Yokohama to Tokyo to Haneda Aiport

We will be arriving in Yokohama cruise terminal and be off the ship and ready for pick up around 8:30am.
We have a flight to catch at Haneda Airport on the same day so we need to be at the Airport by 3:30pm. What sites should we not miss? We are assuming we will have to hire a car since we will have our luggage with us.

We want to see as much as we can

Thanks

I think you have two options:

1. Hire a car at the port of Yokohama and explore Yokohama (or maybe Kamakura). Then Taxi or bus to Haneda Airport.

2. Take taxi to Haneda Airport. Check in your luggage. You can take taxi from there but you can also use public transportation. Basically Tokyo was destroyed during the WWII so there seems to be not so many historical buildings. For me, Tokyo tower and Yurikamome are the must see in Tokyo which are easily accessible by public transportation.

I believe renting and driving a car would be an unnecessary hassle when the public transport in both cities is so convenient, frequent and cheap. As for the luggage, all major train and metro stations have luggage storage facilities or coin lockers, so you can temporarily leave your stuff there.

Oh, I meant to say hire a taxi, not renting a car. I (am a Japanese living in rural area in Japan) don't want drive in the big cities.

it will be convenient for you to hire one taxi for 7 hours, because your time in Japan is limited.
I think some taxi companies have English-speaking drivers.

I don't think you can "check in" luggage at an airport way beyond your departure time, but you can certainly have it kept inside coin lockers and over-the-counter lockers.

Perhaps you can hire a car to see Yokohama with your luggage. A lot of taxis can do random tours for a fee, or your cruise may have more information on other options such as tour buses.

Then you can head straight to Haneda Airport using either the same car, a Limousine Bus or the Keikyu train. All three go directly to the airport without you having to transfer in the middle (except that some Keikyu trains go the other way, so make sure you board the correct one).

Haneda is located in central Tokyo toward Yokohama. So, once you have your luggage kept at Haneda, you can take trains to see the city. Tokyo is not car-friendly, so it's better to use trains.

If you intend to fly domestic from Haneda, another option about your luggage is to send it directly from your port in Yokohama to your next accommodation.

As for sites to see, there are too many. So, you need to narrow it down depending on your preferences. Below are just for reference:

https://www.yokohamajapan.com/
https://www.gotokyo.org/en/index.html

By the way, the percentages of undestroyed old buildings are about the same in Yokohama and Tokyo (and Yokohama was as bombed as Tokyo was). It's just that Yokohama Bay tends to promote old brick buildings for weird some reason. In any case, both cities offer old brick buildings and old wooden houses as long as you go to the right places.

I hope it helps.

You can store (then collect) your luggage
and catch a bus for HND in YCAT,
which is near Yokohama Station (JR) East Exit.
(Check in advance the timetable for airport buses.)

Yokohama �gAkai Kutsu�h sightseeing buses
start from Sakuragichō Station,
and run not via Yokohama Station.

We will be arriving in Yokohama cruise terminal and be off the ship and ready for pick up around 8:30am.
We have a flight to catch at Haneda Airport on the same day so we need to be at the Airport by 3:30pm.

Akai Kutsu loop bus service begins with the first bus departing
at 10:02 from Sakuragichō Station.

I suppose you can visit the baggage storage counter in YCAT
then get to Sakuragichō Station before noon.

The mentioned Akai Kutsu (or Red Shoes) buses make stops at places like Osanbashi Terminal and Hammerhead which would be convenient if your cruise is arriving to either of these ports.

They're cute affordable buses that don't really provide sightseeing guidance per se but is more like a bus for both residents and visitors.
https://www.yokohamajapan.com/information/getting-around-yokohama/akai...

These kind of buses are increasingly common in cities throughout Japan. One of the oldest ones in Tokyo is the extensive Megurin Bus that would even go into narrow grocery streets.
https://www.city.taito.lg.jp/kenchiku/kotsu/megurin/index.html