Caribbean
The Ultimate World Sailing Calendar for 2025
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, we 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.
Katrina Lawson, Head of Brand and Acquisition at Sunsail has also shared her thoughts on why specific destinations are ideal for different types of sailors, from professional sailors to groups, nature lovers and adventure seekers.
Jump to:
Where to Go Sailing in 2025?
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.
July Sailing Highlights:
- For Families: Croatia – Average temperatures range from 26°C-30°C across July and August which is ideal for sunbathing on golden sands, island hopping and sailing as a family. Split Summer Festival, also runs from mid-July to mid-August every year and is a great opportunity for everyone to immerse themselves in local culture. Find out more about when to sail around Croatia, including Dubrovnik and Agana.
- For First-Time Sailors: Balearic Islands – July is one of the peak months of the year for sailing around the Balearics, offering beautiful sailing conditions, exceptional water visibility and sizzling temperatures. It showcases the Balearics in all its glory, and is the perfect time to pay your first visit to this part of the world.
- For Sailing Enthusiasts: There are lots of brilliant events in the Seychelles throughout July, including the brand new Seychelles Challenge Regatta, a seven-day sailing extravaganza around the stunning islands. Learn more about the best things to do in The Seychelles.
August Sailing Highlights:
- For Explorers: Corsica – Like most Mediterranean sailing destinations, August is the hottest month of the year in Corsica and offers the perfect sailing conditions for island hopping between Corsica and Sardinia.
- For couples: Italy – August is one of the busiest times of the year for sailing around Italy so it’s great for couples who love socialising. Average temperatures range from 20°C to 30°C and there’s very little rainfall (around 3mm). Find out more about where to sail around Italy in August.
- For every type of sailor: United Kingdom – Cowes Week takes place annually in August and is one of the most popular sailing events of the year. It’s perfect for sailors of all experience levels, from Olympians and professional sailors to novice and weekend sailors.
September Sailing Highlights:
- For couples: Greece – While it still boasts temperatures of 24°C and idyllic sailing conditions, September tends to be quieter than June, July and August so you can explore this cultural wonderland in peace, tranquillity and privacy.
- For nature lovers: Norway – September is part of the shoulder season in Norway so, while it’s slightly cooler, sailing conditions are still great. Plus, from September to March, you’re more likely to be able to experience the stunning beauty of the Northern Lights from your yacht, and you may even spot some Orcas.
- For families: Seychelles – Water conditions are at their best in the Seychelles in September, with average temperatures of around 27°C, calm waters and consistent winds. This makes it the ideal time to go sailing, swimming and snorkelling as a family.
October Sailing Highlights:
- For Experienced Sailors: Croatia – For those who enjoy a bit of a challenge, October brings slightly stronger winds than summer months, adding an extra thrill to your sailing trip along Croatia’s beautiful Dalmatian coast.
- For Water Sport Enthusiasts: French Polynesia – With temperatures between 22°C and 28°C, the climate is ideal for beach days, water activities, and leisurely sailing. Every October, the islands also celebrate the Hawaiki Nui Va’a, a thrilling three-day canoe race that draws crowds and is a must-see event for sports lovers. Learn more about when to sail around French Polynesia.
- For Nature Lovers: Whitsundays – October is your last chance to see migrating humpback whales in The Whitsundays. These gentle giants make for an awe-inspiring sight, and the calm waters of the region make spotting them a joy. Want to protect local marine life during your yacht charter? Take a look at our sustainability policy and top tips for eco-friendly sailing.
November Sailing Highlights:
- For First-Time Sailors: Thailand – November marks the start of Thailand’s dry season, so you don’t have to worry about humidity and monsoons affecting your sailing. It’s a paradise for sailors of all experience levels, and if it’s your first time sailing around Thailand, Loi Krathong, Thailand’s festival of lights is a must-see. It always takes place on the evening of the full moon in the 12th month of the Thai lunar calendar, which usually happens to be the first half of November.
- For scuba divers: Belize – With crystal clear waters, an abundance of marine life and beautifully warm temperatures, November is undoubtedly one of the best times for going scuba diving in Belize. Will you explore the Belize Barrier Reef, Gladden Spit or The Blue Hole?
- For Exploration: St Lucia – November is the beginning of the peak sailing season in St Lucia so you get to enjoy warm, gentle waters, with the trade winds also starting to pick up. This makes it ideal for setting sail around secluded coves, uninhabited islands and the iconic Pitons.
December Sailing Highlights:
- For Stargazers: Antigua – On clear nights throughout the year, the Milky Way is easily visible from Antigua, and in December you’ll be able to watch the annual meteor shower Geminids due to the clear skies and dark surroundings.
- For Peace and Quiet: Bahamas – Want to switch off from the hustle and bustle of the festive season? You can disconnect from the world and uncover unspoiled landscapes, secluded beaches and laid-back island living in The Bahamas.
- For Winter Sun: British Virgin Islands – The British Virgin Islands are a sailing paradise with consistent trade winds, warm temperatures, and clear waters in December. Whether you’re a first-time sailor, or experienced professional, the BVI is a delight this time of year.
Conclusion
So, there you have it…our 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 our 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 our 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, please get in touch with us today.
Contributor
hannah
Step Aboard Here
Start your experience with Sunsail on land and sign up to receive e-mails from us about yachts, offers and destinations.
By clicking 'Sign up' you confirm that you have read and understood our Privacy Policy and consent to our use of your information.