Best Caribbean island to visit in October

13 Best Caribbean Islands To Visit In October From An Expert Traveler (2024)

The Caribbean is a paradise for beach lovers, but with its peak season comes high prices, jam-packed beaches, and crowded resorts. This is why you need to know about the best Caribbean islands to visit in October – the shoulder season.

I have traveled the Caribbean region for five years, so it is safe to say I have a crush on tropical islands. From white sandy beaches to tours, local festivals, and celebrations, I will help you explore the top 13 Caribbean islands that come alive during this time of year.

Although October is the last month of the wet season, the sun is mostly out, and the temperatures are wonderful. There are many benefits to visiting these incredible destinations in October, like lower prices, great temperatures, and unique cultural experiences.

Affiliate disclosure: I only recommend tours, services and purchases I know and love on this website.

1. Jamaica

Jamaica, overview photo taken from the Blue Mountains towards Kingston Town. A spectacular view over green hills, with the city and the sea in the distance under light white clouds.
The Blue Mountains in Jamaica are perfect for a visit after the wet season

For those seeking a destination that’s full of life and an energetic, unique vibe, Jamaica is the perfect island to visit.

I traveled around Jamaica for over a month, an island that offers a plethora of activities, from exploring the lush rainforests to soaking up the sun on one of its many beaches.

Jamaica is known for its vibrant culture, particularly its music, art, Rastafari culture, and food. You can easily explore the local culture by visiting one of the many Kingston street markets or attending a reggae concert.

If you’re a foodie, you have to try some of the local delicacies, like the famous jerk chicken or ackee and saltfish.

October coincides with the island’s annual music festival, “Reggae Sumfest.” The week-long festival features some of the best reggae artists from around the world, making it a must-see event for music lovers.

But Jamaica isn’t just about the culture and nightlife. The island is home to some of the most stunning natural landscapes in the Caribbean. Take a hike through the Blue Mountains or visit Dunn’s River Falls for an unforgettable adventure.

If you’re looking for a destination that offers a little bit of everything while being truly unique, Jamaica is a great choice.

Top-rated places to stay in 4 Jamaica destinations:

Top-Rated Tours Jamaica:

Most tours here can also be arranged with pick-up from other destinations.

2. Dominican Republic

Island Isla Saona beach surrounded by palm trees under a blue sky in the Dominican Republic.
Beach life Isla Saona Dominican Republic

The Dominican Republic is a top pick for those seeking a blend of adventure, relaxation, and rich culture.

I spent more than one month traveling around the Dominican Republic, exploring the northern shores, the Blue Mountains, eastern beaches, and the historic Zona Colonial in the capital.

In the DR, you can go trekking through the lush greenery of the Samaná Peninsula up north, go whale watching, visit the historic Zona Colonial in the capital, Santo Domingo, or lounge on the sun-kissed beaches of Punta Cana.

From anywhere, you can enjoy the lush beaches, hotels, resorts, and a multitude of water activities like scuba diving or spectacular snorkeling.

For a unique DR experience, take a dip in the crystal-clear waters of the Hoyo Azul lagoon, nestled in the heart of the jungle!

The island boasts a vibrant music and dance scene, showcased in the lively merengue and bachata rhythms.

Sample the local cuisine, influenced by African, Spanish, and Taíno Indian cultures, and savor dishes such as mangu, a breakfast staple made of mashed plantains.

Top-rated places to stay in the Dominican Republic:

Top-Rated Tours Dominican Republic:

3. Bahamas

Best Caribbean islands to visit in October: A Bahamas beach with cute wooden lounge chairs directly on the sand
The beaches in Nassau are unsurpassed in their tranquil beauty

When considering a vacation in the Caribbean, the Bahamas is often one of the first destinations that come to mind.

And with good reason! Known for its clear turquoise waters, vibrant marine life, and luxurious resorts, the Bahamas is a dream come true for any traveler.

Visiting the Bahamas in October is an excellent choice for those looking to avoid crowds and enjoy a more relaxed atmosphere. Not only are the prices lower during this time, but the weather is perfect for swimming, sunbathing, and water sports.

One must-see attraction is the Exuma Cays Land and Sea Park, a protected area with stunning coral reefs, white sandy beaches, and crystal-clear waters. And naturally, you need to go swimming with the famous pigs.

If you’re interested in history, visit the Pompey Museum of Slavery and Emancipation to learn about the country’s complex past.

Best Caribbean Islands to visit in October

Of course, no trip to the Bahamas is complete without indulging in some fresh seafood. You’ll find plenty of mouthwatering options, from conch fritters to grilled lobster, to satisfy your cravings.

There is no shortage of places to stay on the island in general, whether you prefer simple quarters or want to indulge in a bit of pampering and luxury in some of the best all-inclusive resorts in the Bahamas.

Overall, the Bahamas offers a unique blend of natural beauty, cultural experiences, and relaxation at a lower cost and with fewer crowds in October, making it an ideal destination this time of year.

Top-Rated Places to Stay in Nassau, the Bahamas:

Top-Rated Tours in the Bahamas:

4. Grenada

Carriacou Island in the Grenadas
Carriacou Island in the Grenadas

Grenada, which is also known as the “Spice Isle,” is a hidden gem tucked away in the southern Caribbean.

The island is famous for its spices, including nutmeg, cloves, ginger, and cinnamon, which are grown in the lush forests that cover much of the terrain.

In addition to the aromatic spices, Grenada also boasts breathtaking waterfalls, idyllic beaches, and crystal-clear waters perfect for snorkeling and diving. One epic and unique experience in Grenada is snorkeling at an underwater sculpture park.

Be sure to visit St. George’s, the island’s capital, home to a picturesque harbor and a colorful market. The market is a great place to sample local delicacies and purchase handmade crafts.

The island is relatively untouched by mass tourism, allowing you to experience more of the authentic Caribbean lifestyle and immerse yourself in the warm, vibrant culture of the locals.

Top-rated places to stay in Grenada:

Top-rated tours in Grenada:

5. Antigua (And Barbuda)

St Johns in Antigua & Barbuda
St Johns in Antigua Barbuda

Antigua is another Caribbean gem to add to your bucket list travel itinerary. With a vibrant culture and stunning beaches, this island has so many incredible things to do and see.

If you want to do some island hopping and visit both, the sister island, Barbuda, is only a short ferry ride away. This smaller island is also known for its lively nightlife and thriving music scene. Don’t be surprised if you stumble upon a street party here during your visit.

From historic sites in the island capital, St. Johns, to water activities, spectacular hiking, great dining, and nightlife, you will have fun in Antigua.

One of the island’s main draws is its well-preserved history and architecture, with Nelson’s Dockyard being a prime example. This historic site is a reminder of the island’s colonial past and is now home to shops, restaurants, and museums.

Apart from exploring history in Antigua, there is a wide variety of activities here and on the sister island of Barbuda as well.

And, of course, the beaches are otherworldly, with bright blue waters and soft sands that will leave you feeling refreshed and relaxed.

Top-rated places to stay in Antigua:

Top-rated tours Antigua and Barbuda:

6. Puerto Rico

A lush green El Yunque National Forest in Puerto Rico
The lush green El Yunque National Forest in Puerto Rico

Puerto Rico is a destination that offers a little bit of everything for travelers. The island has everything from a vibrant culture and delicious cuisine to stunning natural scenery.

Being a US overseas territory, Puerto Rico is also a super easy destination for American citizens; you don’t need a passport to travel here.

One of the major draws of this Caribbean island is its historical landmarks. San Juan Old City is a must-visit for history buffs, featuring colorful Spanish colonial architecture and charming streets. It is even protected on the UNESCO World Heritage Site list.

Beyond its rich history, Puerto Rico also boasts some of the most beautiful beaches in the Caribbean; the city beach of the capital, San Juan, is stunning.

Also, Playa Flamenco on the island of Culebra consistently ranks as one of the best beaches in the world, with its soft white sand and crystal clear waters.

The lush El Yunque National Forest is also a must-see for those looking for more adventure.

In addition to natural and historical wonders, the island also offers a vibrant nightlife scene, particularly in the capital city of San Juan. There’s no shortage of entertainment options, from rooftop bars with stunning views to live music venues.

Top-rated Places to Stay Puerto Rico San Juan:

Top-Rated Tours from San Juan Puerto Rico:

7. Trinidad & Tobago

Located just off the coast of South America, Trinidad and Tobago is a unique Caribbean destination often overlooked by travelers.

But those who do venture here are rewarded with a vibrant culture, beautiful beaches, and delicious cuisine.

While Trinidad is known for its lively carnival celebrations, Tobago is a quieter island with more secluded beaches and tranquil forests.

One of the highlights of Trinidad and Tobago is its diverse culinary scene. From savory street food like doubles and roti to fresh seafood dishes like crab and callaloo soup, there’s something new and exciting to try here for every palate.

Check out Kervon Seafood, which has excellent reviews for its seafood cuisine.

And for those looking for a taste of the local nightlife, Trinidad’s capital city of Port of Spain offers a lively scene with plenty of bars and clubs.

But the real draw of Trinidad and Tobago is its natural Caribbean beauty. Explore the lush rainforests of Tobago, where you can spot exotic birds and even go on a guided night hike to see bioluminescent mushrooms (which I had no idea existed).

And for beach lovers, there are plenty of options, including the popular Store Bay and the secluded Pigeon Point!

Top-rated places to stay Trinidad and Tobago:

Top-Rated Tours Trinidad and Tobago:

8. Barbados

Stunning picturesque beach in Barbados surrounded by palm trees on one side, and the beautiful ocean on the other.
Stunning misty beach in Bathsheba Barbados

Located right in the middle of the Lesser Antilles, Barbados is a tiny island that packs a big punch!

Boasting a unique blend of British and West Indian culture, Barbados is an ideal destination for those seeking a taste of the Caribbean with a touch of sophistication.

One of the island’s biggest draws is its stunning beaches. Dozens of stretches of white sand and crystal-clear waters can be found all around the island, making it easy to find a spot to suit your tastes.

If you’re looking for a lively scene, head to the south coast, where you’ll find a variety of bars and restaurants lining the shore.

For a more serene experience, the west coast is dotted with quiet coves and secluded spots.

Apart from its beaches, Barbados has plenty of other attractions to keep you entertained. History buffs will enjoy exploring the island’s colonial past at sites such as St. Nicholas Abbey, a beautifully restored plantation house.

Those seeking adventure can hike through the verdant hills of the interior or go on a thrilling catamaran ride to swim with sea turtles!

Top-rated places to stay in Barbados:

Top-Rated tours in Barbados:

9. Cuba

Narrow old colonial streets in the Old City in Havana Cuba.
Old Havana streets in 2023

Cuba is an island nation that has remained largely unexplored for Americans due to former travel restrictions. It offers a peek into an enigmatic history and culture like no other.

I have traveled regularly to Cuba for five years, and I really want you to see what this mesmerizing and contradictory island has to offer.

Buzzing Havana is a must; you want to stroll around the cobblestone streets of Old Havana, visit the Fusterlandia art installation, go for a classic American car tour, and listen to the beats of live salsa music at one of the many bars, restaurants, or clubs.

Other must-see destinations are the colonial city of Trinidad, the lush green Vinales Valley with Cuban cigars, and the infamous Bay of Pigs, where you can go scuba diving.

If you are fascinated by Cuban history, you should also visit Santa Clara, where one of the most important battles of the revolution took place.

For travelers just looking for Caribbean luxury and pampering, either Varadero (the largest resort area in the Caribbean), or one of the Cuban Keys might be perfect.

Check out Cayo Coco and Cayo Santa Maria along the northern shores of the island.

If you have the time, I also strongly recommend a less traveled destination: visit Santiago de Cuba on the eastern side of the island. Santiago is also known as the “Cuban capital of the carnival,” happening in July every year.

Embrace Cuba’s diverse nature by hiking in the lush green forests of Topes de Collantes or scuba diving in the pristine waters of Jardines de la Reina.

Cuba will leave you spellbound from its rich history to its vibrant present.

Top-rated casa particulares in Cuba:

Remember that Cuba is not like “other destinations,” which amenities and standards will reflect!

However, what is lacking in the luxury department is that the Cubans often give back in service and friendliness.

Also, remember that US citizens in Cuba can not stay in hotels and resorts owned by the Cuban government, according to the Cuba restricted list. There are a lot of privately owned casa particulares for rent, so that is not gonna be a problem!

Top-rated Tours in Cuba:

If you are curious, you can read more about Cuba here.

10. Aruba

Chilling with the famous flamencos in Barbados
Chilling with the famous flamencos in Barbados

As you continue your Caribbean adventure, Aruba is a must-visit destination. With its fine sandy beaches and crystal-clear waters, Aruba boasts some of the best views in the Caribbean.

Spend your days lounging on the beach or snorkeling in the calm waters, but don’t forget to explore the island’s rich history.

Visit the California Lighthouse, a historic landmark that offers stunning panoramic views of the island.

Head to Arikok National Park to hike through Aruba’s natural wonders, including the Hooiberg, a volcanic formation with 360-degree views of the island.

Aruba’s cultural diversity also shines through in its cuisine, with influences from Dutch, Caribbean, and Latin American cultures. Be sure to try some of the island’s local dishes, such as Keshi Yena (stuffed cheese) or Balashi beer.

Top-rated places to stay in Aruba:

Top-rated tours in Aruba:

11. British Virgin Islands

Cane Garden Bay on Tortoga, British Virgin Islands
Cane Garden Bay on Tortoga British Virgin Islands

When you set off from Aruba to explore the Caribbean, an excellent stop is the British Virgin Islands.

This cluster of islands offers something for everyone, from pristine beaches to world-renowned diving and snorkeling sites.

The islands’ natural beauty is still largely untouched by commercialization, making the British Virgin Islands an excellent destination for nature enthusiasts. A great excursion option is paddling in Beef Island Lagoon.

One of the British Virgin Islands highlights is The Baths, a unique rock formation that sits on the beach and creates natural pools and tunnels for exploration.

This is a popular spot for swimming, snorkeling, and diving, and visitors can also enjoy hiking in the surrounding area.

Another must-see destination in the British Virgin Islands is the island of Anegada, famous for its coral reef and pink sand beaches. It’s an excellent spot for fishing and diving, and the island’s locals are known for their hospitality.

If you’re looking for a livelier scene, head to Jost Van Dyke Island, where you can enjoy beach bars, live music, and a vibrant atmosphere.

The island is small enough to explore on foot, making it easy to find a spot that suits your style.

Top-rated places to stay in the British Virgin Islands:

Top-Rated Tours in the British Virgin Islands:

12. Turks & Caicos Islands

A true paradise with pristine beaches and amazing waters, the Turks and Caicos Islands are a true paradise for lovers of the Caribbean Sea and marine life.

Comprising 40 islands and cays, the Turks and Caicos Islands offer a perfect retreat for those looking to escape their busy lives.

One of the most popular activities on these islands is exploring the spectacular coral reefs, home to abundant marine life.

You can go snorkeling or diving and experience the beauty of the underwater world. If you are lucky, you may even catch a glimpse of humpback whales during their migration season.

For those looking for more land-based adventures, Turks and Caicos Islands offer various hiking trails and nature reserves.

You can also explore the island’s rich cultural heritage by visiting the Turks and Caicos National Museum, which gives an insight into the country’s fascinating history.

Top-rated places to stay in the Turks and Caicos Islands:

Top-Rated Tours Turks and Caicos Islands:

13. Grand Cayman

Kissing a stingray in Stingray City, Grand Cayman Island in the Caribbean.

The largest of the Cayman Islands, Grand Cayman is a perfect addition to any Caribbean island-hopping itinerary.

The authentic charm of Grand Cayman lies in its crystal-clear waters, ideal for snorkeling and diving. The island is famous for its shipwrecks, offering a unique opportunity for underwater exploration.

Seven Mile Beach is a must-visit spot if you’re looking for a more serene experience. The powdery shorelines are perfect for sunbathing and relaxing.

For a bit of thrill, you can swim with the gentle stingrays at Stingray City, a unique experience you won’t find anywhere else.

Grand Cayman is also known for its culinary scene, with an array of fine dining options and street food stalls. Don’t forget to try local dishes such as conch fritters and fish tacos.

October is a great time to visit Grand Cayman as the island is less crowded, and the prices are comparatively lower.

You can enjoy all the island’s activities without the hustle and bustle of peak season. So pack your bags and head to Grand Cayman for an unforgettable Caribbean getaway!

Top-rated places to stay on Grand Cayman Island:

Top-Rated tours in Grand Cayman:

Why October Is A Great Month To Visit the Caribbean

Best Caribbean islands to visit in October.

October may not be the most obvious time to visit the Caribbean, but it is actually the perfect month to experience everything this stunning region has to offer.

As October is the last month of the wet (hurricane) season, when the risk of hurricanes is lowering, but the risk of afternoon showers is still there.

The temperatures are warm and pleasant, and the crowds are still thinner, allowing you to enjoy a more secluded and peaceful tropical vacation.

Plus, the prices are often lower than during peak season. At the end of this article, you can read more in-depth about the perks and advantages of visiting the Caribbean region in October.

Perks Of Caribbean October Travel

Visiting the Caribbean in October offers more than just stunning scenery and crystal-clear waters.

Lower Prices and Fewer Crowds

E-bike tour in Grand Cayman island: the bike parked in front of a golden sandy beach.

Traveling during the off-season means reduced prices and fewer crowds. It’s the perfect opportunity to explore the islands without dealing with peak-season crowds, long lines, and sold-out tours.

Lower prices mean that you can experience luxury resorts and enjoy fine dining without breaking the bank. Local vendors also tend to offer special deals during the off-season.

Take advantage of this and try local cuisines, such as the famous conch fritters and fish tacos in Grand Cayman.

Fewer tourists also mean enjoying popular tourist spots with less hustle and bustle. You’ll have more opportunities to soak in the Caribbean’s natural beauty without competing for space.

Whether hiking through lush rainforests in Puerto Rico or lounging on a secluded beach in the Bahamas, you’ll have more flexibility to explore the islands on your own terms.

Not to mention, traveling during the low season means that you’ll be able to snag the best deals on flights and accommodations.

More affordable options allow you to extend your stay and truly immerse yourself in the Caribbean’s culture and activities.

The perks of traveling to the Caribbean in October don’t stop there. In addition to lower prices and fewer crowds, you can also enjoy perfect weather conditions.

Perfect Weather Conditions

October is undoubtedly a perfect month to visit the Caribbean, and the perfect weather conditions are a big part of why.

Temperatures remain pleasantly warm, hovering around the high 80s and low 90s, making it easy to take advantage of the region’s beautiful beaches and outdoor activities.

The humidity drops, and rainfall decreases, so you won’t have to worry about getting caught in the rain or feeling sticky all day.

The Caribbean can be prone to hurricanes during this time of year, but the good news is that the peak of the hurricane season usually ends in September.

By October, the likelihood of a hurricane hitting is significantly reduced. The water is still warm, and snorkelers and divers will appreciate the improved visibility.

The perfect weather conditions in October also set the stage for excellent diving and snorkeling opportunities.

With less rainfall and calmer waters, underwater visibility increases, allowing visitors to see more of the colorful marine life and coral reefs.

In the next section, we’ll explore some of the best spots for snorkeling and diving in the Caribbean during October.

Excellent Diving and Snorkeling Opportunities

Scuba diving in Grand Cayman, here with a turtle!

The excellent news for diving and snorkeling enthusiasts is that October is the best time to explore the Caribbean’s underwater world.

With the hurricane season coming to an end and the water still warm, the calm and clear seas provide the perfect conditions for experiencing the vibrant marine life and coral reefs that the region is famous for.

Less rainfall and calmer waters also mean better visibility, allowing you to witness the underwater world in all its glory.

Whether you’re an experienced diver or a beginner, there are plenty of diving and snorkeling spots throughout the Caribbean that cater to all levels.

From the diving sites of Bonaire to the turquoise waters of the British Virgin Islands, the Caribbean offers something for everyone.

In the next section, we’ll take a closer look at some of the best festivals and celebrations that you can experience during your October visit to the Caribbean.

Experience Local Festivals and Celebrations

The annual carnival in Santiago de Cuba, a truck with dancers in colorful costumes at night.

In addition to the perfect weather conditions, October is also a great time to experience the vibrant local festivals and celebrations found throughout the Caribbean islands.

From the lively and colorful Carnival celebrations in Trinidad and Tobago to the traditional music and dance festivities of the Dominican Republic’s Merengue Festival, there are plenty of opportunities to immerse yourself in the unique culture of each island you visit.

One must-attend event during this season is the Bahamas Junkanoo Festival, where you can witness the colorful and spirited parade of costumed dancers and musicians in the streets.

In Jamaica, the National Heroes Day celebrations, held on the third Monday of October, offer an opportunity to honor and pay tribute to the country’s national heroes with a grand parade and cultural performances.

For food lovers, the Cayman Islands’ annual Restaurant Week offers a chance to sample the island’s best culinary offerings.

And if you’re looking for some spooky fun in the spirit of Halloween, head to the Dominican Republic for their Dia de Los Muertos celebrations, where locals honor their deceased loved ones in a festive and heartwarming way.

With so many unique and lively celebrations to experience, you’re sure to have an unforgettable cultural experience during your October visit to the Caribbean.

But don’t forget to also take some time to explore the beautiful beaches and hiking trails that each island has to offer, which we’ll cover in the next section.,

Explore Beautiful Beaches and Hiking Trails

Hiking in the Blue Mountains in Jamaica on a rainy day surrounded by green forest.

While the Caribbean is synonymous with pristine beaches and crystal-clear waters, many of these islands also boast breathtaking hiking trails with unparalleled views.

In October, the weather is perfect for exploring these natural wonders without the sweltering heat of the summer months.

For example, in St. Lucia, visitors can hike the iconic Gros Piton trail, which offers panoramic views of the surrounding landscape. The trail can be challenging, but the stunning vistas at the top make it all worth it.

Similarly, in Puerto Rico, the El Yunque National Forest boasts several hiking trails ranging in difficulty, including one that leads to a stunning waterfall.

Of course, the beaches are not to be missed either. With the peak tourist season winding down in October, visitors can enjoy the picturesque shores with fewer crowds.

Curacao’s Playa Porto Mari is a hidden gem with crystal waters and vibrant coral reefs, perfect for snorkeling or simply lounging on the beach.

Pink Sand Beach lives up to its name in the Bahamas with stunning pink-hued sand against the backdrop of turquoise waters.

While immersing yourself in local culture and cuisine is a must during any Caribbean trip, don’t forget to take advantage of each island’s natural beauty.

Next, we’ll dive into some of the best local cuisine and cultural experiences that are definitely will delight your taste buds and offer a deeper connection to the vibrant Caribbean culture.,

Savor Local Cuisine And Culture

Traditional Ropa Vieja, pulled pork with rice and vegetables, in Cuba

While the Caribbean is known for its stunning beaches and crystal-clear waters, its diverse cultures and cuisines are equally enticing.

Embarking on a culinary journey through the Caribbean is a must for any foodie, as each island offers its unique flavor palette and traditional dishes.

Jamaica, for instance, is famous for its jerk chicken, a flavorful dish marinated in a blend of spices, including scotch bonnet peppers, thyme, and allspice.

The island’s street food scene also boasts a variety of tasty options, including patties, a savory pastry filled with spiced meat or vegetables. In Puerto Rico, mofongo is a must-try dish made from mashed plantains and typically served with seafood or meat.

While exploring the island’s cuisine, be sure to try the refreshing drink, coquito, a coconut-based cocktail similar to eggnog.

Visitors to the Dominican Republic are in for a treat with dishes like sancocho, a hearty stew made with meat, root vegetables, and plantains.

Meanwhile, Spanish, African, and Caribbean flavors heavily influence Cuba’s cuisine, resulting in dishes like ropa vieja, a shredded beef stew, and Moros y Cristianos, rice, and beans cooked together.

Beyond the food, immersing yourself in local cultural experiences is vital to any Caribbean trip.

From attending a carnival in Trinidad and Tobago to exploring the colonial architecture of San Juan, Puerto Rico, the region’s cultural offerings are as diverse as its people.

Savoring the local cuisine and culture of the Caribbean offers a chance to connect with the region’s history and traditions while indulging in its vibrant flavors and experiences.

As October offers a quieter tourist season, it’s the perfect time to explore the islands and immerse yourself in everything they have to offer.

Wrap-Up Best Caribbean Islands To Visit In October

In conclusion, October is the month to visit the Caribbean, regardless of your traveler category. Lower prices, fewer crowds, perfect weather, and cultural celebrations make it an ideal time for a dream vacation.

From stunning beaches to unique cuisine to excellent diving opportunities, the 13 islands on this list really should have something for everyone as the winter months come closer!

As the famous quote goes, “The world is a book, and those who do not travel read only one page.”

Don’t let yourself be limited to one page – explore the beauty and diversity of the Caribbean islands this coming October.

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