Charter Advice for First-Timers

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Never chartered? No worries. A vacation under sail can be the most memorable time of your life. That said, it also pays to be prepared by doing some reading, building your skills and listening to what the experts say.

First and foremost, not all charter grounds are created equal. Some, like the British, U.S. and Spanish Virgin Islands, are as user-friendly as they come. Here you’ll find steady winds, line-of-sight navigation, easy anchoring, good nav aids and plenty to do ashore when traveling with non-sailors and kids. Other areas, though, can be a bit more challenging. The winds in Greece’s Cyclades Islands, for example, can quickly kick up into a Meltemi; anchoring around the Balearics can get rocky; docking in Croatia calls for an almost daily Med moor (which can be intimidating even for those with experience), and the remote nature of the Sea of Cortez in Mexico means no calling for help in the event something goes wrong.

Once you’ve settled on a location, you’re also going to want to think through some of the logistics—things like where you’ll want to go, what you’re going to wear and what you’re going to do. Here are a few words of wisdom from a number of charter-industry reps based on the countless newcomers they’ve seen setting out on their first charter over the years.

Ian Pedersen, Senior Marketing Manager

The Moorings and Sunsail (


Set your itinerary. My personal preference when on charter is to pick one spot per day. It’s a steady, relaxing pace, simple to follow and helps ease any unnecessary hassle over trying to do too much. Wake up early in the morning, have your coffee, watch the sunrise and then head off to your next stop. This will help ensure there are plenty of mooring balls or space to anchor. Once you’re set in your new anchorage, you’ll have the entire day to explore, snorkel, go ashore or enjoy an afternoon nap. Equally important, remember to remain flexible, as the weather may prevent you from seeing or experiencing certain things on the day you originally planned.

To ensure a smooth start, be sure to speak with your charter company to determine the exact time of day you will be able to access your yacht. Do they have a pickup time of noon or 1700? The times vary from company to company and will play a large role in determining whether you can leave the dock the day you arrive. The same is true for the time when the yacht will be due back at the charter base.

Lesley Hayes, Reservations Assistant

Horizon Yacht Charters, Grenada & St. Vincent (


First-time chartering can be daunting in unfamiliar waters. We, therefore, provide a cruising guide to the Windward Islands that can be posted to [the guest’s] address prior to arrival. For first-timers, I would suggest they use our sample itineraries for their first cruise of the Grenadines. We have a selection including seven-night, 10-night and 14-night charters, one-way charters, and Grenada to Grenada and St. Vincent to St. Vincent routes. These are all tried and tested and give a good flavor of what the Grenadines have to offer.

As our charters start at midday, it really is worth flying in the day before and opting for a sleepover aboard or spending a night at the on-site hotel. I know I always feel a little disheveled after a flight, and the start of a charter can be a little frantic, especially if there are other charters starting the same day.

Karen Johnson, Charter Sales Manager

TMM Yacht Charters, British Virgin Islands (


First of all, remember that every seasoned client was once a first-timer, just like you! It is not your everyday vacation, so a good first step is to speak to a knowledgeable reservationist by phone. Having your dates, number of crew and any questions you have ready is helpful. Soon, you should feel well-informed and confident to proceed with a booking.

From this initial phone call to pushing off the dock you should feel valued and appreciated. Countless first-time charterers have become multiple repeat clients of ours for this reason. Finally, I offer two of my favorite charter phrases: “Boat hair, don’t care!” and “pack your patience!”

Sylvia Driver, Director

Horizon Yacht Charters, British Virgin Islands (


Don’t try and achieve too much on your charter. Remember, you can always come back another time for more! You are on holiday, so relax and enjoy the beauty of the islands and our amazing oceans and sea life. Don’t rush the experience just because you want to tick something off your list, especially since in the end it’s the weather and sea state that will dictate your itinerary.

Respect Mother Nature and please also respect the environment—it’s both very fragile and precious. Don’t throw cigarette butts in the water or on land, make sure plastic items do not blow off your boat into the sea, wear reef-safe sunscreen, never stand on or touch coral, and when in the BVI, always be sure to report any lionfish sightings to the staff so we can inform the local hunters to cull them. (They are an invasive species and eat all the juvenile reef fish). Take only photos, leave only footprints.

Cindy Chestnut, Sales & Marketing Manager

Conch Charters, British Virgin Islands (


First-time bareboating in the BVI can be an amazing experience. Planned itineraries “arr” (as the pirates of the Caribbean say) more like guidelines. Be prepared to “trim your sails” based on the weather situation. Another good rule to follow is to arrive at your destination before noon. That way you’ll have your pick of mooring balls. Once the boat is secure you can enjoy the rest of your day exploring. Provision for the sun—bring a ton of drinking water and remember that ice cream melts! For the vacation of a lifetime, bring half as many clothes as you think you’ll need and twice as much money.

Dan Lockyer, VP Global Tourism

Dream Yacht Charter Worldwide (


So many first-timers focus on vacation research and forget about capturing the memories, often relying on just an iPhone. To perfectly capture your sailing vacation, you need a decent camera and, ideally, a drone. The most popular types of drones used by our videographers are the Mavic Mini or Phantom 4 Pro. You won’t regret it, and you can have fun making a video when you get back. I would also recommend that you bring an underwater casing for your camera so you can take those classic sailing photos of a mid-air jump off the side of the boat and a half underwater/half above the waterline shot of the boat and hull. Have fun!

Maryline O’Shea, Global Marketing Director

Navigare Yachting (


When packing for a week of sailing in the Med, like Croatia where the weather is fairly consistent throughout the season, less is more. Packing light means you’ll get the best airfare deals with connections via London using the low-cost airline EasyJet (direct to Split, Croatia). Having only a carry-on also guarantees you won’t ever find yourself left empty-handed by the luggage belt as the result of a tight layover.

If you’re new to chartering in the Mediterranean, also be aware that checkout is usually later in the afternoon. By paying for an expedited check-in when available, you’ll also get in an extra half-day of sailing upfront. Finally, don’t hesitate to hire a local skipper if you’re so inclined. Such a person will be an invaluable guide for everything from secluded sunbathing to top-notch snorkeling and not-to-be-missed dining and cocktails.

Chip Needham, Technology & Marketing

CYOA Yacht Charters (


Pre-charter planning with the entire crew is often overlooked by first-timers and is especially useful when chartering with a large group. Have everyone do some independent research on things they might want to do. Collect details on what island people want to visit, the food ashore they want to try, preferences on things like moorings or anchoring, etc. Have a party or meet virtually to share what you’ve found and plan a route and loose itinerary. This will help everyone better understand what to bring and help decide what meals will be had, both aboard and onshore. 

For more charter advice read Chartering Again for the First Time, Your First Day on Charter and check out A Brief History of Chartering.

For the latest on chartering and border openings, visit SAIL's Charter Resource Directory

October 2020



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