How to Do a Sailing Holiday in the Caribbean

Image of Tobago Cays
Image of sailboat at sea

Bunny doesn’t think there are many holidays that can top the experience of chartering your own yacht in the tranquil waters of the Caribbean Sea. Sailing through the aquamarine bays, stopping at deserted islands (literally), strolling on palm-fringed beaches, snorkeling with turtles and sipping cocktails on a hammock on deck - what could be better than that?

It is expensive, yes, but not more so than treating yourself to a luxury safari holiday in Africa or a stint in an over-water villa in the Maldives. The best part is that it is worth every penny you spend. 

Here is Bunny’s guide on how to do a sailing holiday in the Caribbean as a first-timer.

Choose the Grenadines

The Caribbean offers a number of excellent sailing destinations, including the British Virgin Islands, the Leeward Islands, and the Grenadines - Bunny’s favourite.

The Grenadines are part of the southern, so-called Windward Islands, of the Caribbean. They comprise 32 lovely tropical havens between the island nations of St. Vincent & the Grenadines and Grenada. According to many experts, the sailing in the Grenadines is among the best in the world.

Image of Salt Whistle Bay

Bunny has visited the Grenadines a number of times and absolutely loves this fabulous little corner of the world. The small, often uninhabited, islands that belong to Grenada and St. Vincent & the Grenadines are beautiful and unspoiled. There is little to no development, clear and tranquil waters, the softest possible sand, beautiful sunsets and excellent snorkeling. 

The enchanting tropical islands are very close to each other and sailing from one to another is easy and pleasurable. It is no exaggeration to say that you can start your morning swimming with turtles and rays in the Tobago Cays Marine Park, sail to an uninhabited island for a picnic lunch on the beach and finish the day in Mayreau, on the picturesque Salt Whistle Bay, where you can sink your toes in the powder white sand and enjoy a pre-dinner drink at one of the colourful rum bars. 

Image of Tobago Cays
Image of turtle

Go Through a Broker the First Time

When Bunny first got the idea of doing a sailing holiday in the Caribbean, she didn’t know a thing about sailing. She hadn’t even set a paw on a sailing boat before! So she wasn’t quite sure where to begin.

She was encouraged to go through a yacht broker to find the perfect boat for her needs. Bunny happily followed that advice. After having checked a couple of broker websites, Bunny opted for Ed Hamilton & Co Yacht Charter Agents

Their website was easy to navigate and full of useful information, including links to available crewed yachts and prices. Bunny spent a bit of time poking around different options before contacting Ed Hamilton via their detailed request form, specifying the type of yacht needed, the timeframe, the desired location and other essential elements of her trip.

Image of perfect beach

Choosing the Yacht

With no sailing experience under her belt, Bunny naturally had to opt for a crewed yacht as opposed to a bareboat charter, where you just rent the boat and are in charge of the sailing yourself (gulp). 

Naturally, the crewed yachts are more expensive as you will benefit from the services of a captain and a chef during the course of the sailing. The price usually includes all meals, prepared to your own taste, as well as house wines and bar drinks. 

As a rule, the prices are set for weekly increments, although it is often possible to reserve a shorter charter too, depending on the boat. Economically-speaking, going for the full week is usually the best option.

Top Tip

Go for a catamaran. When picking a boat, your choice is between a catamaran and a monohull. As a first-time sailor, you will appreciate the stability and spaciousness provided by a catamaran. Monohulls may generate more excitement and the feeling of ‘true’ sailing but catamarans are more relaxing and comfortable, Bunny says.

Image of Bunny in a bar
Image of Mayreau
Image of sunset in Carriacou

Interaction with the Yacht Broker

After having submitted her initial request form, Bunny was contacted by a friendly and helpful yacht broker. Based on Bunny’s requirements, the broker had put together a list of crewed yachts matching the availability of Bunny’s indicated timeframe. Bunny was able to study the information in peace, make comparisons and eventually get back to the broker with some questions. 

The process was very easy and straightforward. Bunny was happy with the answers and recommendations she received from the broker. Communication was conducted by email (Bunny prefers emails to phone calls) and Bunny was soon able to identify the yacht she preferred.

The next step was to place a hold on Bunny’s requested dates. A hold didn’t yet commit her, but blocked the dates while she finalised travel plans and looked at flights and other details. In effect, it gave Bunny a 48 hour right of first refusal on the boat.

Image of sailboat at sunset

Signing the Contract

After deciding on the boat, timeline and destination of your trip, you will have to sign a contract to actually book the sailing yacht. This is usually a straight-forward process as the brokers use “standard” contracts. 

Just check that all the details are acceptable to you and pay particular attention to the cancellation policies. For example, usually no refunds will be entertained if the sailing is curtailed due to severe weather. This is the one type of holiday you should absolutely have cancellation insurance for.

"Take out cancellation insurance!"

Bunny logo

Agreeing on the Sailing Details

Once you have signed the contract, you usually have a chance to talk to the crew directly. This is useful to agree on further details of the itinerary and discuss dietary preferences etc.

Bunny is usually a control freak when planning holidays but when discussing the exact sailing itinerary, she was happy to simply follow the captain’s recommendations. No amount of googling will make you a better expert of the locations than the yacht captains.

Image of sailboat
Image of turquoise sea
Image of Sandy Island

As long as you make the captain aware of your preferences (quiet vs. livelier spots, snorkeling/diving vs. beach life, fancy restaurants vs. beach shacks etc.), they will be able to put together the perfect itinerary for you. 

The great thing about chartering a boat is that you have the freedom to change the itinerary on the go too. If you go through a broker, they usually send you a cruising guide of the area in advance, so that you can think about your preferences before talking to the captain.

Time Your Holiday Wisely

Bunny’s preferred time to go sailing in the Caribbean is late November/early December. That is when the weather is miserable in Europe and glorious in the Caribbean (most of the time anyway). The prices are still lower too as the real high season starts a bit later in December, and there are still fewer chartered boats around.

If you go during the high season, approximately from Christmas to early April, you will have to pay more for the exact same experience and you should also be prepared to share the sea and islands with more fellow sailors, especially in the most popular places.

Image of sunset
Image of Bunny drinking Margaritas
Image of Anse La Roche

Prepare for Life Onboard

A sailing holiday is expensive, but the boat will not be a 5-star establishment. It is precisely what it is: a boat. So prepare for some mild discomfort. It is most probably going to be a bit cramped, damp and you may find the bathroom facilities and routines well, hmph, a little interesting.

You should not bring too much luggage as no fancy clothing is needed. Swimsuits, beach coverups, hats, light dresses, shorts and t-shirts - that is all you need really. High heels can safely be left at home. They are not only painful to wear but also totally useless on the sandy shores, Bunny says. Plus, almost all sailboats enforce a strict no shoes policy on deck anyway, so let this be your barefoot luxury holiday.

The yacht you charter is likely to have a list of rules for you to follow onboard. Pay heed to these. They are drawn up for your safety and wellbeing as well as for the comfort of other guests and the crew onboard. Following the rules will also help preserve the marine life and ocean.

As long as you recognise and accept these realities from the beginning, you will love your time onboard. The luxury aspect comes from the freedom of being out on turquoise waters, enjoying quiet anchorage time and marveling at the pristine and gorgeous nature and wildlife around you…

Top Tip

Tipping is always a bit of a headache for Bunny who comes from a country where no tipping is the rule. For sailing trips, Bunny was advised that a gratuity of 10-20 percent of the charter fee to the crew is appropriate.

Make Sure You Like Your Sailing Companions

Now this is a tricky one. There is no escape once you are onboard. There is not a lot of room in the boat unless you are a multi-millionaire and can afford a truly luxurious yacht. In that case, you should have better things to do than reading this blog.

If you are on the brink of a divorce, maybe choose some activity other than a sailing trip in the Caribbean to patch things up with your future ex. Yachting should be left for those whose romance is still well and truly alive.

Imagination - Bunny’s Boat of Choice

Image of Imagination
Image of Bunny on catamaran
Image of sail

Bunny has twice sailed in the Caribbean on a catamaran called Imagination. Imagination is a lovely 46-foot ship that has room for up to 6 guests. The Bunnies, anti-social as they are, sailed alone both times for the added privacy and luxury.

Imagination is crewed by a friendly and easy-going couple from the UK: Shawn and Ally. They are expert sailors who know every nook and cranny of the Grenadines. Bunny has trusted them to put together wonderful itineraries for her two sailing holidays on Imagination. Bunny has also appreciated Shawn and Ally’s great recommendations for activities in the area, whether it is an interesting hiking route on a picturesque island, the best snorkeling places or perfect picnic spots on secluded beaches.

Shawn has restored Imagination from scratch and is deservedly proud of his beautiful catamaran. Imagination has three en-suite cabins (with marine toilets) in addition to the separate crew quarters, solar panels, wind generators, and is A/C free - making it also quite a green holiday option. An array of water toys, such as a kayak and SUP boards are also available for active guests.

Image of Sandy Island

Shawn is also a dive master instructor who can accompany you on dives. Bunny is not a diver, so she best appreciates Shawn’s skills as a cocktail master. Every evening, Shawn indulges his guests with different creations from his cocktail menu. Sometimes the drinks are enjoyed in the sea, as a floating bar!

Ally, the first mate and chef, cooks wonderful meals (fully vegetarian ones for the Bunnies) in the galley of Imagination. The Bunnies have been impressed with the freshness, variety and tastiness of all foods served onboard.

Bunny’s favourite spot on Imagination is the hammock strung up on deck. There’s nothing like chilling out in the hammock after a delicious dinner, enjoying the gentle breeze and admiring the seemingly endless number of twinkling stars in the sky above. There is no better holiday than that.

Bunny’s Conclusions

Image of the Grenadines
Image of Tyrell Bay

A sailing trip in the Grenadines is one of those bucket list things to do before you die. It does not even have to break the bank, particularly if you go with a group of friends or family. You will be totally mesmerised by this alluring, one-of-a-kind holiday, Bunny says.

Image of Bunny paw prints

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