Erin De Santiago a RoamRight Blog Author

What You Need To Know Before Booking A Sailing Charter

Photo source: Ecologic Cats Sailing Charters

With some travelers looking for alternatives to the large cruise ship experience, the popularity of private yacht and sailing charters continues to boom. What was seemingly an unaffordable luxury for many is now the best bet for travelers who want to spend their entire vacation on the water – literally. Not sure what goes into booking a sailing charter? Here are some of the most important aspects to consider.

Bare Boat or Crew Chartered Boat

Sailboat charters are typically either "bare boat" or crewed. One of the questions you have to ask yourself is, "Are you going on vacation to hoist sails and cook your meals, or do you want others to do the heavy lifting and feed you better than you’ll eat at home?" Experts point out that travelers considering bare boat charters need to be capable yachtsmen and sailors. Also, not all destinations’ regulations allow for bare boat charters, so it’s important to do your research if that’s your most important criteria.

Seasons and Sailing Conditions

The most popular destinations for charters tend to be in tropical locations, which means seasonality is key. If you book a charter in the Caribbean during hurricane season, it’s quite possible that you find yourself seeking out alternative lodging on dry land if the seas are too rough. Definitely do your research on the best times to go based on your ideal destination. Charters aren’t just popular in the Caribbean either – consider destinations like French Polynesia, Croatia, or the Greek Islands for some stunning sailing vacations. Wherever you ultimately decide to go, travel insurance for a sailboat charter is a necessity to protect you in case of unforeseen conditions.

Planned Activities

Another key element to consider when booking a charter is balancing your activity goals versus what is realistic. If you’re hoping to do a number of dives each day, experts suggest people opt for a live-aboard experience geared towards hard-core divers. Realistically, with transit times and a smaller crew, most professionals say that customers will be lucky to get in two dives per day at most. The idea of a sailing charter is for the "nice and easy experience," not a dive vacation.


The biggest mistake experts encounter once people book their charters is the amount of luggage they show up with. The fact is that boats aren’t big and every inch of space taken up by your stuff is space you can’t enjoy.

Don’t bring hard suitcases and limit the amount of clothes you bring. The reality is you’re likely to be in a swimsuit the majority of time, so how much clothing do you really need? Opt for clothes that dry fast, get toiletry bottles that float, and bring extra hair ties and hats, bug spray, sunscreen and lip balm with SPF as your lips will get chapped and burnt out after being on the water for days on end. Consider a rash guard for snorkeling to help lessen sunburn risk as well – there’s nothing worse than ruining your vacation with a nasty sunburn right at the start. Also, scale back the amount of electronics you bring, as the boat’s power supply is obviously limited as compared to a hotel.

Ask Questions

Before booking, be sure to ask ample questions of your broker or charter company directly. This is their passion, and they want everyone to experience a dream sail rather than be disappointed over miscommunication. Ask questions and be specific about the details that are most important to you up front. This way there are no surprises, and it gives the charter company time to fulfill your wish list rather than scramble as you’re preparing to set sail.

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Note: Available plans and coverages may have changed since this blog was published.

About the Author

Erin De Santiago

Erin De Santiago, a RoamRight Blog Author Erin is a travel and food writer who currently splits her time between the Netherlands and Belize. She's traveled to 60+ countries on 5 continents with a passion for culinary travel, luxury hotels, and all things Disney. Her writing has appeared in numerous online outlets including Gadling, BootsnAll, CNN, Art of Backpacking, TravBuddy, CBS, and more. She was the major author of Belize's official visitor magazine, Destination Belize 2013; wrote the official AFAR Guide to Belize; and is also AFAR Magazine's local Belize expert.. In addition to writing for other publications, Erin maintains several blogs, Our Tasty Travels, No Checked Bags, Pooh's Travels, and the brand new Caye To Belize. Follow Erin on Facebook, Twitter, Pinterest and Google Plus.

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