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Konnichiwa, fellow digital nomads! Ready for an unforgettable Hokkaido adventure? As your tech-savvy, globe-trotting guide, I've crafted this itinerary for four business-minded travelers seeking a blend of productivity and autumnal bliss in Japan's northern island. Prepare for crisp air, stunning landscapes, and cultural immersion unlike any other!

Hokkaido in autumn boasts mild winter temperatures, making it perfect for exploring. Expect average highs around 10-15°C (50-59°F) and crisp, clear skies. Pack layers – it can get chilly, especially in the evenings. The changing leaves paint the landscape in fiery hues of red, orange, and gold, creating picture-perfect backdrops for your Instagram stories (and those all-important business calls).

Our journey begins in Sapporo, Hokkaido’s capital city. The architecture blends modern designs with influences from Japan's Meiji era – a fascinating mix. We'll explore Odori Park, a green oasis in the city center, and sample local delicacies like Jingisukan (grilled mutton), a Hokkaido specialty. Dinner at a traditional Izakaya (Japanese pub) will be around ¥4,000-¥6,000 per person. Transportation within the city using public transport will average ¥500-¥1000 per day per person.

Next, we'll journey to Hakodate, known for its stunning views from Mount Hakodate. Consider a ropeway ride up the mountain (around ¥1,200 per person) for breathtaking panoramic views at sunset. Don't miss the fresh seafood; Hakodate is famous for its squid! A delicious seafood dinner will set you back around ¥5,000-¥7,000 per person. Travel to Hakodate by express train costs approximately ¥5,000 - ¥8,000 per person.

Throughout our travels, we’ll experience the warm hospitality of the Hokkaido people. While reserved initially, they're incredibly friendly and helpful once you break the ice. You'll notice a blend of traditional and modern sensibilities in their lifestyles. The subtle sounds of traditional Japanese music might drift from temples, contrasting with the modern buzz of city life. Keep an eye out for Shiba Inus – they're popular pets here! And don’t forget the stunning landscape - the rolling hills covered with birch trees are truly something to behold.

We'll also delve into some local traditions, like attending a traditional tea ceremony (around ¥2,000 per person) or visiting a local shrine or temple. Keep your eyes peeled for festivals during your trip; these vibrant cultural events are a fantastic way to engage with the local community.

Finally, for our business travelers, we’ll ensure ample time for co-working, with access to high-speed internet in all our accommodations and selected cafes. We'll even schedule time for networking events to connect with other entrepreneurs. Remember to bring your business cards!

Estimated total cost per person (excluding flights): ¥30,000 - ¥40,000 (approximately $200 - $270 USD). This is an estimate, and the actual cost may vary depending on your choices and spending habits.

Total estimated cost for the group of four: ¥120,000 - ¥160,000 (approximately $800 - $1080 USD).

So, are you ready to embark on this adventure? Let's explore Hokkaido's autumnal magic together!