While in our opinion, anytime is a perfect time to visit Kona, many would argue that the best time to visit the Big Island of Hawaii is December to March. But… if you are looking for a more affordable trip, the best time to visit the Big Island is definitely from September to November. With fewer visitors on the island during the autumn months, you are likely to see a pretty major drop in prices. In addition to fewer visitors and better prices, the weather is much cooler and  and there is no shortage of things to see and do this time of year. Here are a few events that you will not want to miss when visiting the Big Island this fall….

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Kokua Kailua Monthly Stroll

The Kokua Kailua Montly Stroll, is popular local event that takes place along Alii Drive one Sunday each month during the fall months. Kona’s Historic Kailua Village closes to street traffic and becomes a festive, pedestrian-only outdoor market that makes for a fun family-friendly day. Stretching from the Kailua Pier all the way through the Historic Village of Kailua this event showcases close to 100 vendors including local artisans, musicians, and merchants offering a fantastic array of shopping and dining options.

This event takes place from:

September – December 

Street Eats, A Kailua Village Food Truck Festival

Join us on a true culinary adventure at the Street Eats Food Truck Festival in Historic Kailua Village this fall. Discover a wide variety of delicious local cuisine from food trucks and vendors from all around the Big Island. Alii Drive closes to street traffic as food trucks line up in Historic Kailua Village offering the island’s best food trucks and food vendors of all kinds.

This event takes place from:

October – December 

The VinFast Ironman World Championship

13th Annual Hawaii Food & Wine Festival

The Hawaii Food & Wine Festival is the premier culinary destination event in the Pacific. This three-weekend culinary experience spans three islands each fall, the Hawaii Food & Wine Festival (HFWF) is the largest food festival in Hawaii. Co-founded by two of Hawaii’s own James Beard Award-winning chefs—Roy Yamaguchi and Alan Wong—the Festival showcases Hawaii’s rich agricultural diversity and homegrown culinary talent through world-class culinary experiences.

Each year, more than 150 internationally renowned master chefs, culinary personalities, sommeliers, mixologists, and wine and spirit producers are invited to participate in roughly 20 events, from grand tastings and wine dinners to kids cooking classes, wine seminars and more. Unlike other food festivals across the country, HFWF challenges participating chefs to use at least one locally grown, raised or caught ingredient in their dish, connecting Hawaii’s farmers, ranchers and fishermen to thousands of attendees each year.

This event takes place from:

The Big Island

October 20-21, 2023

November 03, 2023 – November 12, 2023

Visiting Hawaii during autumn months allows you to take in the island’s natural beauty and participate in tourist activities and an excellent selection of local festivals & events at more reasonable rates.

Find the perfect accommodation now by visiting us at Casago Kona. Our rental properties are located on the beautiful Kona coast of Hawaii on the Big Island. We proudly manage 1 – 4 bedroom properties with a great range of options for all your personal and budget needs. Our team of experts will help you find your perfect Vacation Rental and make your dream vacation a reality! 

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🌺 Website: www.CasagoKona.com 🌺
📩 Email: reservations@casagokona.com 📞 Call: 1-808-466-1878
Casago Kona
75-5870 Kahakai Rd Kailua Kona, HI 96740
license # #23869