The 7 Useful Tips On How To Plan The Perfect Sailing Adventure

July 08, 2020

Planning for the perfect sailing or boating adventure need not be stressful or intimidating if you follow these 7 useful tips.

A sailing adventure goes beyond just satisfying your craving for the sun and water. It is, in fact, an adventure that is exciting and hard to forget. At the same time, being in the middle of the water with the strong wind blowing can be a relaxing and somehow meditative experience. 

Use these 7 practical tips on how to plan the perfect sailing adventure
Photo courtesy of Tropicalboat Charters & Rentals

The 7 Useful Tips On How To Plan The Perfect Sailing Adventure

    What to expect in your sailing adventure 

    Spending a day or two in a boat while cruising leisurely through the waters is an experience that you will definitely love. It is a different kind of thrill that is definitely worth trying at least once 

    If you are living near the ocean or close to a lake, then consider yourself lucky because that gives you more options to easily plan out and embark on your fun sailing adventure. 

    Nevertheless, it is still possible to achieve the perfect sailing adventure even if you live far from a body of water. All you have to do is to plan ahead and prepare carefully to ensure that you have everything that you need before heading out to your boating escapade. 

    In terms of things to expect, you can look forward to a lot of sun, fun, wind, and water. Depending also on your itinerary, you can visit nearby islands and beaches. And if you are lucky, you might even spot a group of dolphins or a whale. Of course, swimming is highly-encouraged. 

    Things to remember when planning your sailing adventure 

    When you have finally decided to realize your boating adventure, it’s really simple and easy to plan for it. Needless to say, start by getting a headcount of your friends and family whom you would like to bring with you in this sailing excursion. 

    Furthermore, keep these seven tips in mind to make your boating experience unforgettable and exciting. 

    1. Find the best charter service based on your needs 

    Unless you have your own boat or are friends with someone who regularly operates their own vessel, you will have to look for a charter service to manage and operate your cruise. 

    Most charters offer packages that include a captain and a full-service crew to operate the boat. Individuals who live on or near the coast usually have a large selection of charter boat services to choose from. 

    In some countries, like in the United States, boat operators such as Tropical Boat Charters & Rentals give customers the option to charter a boat for a number of days. This will turn the tour into an exotic vacation across, for example, the Florida coastal waters. 

    It is good to ask your local boat operator if they have the option to take a cruise for multiple days so that you and your companions can fully enjoy your sailing adventure. 

    2. Make safety your top priority 

    Above anything else, the first and most important thing to consider when boating is safety. Most charter services have life jackets as part of their standard safety protocol. However, it still would not hurt to check with your charter service that they indeed have life jackets for all their passengers – one jacket per guest. 

    It also goes without saying that you should never consider a boat service that does not have enough life vests for all guests. Emergencies may happen when you least expect it and, in a lot of times, in an instant. Life jackets are thus necessary, even for strong swimmers.

    Moreover, make sure to avail of travel insurance if you can. Again, unfavorable things happen unexpectedly so it is better to be on the safe side all the time.    

    Remember also that it is also important to focus on sun exposure safety for everyone on the boat. Sailing on the water may leave you and your guests more vulnerable to the harmful effects of the sun. However, when you are having fun, it is easy to forget that you have been under the sun for so long. You will only notice the redness when it has become painful and blistered. 

    As such, bring with you plenty of strong sunscreen, preferably reef-safe brands, to protect you against burning or sun damage, and apply it before any outdoor activity. 

    Lastly, as a precaution, you may want to bring with you a first-aid kit and a list of possible emergency numbers that may help you in case of any untoward incident. In the end, strictly follow your boat’s safety protocols. 

    3. Prepare a good itinerary 

    Yes, you can also come up with an itinerary for your sailing adventure. You can customize an itinerary based on your interests, the things that you would like to see, or the activities that you would like to do during your cruise. 

    A few of the popular activities when sailing are wildlife sightings, such as whale watching, dolphin cruises, migratory bird sightings, or coral reef observations. On the other hand, you may also want to try more physically-intensive activities like snorkeling, diving, or fishing. 

    To prepare your itinerary, all you have to do is to research the options available in your area. You can check for nearby islands, fish and coral sanctuaries that allow visitors, or diving sites that are available. From there, you can search for a cruise charter that can help you fulfill your itinerary. 

    4. Plan a sumptuous seafaring food spread 

    Some charter services provide food options for its passengers, usually composed of a menu of lite yet tasty fare and drinks. If you are planning a day on a boat, you may want to review the charter service's menu. Alternatively, you may also want to prepare your own food if you choose to do so and if this option is allowed by the cruise provider. 

    You do not really need to prepare a grand buffet spread. You can just opt to keep it simple and easy-to-prepare if you have to bring your own food. Go for dishes that you can make ahead of time that are lite, quick, and easy, like sandwiches, chips, and bottled or canned drinks. Each guest can just take the food and drink that they prefer from the table. 

    5. Wear comfortable clothes 

    Remember that being out in the open water can expose you to a lot of elements. There is strong wind and waves, and intense sun, that is why it is important to be prepared and dress accordingly. 

    For most cruises in warm and sunny weather, you will need to wear your bathing suit underneath light clothing if you plan on getting in the water. If you want to protect yourself from the sun, consider wearing light, long-sleeved garments with a hat, and sunglasses. 

    6. Bring your camera 

    It is important to capture the sights and spots you visit on your cruise so that you and your guests can relive the memories forever. Hence, it is a mortal sin to forget your camera while embarking on a memorable boat trip. 

    You can opt to bring a waterproof camera to eliminate your worries about ruining your device with seawater. There are also disposable waterproof cameras in the market if this is what you choose. 

    As a safety precaution for your non-waterproof gadgets, wrap your smartphones or tablets in a plastic storage bag for protection 

    7. Be mindful of the weather 

    A few days before your scheduled sailing adventure, carefully monitor weather reports to make sure that there are no incoming typhoons or weather disturbances. If there are reported severe weather conditions, never push through with your trip no matter what.

    Again, your safety should be your utmost priority. In cases of cancelled trips, get in touch with your cruise provider on a how you can re-schedule your boating trip. 


    While boating and sailing adventures may not be as popular as, say mountaineering or backpacking, it is still something that is worth considering. It is a unique and memorable activity that you can experience for yourself, and fairly easy to put together with careful planning and preparation. 

    Plan the perfect sailing adventure with these 7 practical tips
    Photo courtesy of Tropicalboat Charter & Rentals

    Thus, if you are considering going on a sailing adventure but have doubts about whether you should push through with it, just go ahead and do it.

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    1. Not gonna lie, the ocean scares the hell out of me, but the tips you mention make it look like sailing could be lots of fun. I will think about it since we live relatively near the sea. Thanks for your post.

    2. My husband loves the idea of a sailing holiday. It's not something we've done before and it sounds like it would be a great experience.

    3. Great tips. I’m about to visit another country and some of the excursions are the same as the ones you shared.

    4. My husband would love to go on a sailing trip! I love the idea of a sailing holiday myself and will make sure to heed your tips to ensure the best experience when I do ;)

    5. I've never done sailing before, i would love to do it one day, it is quite an adventure...

    6. We love to sail and some great tips here for sure. Just near us in the UK we have a fab sailing school and it is very cool to learn the ropes so to speak and enjoy the waters x

    7. Yes to checking and rechecking the weather. An enjoyable day on the boat depends on it!

    8. Such great tips. Even though I'm a bit fearful of the water, I think I'd enjoy sailing.

    9. I have not thought about sailing before, but this could be so fun to do this summer! Thank you for the tips!