Your first sailing trip is exciting and a little scary, too. Even if you have been on a boat before, being on your own is a completely different challenge. However, it will be a rewarding challenge. Solo sailing can be a great way to travel, but you won’t know until you try it. Even if it is not for you, that is completely okay.
For example, I have sailed alone on calm waters. Even on windy days, I was fine. It is all about being prepared, planning in advance, and knowing your limits.
How to Prepare for Your First Solo Sailing Trip
Planning some things before you get on a boat will help your solo sailing go as planned.
- Know your boat – Every boat is different in how it moves. When starting out, opt for a smaller yacht or a catamaran that is easy to manage on your own.
- Pack smart – You need life jackets, waterproof jackets, a first aid kit, a reliable phone charger, and a lot of sunscreen.
- Check the weather – Even if you feel ready, make sure to check the weather, forecast, and wind conditions.
- Plan your route – Stick to short trips and gradually increase to longer open-water stretches.
- Share your plan – Tell someone your route and expected return time. Land checkers can be a friend or family member.
Preparation can be as easy as a checklist. Checklists give a sense of accomplishment and confidence before your solo journey.
How to Choose Your Solo Sailing Destination
To make your first solo trip easy, plan to sail in calm and sheltered waters. Stay close to shore and identify areas with lots of marinas and places where you can easily get help. Some of my favorite places to recommend are:
- Croatia or Greece – They have great views and calm water bays and will be a great option with a lot of places to stop.
- Italy – The views from the Amalfi Coast offer a wonderful opportunity to stop and sightsee.
- The Caribbean – Many islands offer calm and warm waters.
- Northern Europe – Norway’s fjords are a sight, and the Baltic Sea has wonderful views.
Always be aware of where support is located: marinas, sailing schools, or emergency services. This is even more important for someone on their first solo sail. Knowing help is near is very comforting.
Traveling Insurance When Going on a Solo Sail
Planning for insurance may not be the most exciting, but believe me, for solo sailors, it is one of the most sensible things. There is a slightly greater risk of accidents while sailing than on other vacations, so getting the best travel insurance for sailing holidays is a must.
- Ensure your insurance covers sailing, as many standard policies do not. This is very important.
- If something serious happens far from the shore, emergency medical evacuation will save your life.
- Covering your gear is helpful and often needed; sails, ropes, and any personal equipment are expensive.
- Trip Cancellation insurance will save your life when adverse weather or other issues abruptly change your plans.
When your insurance is set, you can focus on your trip and stop worrying.
The Best Way To Self-Teach Basic Sailing Skills
There are a number of ways you can learn to sail from the marina before you depart, even if you are going to be sailing on your own.
- Online courses – They allow you to learn about knots, navigation, and basic techniques of sailing at your own pace and convenience.
- Local sailing clubs – There’s no substitute for actual hands-on training. You will have the opportunity to practice steering, docking, and sail-raising under supervision.
- Short charter trips – For some practical experience without undue pressure, you can rent a boat for a few hours with a trained professional.
- Mobile apps and simulators – These provide a great opportunity to practice sailing virtually before actually going on the water.
Start with the basics first. These include managing the sails, steering the boat, and learning the different wind positions. Once you gain some confidence, you can work on different routes and go to new areas.
Safety Tips for Solo Sailing
For some people, sailing alone may be scary, but using a few common-sense techniques can help reduce the risk and build your confidence.
- Stay in touch – Carry a phone, a VHF radio, and a satellite communicator. For easy access to Google Maps and WhatsApp, you can use a data eSIM and a VHF radio.
- Carry safety equipment – Life jackets are essential even in calm water. I always have one on. Non-slip shoes and waterproof clothing are great additions to your safety equipment.
- If a marina or anchorage does not feel safe to you, do not stay. You do not feel safe, do not stay. Your comfort should always come first.
- Learn a few simple emergency skills. You should know how to deal with a man overboard, signal for help, or do a few simple repairs on your boat.
Sailing alone can be very rewarding. It should be an enjoyable experience, not a scary one, and feeling prepared first will make it so.

