Things to Consider When Visiting the Caribbean on a Sailing Trip

Sailing holidays are no longer the sole preserve of the uber rich and famous. Specialist websites pool together thousands of private yacht charters into one convenient place, creating an affordable and user-oriented service for even the most inexperienced seafarer.

Catamarans are a great choice for first time sailors since their twin hull design offers superior stability at sea – ideal for those that haven’t yet found their sea legs. You can search here to find the perfect size vessel for your party, both engine and wind powered and crewed or bareboat.

If you want to take all the hassle out of the process opt for a skippered cat which takes care of all the necessary provisions, so you need only sit back and enjoy the journey.

Where Should You Choose to Travel To?

The Caribbean is high up on the list of great sailing destinations for good reason. Year long great weather and a host of idyllic landscapes invite bustling itineraries and a multitude of island hopping opportunities.

The volcanic Antillean Archipelago was formed approximately 200 million years ago in the Jurassic period and now comprises almost 700 islands. The Greater Antilles is made up of Cuba, Puerto Rico, Jamaica, the Cayman Islands and Hispaniola, which is shared by Haiti and the Dominican Republic.

The Bahamas and Turks and Caicos lie to the northeast in the Lucayan Archipelago and the Lesser Antilles, to the south – where you can find dozens more island nations and overseas territories. Among the most popular for sailing vacations are Antigua and Barbuda, The British and US Virgin Islands and the Dutch Caribbean but that’s really only scratching the surface. 

• Swim with the stingrays at Stingray City – the largest of the Cayman Islands, Grand Cayman is home to one of the planet's most abundant communities of southern stingray. Between Morgan Harbour and Rum Point, two shallow sandbars in the northwest corner of the island’s North Sound provide people with the chance to get up close and personal with the very safe southern species of stingray (not to be confused with their more dangerous cousin the short-tail).

The deeper of the two regions are perfect for divers while the shallower is fine for paddlers and even supervised kids. 

• Unwind at Grand Case Beach – the French owned Saint-Martin is part of the Caribbean’s Leeward islands, and one of its most heavenly ports of call is the beautifully sheltered Grand Case Bay. Drop anchor and swim or row to shore through crystal clear, turquoise waters towards impossibly white sands.

Do absolutely nothing but relax in paradise for as long as you possibly can before sampling the local cuisine of callaloo soup and conch and dumplings from one of the shoreline’s prestigious eateries.

• Sport fishing and snorkelling at Sapphire Beach – Saint Thomas is the second largest of the US Virgin Islands and where you can find the capital, Charlotte Amalie. After docking at Sapphire Beach Marina and immersing yourself in the rich Danish colonial history, head to Pretty Klip Point to snorkel among the local turtle population and shoals of tropical fish.

The angling inclined can also use Sapphire Beach as a base from which to inshore fish for blue marlin and kingfish. The experienced or adventurous can try to land some huge yellowfin tuna and mahi mahi at the island’s offshore spots.

What Should You Pack?

If it’s your first time planning for a sailing holiday, there are a few key differences to bear in mind when compared to a conventional getaway. Firstly, storage space is at a premium on boats so a bulky suitcase isn’t always the best option. Instead opt for a soft sided hold-all that you can stow more easily.

The sun can obviously be more intense at sea, so solar protection is a must. Take high factor waterproof sunscreen, a sun hat and some cool long sleeved clothes to cover up during the hottest parts of the day.

A sailing holiday is the perfect place to try your hand at a range of watersports. Kayaking and paddleboarding, diving and snorkelling, water skiing and fishing, and of course sailing itself are just a few of the activities you can find yourself partaking in whenever the feeling takes you.

If you consider yourself part amphibian and can’t get enough of dipping in and out of the sea, a waterproof camera (or a waterproof case for your existing camera) is a great way to capture those moments from right in the middle of the action.

Evenings will often be spent moored in a harbour or bay where you can disembark and enjoy a different town or sleepy fishing village each night. Winter temperatures are cooler in the evenings – around the low twenties depending on your destination – so take some layers to ensure you don’t get too chilly. The locals refer to easterly trade winds as the “Christmas winds”, which not only aid sailing but are a welcome respite from the heat.

What Else?

If you’re not sure whether a yacht or a catamaran experience is the right one for you, here are some things to consider. Typically, a yacht is a monohull boat and is more susceptible to heeling (gently leaning as it travels). 

This makes for a more exhilarating sailing experience but is arguably less relaxing, especially for first timers. Along with the improved stability of a catamaran, the wide deck provides ample space inside so can be roomier, especially for larger parties.

Thanks to modern technology, sailing tours have become more affordable. If you haven’t experienced a vacation at sea already, then ensure it’s added to the top of your travel bucket list.