Yacht charters in Mediterranean, Caribbean, Indian Ocean, Thailand, Whitsunday Islands & more
Catamaran cruising
Cruising aboard a sailing catamaran means you’ll enjoy a spacious onboard lifestyle and an impeccable balance between performance and manoeuvrability. The Sunsail charter fleet includes sailing catamarans from the world’s leading innovators in build, design, and performance with both Robertson and Caine's, Leopard Catamarans and Lagoon Catamarans ranging in size from 38’ to 48’ in our worldwide charter fleet.
By design, the build of a catamaran offers spacious proportions not only in full height cabins, on-deck lounging areas, and wide outdoor living spaces but also in the main salon and galley where expansive open designs and large windows create a bright interior for you to enjoy during your sailing vacation. Thoughtfully designed cabins in both port and starboard hulls means more privacy for you and your guests during your charter.
Whether you’re at anchor or in full sail, a catamaran keeps your experience steady and balanced throughout your sailing vacation. All of our sailing catamarans benefit from a shallow draft, allowing you to explore intriguing shorelines and anchor in shallow waters. With the ease of manoeuvrability and performance in mind, sailing a catamaran is ideal for sailors of all experience levels.

Monohull sailing
With its classic, single hulled template, the monohull is the original sailboat. Designed by Jeanneau with performance in mind, our monohulls give you optimal control whether the conditions are flat and calm or rough and wild.
Choose from our world-class fleet of monos, ranging from compact 32 footers to spacious 53 footers. Our scrupulously maintained, well appointed yachts offer every creature comfort, as well as power aids including electric winches and the latest furling systems. Catch a mistral in the Med or tame Vancouver’s Salish Sea—these elegant yachts deliver whether you’re heading upwind or down.

Yacht Charter Holidays: Discover A New Way To Explore The World's Most Beautiful Islands
Why stay in one resort when you can wake up somewhere different every day?
For many South Africans, a tropical island holiday means checking into a beautiful beachfront resort and spending a week relaxing beside the ocean. While that remains a wonderful way to holiday, more travellers are now discovering a completely different type of adventure: yacht charter holidays.
Imagine waking up to a new island every morning, swimming in secluded bays, enjoying breakfast on deck, and watching spectacular sunsets from your own private yacht.
The best part? You don't need any sailing experience.
At IslandStays, we're excited to introduce yacht charter holidays in partnership with Sunsail, one of the world's leading yacht charter specialists. Their professionally organised sailing experiences open up a whole new world of travel possibilities.
Whether you're celebrating a milestone birthday, planning an anniversary, travelling with family or ticking off a bucket-list adventure, a yacht holiday could be one of the most memorable experiences you'll ever enjoy.
What Is A Yacht Charter Holiday?
A yacht charter holiday allows you to explore multiple destinations while travelling aboard a comfortable sailing yacht or catamaran.
Think of it as your:
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Hotel
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Transport
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Private viewing platform
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Restaurant
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Adventure base
All combined into one extraordinary experience.
Rather than unpacking at a single resort for seven nights, you'll wake up in a different bay or island destination almost every day.
You'll discover places that most tourists never see.
Do I Need Sailing Experience?
Absolutely not.
This is one of the biggest misconceptions.
Many first-time travellers choose a Skippered Charter, where an experienced professional captain takes care of all the sailing and navigation while you simply relax and enjoy your holiday.
This makes yacht charters ideal for:
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Couples
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Families
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Groups of friends
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Multi-generational holidays
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Anniversary celebrations
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Bucket-list travellers
If you are an experienced sailor, there are also Bareboat Charters available that allow you to captain your own yacht.
For those who enjoy meeting fellow travellers, Flotilla Sailing holidays combine independent sailing with the support of a lead crew.
Three Ways To Enjoy A Yacht Holiday
1. Skippered Charter (Our Top Recommendation)
This is by far the easiest and most popular option for first-time travellers.
A qualified skipper handles:
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Navigation
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Mooring
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Route planning
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Local knowledge
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Safety procedures
You simply enjoy the experience.
This option allows you to completely switch off and immerse yourself in the destination.
2. Bareboat Charter
Perfect for experienced sailors.
You captain your own yacht and create your own itinerary.
This option provides complete freedom and flexibility.
3. Flotilla Sailing
Ideal for social travellers.
You'll travel as part of a small group of yachts while still enjoying your own private accommodation and independence.
Expert support is available throughout the journey.
Why South Africans Are Falling In Love With Yacht Holidays
Yacht charter holidays offer several advantages over traditional resort holidays.
Experience More Destinations
Why visit one island when you can visit several during a single holiday?
Access Hidden Beaches
Many beautiful beaches and coves are inaccessible by road.
Yachts allow you to discover untouched locations away from crowds.
Unpack Once
Your accommodation travels with you.
No repeated check-ins or transfers.
Incredible Snorkelling
Anchor directly above vibrant coral reefs and enjoy exceptional marine life.
Ultimate Privacy
Avoid crowded hotel pools and busy beaches.
Enjoy your own floating sanctuary.
Unique Dining Experiences
Enjoy breakfast at sunrise and dinner under the stars.
Few holiday experiences compare to dining on deck surrounded by the ocean.
Our Favourite Yacht Charter Destinations
Seychelles
The Seychelles may be one of the world's greatest yacht charter destinations.
This spectacular island nation offers calm waters, short sailing distances and stunning scenery.
Highlights include:
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Giant tortoises
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White sandy beaches
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Crystal-clear lagoons
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Excellent snorkelling
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Beautiful granite islands
Perfect for:
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Couples
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Honeymooners
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Nature lovers
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First-time yacht charter guests
Greece
The Greek Islands are ideal for travellers seeking culture and history alongside beautiful scenery.
Expect:
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Whitewashed villages
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Traditional tavernas
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Ancient ruins
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Spectacular sunsets
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Beautiful island-hopping routes
Perfect for:
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Couples
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Food lovers
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History enthusiasts
Croatia
Croatia has become one of Europe's fastest-growing sailing destinations.
Highlights include:
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Medieval coastal towns
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Scenic islands
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Calm waters
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Excellent cuisine
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Beautiful marinas
Perfect for:
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Families
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Groups of friends
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Active travellers
British Virgin Islands
The Caribbean's most famous sailing destination offers easy sailing conditions and breathtaking scenery.
Perfect for:
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First-time sailors
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Couples
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Adventure seekers
Thailand
Thailand offers a wonderful combination of exotic culture and tropical beauty.
Expect:
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Limestone cliffs
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Hidden lagoons
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Incredible seafood
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Warm waters year-round
Perfect for:
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Adventure travellers
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Couples
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Experienced sailors
Is A Yacht Holiday Expensive?
Many people assume yacht charters are only for the ultra-wealthy.
This is often not the case.
When shared between several travellers, yacht holidays can offer excellent value for money.
Remember, your holiday includes:
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Accommodation
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Transport between islands
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A unique travel experience
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Access to exclusive locations
The overall value can compare favourably with many premium resort holidays.
Who Is This Holiday Perfect For?
A yacht holiday may be perfect if you are:
A Couple
Celebrate anniversaries, honeymoons or simply enjoy quality time together.
A Family
Create unforgettable memories with children through adventure and exploration.
A Group Of Friends
Share a unique experience while enjoying privacy and flexibility.
Celebrating A Milestone
Birthdays, anniversaries and retirement celebrations become even more special on the water.
A Bucket-List Traveller
If you're seeking something truly different, yacht charters offer an extraordinary alternative to traditional holidays.
Why Book Through IslandStays?
At IslandStays, we have spent many years helping South Africans discover exceptional island destinations.
We understand what South African travellers value most:
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Great value for money
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Ease of travel
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Safety
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Authentic experiences
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Expert advice
We'll help you choose the right yacht charter destination, itinerary and style of holiday to match your travel goals.
Whether you're dreaming about sailing the Seychelles, exploring the Greek Islands or discovering Croatia's stunning coastline, we'll help make it happen.
Ready To Discover A New Way To Travel?
A yacht holiday isn't simply another holiday.
It's a completely different way to experience the world.
Instead of staying in one place, you'll explore multiple islands, discover hidden gems and create memories that will last a lifetime.
If you've already experienced Mauritius, Seychelles or Zanzibar from a resort, perhaps it's time to see these beautiful destinations from a completely new perspective.
Your next great adventure may begin on the water.
Contact IslandStays today and let us help you plan your first yacht charter holiday.
