The Best Sailing Destinations by Month: Your 12-Week Sunsail Yacht Ownership Guide
With Sunsail, you are not limited to a single cruising ground, a single yacht, or a single idea of what a sailing vacation or yacht ownership should look like. With 12 weeks of stress-free sailing across our global network, the real luxury isn’t just the boat; it’s the ability to follow the best sailing conditions around the globe.
This is your guide to the best places to sail month by month, designed to help you make the most of every one of your 12 weeks of ownership use a year. Whether you want to beat the crowds, be part of the action, or simply chase the best winds across the planet, this is exactly the kind of freedom Sunsail ownership was designed for.
And with Sunsail it’s never a case of been there done that. Across our more than 20+ destinations, there is always another route to take, another hidden anchorage in your favorite cruising ground, and another stretch of coastline that never quite made it into the guidebooks. You can plan every detail months in advance or leave space for spontaneity, and simply use your short-notice points to slip away when the timing feels right.
Because when it comes down to maximizing your ownership perks and using all 12 weeks of your sailing privileges in a year, it comes down to one simple thing: Knowing when and where to go.
To help you do exactly that, we have mapped out the best sailing destinations by month across the Sunsail network. Whether you are chasing the perfect winds, looking for peace and quiet, or planning to be part of the action in the peak holiday season, this is your year-long plan to make every one of your 12 weeks count.
January Sailing in The British Virgin Islands: The Ultimate Winter Escape
If there was ever a perfect way to start the year, this is it.
With short, rewarding passages through the Sir Francis Drake Channel, easy line-of-sight navigation, and over 60 islands to explore, there’s a reason the BVI is considered one of the best sailing grounds in the world.
And by mid-January, the peak holiday crowds have died down, and the steady trade winds, warm turquoise waters, and effortless island hopping create the kind of conditions that remind you exactly why you chose to own with Sunsail.
With the frantic holiday season scramble for mooring balls and anchorages done, the beach bars are still alive, and the usual stops still carry their familiar buzz, just without the sense that you are competing for space at every turn. It is that rare sweet spot that offers the absolute best of the BVI.
And just a quick flight from the U. S mainland and outside of the peak holiday season, mid-to-late January is the perfect way to use up some of your short-notice sailing points for a last-minute Caribbean sailing getaway.
Other Great January Sailing Destinations:
Sailing the Caribbean in January offers ideal conditions. And if you are looking for something a bit more dramatic and laid back, set sail from our St. Lucia base for world-class fishing, steady winds, and sporty sailing.
But if something a little bit more remote is how you would like to kick off your year, then the Seychelles has a boat with your name on it. January is the shoulder season for sailing in the Seychelles, and although it is still part of the rainy season, the moderate to light Tradewinds create the ideal conditions for easy and relaxed sailing, perfect for remote island-hopping without the autumn and spring crowds.
February Sailing in Phuket, Thailand: The Ultimate Exotic Escape
Trade the Atlantic for the Andaman Sea as February is prime sailing season in Thailand. November to April is the dry season in Thailand and brings with it sunny weather, calm seas, and steady winds, creating the perfect sailing conditions to explore the scattered limestone islands this cruising region is renowned for.
Setting sail from our base in Phuket, you have access to it all: Phang Nga Bay delivers those dramatic, almost otherworldly landscapes, while further afield, the islands of the Andaman Sea offer a mix of quiet beaches, clear water, and just enough infrastructure when you feel like stepping ashore.
February is also the peak snorkeling and diving season in Thailand, offering some of the best visibility of the year, often reaching up to 100ft. Expect numerous day boats filled with divers crowding the most popular diving spots this time of year. But with thousands of islands scattered across Phang Nga Bay, it’s always easy to find a quiet bay to escape the crowds.
Other Great February Sailing Destinations:
For those still looking for something different and off the beaten path, set sail in the Sea of Cortez from our base in La Paz, Mexico. This cruising ground offers very little to no man-made infrastructure once you leave the base. Making it the ideal February sailing destination for those who want to escape it all and simply marvel at desert landscapes, azure seas, and abundant marine life.
March Sailing in Belize: Exploring the World’s Second-Largest Barrier Reef
March is the sweet spot for the Western Caribbean, and the perfect time to set sail in Belize.
Set along the edge of the world’s second-largest barrier reef, this is a cruising ground that is naturally protected, comfortable, and calm even when the breeze picks up. With short, comfortable passages, minimal swell, and water that stays flat and glassy more often than not. It is the kind of environment that lets you slow things down a little, spend more time in the water, and less time thinking about the weather.
March also brings some of the best visibility of the year, making it prime time for snorkeling and diving along the Belize Barrier Reef, with coral reefs and thriving marine life never far from your anchorage. Sailing in Belize in March also coincides with the start of the whale shark season, giving Sunsail owners the rare opportunity to swim with these gentle giants.
And sailing from the Sunsail Base in Placencia, you are perfectly positioned to access it all. From the laid-back charm of the Southern Cayes to more remote stretches of reef that feel completely untouched, this is a destination that rewards a slower pace and a bit of curiosity.
Other Great March Sailing Destinations:
If more underwater exploration is calling you in March, consider setting sail to the Whitsundays in Australia to dive into the Great Barrier Reef. Or if staying dry and soaking up the sun is your ideal spring getaway, Antigua’s 365 beaches are just a short flight from the U.S mainland.
April Sailing in the Seychelles: The Ideal Window for Calm Seas and World-Class Diving
April is widely regarded as the calmest month of the year for a Seychelles yacht charter, with gentle breezes and almost glass‑like seas that create picture‑perfect conditions for both sailing and diving.
These calm conditions create excellent visibility and are the perfect time to spot manta rays, hawksbill turtles, octopus, reef sharks, and the elusive whale sharks that call these warm tropical waters home.
Above the surface, the 115 islands that make up this remote Indian Ocean Island chain are home to numerous rare plant and animal species that can only be found in the Seychelles. From giant tortoises, coconut crabs, carnivorous plants, rare birds, and the largest nut in the world, sailing in the Seychelles is an absolute delight for those looking to explore both above and below the water.
Other Great April Sailing Destinations
If you are looking for more excellent snorkeling and diving and unique landscapes to explore, head to French Polynesia for lush landscapes, gentle winds, and incredible snorkeling outside of the peak cyclone season.
The Exuma Cays in The Bahamas are another great April sailing destination for wildlife encounters both above and below the water. Swim with the nurse sharks at Compass Cay, feed the rowdy swimming pigs at Big Majors Cay, and snorkel the famous Thunderball Grotto, or simply watch nurse sharks swimming off your stern from a desolate cay.
May Sailing on the Amalfi Coast: The Perfect Start to the Italian Summer
If the start of the European sailing season has you itching to dip your toes into the Mediterranean ocean, then there is no better way to scratch that itch than exploring Italy’s glamorous Amalfi Coast.
Launch from our base in Procida just as the wisterias begin to bloom, and head to the iconic ports of Positano and Amalfi without the sweltering heat and crowds of peak summer.
Sailing the Amalfi coast in May means the weather is warm but comfortable, anchorages are not crowded, and you can more likely than not always find a last-minute spot in a marina. Distances along the Amalfi Coast are also short and manageable, making this an ideal cruising ground for relaxed island hopping with plenty of time ashore.
From Procida, you are perfectly positioned to explore the Bay of Naples and beyond. Sail west toward the volcanic landscapes of the Phlegraean Islands, or venture further to the Pontine Islands, where places like Palmarola offer some of the most untouched and dramatic anchorages in the Mediterranean. Clear water, rugged cliffs, and fewer crowds make this stretch feel like a hidden side of Italy that many travelers never experience.
Heading south, the coastline transforms into the iconic Amalfi scenery with steep cliffs, pastel villages, and lively harbors. Capri delivers on its reputation with upscale boutiques and polished marinas, while Sorrento offers a more relaxed charm with easy access to historic sites like Pompeii and Mount Vesuvius.
And for a more social and guided experience, Sunsail also offers flotillas from Procida, including specialty itineraries like the SailEatalia Italian Cuisine flotilla, combining independent sailing with local expertise, curated stops, and a focus on authentic regional food, culture, and local insights.
Other Great May Sailing Destinations:
If sailing in Europe isn’t on your radar for May, yet you still want the elegance and flair of the Amalfi Coastline, St Maarten, and St Barts are your ideal May sailing destinations. With all of the glitz and none of the long flights, these French and Dutch Islands offer the best of European cruising right in the heart of the Caribbean.
June Sailing in the Ionian Islands: Greek Island Hopping
Kick off your summer with a sailing adventure in the lush, sun-drenched Ionian Islands. Cast off from our base in Lefkas and discover why June is one of the best months to sail the Ionian Islands.
The islands are at their greenest, flowers are in full bloom, and the notorious Meltemi winds haven’t yet reached their summer peak, giving you gentle breezes in the morning and some more lively afternoon sailing, keeping the adventure exciting and your hands solidly on the reefing lines.
But what sets the Ionian islands apart from other Greek sailing grounds is how forgiving and varied they are. The sailing distances are short, the seas are typically calmer than the Aegean, and line-of-sight navigation makes it an ideal destination for both newer and experienced owners. From Lefkas, you can easily reach Kefalonia’s dramatic limestone cliffs, the sheltered bays of Meganisi, and the iconic turquoise waters of Porto Katsiki.
Other Great June Sailing Destinations:
If easier line of sight sailing is what you are craving in June, the BVI’s never disappoint with its relaxed and easy sailing conditions. And even if you have been-there-and-done-that earlier in the year, with over 60 islands to explore, there’s always a new anchorage or a hidden bay calling your name.
The Abacos is another great sailing destination for easier line of sight cruising, perfect for new owners or families looking for an easy and relaxed week on the water.
July Sailing on the Dalmatian Coast: Sailing the Heart of the Adriatic
July offers the peak, warmest sailing conditions in Croatia. With hot days, warm calm seas, and reliable afternoon winds of 10 to 15 knots, this is the perfect time to explore the Adriatic.
Setting sail from one of our two Sunsail bases in Croatia, either Marina Agana or Dubrovnik, you get to choose exactly how you want to explore the 1244 islands, rocks, and islets that make up this charming and historic stretch of the Dalmatian Coast.
What makes Croatia so compelling in July is the sheer variety packed into short, manageable sailing distances. From Marina Agana, you can easily reach Brač for quiet anchorages and beaches, Hvar for a mix of nightlife and historic charm, Vis for more remote, authentic cruising and clear-water bays, and Korčula for its walled old town and relaxed island atmosphere.
From Dubrovnik, your route opens to the southern Dalmatian islands, with Mljet offering a peaceful national park setting and saltwater lakes, Korčula blending historic architecture with lively harbors, and the Elafiti Islands providing easy first and last day stops with sheltered anchorages and quiet village charm.
Other Great July Sailing Destinations:
If you want more rich history this July, then set sail for Portsmouth, England. With thrilling sailing conditions and famous races and regattas happening throughout the summer, this is the ultimate playground for experienced sailors.
But if you prefer your history paired with easy sailing and 365 palm-lined beaches, then sailing in Antigua in July is the perfect way to explore its rich pirate and naval heritage, just a short flight from the U.S. mainland.
Sailing Sardinia in August: Navigating the Rugged Elegance of the Costa Smeralda
Start your sailing vacation from our base in Cannigione and discover the rugged elegance of Sardinia’s Costa Smeralda. With its dramatic coastline, strong summer winds, and narrow tidal range, this is the perfect Mediterranean playground for more experienced sailors.
Set in the resort town of Cannigione, the Sunsail base in Sardinia is the perfect place to get in a round of golf, enjoy dazzling white beaches, and rub shoulders with the rich and famous before setting sail to explore Sardinia, the Maddalena Archipelago, and Corsica.
Out on the water, the cruising is varied but easy to manage. The Maddalena Archipelago offers short, well-spaced passages with clear channels and reliable winds, so you can cover multiple stops without long sailing days.
And then there is the food! This is reason enough to plan your route carefully. Sardinia blends Italian classics with its own distinct identity. From fresh seafood and handmade pastas to local specialties like porceddu and pane carasau, no matter where you stop, you’re in for a great meal in this part of the world.
If you want to take the stress out of exploring the Costa Smeralda coast, join a Sunsail flotilla in Sardinia to sail with a group of like-minded Sunsail owners on the hunt for good food, good sailing, and good anchorages.
Other Great August Sailing Destinations:
If you love the sunny, breezy sailing of Sardinia in August, Corfu, Greece, is a perfect alternative. With steady summer winds, turquoise waters, and charming harbors to explore, Corfu offers the same mix of effortless sailing, Mediterranean culture, and picture-perfect anchorages.
September Sailing in Turkey: Discover the Newest Base on the Turquoise Coast
September is the perfect time to set sail from the latest base in the Sunsail network, Fethiye, Turkey.
As the peak summer heat begins to ease, the crowds dwindle whilst the water temperatures remain warm and inviting, and the best of the season’s steady breezes make for effortless sailing across the Göcek Archipelago.
From Fethiye, Turkey’s Aegean Coastline beckons with dozens of tranquil anchorages, crystal‑clear water perfect for swimming and snorkeling, and short sails that leave plenty of time ashore. Along the way, ancient Lycian ruins and historic harbors dot the shoreline, while quiet seaside villages invite you to wander cobblestone streets and sample local Turkish cuisine.
And Turkey’s coastal cuisine is as warm and inviting as the sailing conditions. From fresh seafood and mezze plates to grilled specialties prepared with vibrant local flavors. It is easy to see why this coastline has been captivating sailors for centuries, and why it is the latest addition to the Sunsail network.
Other Great September Sailing Destinations:
As the summer season in the Mediterranean comes to an end, September is the perfect chance to get your last dose of European charm in before the cold weather and rough seas start rolling in. Sailing the Saronic Islands in Greece from the Sunsail base in Zea Marina near Athens in September offers mild winds and calm seas alongside its historic harbors.
Sailing French Polynesia in October: Cruising the Society Islands and Bora Bora
Escape to the South Pacific in the shoulder season of October, when the weather is warm, the seas are calm, the crowds have died down, and the islands are at their most inviting.
From our Sunsail base in Raiatea, you will be right in the heart of the 118 islands that make up French Polynesia. With the vast majority of these isolated islands spread apart by long, exhilarating open ocean sailing, these cruising grounds demand skill behind the helm and are not recommended for new or inexperienced owners.
But for those who have earned their miles behind the helm and have proven their sea legs, no other destination in the Sunsail network is as rewarding as experiencing the scale and diversity of French Polynesia.
Sailing through the lagoons of Tahiti, Raiatea, Taha’a, and Bora Bora, you will find dramatic volcanic peaks, black pearl farms, vanilla plantations, otherworldly blue waters, and one of the richest and most diverse marine ecosystems on Earth.
In these waters, the scale of the adventure matches the skill required to find it, making this a bucket list sailing trip for any Sunsail owner.
Other Great October Sailing Destinations:
If dropping off the map is your ideal October sailing trip, then setting sail from our base in Nassau offers the perfect opportunity for isolation in the mostly uninhabited Northern Exuma islands before the holiday crowds arrive.
But if being part of the action is more your speed for the perfect sailing trip in October, look no further than Tortola in the British Virgin Islands. As the social heart of the Caribbean, the BVI is constantly humming with an energy that’s hard to beat. And as the Atlantic hurricane season draws to a close, the crowds return, yet it’s still not as overcrowded as the peak winter holiday season.
November Sailing in Grenada: Spice Island Adventures and Southern Caribbean Freedom
With the Caribbean hurricane season officially coming to a close by the end of the month, November is one of the best times to set sail in the southern Caribbean. Grenada sits just outside the main hurricane belt, making it a reliable and rewarding destination for early-season cruising, with steady trade winds, warm temperatures, and far fewer crowds than the peak winter months. From our Sunsail base in St. George, you can explore a diverse cruising ground that blends exhilarating open-water sailing with some of the world’s most pristine white and black sand beaches. Sail north along Grenada’s lush, mountainous coastline, where waterfalls spill through dense rainforest, and the smell of spice plantations fills the air, or venture further to the Grenadines for some of the most iconic fishing and sailing in the Caribbean.
Drop anchor in the Tobago Cays to snorkel alongside sea turtles in crystal-clear waters, explore the vibrant marine life around the reefs, or enjoy laid-back Caribbean cuisine and classic island cocktails right on the beach. Back in Grenada, experience the island’s rich culture through bustling spice markets, waterfront dining, and lush tropical hiking.
November sailing in Grenada offers a blend of culture, adventure, and laid-back Caribbean charm that every Sunsail Owner should experience at least once
Other Great November Sailing Destinations:
If something more exotic is calling your name in November, this month marks the start of the dry season in Thailand and the return of calm seas, sunny skies, and light to moderate winds across the Andaman Sea. Setting sail from Phuket, you can explore dramatic limestone karsts in Phang Nga Bay, hidden lagoons, and quiet island anchorages before the peak season crowds arrive. It’s the ideal time to experience this exotic cruising ground at its most peaceful, with excellent conditions for both relaxed sailing and world-class snorkeling.
December Sailing in St. Martin and St. Barts: The Heart of the Caribbean Festive Season
There’s no better place to celebrate the festive season than the French and Dutch Caribbean, and nowhere is more glamorous than St. Barts. Cast off from our St. Martin base to sail into a world where turquoise waters meet designer boutiques, gourmet dining, and the kind of yacht-filled harbors that attract celebrities, royalty, and the world’s most elite travelers.
Explore the beaches of St. Martin and Anguilla for a few days before joining the buzz of St Barts’ Gustavia harbor. This is where luxury yachts glisten under festive lights and exclusive beach bars host elegant holiday gatherings for the rich and famous. It’s a season of glitz, glamour, and unforgettable tropical indulgence that you won’t find anywhere else in the Caribbean.
Other Great December Sailing Destinations:
If your December sailing plans include partying the night away at some of the best New Year’s celebrations in the world, but St Barts doesn’t quite tickle your fancy, the BVI is your port of call. Home to the legendary Foxy’s New Year’s Eve party on Jost Van Dyke, there’s no other place quite like ringing in the New Year in the BVI.
But if avoiding the crowds and escaping it all is your New Year’s resolution, head to Martinique for a quiet Caribbean retreat. The island combines laid-back beaches with charming French-inspired cafés, vibrant markets, and gourmet dining, making it the perfect relaxed alternative to the bustling harbors of St. Barts.
Maximize Your Sunsail Yacht Ownership
The Sunsail Yacht Ownership program is designed for those who want the world to be their playground. By strategically planning your owner sailing weeks month by month across these prime sailing destinations and seasons, you’re not just owning a yacht; you’re experiencing the globe on your terms.
From crystal-clear Caribbean waters to the sun-drenched Mediterranean and the exotic beauty of the Indian and South Pacific Oceans, every week is an opportunity for a new sailing adventure.
Ready to plan your next escape? Log in to your Owner Portal or contact your dedicated Owner Services team to see which bases are available for your upcoming owner-use weeks, and start turning your sailing dreams into reality. Because why just sail, when you can Sunsail.
Hanrie Bosch
Guest blogger, Hanire Bosch, is a professional yacht chef. Based in the Caribbean and Bahamas, since 2013, she has worked on boats ranging from 48 ft Leopards to 160 ft superyachts.