The Ultimate World Sailing Calendar for 2025

Discover the ultimate sailing destinations with the first 6 months of Sunsail's 2025 calendar. Enjoy stunning views, vibrant cultures, and beautiful weather

With so many incredible sailing destinations around the world offering exceptional water visibility, strong trade winds, beautiful weather, breathtaking natural beauty and vibrant cultures, choosing where to book your next sailing holiday can feel like an impossible task. 

To make planning your next sailing holiday as hassle-free as possible and help you feel confident in your choice of destination, Sunsail have put together a new 2025 sailing calendar, showcasing the very best sailing destinations for each month of the year.

It comes as new research on the future of travel indicates that travellers are becoming more informed, conducting thorough research before their trips. People aren’t just making bookings, but actively seeking confidence and reassurance in their choices. Additionally, online searches for “stress-free travel” have increased by 22% in the past quarter. 

January Sailing Highlights:

For Sunbathing: Antigua – January offers the perfect temperatures for sunbathing on the deck of your yacht or on one of Antigua’s 365 breathtaking beaches, many of which are tucked away and offer a tranquil place to relax and soak up the sun. For the ultimate sense of isolation, visit Green Island Beach which is just off the coast of Antigua. Learn more about the best time to sail around the Caribbean.

For Multigenerational Sailors: Grenada – Exploring the open waters with children, parents and grandparents who all have unique needs and interests? Keep everyone happy and entertained by sailing around Grenada in January. Whether you’re interested in water sports, hiking, or simply lounging on the beach, Grenada provides a wide range of activities to suit various interests.

For Active Families: Cuba – If you’re an active family who want to spend days exploring islands, taking part in water sports and mooring up to go hiking, you’ll love Cuba in January. It’s cooler and less humid than other peak months of the year but still offers plenty of sunshine so you can channel your inner adventurers without worrying about the heat.

February Sailing Highlights:

For Beaches: St Martin – St. Martin is home to some of the world’s most secluded beaches, particularly on the French side of the island. With average temperatures of around 25°C in February, you can spend your days sunbathing, reading, swimming, snorkelling and resting away from everyone. Some of the quietest beaches include Plum Bay, Anse Marcel Beach and Friars Bay.

For Families: Key West – February falls right in the middle of the peak sailing season in Key West, making it perfect for families who want to socialise, meet new people and create magical memories. Offering average temperatures of around 24°C, you can explore the crystalline waters, soak up the sun and enjoy hours of snorkelling, scuba diving and swimming as a family.

For couples: British Virgin Islands – Spend a Valentine’s Day unlike any other by sailing around the BVI in February. The islands offer unspoiled natural beauty with white sandy beaches, coral reefs, lush hillsides and exceptional water visibility for sailing. There’s no setting more romantic! Find out more about when to sail the BVI.

March Sailing Highlights:

For Scuba Diving: Thailand – Colourful coral reefs, diverse fish species, and the opportunity to encounter larger marine life such as whale sharks and manta rays – March is a paradise for sailors who want to spend days scuba diving in Thailand and exploring the depths of the crystal clear waters. Will you visit Anemone Reef or King Cruiser Wreck?

For Nature Lovers: Martinique – Martinique’s natural beauty is unmatched. With the perfect blend of lush rainforests, pristine beaches and extraordinary biodiversity, Martinique is somewhere you can feel connected to nature everywhere you turn, particularly in March when visibility and temperatures are still at their best.

For Switching Off: St Lucia – Looking for somewhere to go sailing in March where you can relax, unwind and switch off from the world? St. Lucia’s majestic beauty, characterised by the iconic Pitons and lush rainforests, creates the perfect backdrop for rejuvenation. You can unwind in off the grid bays and refreshing waterfalls while also enjoying rejuvenating spa treatments such as mud baths.

April Sailing Highlights:

For Adventurers: British Virgin Islands – If you want to channel your inner adventurer and immerse yourself in the wonderful world of sailing, The BVI Spring Regatta and Sailing Festival takes place annually at the end of March-beginning of April. Embrace the crystal clear waters and take part, or celebrate from the sidelines.

For Nature Lovers: Grenada – Part of Grenada’s dry season, April is a fantastic time to go sailing as you’ll come face to face with vibrant marine life and rare wildlife. From armadillos and mona monkeys to breathtaking coral reefs, it’s a natural paradise!

For First-Time Sailors: The Bahamas – With stable trade winds blowing in from the East, the sailing conditions in The Bahamas are wonderful in April and there is lots of line-of-sight sailing which means it’s ideal for beginner sailors. Learn more about when to sail around The Bahamas.

May Sailing Highlights:

For Competitive Sailors: Antigua – Antigua Sailing Week usually takes place at the end of April into the start of May. It’s the perfect place for sailors to meet likeminded people and immerse themselves in local sailing culture.

For Families: Italy – It’s starting to warm up across the Mediterranean as the sailing season begins, but it’s not as hot as June, July and August which is ideal if you’re setting sail with young children who may not cope well in the heat of the high summer. Find out more about the best time to sail the Mediterranean.

For Couples: St Lucia – If you’re looking for an intimate, romantic sailing holiday, visiting St Lucia in May is ideal as there are less crowds and more opportunities for privacy. The weather is still similar to the high season (December-April) but you’ll experience tranquil beaches, lower prices and more alone time.

June Sailing Highlights:

For Culture: Greece – As well as exceptional sailing conditions, there are many festivals across Greece to enjoy in June, including the Miaoulia Festival on Hydra Island (mid-June), Nafplio Festival (late June) and the Athens & Epidaurus Festival (June to August). It’s a cultural wonderland for all the family to enjoy! Learn more about the best time to sail around Greece.

For Peace and Quiet: United Kingdom – The best time to sail in the UK is the summertime, where the weather is far more favourable and the days are longer. However, June is particularly great if you want to avoid large crowds and make the most of the peace and quiet, as the School Summer Holidays don’t start until July.

For Exploration: Norway – With longer days, clearer skies and calm waters, June is a brilliant time to set sail around the Norwegian Fjords and explore the treasures that await you.

So, there you have it… the first 6 months of Sunsail's 2025 sailing calendar. The best part about choosing a sailing charter for your next holiday abroad is, no matter what time of year you want to explore the open waters, there’s always somewhere around the world with the perfect conditions for you.

Whether you are already planning a 2025 sailing holiday at one of Sunsail's world-class bases and looking forward to exploring uninhabited islands, secluded coves and hidden beaches, or still looking for inspiration on where to book for your next sailing trip, we hope Sunsail's ultimate sailing calendar for 2025 helps you find somewhere you can create memories for life.

If you have any questions about planning your next bareboat, skippered or flotilla sailing holiday, or want to learn more about our sailing schools, get in touch with Sunsail today or phone the Sunsail team on 0330 029 2500.