Top 10 Bucket List Sailing Trips for 2025: Elevate Your Yacht Owner Experience With Low Season Sailing

Top 10 Bucket List Sailing Trips for 2025: Elevate Your Yacht Owner Experience With Low Season Sailing

Why sail with the peak season crowds when you can embrace the tranquility of off-peak sailing in some of the world’s most stunning destinations? As a Sunsail yacht owner, you enjoy exclusive access to 20+ premier sailing locations worldwide through our flexible and innovative yacht ownership program. Whether planning a bucket-list adventure months in advance or a spontaneous getaway, our 84-point system empowers you to customize your journeys and maximize your time on the water.

With 42 points for advanced bookings and 42 for last-minute trips booked 7–16 days in advance, Sunsail’s points system is designed to fit your lifestyle. Instead of the two points per day in the high season, low-season trips require just one point per day, letting you explore more while stretching your points further. This means you can enjoy up to 12 weeks of sailing annually with no blackout dates. Plus, Sunsail yacht owners can book comparable Moorings yachts at no extra cost, offering even greater flexibility.

Whether you’re dreaming of soaking up some Mediterranean charm, basking in Caribbean tranquility, or falling off the map in far-flung exotic adventures in the Indian Ocean, low-season sailing lets you explore bucket-list destinations at their most peaceful. Check out our top 10 picks for unforgettable low-season sailing trips in 2025 and start planning your next unforgettable 12 weeks of sailing with Sunsail.

Top 10 Bucket List Sailing Trips for 2025: Elevate Your Yacht Owner Experience With Low Season Sailing

Seychelles – Indian Ocean

Point High Season:         Dec 1 – Apr 30

Points Low Season:        May 1 – Nov 30

Sailing Experience Level 3

Sailing in the Seychelles during the low season offers a peaceful, unhurried experience, perfect for those seeking serenity without the crowds. Located in the remote Indian Ocean, and with nearly half of its landmass – compromised of over 100 islands – set aside for national parks and reserves, the Seychelles offer an abundance of pristine beaches, sheltered coves, remote anchorages, and arguably, the most crystal-clear waters in the world, with visibility reaching up to 100ft between April and May, and October to November! Falling outside of the hurricane belt and experiencing ideal weather year-round, sailing the Seychelles is a perfect low-season sailing destination.

Passages in these remote islands combine a mix of open water sailing in fair winds and short island hops between Mahé, Praslin, and La Digue, allowing you to enjoy a variety of top-notch sailing experiences between the islands. As you cruise the islands, you’ll discover pristine beaches, lush forests, and majestic mountains. The Seychelles is home to rare wildlife, including giant tortoises, the Seychelles black parrot (which is actually brown), and diverse marine life, such as whale sharks and vibrant coral reefs. On land, explore the charming streets of Victoria or unwind in peaceful anchorages, far from crowded ports and noisy tourist hubs.

With crystal-clear waters and excellent visibility, the Seychelles is a prime destination for diving and snorkeling. The marine life is diverse, including vibrant coral reefs, sea turtles, and the occasional whale shark. The Seychelles also offers fantastic fishing opportunities, where you can fish for tuna, sailfish, and giant trevally, and even cook your fresh catch on the boat – no fishing license needed!

Top 10 Bucket List Sailing Trips for 2025: Elevate Your Yacht Owner Experience With Low Season Sailing

Best Time To Visit The Seychelles To Maximize Your Owner Points:

Falling outside of the hurricane belt and experiencing most of their stormy weather during the peak summer months of January and February, Seychelles is a perfect destination to take advantage of any time during the low season.

May ushers in the dry season with cooler temperatures, low humidity, and southeast trade winds of 8-20 knots, making it perfect for sailing. From June to August, the winds remain steady, and temperatures stay mild, though humidity rises slightly. September brings calmer conditions and warmer weather. October and November offer mild winds and warmer temperatures as the northwest monsoon approaches. The low season is generally marked by excellent visibility, perfect for diving, snorkeling, and exploring the pristine beaches and coves.

Highlights Of Low Season Sailing In The Seychelles:

Relax On Anse Lazio Beach:

This breathtaking white-sand beach framed by granite boulders and crystal-clear waters is consistently ranked as one of the world’s top beaches. It’s ideal for swimming or snorkeling with sea turtles and colorful tropical fish near the rocky edges, with nearby hidden bays offering peaceful spots to explore vibrant marine life.

Get Nutty on Curieuse Island:

Not only is Curieuse Island a designated marine national park, but it is also one of just two places in the world where you’ll encounter the heaviest nut in the world— the coco-de-mer also known as the double coconut. You can also spend some time exploring the ruins of a leper colony and meeting hawksbill turtles at the island’s rookery.

Cousin Island

Cousin Island, a protected nature reserve, is a sanctuary for incredible wildlife. Visitors can encounter Aldabra giant tortoises roaming freely and spot hawksbill turtles nesting on the pristine beaches. This island is also home to vibrant birdlife and lush vegetation.

Top 10 Bucket List Sailing Trips for 2025: Elevate Your Yacht Owner Experience With Low Season Sailing

The Exumas – Bahamas

Points High Season:      Dec 16 – Jan 2 And Feb 16 – July 31

Points Low Season:       Jan 3 – Feb 15 And Aug 1 – Dec 15

Sailing Experience Level 3

Just a short hop from Florida, and with numerous direct flights from various US and European cities to Nassau, sailing in the Exumas is the perfect destination to use up those short notice points and take advantage of perfect low-season sailing conditions.

For seasoned sailors, the Exumas offer a thrilling and rewarding experience unlike any other. Famous for their crystal-clear waters, hidden sandbanks, and abundant marine life, these 365 islands are a dream destination for those looking to combine adventure with tranquility.

Nothing beats island-hopping in the Exuma Cays, with each island offering a different type of laid-back Bahamian charm, whether it’s the (sometimes) friendly swimming pigs at Big Major Cay, snorkeling the famous Thunderball Grotto, or simply reveling in the unspoiled beauty of the Exuma Cays Land and Sea Park.

Due to the challenging sailing conditions throughout the Exumas, you will need to have some miles under your belt to take on this cruising ground. But if you have proven your sea legs and you are not afraid of terrifyingly shallow water, navigating massive coral heads across the yellow bank, ripping currents through narrow cuts and shifting sand banks, you will be rewarded like no place else on earth with spectacular crystal clear water, an abundance of marine life, strolling on isolated sand banks in low tides and of course the endless bragging rights of having navigated the Exumas.

Top 10 Bucket List Sailing Trips for 2025: Elevate Your Yacht Owner Experience With Low Season Sailing

Best Time To Visit The Exumas To Maximize Your Owner Points:

Mid-October to mid-December is the ideal time to maximize your owner points and take advantage of the Exumas without the crowds. Although the official end of hurricane season in the Caribbean is November 30, the chances of a hurricane in these shoulder months are considerably lower than the peak summer months of July, August, and September.  

Mid-October to mid-December also sees pleasant weather, great sailing conditions, and a very low likelihood of any cold fronts sweeping through bringing potential nasty weather to Exumas – making it nearly impossible to navigate, as is sometimes the case in December, January, and February.

Highlights Of Low Season Sailing In The Exumas:

Spectacular Wildlife:

No matter the season, majestic wildlife is abundant in the Exumas. From spotting nurse sharks and eagle rays in the crystal-clear water right from the comfort of your boat to getting up close and personal by diving into one of the many spectacular snorkeling or diving spots. Or stay dry by visiting the infamous Staniel Cay Pigs or giant iguanas on Bitter Guana Cay.

The Ultimate Isolation:

The Exumas are made up of over 365 Islands and Cays! Offering the ultimate playground to escape everyone and everything and find that perfect secluded anchorage or sandbar, especially in the low season.

Explore the Exuma Cays Land and Sea Park:

Sail through the Caribbean’s largest marine park, which covers over 450 square kilometers and offers some great hiking on Warderick Wells.

Top 10 Bucket List Sailing Trips for 2025: Elevate Your Yacht Owner Experience With Low Season Sailing

Dubrovnik – Croatia

Based Closed Ded, Jan, Feb

Point High Season:         June 16 – Sept 22

Points Low Season:        Sep 23 – June 15

Sailing Experience Level 1

Often overlooked by other Mediterranean destinations like Spain, France, or Italy, Croatia is more quintessentially Mediterranean than you might expect.

Begin your adventure at our Dubrovnik base, just minutes from the historic Old Town. Walk along the medieval walls for breathtaking views of terracotta rooftops and the sparkling Adriatic Sea. From there, set sail to the idyllic Elaphiti Islands, where peaceful anchorages, lush greenery, and crystal-clear waters await. Snorkel off Koločep, explore the scenic trails of Lopud, or unwind in Šipan’s quiet charm.

For nature enthusiasts, Mljet National Park is a must-see. Its saltwater lakes, dense forests, and secluded bays offer a tranquil escape. Further afield, Korčula enchants with its cobblestone streets, rich history, and delicious local seafood paired with Croatian wines.

Avoiding the summer crowds in the shoulder seasons, you’ll enjoy calm seas, steady breezes, mild weather, easy line-of-sight navigation, and tranquil harbors.

Top 10 Bucket List Sailing Trips for 2025: Elevate Your Yacht Owner Experience With Low Season Sailing

Best Time To Visit Dubrovnik To Maximize Your Owner Points:  

Croatia has the perfect low-season sailing conditions from May to mid-June or in October. Sailing in the spring will see temperatures in Croatia warming up and getting even hotter as the month progresses. The days are getting longer, with plenty of sunshine and the winds are steady, but they won’t be as strong as they were in April, and there are still little to no crowds before the peak summer months hit. The sea is also still warming up after the winter, and you might be able to swim but don’t expect balmy tropical waters during these months.

October is post-season time, with shorter days, steady winds, and thin to non-existent crowds. And thanks to the hot summer months, the sea is still warm and perfect for swimming and snorkeling, unlike the shoulder season of May to June.  

Highlights Of Low Season Sailing In Dubrovnik:

Dubrovnik Old Town:

Just minutes from the Sunsail base, Dubrovnik’s Old Town is a captivating blend of ancient history and modern charm not to mention a crowded nightmare in the peak summer months. Take full advantage of the sparse low-season crowds and spend your first day exploring the “Pearl of the Adriatic.” Stroll the marble-paved streets, visit landmarks steeped in history, and savor local delicacies at charming eateries. Ride a cable car to the summit of Srd Hill for breathtaking views of the Old Town and unwind at night with the vibrant culture of this medieval city.

Mljet National Park;

Explore this expansive lush national park by dropping anchor in one of the many protected bays. Polače Bay is surrounded by smaller islands and home to an ancient Roman palace, Pomena Bay provides easy access to park trails for hiking or biking (perfect activities for October), while Lokva Bay offers a tranquil anchorage.

Explore stunning beaches like Saplunara, a white sandy stretch framed by pine forests, or discover the serene lakes of Veliko Jezero and Plitko Jezero. Don’t miss Odysseus Cave, just outside the park, for a magical snorkeling experience.

Stunning Korčula Town.

Korčula Town, often called “Little Dubrovnik,” is renowned for its stunning Old Town, showcasing Venetian-era charm with stone gates, lion-adorned statues, and elegant palazzos lining its cobbled streets. A hub of culture and history, it’s home to museums, galleries, and fine dining spots, as well as being a bustling tourist hotspot in the peak winter months.  

The island is also famed for its local wines, particularly the white grape varieties of Pošip and Grk. Join a wine-tasting tour to sample the offerings of the numerous family-run vineyards dotting the island.

Top 10 Bucket List Sailing Trips for 2025: Elevate Your Yacht Owner Experience With Low Season Sailing

Belize – Central America

Points High Season:       Dec 16 – Apr 15

Points Low Season:        Apr. 16 – Dec 15

Sailing Experience Level 3

Sailing in Belize is an adventure best suited for experienced sailors. Although the sailing here is mostly short hops between the islands, it’s the shallow waters, hidden coral heads, and minimal navigational markers, that make this a destination that demands sharp navigation skills and constant attention to charts and depth sounders. For a more relaxed experience, there is also always the option of hiring a skipper to let you enjoy the journey without the stress.

Whichever way you choose to navigate these jungle-lined tropical waters, heading to the Belize Barrier Reef – the second largest barrier reef in the world – is definitely one of the main draws of this South American paradise. But Belize’s appeal extends beyond the reef, where you can explore sites like the ancient Mayan ruins of Lamanai, venture into lush rainforests teaming with wildlife, discover a plethora of secluded islands and pristine beaches, dine on fresh local seafood and discover unique Creole culture in the isolated community of Monkey River town.

Compared to other Caribbean destinations, Belize is not considered a tourist hotspot and generally tends to have a more relaxed and less crowded atmosphere year-round, but that said, Belize does still get pretty busy in the peak winter months. Blessed with near-perfect year-round sailing conditions of consistent trade winds blowing from the east or southeast, the protected waters of the barrier reef where waves remain minimal no matter the weather, and an average year-round temperature of around 80°F, it makes for the perfect destination for low season sailing to maximize your Sunsail Owners benefits.

Belize offers the kind of sailing destination that rewards both the seasoned sailor and those looking to find something off the beaten path. Whether you’re after thrilling sailing or simply dropping anchor to unwind, Belize is a must-sail low-season destination for anyone worth their salt.

Top 10 Bucket List Sailing Trips for 2025: Elevate Your Yacht Owner Experience With Low Season Sailing

Best Time To Visit Belize To Maximize Your Owner Points:

Set your sails for Belize in either late May to early June or mid-October to mid-December to skip the crowds and stretch your owner usage. These months bring clear skies, calm seas, and steady trade winds, all while maintaining warm temperatures perfect for sailing. While occasional rain showers can occur, the weather generally remains favorable for cruising.

The dry season in Belize runs from December to May, with little rain and clear skies. The wet season runs from June to November, with more rain and higher humidity. As November is still part of hurricane season, it’s wise to stay updated on weather forecasts during your trip.

Highlights Of Low Season Sailing In Belize:

Explore The Belize Barrier Reef:

The best way to see the magnificent Belize barrier reef at its uncrowded best is to navigate the shallow waters through the patchy reef that leads to South Water Caye. Grab a mooring buoy and dinghy ashore to unwind on a hammock and dine on fresh local lobster or dive right into the barrier reef laying just offshore.

Swim With Whale Sharks:

Whale sharks can be seen in Belize from March through June, usually starting two days before a full moon and lasting about 10 days. The best time to see them is a few days after the full moon. April and May are typically the best months to see whale sharks. The most popular spot to see whale sharks is Gladden Spit Marine Reserve, off the coast of Placencia.

Visit Monkey River Town:

Sail to No Name Point, a peaceful anchorage surrounded by mangroves teeming with wildlife. From here, visit Monkey River Town, one of Belize’s last traditional Creole fishing villages. Immerse yourself in authentic Caribbean culture while exploring this charming community. Don’t miss a guided river tour to spot black howler monkeys, manatees, and exotic birds.

Top 10 Bucket List Sailing Trips for 2025: Elevate Your Yacht Owner Experience With Low Season Sailing

La Paz Mexico – Sea of Cortez

Points High Season:        Mar 1 – May 31 And Oct 1 – Nov 30

Points Low Season:         Jun1 – Sept 30 And Dec 1 – Feb 28

Sailing Experience Level 3

Dubbed “The World’s Aquarium”, the Sea of Cortez does not disappoint as a spectacular sailing and wildlife destination. Teeming with a dizzying array of wildlife year-round, you will have the opportunity to swim alongside whale sharks, witness breaching humpback whales, or snorkel vibrant coral reefs teeming with colorful fish. From April to August and again from late November to January, Mobula rays perform mesmerizing acrobatic displays, while pods of dolphins and colonies of sea lions make for unforgettable encounters year-round.

For those visiting from December to April, the Bay of Cortez is one of the best places in the world to spot orcas, as these magnificent creatures migrate through the area in search of food. Beyond the water, hiking trails lead to stunning viewpoints, and birdwatchers can spot rare species unique to the Baja Peninsula.

With all the hustle and bustle below the waves, don’t expect to find any of that on land sailing in the Baja peninsula. Besides the town of La Paz, where you will start and end your sailing journey, the rest of your sailing trip in the Sea of Cortez will have no beach bars, restaurants, or pretty much any man-made facilities. It’s just you and your boat, 244 uninhibited islands, and about 900 species of fish.

Find out how to make the most of sailing this isolated gem with our perfect 7-day itinerary here.

Top 10 Bucket List Sailing Trips for 2025: Elevate Your Yacht Owner Experience With Low Season Sailing

Best Time To Visit La Paz to Maximize Your Owner Points:

Make the most of La Paz in February when the weather is dry, the winds are constant, between 10 to 25 knots, and temperatures range between 61°F to 77°F. This is also the perfect time to see orcas and other whale species. Or opt for an early summer retreat in June when temperatures range between 72 °F to 97°F and winds range between 10-20 knots. June is also the perfect time to see the dancing Mobula rays.

Highlights Of Low Season Sailing In La Paz:

Isla Espíritu Santo

A popular anchorage with secluded coves, white-sand beaches, and dramatic rock formations, this island is renowned for its dramatic red cliffs, white-sand beaches, and turquoise waters. Visit the playful sea lions at Los Islotes, kayak along rugged coastlines, relax in serene anchorages like Ensenada Grande, or hike the island’s trails for breathtaking views.

Discover Mobula Rays in the Sea of Cortez:

The Sea of Cortez offers one of the most spectacular wildlife experiences out on the water, with the seasonal migration of Mobula rays. From April to August and again from late November to January, hundreds of thousands of Mobula rays perform synchronized acrobatic displays, leaping up to two meters out of the water. Mobula rays are gentle and curious creatures, typically shy around humans, offering a unique opportunity for snorkelers and freedivers to get up close. Scuba diving with them is prohibited.

The Ultimate Escape:

Unlike any other Sunsail destination on our list, sailing in La Paz truly offers the opportunity to escape it all. With no beach bars, restaurants, or any facilities at all once you leave La Paz, you will truly be able to enjoy the freedom of sailing and immerse yourself in the rugged beauty of the arid coastline, crystal clear waters, and diverse wildlife and sail into the ultimate escape.

Top 10 Bucket List Sailing Trips for 2025: Elevate Your Yacht Owner Experience With Low Season Sailing

Tahiti – French Polynesia

Point High Season:         May 1 – Aug 31

Points Low Season:        Sep 1 – Apr 30

Sailing Experience Level 3

Sailing in Tahiti is a breathtaking experience year-round, but there’s something truly special about visiting during the low season and having this sought-after sailing destination almost to yourself.

Exploring Tahiti in the quieter months offers the perfect balance of ideal weather conditions and fewer crowds. The shoulder season in Tahiti generally falls between May to early June and September to October. During these months, the weather remains warm and pleasant, with steady trade winds ideal for sailing, but without the influx of tourists that arrive during peak season.

In addition to the tranquil waters and fewer tourists, sailing in Tahiti during the shoulder season offers a chance to experience the islands in their natural beauty, as flora is often in full bloom, and marine life is abundant. You can enjoy activities like snorkeling with rays, exploring lush trails, and immersing yourself in Tahitian culture without the pressure of crowded harbors and overbooked excursions.

While sailing in Tahiti, you can explore the famous Bora Bora Lagoon, where you can snorkel or dive alongside manta rays and colorful marine life. Visit the lush island of Moorea for a hike through its tropical rainforests, or experience the vibrant Tahitian culture in the capital, Papeete. For nature lovers, the island’s stunning landscapes offer hiking trails with panoramic views, and the clear waters are ideal for kayaking and paddleboarding.

Whether you’re after romantic tranquility, adventurous sailing, or a perfect mix of both, Tahiti’s shoulder season delivers on all fronts. As one of the world’s most remote sailing grounds, French Polynesia offers unparalleled tranquility during the quieter months.

Top 10 Bucket List Sailing Trips for 2025: Elevate Your Yacht Owner Experience With Low Season Sailing

Best Time To Visit Tahiti To Maximize Your Owner Points:

Sailing in Tahiti during the beginning of the low season in September and October offers calm seas, steady trade winds, and mild weather, ideal for smooth navigation. It’s also humpback whale migration season, with chances to spot manta rays too. With fewer tourists, anchorages at Bora Bora, Raiatea, Taha’a, and Huahine are peaceful.

While December to February falls in the peak rainy season, brief showers don’t diminish the charm of exploring Tahiti, especially as this is when the islands are in full bloom.  However, it’s important to note that cyclone season runs from November to April, and although cyclones are rare in this part of the Pacific, they can still happen.

Highlights Of Low Season Sailing In Tahiti:

Tahiti Carnival:

The Tahiti Carnival, held annually in October in Papeete, is a lively celebration of culture and tradition. The streets come alive with vibrant colors, spectacular floats, energetic dancing, and joyous street parties. The parade draws over 10,000 spectators, offering a unique chance to experience the island’s rich heritage and lively atmosphere.

Take Your Dingy On A River Cruise:

Take your dinghy up the tranquil Faaroa River, the only navigable river in French Polynesia. Lined with lush jungle and vibrant flora, this peaceful journey offers a glimpse into Tahiti’s natural beauty. Explore the river’s serene waters surrounded by towering peaks and tropical landscapes without the crowds.

Swim With Giant Manta Rays:

Swim with giant manta rays in Bora Bora during September, when these graceful creatures are most active. Bora Bora’s calm, clear waters make it an ideal spot for snorkeling or diving alongside mantas, with their impressive wingspans gliding effortlessly through the sea. While exploring, you may also encounter gray sharks, turtles, and vibrant coral reefs. With minimal currents, the conditions are perfect for divers of all levels.

Top 10 Bucket List Sailing Trips for 2025: Elevate Your Yacht Owner Experience With Low Season Sailing

Thailand – Phuket

Point High Season:         Dec 1 – Apr 31

Points Low Season:        May 1 – Nov 30

Sailing Experience Level 1

If you are looking to escape the world and not see another soul for days on end and have quiet anchorages all to yourself, a sailing adventure in Thailand – even in the low season – might not be the place for you. But if your dream sailing destination includes incredible culture and cuisine, extravagant nightlife, and beach bars surrounded by spectacular scenery, then it’s time to set sail for the dramatic limestone cliffs of the Andaman Sea in Phuket, Thailand.

Famed for its wild Full Moon beach Parties, dramatic limestone cliff scattered islands, spectacular snorkeling and diving, and the famous Phi Phi and Similan Islands. Phuket offers no shortage of opportunities to explore both above and below the crystal-clear waters.

Below the water, you will find exotic whale sharks and manta rays in excellent visibility and an abundance of hidden caves to explore. Beyond the water, Phuket offers a blend of ancient culture and lively modern life. You can visit local villages on smaller islands nearby, experience authentic Thai cuisine, take in the vibrant nightlife with beach bars and Full Moon parties, or simply take in the breathtaking sunsets with a cold Thai beer from your aft deck.

The warm waters, along with the steady trade winds, create excellent sailing conditions, especially from November to April during the dry season, and easy line-of-sight navigation, making it accessible for sailors of all levels.

View our perfect 7-day Phuket sailing literary here.

Top 10 Bucket List Sailing Trips for 2025: Elevate Your Yacht Owner Experience With Low Season Sailing

Best Time To Visit Phuket To Maximize Your Owner Points:

Sailing around Phuket in October and November offers favorable conditions as the southwest monsoon season ends. In October, the weather is warm with less frequent rainfall and light to moderate winds (5-15 knots), making for pleasant sailing.

Average temperatures range from 77°F to 88°F, and seas are calm to moderate. November marks the start of the dry season, with even calmer waters, clear skies, and ideal conditions for island hopping, making it a prime time to set sail before the peak tourist season arrives.

Highlights Of Low Season Sailing in Phuket:

Experience A Full Moon Party:

Expect live music, fire dancers, neon lights, and dancing under the stars. These lively events draw travelers from all over, creating an unforgettable experience amidst Phuket’s tropical beauty.

Dive Into An Underwater Art Gallery

Dive into Ko Racha Yai’s submerged sculpture park to come face to face with giant stone elephants and other incredible underwater art in crystal-clear waters. The visibility in October and November is exceptional, often reaching up to 30 meters, making this a perfect time to discover the stunning artwork and vibrant marine life that surrounds it.

Visit Koh Panyee:

This floating Muslim fishing village in Phang Nga Bay offers a unique glimpse into local life. Built on stilts over the water, you can wander through narrow walkways, visit the bustling market, and enjoy fresh seafood at one of the floating restaurants.

Get a Massage On The beach:

What would a trip to Thailand be without indulging in a traditional Thai massage? And the best way to treat yourself to this national pastime is to get a massage right on the beach. Most beaches offer beachfront spas or local beachfront huts where you can enjoy traditional Thai massages while listening to the soothing sounds of the waves.

Top 10 Bucket List Sailing Trips for 2025: Elevate Your Yacht Owner Experience With Low Season Sailing

Athens – Greece

Based Closed Ded, Jan, Feb

Point High Season:         June 16 – Sept 22

Points Low Season:        Sep 23 – June 15

Sailing Experience Level 3

Who hasn’t dreamt of escaping to a Greek island at some point? And by the looks of the summer crowds in this iconic Mediterranean destination, literally everyone has! Forget sailing this Mediterranean hotspot in the peak summer and tourist months of June, July August, and September, as this is truly a destination where you do not have to sacrifice prime sailing conditions to beat the crowds.

Sailing in Athens and the Aegean Sea offers some of its best sailing outside of the peak tourist season. The predominant Meltemi winds in the summer can make for some sporty sailing conditions and affect ocean visibility, not always ideal for everyone’s sailing vacation dreams and preferences. These winds can start to occur in May but are most common from June to September, reaching their peak in July and August.

The Meltemi winds can blow at speeds between 17-33 knots, and can sometimes gust even stronger, especially in narrow channels between islands: making them a significant challenge for sailors in the Aegean Sea, particularly during the summer months, hence this destination ranking at a level 3 experience level.

Avoiding the crowds and starting your Greek sailing adventure in the shoulder season months at the Sunsail base in Zea Marina, just outside central Athens, you’ll be close to the iconic landmarks of the Acropolis and Parthenon, giving you the opportunity to explore some ancient Greek history before setting sail

Once on the water, set sail towards the nearby islands of Hydra and Spetses. Known for their picturesque harbors, car-free streets, and laid-back atmosphere. Discover charming villages, soak in stunning coastal views, and enjoy quiet anchorages ideal for swimming, snorkeling, or kayaking.

The Saronic Gulf offers easy island hopping with its calm seas and beautiful surroundings. For a mix of adventure and relaxation, visit Kea, a short sail from Athens. This island is known for its traditional fishing villages, sandy beaches, ancient ruins, and hiking trails with breathtaking vistas.

Top 10 Bucket List Sailing Trips for 2025: Elevate Your Yacht Owner Experience With Low Season Sailing

Best Time To Visit Athens To Maximize Your Owner Points:

The weather in May/June offers mild temperatures and pleasant winds, ideal for a comfortable sail. In October, the weather remains warm with fewer tourists, and the winds are calmer, making it perfect for relaxed island-hopping. This time of year, you’ll enjoy clear waters for swimming and snorkeling, with average temperatures ranging between 68°F and 77°F. It’s also a great time for hiking and exploring ancient ruins.

The iconic Meltemi winds, which peak in the summer months, subside in October, offering more favorable sailing conditions outside of the busy summer months.

Highlights Of Low Season Sailing In Athens:

Explore Athens:

A tourist hotspot in the summer months, Athens in the shoulder seasons offers a perfect mix of history and relaxed exploration. Visit the Acropolis Museum at a leisurely pace and stroll up to the iconic Parthenon for breathtaking views of the city. The Sunsail base at Zea Marina is just a short ride from central Athens, making it easy to explore bustling markets, local tavernas, and cultural treasures.

Spetses Islands:

This pine-covered island, dotted with aristocratic mansions, offers a peaceful escape near Athens. Anchor in the old harbor or at Dapia, the bustling main port, and enjoy waterfront cafes, local tavernas, and boutique shopping. With fewer crowds, stroll along scenic coastal paths or explore by bike or horse-drawn carriage, soaking up the island’s rich history and laid-back Mediterranean vibe.

Hydra island:

Hydra, a completely car-free island, is best explored during the shoulder seasons when the crowds thin, and you can comfortably wander the steep cobblestone streets, visit historic fortresses, and soak in stunning sea views. With donkeys as the main mode of transport, this tranquil island offers a slower pace of life. Enjoy Grecian cuisine at waterfront tavernas, explore elegant mansions, and relax on idyllic beaches—perfect for swimming and snorkeling.

Top 10 Bucket List Sailing Trips for 2025: Elevate Your Yacht Owner Experience With Low Season Sailing

St. Lucia – Caribbean

Points High Season:           Dec 16 – Apr 15                                

Points Low Season:            Apr. 16 – Dec 15

Sailing Experience Level 3

Sailing in St. Lucia offers all the best of the Caribbean in one condensed little island. With an incredibly varied landscape ranging from breathtaking mountains, lush rainforests, volcanic sand beaches, colorful coral reefs, natural hot pools, and bubbling volcanic mud springs, it’s easy to forget that you are on one island.

But if you are looking to set your sails into the wide-open ocean then St. Lucia is also the perfect jumping-off point to see the scattered islands of St. Vincent and the Grenadines, enjoy a long open ocean sail to Bequia, dive into the marine parks of the Tobago Cays and enjoy powder-fine white sand beaches and fresh lobster on the tiny island of Mayreau.

Wherever your sailing journey into the heart of the Caribbean will take you, these Windward Islands see considerably fewer tourists than the major Caribbean sailing destinations of the BVI, St. Maarten, and The Bahamas, making it the perfect destination to splurge on using up some of your high season owners’ points during the winter months – should the craving for a mid-winter Caribbean escape arise. But St Lucia and its surrounding islands is also the perfect last minute low season retreat to stretch your owner use even further.

Top 10 Bucket List Sailing Trips for 2025: Elevate Your Yacht Owner Experience With Low Season Sailing

Best Time To Visit St. Lucia To Maximize Your Owner Points:

The fall shoulder season from mid-April to mid-June offers perfect sailing conditions, and even fewer crowds, and is still outside of the peak hurricane season and sweltering mid-summer Caribbean heat.  The same goes for the tail end of the hurricane season in the spring with ideal sailing conditions between mid-October and mid-December with steady Tradewinds of 10 -15 knots and generally calm seas.

Highlights Of Low Season Sailing In St. Lucia:

Take a Hike:

Hiking the Pitons in St. Lucia provides an opportunity to explore two iconic volcanic peaks, Gros Piton and Petit Piton. Gros Piton is the more accessible option, offering a variety of trails suitable for all fitness levels, while Petit Piton is steeper and more challenging. The trails feature diverse flora, including an abundance of colorful orchids, as well as numerous unique bird species such as the endangered Saint Lucian parrot. Don’t forget to pack a swimsuit so you can enjoy a dip at the base of one of many majestic waterfalls!

Cast Your Lines:

St. Lucia’s deep Caribbean waters support year-round fishing, offering opportunities to catch species such as blue marlin, sailfish, yellowfin and blackfin tuna, dorado, barracuda, king and Spanish mackerel, wahoo, rainbow runners, horse-eye jacks, and yellowtail snapper. But don’t fire up your grill just yet, as St. Lucia has a catch-and-release policy for tourists. Fishing gear rentals are available from the Sunsail base in Rodney Bay marina.

Volcanic Spa Treatments:

Moor in Soufrière Bay to visit the volcanic mud baths at Soufrière Volcano, located near the Sulphur Springs Park. The mineral-rich mud is known for its high sulfur content, which is believed to have therapeutic properties, including potential relief for sunburns, eczema, and sore joints. Take a dip in this healing mud before rinsing off in the nearby warm pools.

Don’t Go Camo!

Not so much a highlight as just a useful and somewhat bizarre fact to keep in mind before arriving in St Lucia: Camouflage clothing, bags, and accessories are prohibited in St. Lucia, as they are reserved exclusively for use by military personnel. This includes all types of camo-patterned items, such as hats, shoes, and backpacks. Avoid packing or wearing anything camouflage, as these will be confiscated by customs or whilst out and about on the island.

Top 10 Bucket List Sailing Trips for 2025: Elevate Your Yacht Owner Experience With Low Season Sailing

British Virgin Islands – Caribbean

Points High Season:          Dec 16 – Apr 15

Points Low Season:          Apr. 16 – Dec 15

Sailing Experience Level 1

No top sailing destination list would be complete without mentioning the ultimate sailor’s playground – The British Virgin Islands.

With its consistent trade winds, well-built-up infrastructure, protected deep waters, and close proximity and easy line of sight navigation between the 60 odd islands and cays that make up this sailors’ paradise, it’s easy to see why it can be hard to beat the crowds here any time of year.

Visiting the BVI during the crowded winter months requires some advanced strategic planning: restaurant bookings need to be made well in advance and to get to the prime tourist attractions of The Baths, Soggy Dollar, Anegada, Cooper Island, or any of the numerous popular snorkeling spots you will need to arrive at strategic early morning times to grab a mooring ball or anchoring spot, as these will quickly fill up by mid-morning. Exploring popular destinations like The Baths on Virgin Gorda can feel more like a queue at some bizarre marine-themed Disneyland than a relaxing Caribbean getaway.

Besides the crowds, the peak winter season can also bring with it strong winds and choppy waters, making the Sir Francis Drake channel quite sporty and, depending on the wind and swell directions, leaving some popular bays impossible or extremely uncomfortable to spend the night in.

This is exactly why the world’s premier sailing playground earns its spot as one of our top 10 destinations to rather sail in the low season to beat the crowds, stretch your points, and enjoy paradise (almost) to yourself.

Top 10 Bucket List Sailing Trips for 2025: Elevate Your Yacht Owner Experience With Low Season Sailing

Best Time To Visit The BVI’s To Maximize Your Owner Points:

Sailing the BVI in the spring shoulder season offers warm weather, occasional rain showers, steady trade winds between 10-20 knots, and fewer crowds and still falls outside the prime hurricane season of July, August, and September.

Mid-October to mid-December also offers excellent sailing conditions and sees the rain dry up a bit and the heat subsides, as well as falling outside of the prime hurricane season and the droves of crowds in the peak winter months. 

Just keep in mind the Caribbean hurricane season officially runs from June to November and storms are still possible anytime during these months.

Highlights of Low Season Sailing In the BVI:

Lobster dinner on Anegada:

Set sail to the unique coral atoll of Anegada for a prolonged spell of blue water sailing. Known for its pristine beaches and laid-back charm, no trip to Anegada is complete without dining on cooked-to-order local fresh-caught lobster at one of the many beachside restaurants. Hire a scooter or quirky little Moke to explore the island and visit the Salt Ponds to spot flamingos.

The Baths National Park:

Avoid the Disneyland-type lines to walk through the awe-inspiring geological wonders of The Baths in the peak winter months, and arrive there early in the low season, either by taxi from the docks in Spanish town or catch a mooring ball right in front of The Baths and swim in to have this must-see attraction all, or nearly all, to yourself!

Explore the beach bars on Jost Van Dyke:

Jostling for a spot in the iconic and crowded White Bay during the winter months can be frustrating and a tight squeeze, to say the least, but when the crowds die down in the shoulder seasons grab a comfortable anchorage and swim through crystal clear waters to the numerous beach bars lining this pristine white sand beach.

Go with The Flow:

Unlike planning for a trip in the BVI in the peak winter months and having to book restaurants months in advance or wake up at 7 am to book a BoatyBall, or risk fighting for a mooring ball or anchorage in overcrowded bays. You will have the leisure of going with the flow and seeing where each day takes you and leave your BVI adventures up to spur-of-the-moment impulses.

Whether it’s diving the wreck of the Rhone, exploring the Baths, or a last minute decision to dine out, the low season in the BVI is the perfect time to unwind and not think about anything besides which direction to point your sails.

Top 10 Bucket List Sailing Trips for 2025: Elevate Your Yacht Owner Experience With Low Season Sailing

Don’t Just Sail, When You Can Sunsail

Whether it’s the Mediterranean culture and cuisine that beckons your sails, the consistent Tradewinds of the Caribbean, or sailing off into the far-flung exotic sunsets of the Indian or Pacific oceans, the Sunsail Yacht Ownership program offers you the freedom to chart your own course.

Find out more about the Sunsail Yacht Ownership Program here.

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Sunsail Yacht Ownership