A Guide to Group Sailing Vacations

October 19, 2023 7 min

From team-building retreats and corporate events to birthday celebrations and bachelor/bachelorette parties, there are countless reasons why you might be looking for a thrilling, utterly unique group vacation. If you want to give your guests the chance to make incredible memories, see the wonders of the world and disconnect from the hustle and bustle of everyday life, we think you’ll love a group sailing vacation.

Group sailing vacations have all the ingredients for an unforgettable trip: adventure, relaxation, freedom, beautiful weather, culture, breathtaking views, and an intimate setting. Whether you hire 5 yachts and sail around the stunning islands of the Caribbean, such as the BVI and Grenada, or join a flotilla in the Mediterranean, there is something to suit everyone’s needs on a group sailing charter.

We know it can feel overwhelming planning a vacation for a large group of people, so as part of our commitment to supporting you every step of the way with your yacht charter, we have put together a guide to group sailing vacations. You’ll find everything from the best sailing destinations to what your itinerary could look like.

Benefits of booking Group Sailing Vacations

Whether you’re booking a large or small group sailing vacation, we know you’ll have an incredible time as you cruise around crystal clear waters and take in breathtaking landscapes, surrounded by friends, family or colleagues.

If you haven’t been on a group sailing charter before, you might be wondering what makes them so special.

Here are our top 5 benefits of booking a group sailing vacation:

– Sociable – Group sailing charters are perfect if you want a particularly sociable vacation, with plenty of opportunities for privacy. Our yachts are spacious and ideal for hosting guests, so you can invite people to sip cocktails on deck with you before heading off to explore nearby islands. However, you always have the freedom to return to your own cabin anytime you want a moment of quiet.

– Something for everyone – When you plan a vacation for a large group of people, you may feel pressure to find something that caters to everyone’s needs. Group sailing vacations offer something for everyone, no matter who you are or what you enjoy. Whether you want to sunbathe on the golden sands of the Seychelles, island hop around Greece or immerse yourself into the local culture of Thailand, you and your group can create an itinerary that suits everyone.

– Distraction-free – Are you wanting to book a group vacation to enjoy some well-needed bonding time? Whether you’re team building or preparing for a wedding, a group yacht charter provides a sociable space away from the distractions of the world, including social media. As you set sail into the sunset, the only thing you need to focus on is each other.

– Glamorous – Do you want to impress clients at a corporate event? Are you planning a bachelor/bachelorette party for your best friend? Trying to find a beautiful wedding gift? No matter the reason for booking a group sailing vacation, you can rest in the knowledge that it offers a glamorous, stylish and luxury experience for everyone on board.

Magical memories – Above all, group yacht charters create magical memories that will last a lifetime. From watching the most beautiful sunset of your life to snorkelling among the coral reefs for the first time, nothing compares to the memories you will make on a group sailing vacation.

Get in touch with us today to learn more about booking a group sailing vacation.

Best destinations for Large and Small Group Sailing Vacations

With so many sensational sailing destinations around the world, you might be wondering which are the best for group sailing vacations.

Every destination has its own unique features and benefits, including sizzling sunshine, world-class snorkeling opportunities, authentic cuisine, brilliant sailing conditions, a lively culture and so much more.

Ultimately, wherever you choose for your group sailing vacation is completely your decision, but to help you get started, here are our top 5 sailing destinations for groups:

Italy – The home of the SailEATalia Sail, Wine, and Taste of Italy Flotillas, Italy is one of the best destinations in the world for group sailing vacations. With exquisite food and drink, wonderful cruising conditions, beautiful weather and breathtaking landscapes, book a group sailing vacation in Sicily, Procida or Sardinia and blow your guests away.
BVI – If you’re looking for a Winter group sailing vacation to kick the New Year off in style, visit the British Virgin Islands. With secluded coves, golden beaches, gorgeous turquoise water, famous beach bars such as the Soggy Dollar, and the iconic BVI Spring Regatta, there’s nowhere you’ll love more for your group sailing charter than the BVI.
Croatia – Group sailing vacations in Croatia offer the perfect blend of cultural sights and blissful beaches. There’s truly something for everyone on a Croatia group sailing vacation, whether people want to spend their days wandering around Corfu Old Town or relaxing on Sakarun Beach.
Antigua – One of the best ways to develop team building and leadership skills is through friendly competition. Sailing races and regattas are fun, fierce and thrilling – perfect for an extraordinary corporate event. Antigua is renowned as one of the best destinations in the world for regattas, hosting Antigua Sailing Week annually which makes it ideal for a group sailing vacation.
Greece – Group sailing vacations in Greece are some of the most popular in the world, especially if you have guests with varying interests. Whether you soak up the sun in Corfu, uncover the treasures and ancient history of Athens, or island hop around any of the 2,000 Greek islands, you’ll have a once in a lifetime adventure on a group sailing vacation in Greece.

Take a look at our sailing destinations around the world and find the best one for your group’s requirements.

Women on SUP in Magen's Bay St Thomas in the USVI

What can you do on a group sailing vacation?

As you prepare for your group yacht charter, you’ll likely be thinking about what your itinerary might look like and what you can expect to get up to each day.

Your itinerary will depend on who you’re traveling with and where you’re sailing around, as every destination is unique and offers its own treasures to uncover.

Whether you visit Tahiti on a skippered charter, Grenada on a bareboat charter or Belize on a crewed charter, here are some of our favorite things to do on a group sailing vacation:

Take part in unique team-building activities, from watersports to hiking
Develop leadership skills by taking the helm on a bareboat charter
Spend time reflecting and socializing on deck as you watch beautiful sunsets (or sunrises if you’re awake early enough)
Treat yourselves to the finest, most authentic cuisines in the world
Rest and recuperate on some of the most sensational beaches in the world, from The Baths on Virgin Gorda in the BVI, to Anse Chastanet Beach in St Lucia
Encourage everyone in your group to try something new, whether that’s snorkeling in St Thomas, visiting a new island in Thailand or tasting a new dish in Italy

To learn more about the best things to do on a group sailing charter, take a look at our individual sailing destinations, where you will find everything from an Abacos itinerary to an Athens itinerary.

Couple snorkeling on St. John, U.S. Virgin Islands

Exceptional yacht charters for groups

To suit everyone’s requirements in your group, we offer an impressive selection of group sailing charter types and yachts. You have the freedom to choose the best charter for your group, whether that be a bareboat, skippered or crewed charter.

Do you love the sound of a sociable group sailing vacation but want a more exclusive charter without others joining? Create your own mini-flotilla and book a bareboat yacht charter. Choose the best sailors in your group to take the helm as you all board several yachts and navigate yourselves around the open waters. Your group can all follow the same itinerary, or split up and make your own paths.

Bareboat charters are ideal if you want to challenge yourselves, or even have some friendly competition when it comes to who is the best skipper. However, if you’d prefer to spend quality time with your group on deck as you relax and sip cocktails, you can hire a skipper or book a crewed yacht charter. On an all-inclusive yacht charter, your guests will be taken care of every second of the day, with a team of skippers, chefs and housekeepers tending to your every need.

We also have a world-class fleet of yachts ready and waiting for your group. Whether you’re trying to impress a new client or celebrating a special occasion with family, our sailing catamarans and monohulls are stylish, high-performing and very spacious. With some yachts having as many as 5 cabins, say hello to wonderful group sailing vacations with The Moorings.

At some of our sailing destinations around the world, we also offer exceptional power catamarans. Sleek, fuel-efficient and technologically advanced, power catamarans can host up to 12 people which make them ideal for small group sailing vacations.

Book your group sailing vacations with The Moorings

Now you know everything there is to know about group sailing vacations, all that’s left to do is book your very own. Whether you are hosting corporate clients or throwing an iconic family reunion, take to open waters and uncover the beauty of a group yacht charter.

From flotillas in the Mediterranean and bareboat charters in the Exotics to skippered vacations in the Americas and crewed charters in the Caribbean, we have an extensive range of group sailing vacations ready for you to book. To ensure everyone on board is well-looked after and living a life of luxury, we also offer charter extras such as provisioning and watersports rentals.

Take a look at our fantastic sailing destinations, incredible charter types and world-class yachts, and build a quote for your idyllic group sailing vacation today. We also have a corporate group program, where you can enjoy a customized, entirely bespoke yacht charter which involves leadership development and customer outings. If you have any questions, contact us today.