Tokyo is more than the world’s largest city, it’s a kaleidoscope of 23 unique wards, each with its own character, history, and charm. From the nostalgic streets of Yanaka to the bustling energy of Shinjuku, the city feels like a collection of mini-worlds. A long weekend here is just enough to scratch the surface, leaving you eager for more.
The best time to visit Tokyo is between September and June, when the weather is mild and inviting. Summers can be overwhelmingly hot and humid, while June brings the rainy season. Getting around Tokyo is effortless thanks to its world-renowned train system, which is both efficient and easy to navigate.
Upon landing, make sure to grab a Welcome Suica card at the JR East train station in the airport. This preloaded transport card eliminates the hassle of buying individual tickets and is valid for trains, buses, and even some convenience stores.
Friday
Start your Tokyo adventure bright and early with breakfast at a kissaten or a retro Japanese café. These establishments serve a traditional “Morning Set,” typically featuring thick, fluffy toast, a boiled or scrambled egg, and a drink. Cafe Tomorrow in Asakusa is a hidden gem, offering both classic Western-style options and Japanese favorites like rice balls with grilled fish.
The nostalgic atmosphere of a kissaten sets the tone for a day of exploration.
From Cafe Tomorrow, take a short walk to Sensō-ji, Tokyo’s oldest and most famous Buddhist temple. As you approach through Nakamise Street, a historic shopping street lined with vendors selling traditional snacks and souvenirs, you’ll spot the iconic red Kaminari-mon gate.
Sensō-ji’s grandeur is undeniable, and its rich history provides a fascinating glimpse into Tokyo’s past. Don’t forget to purify your hands at the Omizuya water station before entering the main hall.
After soaking in the tranquility of Sensō-ji, head toward Kappabashi, also known as “Kitchen Town.” This street is a treasure trove of kitchenware, from beautifully crafted Japanese knives to quirky plastic food models. Strolling along the Sumida River en route to Kappabashi also offers breathtaking views of Tokyo Skytree, a modern icon of the city.
For dinner, head to Shinjuku and discover Kakekomi Gyoza, a bustling izakaya known for its delectable dumplings. This lively eatery serves up a variety of dishes, from sashimi to comforting bowls of oden. What makes it even more special is its philanthropic mission to support local nonprofits.
If Kakekomi Gyoza is full, nearby alternatives like Dengana’s kushikatsu skewers or the eclectic Ningen Restaurant offer equally satisfying options. End your night exploring Shinjuku’s Golden Gai, a maze of tiny bars, each with its own unique character. The buzzing nightlife here is quintessential Tokyo, offering a mix of energy, intimacy, and charm.
Saturday
After a late night, start your morning at a convenience store. Japanese konbini are legendary, offering everything from freshly made rice balls to unique energy drinks like Ukon no Chikara (Ginger Power) for a quick pick-me-up.
Spend your afternoon immersed in the futuristic world of teamLab, Tokyo’s renowned digital art collective. Whether you choose teamLab Borderless in Roppongi or Planets in Odaiba, prepare to be mesmerized. Borderless is an Instagrammer’s dream, with endless mirrored rooms and cascading lights, while Planets offers a tactile experience, including wading through water surrounded by projected marine life.
These immersive exhibits blur the line between art and technology, making them a must-see. Be sure to book tickets in advance, as same-day reservations are rarely available.
For dinner, indulge in the cinematic setting of Gonpachi in Roppongi, famously featured in Kill Bill. The dramatic interior is matched by its excellent menu, which includes sushi, tempura, and vegan-friendly options. As you dine, you’ll feel like a character in a classic Tarantino scene.
If you’re up for more adventure, head to Shimo-Kitazawa, a bohemian district brimming with live music bars and intimate venues.
Sunday
On your final day, embrace Tokyo’s more laid-back side. Begin with coffee at Beasty or Rostro in Tomigaya, where the third-wave coffee scene thrives. Matcha lattes and espresso tonics provide the perfect start to a leisurely morning.
Next, take a picnic to Yoyogi Park, one of Tokyo’s largest green spaces. On Sundays, you might catch rockabilly dancers strutting their stuff near the Meiji Shrine entrance or stumble upon a local festival at the outdoor stage. The park’s relaxed vibe offers a welcome respite from the city’s intensity.
Spend your afternoon in Omote-sandō, a boulevard lined with stunning modern architecture housing luxury boutiques and flagship stores. From Prada’s crystalline façade to the intricate curves of Tod’s building, the street feels like a free art exhibit. For a quieter experience, visit the Taro Okamoto Memorial Museum, a former studio turned gallery showcasing the avant-garde works of this celebrated artist.
End your weekend in Shibuya’s PARCO, a multi-story cultural hub featuring everything from fashion boutiques to themed restaurants. For dinner, adventurous eaters can try Rice and Circus, an izakaya that serves unusual delicacies, or stick to comfort food like vegan ramen at Jikasei Mensho.
Wrap up your night at a music bar like JBS (Jazz, Blues, and Soul) or Bloody Angle, where you can reflect on your unforgettable weekend in this extraordinary city.
Tokyo is a city of endless surprises, blending modernity and tradition in a way few places can. Even after years of living here, I find something new every day. For a long weekend, this itinerary offers a taste of the city’s vibrant culture, rich history, and boundless creativity—enough to leave you dreaming of your next visit.
Photo by SeanPavone
