Dee Caffari MBE on a Sunsail sailing holiday

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Is it really possible to go sailing as a holiday?

By Dee Caffari MBE


Try a sailing holiday they said and I laughed. The reality is however, that more and more people are going on sailing holidays, so before I wrote the whole idea off as a joke I thought I would give it a go. As they say, don’t knock it until you try it!

How can you do what I do professionally, for a job, a career as a holiday? I didn’t really know what to expect and I soon realised I didn’t even know how to pack for my week sailing a Catamaran in The British Virgin Islands.

My usual sailing packing is full of technical clothing, a Leatherman, tape, rule book, sailing instructions, notice of race, wet notes, face wipes and sunscreen. Some items remained the same, sunscreen and well, that was about it.

I could pack swimwear, shorts without practical pockets, dresses and my normal toiletries as washing was suddenly an option to be done daily. Not only was I going to be able to take a shower I could do so with a choice of locations. I could take a shower in the spacious heads or even using the transom shower that ran with hot and cold water.

I was travelling light and despite not requiring so much of my usual packing I managed to fill the space with more clothes. I have to admit that I barely wore half of what I took with me; you really can pack for this week of sailing within one small holdall. The beauty of sunshine holidays is that shorts, dresses and swimwear do not take up much space.

Still day one and I felt as if I was missing something, my pockets were empty and the schedule for the week was looking, how shall we say, rather vague. A comfort for me was that as a first time charterer I needed to attend some briefings on the first morning. This, at the very least, gave me a focus and a structure to my first day. The initial briefing involved hearing the local knowledge of the area. It had been 12 years since I sailed in the Caribbean and in particular the British Virgin Islands and I welcomed the information. The top tips on what time to arrive at certain anchorages to ensure a mooring was invaluable and if you listened then you could avoid the crowds but still make sure you saw all the highlights. However, with a cruising area encompassing over 50 islands, it is pretty easy to find the idyllic bays and anchorages away from everyone else. A route was planning in my mind and once we had the boat brief we were free to go where we pleased.

The boat brief was thorough and reassuring. With a mobile phone allowing free calls to technical support and customer support, covering your every eventuality. There was no need to be an expert at anything as they had that covered. In fact, that is the last thing they want. Follow the system and all will be well. Full of fuel and full of water and well victualled we departed the marina before midday with no intention of returning to a marina before our final day at the end of the holiday. With mooring buoys, an easy to operate anchoring system and a robust dinghy and engine that was also extremely easy to stow and use there was no reason to be stuck in a marina again.

Now, they say when more than one boat is going in the same direction it is considered a race and I pretty much saw a competitor in every boat I saw and waved at. I couldn’t help it. Sails were hoisted and for the wind conditions we were experiencing, the mainsail had a reef. Sailing upwind for four hours that first afternoon, I tweaked and adjusted constantly trying to get the boat sailing efficiently. The concept of cruising was still alien to me. I was loving it, despite not sailing as high as a monohull the boat powered its way through to St Thomas’ Bay off Spanish Town to enable us to be at The Baths for breakfast the next day. Tacking on wind shifts, comparing car positions on each tack, I let the autopilot drive so I could trim the sails to go as fast as possible making a note of the top speed for the day.

In desperate need of a holiday, the aim of the week was to get some sleep, feel the warmth of the sun on my skin and reduce stress levels down to a healthy level again. So early to bed and early to rise was an easy pattern to fall into and it felt great. An early morning swim around the boat before weighing anchor and heading to The Baths for breakfast meant the location was deserted. The northerly ground swell had reduced and it was possible to pick up a buoy and snorkel to my heart’s content. As the bay filled up I was happy to leave and head to Great Dog for lunch. Sailing on the wind to get there. As we arrived two dive charter boat departed and again we had the place to ourselves. Another snorkel before some lunch and then an upwind sail to Virgin Gorda arriving in time for sundowners at Saba Rock.

Cane Garden Bay_ BVI   

Spanish Town_Virgin Gorda

Virgin Gorda was the departure point for the trip to Anegada, an outlying island 12 miles off the rest of the BVI’s. Leaving after breakfast it was a fast reaching sail. I saw a large rain cloud coming and even slowed down to avoid it. I was getting into this cruising mode now. We avoided getting wet and facing strong gusts unnecessarily, this was a breakthrough moment for me. Arriving through the reef late morning made settling into the bay easy.

Now we had time to decide the rest of the schedule. Great winds had permitted us to enjoy some good sailing, but the forecast was not continuing in the same vein. For the first time in a long time there was going to be light winds in the Caribbean. I saw news that even my friends racing in St Bart’s were forced to stay ashore as light winds postponed racing.

The sail the next day back across to the main island cluster around Tortola was perfect conditions, champagne sailing as they say. I enjoyed some swimming, idyllic bays and beautiful lunch stops. The final part of this trip involved the motor as the wind had truly died but I felt happy as this was the first time we had used the engines at all.

We ventured to Diamond Cay and headed ashore to visit the Bubbly pool and enjoy this natural Jacuzzi pool powered by the northerly ground swell through the rocks. We found white sand beaches, solitary palm trees and deserted bays over the next few days. Truly stunning scenery and picture postcard settings were seen on a regular basis.

Late on the penultimate afternoon we went to Grand Harbour and a visit to the infamous Foxy’s. This was my last full night away from the charter base and I was fully into this cruising mode now and feeling sad that it was all coming to an end. I was determined to finish in style and I wanted to fit as much in as possible for the final day. Breakfast was taken on the move as we sailed from Jost Van Dyke to the Indians by Pelican Island. A mooring buoy was secured and I spent the final day as a water baby enjoying one of the finest snorkelling sites in the area. It really was a highlight of the week. The final 5 miles across the channel to Road Town, Tortola and the marina berth sadly had to be under motor as the wind had died out. We arrived as late as we possibly could, docked and had our boat checked off as it was an early departure the next morning to get a flight off the island. The end of the holiday, the end of the tropical paradise and the harsh reality that I was returning back to work.

So how was sailing as a holiday? Surprisingly awesome. I loved it and once I had the boat set up and I managed to change my need for structure and schedules, I felt I adapted well into cruising mode. I was able to be flexible with the wind and weather we faced each morning, I relaxed and did not feel the need for everything to happen at double time with lots of effort. I actually realised sailing as a sport can be relaxed and enjoyable, whilst also being a mode of transport to so many other cool adventures. Would I do it all again? Hell yes, and what’s more, there are so many choices of places to cruise with Sunsail Charter Holidays. I have realised I have only just started.

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