintenance, insurance, and routine upkeep. Then add in food, fuel, personal expenses, and “fun money.” We’ve found we can live on less than we did on land, but that’s because we’re largely self-sufficient and don’t frequent expensive marinas.
4. How do I gain enough sailing experience to feel confident cruising?
Experience trumps certification every time. While certifications (like ASA or RYA) provide a fantastic foundation, nothing beats time on the water. Crew for friends, join local sailing clubs, volunteer to help deliver boats, or even charter a small boat for a week. Practice docking, anchoring, reefing, and handling the boat in various conditions. Confidence comes from competence. Check out Simon’s Sailing Lifestyle Experiences and book a week with him!
5. What are the essential safety equipment requirements for cruising?
Don’t skimp here. Ever. Start with the basics: life jackets, EPIRB/PLB, fire extinguishers, first-aid kit, flares, VHF radio. As you plan longer passages, consider a life raft, satellite communication device, drogue/sea anchor, and robust jacklines/tethers. A good rule of thumb: If it helps you stay on the boat, signal for help, or survive a worst-case scenario, it’s essential. For a full list of all the safety equipment you need, how to use it, and what’s required for servicing and maintenancing along with saftey checklists, get my guide, Boat Safety Checklists.
6. How do I handle internet and communication while cruising?
The game-changer for many cruisers has been Starlink. It’s truly revolutionized connectivity in many parts of the world. However, don’t rely solely on one method. Always have a backup: a good cellular booster for near-shore cruising and perhaps a satellite phone/Iridium Go! for offshore emergencies. And remember, sometimes the best communication is no communication – embrace the digital detox!
7. What’s the best way to get a mailing address and handle mail while living on a boat?
Mail forwarding services are your best friend. They’ll receive your mail, scan it, and forward physical items if needed. Research reputable services in your preferred “home” state or country. Choose a service that understands the transient nature of cruising and offers reliable scanning and international forwarding options.
8. How do I manage power generation and consumption on board?
This is a constant balancing act. Solar panels are non-negotiable for most cruisers. Look into lithium batteries if your budget allows – they offer significant advantages. Most importantly, understand your daily power consumption and learn to be a power miser! Turn things off, unplug devices, and embrace the simple life.
9. What are the challenges of living in a small space, and how do I adapt?
Clutter is the enemy. Organization is key. Every item needs a home, and if it doesn’t, it probably doesn’t belong on the boat. Learn to embrace vertical storage, vacuum-seal clothes, and downsize ruthlessly. The biggest adaptation is often psychological – learning to coexist peacefully with your family/crew in close quarters, respecting personal space (even when there isn’t much!), and finding quiet moments for yourself.
10. How do I manage fresh water storage and production (desalination) on a boat?
Water makers (desalinators) are a must-have for freedom, but they require maintenance and power. If you don’t have one, learn to conserve water religiously. Short showers, washing dishes with minimal water, and collecting rainwater are all part of the game. Regardless of your setup, always know your tank levels and plan your water usage carefully, especially before long passages.
11. What are the best resources for learning about boat maintenance and repairs?
YouTube, sailing forums, and specialized books (like Nigel Calder’s “Boatowner’s Mechanical and Electrical Manual”) are invaluable. Don’t be afraid to get your hands dirty! Start with simple tasks, learn from other cruisers, and document everything you do. Knowing how your boat works is empowering and can save you a fortune. Make sure to get my bestselling book, Checklists for Sailors.
12. How do I deal with seasickness?
Many seasoned sailors still get seasick in certain conditions. Prevention is better than cure: stay hydrated, avoid greasy foods, focus on the horizon, get fresh air, and try ginger. Over-the-counter medications like Dramamine or Meclizine work for many. For some, prescription patches (Scopalamine) are effective. Experiment before you go offshore to find what works for you, and remember, it usually passes after a day or two.
13. What are the best cruising destinations for beginners?
Start close to home! Gaining confidence in familiar waters with readily available resources is crucial. For international cruising, many beginners head to the Bahamas, the Caribbean (especially the Eastern Caribbean), or parts of the Mediterranean (like Greece or Croatia) due to established cruising infrastructure and relatively predictable weather windows. Look for areas with good anchorages, easy navigation, and friendly locals.
14. How do I handle customs, immigration, and foreign port procedures?
It varies wildly from country to country. Research thoroughly before you arrive. Websites like Noonsite.com are fantastic resources. Always be polite, patient, and have all your paperwork meticulously organized. Photos of your crew, boat documents, passports, and crew lists will be your constant companions. Don’t forget your ‘ship’s stamp’ in the Med – it’ll save you a lot of repetitive writing!
15. What are the pros and cons of an outboard vs. inboard engine for a cruising boat?
For anything other than a very small boat, an inboard diesel engine is generally preferred for cruising. They are more reliable, more fuel-efficient, and can produce more power (for charging batteries, etc.). Outboards are simpler, cheaper to replace, and easier to service for some, but they often struggle to push larger boats into strong winds or currents. Prioritize reliability and serviceability for long-term cruising.
16. How do I provision for long passages and remote cruising?
Think non-perishables and things that store well. Canned goods, dried goods (pasta, rice, lentils), long-life milk, root vegetables (onions, potatoes, yams), and plenty of spices. Learn to bake bread, make yogurt, and utilize every bit of fresh produce you can get. Organization is key – label everything and rotate your stock. And don’t forget the treats! Morale food is essential.
17. What are the social aspects of the cruising community, and how do I “fit in”?
The cruising community is incredibly diverse and generally very welcoming. Attend “sundowners” (happy hour on the beach or a boat), help out other cruisers, and be open to sharing experiences. Be a good neighbor – don’t anchor too close, respect quiet hours, and offer help when you see someone struggling. You’ll quickly find your tribe!
18. How do I balance cruising with working remotely or generating income?
This is increasingly common. Reliable internet (see question #6!) is paramount. Be realistic about your work-life balance. Cruising is a lifestyle, not just a vacation, and it demands time and attention. Many cruisers find success with online consulting, writing, photography, or even creating YouTube channels. Flexibility is key! Check out my book, A Sailing Cruiser’s Guide to Making Money.
19. What are the best strategies for anchoring and mooring?
Practice, practice, practice! Learn about different anchor types (Rocna, Mantus, Spade are popular for good reason) and always use enough scope (chain/rode length to depth ratio). Always have a backup anchoring plan. Before dropping, assess the bottom type, look for swinging room, and consider wind and current changes. Don’t be afraid to pick up and re-anchor if it doesn’t feel right. When spending a week with Simon on his Sailing Lifestyle Experiences, you will be a pro at anchoring by the end of the week. I don’t know why sailing schools don’t teach this!
20. Is it really possible to sell everything and just go sailing?
YES! It’s absolutely possible. We did it. Thousands of others have done it. It requires courage, meticulous planning, sacrifice, and a willingness to step outside your comfort zone. The biggest hurdle isn’t the logistics; it’s the mental leap. Address your fears, create a solid financial plan, and commit to the dream. The rewards – the freedom, the adventures, the sunrises, the starry nights – are immeasurable.
Remember, the dream of cruising is achievable, and the community is there to support you. Now, go forth, do your research, get on a boat, and start making those incredible memories! You don’t want to turn 80 and regret not living your dream.
