This was our first time trying to stuff 4 big things into one winter trip with kids. Supposedly staying in 4 accommodations and halfway added a last one due to New Year Holidays in Japan.
Disneyland, Sanrio Puroland, Mount Fuji, a proper 3 day ski block at Nozawa and Legoland Japan, plus New Year shrine and Nagoya Castle.
We did it as a 14 day self drive route with 4 main bases Tokyo Bay, Kawaguchiko, Iiyama / Nozawa and Nagoya.
If you are a parent planning Japan in winter and want theme parks, snow, road trip and still come home on speaking terms with your kids, this is the structure that worked for us.
Trip Overview at a Glance
Duration: 14 days 13 nights (winter, over New Year)
Route:
- Singapore → Tokyo Haneda → Tokyo Bay (Disney / Sanrio) → Kawaguchiko (Fuji) → Iiyama / Nozawa (Nagano) → Nagoya (Legoland, New Year, castle) → Chubu Airport → Singapore
Style: self drive from Day 2, winter gear, 3 ski days, theme parks, some culture, a lot of sushi and ramen
Kids: early primary school, first time Japan island ski trip
Bases and nights:
- Base 1: Tokyo Bay (Comfort Suites Tokyo Bay) – 2 nights
- Base 2: Kawaguchiko (Kawaguchiko Cottage Ban) – 2 nights
- Base 3: Iiyama / Nozawa (Nagano Airbnb) – 6 nights
- Base 4: Nagoya city + Airport Hotel – 3 nights
The rhythm is simple.
Land and warm up in Tokyo, shift to Fuji for views and outlets, go deep into Nagano for temple, snow monkeys and ski, then slide down to Nagoya for Legoland and New Year before flying out.
Driving and Logistics in Short
From Day 2, this trip runs on a rental car.
- Pick up: near Tokyo Bay after Disney and Sanrio, so you do not deal with car straight after landing.
- Drop off: near Chubu Airport at the end. Because the office only opens at 9 am, we returned the car by 7 pm the night before and used an airport hotel shuttle next morning.
- Roads: mix of expressways, mountain roads around Fuji, and real snow and ice around Iiyama and Nozawa
Key lessons.
- Use TA-Q-BIN to ship the ski bag ahead and later back to airport, do not drag it across Tokyo and Nagoya with kids.
- Read parking fine print properly. That “max 1,000 yen” at Sanrio was members only. Our school fee was over 5,000 yen.
- In a storm, Nozawa carparks and village roads can eat your car. Sometimes better to park further and pay for buggy / shuttle than insist on “nearest” option.
If winter driving is new to you, pack in buffer time and do not stack fixed bookings on your ski days. Things will go sideways at least once.
Base 1: Tokyo Bay – Disneyland and Sanrio
Where we stayed: Comfort Suites Tokyo Bay (Urayasu)
Nights: 2
Days covered: Day 0, 1 and part of Day 2
We landed at Haneda at night with two kids and one ski bag. Before the trip, we booked an airport transfer with a 45 minute included waiting time and did one small hack. We used the arrival time of the next flight, one hour later, so the 45 minute timer started later on paper. That gave us enough time for immigration, luggage and TA-Q-BIN ski bag drop without sprinting.
Comfort Suites Tokyo Bay was our Disney base. Big room, kid friendly breakfast, free shuttle to the park. After a late arrival and midnight instant noodles from the convenience store downstairs, we knew there was no way everyone would wake up for rope drop. So we did what many Singapore parents hate to do we let go of “must maximise ticket” and reached Tokyo Disneyland around 11 am.
Day 0 – Arrival
- Flight Singapore → Tokyo Haneda (night flight)
- TA-Q-BIN ski bag drop at Haneda
- Convenience store run for drinks and instant noodles
Day 1 – Tokyo Disneyland
- Shuttle bus to Tokyo Disneyland
- Disneyland
- Shuttle bus back to hotel
Day 2 – Sanrio + Car + Drive Out
- Hotel check out
- Rental Car collection and paperwork
- Drive to Sanrio Puroland
- Sanrio Puroland activities.
- Drive from Sanrio to Kawaguchiko Cottage Ban
- Check in
- Ramen dinner near cottage
Base 2: Kawaguchiko – Mount Fuji and Gotemba
Where we stayed: Kawaguchiko Cottage Ban
Nights: 2
Days covered: balance of Day 2, Day 3 and Day 4
From Sanrio, we drove about 90 minutes to Kawaguchiko. Reception at Cottage Ban closes at 9 pm, so we aimed to reach before that, dropped our bags and immediately went out again for ramen before the shop’s last order. The cottage became our Fuji base, with kids happily eating instant ramen, cereal and bread at the same table like it was a hotel buffet.
We tried to drive up to Fuji 4th Station. Paid 2,800 yen for the toll road, only to find low clouds and very average views at the top. On a clear day, that fee might feel justified. On our day, it felt like paying for fog. Instead of forcing another paid viewpoint, we joined the crowd at the famous Lawson with Fuji backdrop. Snap all the classic shots with the semi visible mountain, then move on.
Day 3 – Mount Fuji and Outlets
- Drive to Mount Fuji 4th Station
- Short walk and viewing area at 4th Station
- Drive to Lawson Fuji viewpoint (photo stop)
- Sushi lunch
- Drive to Gotemba Premium Outlets
- Ramen dinner near Kawaguchiko
Day 4 – Bluebird Fuji, Lake Stop, Matsumoto, Iiyama
- Check out from cottage
- Lake stop at Kawaguchiko area for Fuji photos
- Drive towards Matsumoto
- Visit Matsumoto Castle (castle grounds and interior)
- 2nd Street thrift shop stop
- McDonalds dinner
- Aeon supermarket run (snacks, groceries)
- Drive to Iiyama
- Check in to Iiyama Airbnb
Base 3: Iiyama / Nozawa – Nagano, Snow Monkeys and 3 Day Ski
Where we stayed: Iiyama Airbnb (ex restaurant with huge kitchen)
Nights: 6
Days covered: Day 5 to Day 10
This base is the heart of the winter part. Big industrial kitchen, huge dining table, lots of space for gear explosion. It anchored our Nagano city day, Snow Monkey Park day, 3 Nozawa ski days and one nua reset day.
Day 5 – Nagano City and Gear
- Drive to Nagano city
- Visit Zenkoji Temple
- Xebio sports shop (ski gear)
- 2nd Street (secondhand winter items)
- Yakiniku King dinner
- Drive back to Iiyama
Day 6 – Snow Monkey Park
- Drive to Snow Monkey Park
- Drive to Aeon Town for Late Lunch
- Lunch at food court (McDonalds, KFC, ramen)
- Grocery shopping (wagyu, pork, vegetables)
- Drive back to Iiyama
- Home cooked dinner in Airbnb kitchen
Day 7,8,9 – Nozawa Ski Day 1,2,3
- Nozawa Ski Day 1,2,3
Day 10 – Nua Day and Aeon
- Sushi lunch
- Visit S Cube (helmet with visor)
- Aeon Nagano mall
- Simple food court dinner
- Pack up Iiyama base
Day 11 – Narai-juku and Transfer to Nagoya
- Check out of Iiyama
- Drive to Narai-juku
- Walk along old post town street
- Charcoal yakiniku lunch in Kiso area
- Drive to Nagoya
- Check in to Nagoya apartment
Base 4: Nagoya – Legoland, New Year Shrine and Nagoya Castle
Where we stayed: Nagoya city apartment + Last Night at Airport Hotel
Nights: 3
Days covered: end of Day 11, Day 12, 13 and 14
We used Nagoya as our final base. The main reasons. Legoland Japan, New Year experience and a gentler last few days before flying out.
Day 12 – Legoland Japan
- Drive to Legoland
- Full day in Legoland.
- New Year’s Eve fireworks and countdown (around 6 pm)
- Dinner nearby (sushi)
- Drive back to Nagoya apartment
Day 13 – New Year’s Day Shrine
- Visit Atsuta shrine (hatsumode)
- Buy hamaya arrow
- Explore shrine grounds and food stalls
- Return to apartment, rest and pack
Day 14 – Nagoya Castle
- Return Rental Car
- Visit Nagoya Castle (grounds and interior)
- Return to apartment, final packing
How to Use This 4 Base Itinerary
You can treat this pillar as an overview plus menu.
- Copy the full 14 days if your kids are similar age and you want to do “Tokyo + Fuji + Nagano ski + Nagoya / Legoland” in one shot.
- Pick only some bases. For example.
- Bases 1 and 2 for Tokyo + Fuji in winter without ski.
- Bases 3 and 4 if you want Nagano + Legoland / Nagoya only.
- Adjust night counts. Add an extra night in Iiyama if you want a 4 day ski block, or drop one theme park if your kids are queue allergic.