Nitemare

Specific dates and budget in USD are much easier to work with than phrases like "won't require a second mortgage"

There will be cabs at the pier. Also places to rent bikes and the nearest beaches are in walking distance. There is also shopping and good food in town and the Gingerbread Houses in Oak Bluffs are worth a visit

Don't go by who they promote, those are just ads, and don't book thru them as they are a third party. Use the Iceland Forum where travelers discuss touring options and book directly with a local provider

It's literally less than a 10 minute walk from the Boston Cruise Port to the waterfront, with lots of attractions like restaurants (Yankee Lobster) or Harpoon Brewery, and 5 minutes more to tons of shops, siteseeing boats, etc. And the Silver Line of the MBTA is RIGHT AT the cruisedock. Less than $3/ride, gets you to Faneuil Hall or the Freedom Trail or Fenway Park, etc.

St Patrick's Parade is mostly locals, not as many tourists or visiting participants as something like the Thanksgiving Parade. I wouldn't expect it to have much affect on hotel prices

It's pretty steep and if the sun is shining, it is surprisingly warm there. Great views from the top (or even halfway up) but I'd only do it if I had alot of tiem on the Island, there is so much esle to see and do there

It was enough years ago that I won't mention them as they may no longer be as good as they once were. If you visit the Iceland forum at Tripadvisor, you will see the same few agencies recommended over and over again

No less reliable than that train ride the day before. What time of year is this planned for?

For warmer temps, take route 1 For more foliage, take route 2

I looked on Google Maps to see if it was the closer one. Did you? Hallgrimskirkja is a major site that is considered to be near the center I'm trying to teach you a bit here about Reykjavik, so you'll know more about what to expect

Tripadvisor has great Iceland content on the message forums there, I'd ask on those boards for specific advice. I wouldn't recommend Viator (or Get your Guide, etc). No need to use 3rd parties for booking tours, especially in places like Iceland where docking and weather can be issues. Refunds are so much harder thru third parties, especially Viator.

I'd stay in whatever Midtown hotel you like best that fits your budget and enjoy Manhattan that afternoon and evening. Take a taxi or Uber to the port the next day for your ship. No need to stay in Brooklyn unless you want to stay in Brooklyn, and there are lots of reasons that might be the case.

I would "call" the Uber once you are thru immigration. The car should be there in 10 minutes or so

There are two cruise docks. You can look on Google Maps to see how far they are from the center. If it is the further dock there are usually taxis, or your cruiseline might provide a shuttle. From the closer dock it's a short walk

We really enjoyed our Golden Circle tour. I agree with Hlitner that self driving is easy in Iceland, but we learned SO MUCH from our tour guide, that we found the price more than worth it. Having a driver (it was a minivan tour, just a few bucks more expensive than a full sized bus) take us around on our first day in Iceland and hearing him talk about the country as a whole and the history involved with the Golden Circle really turned it from a great day to a memorable one, that has led to us returning to Iceland again and again. We self drive now, but we always take at least one tour to learn more and to be able to ask questions and meet more people.

Troll and Arctic Adventures are the companies most recommended over on TripAdvisor

I can't tell you but I hope you do a trip report! I check the SP&M forum at TripAdvisor monthly, hoping for updates, as the places fascinate me, and there are almost never any reports

Rome2Rio is useful to start an inquiry, but there info can be WAAAAY out of date. I was searching for ferry info yesterday and R2R gave me schedules and prices, etc, for a service that was terminated in 2021. So always follow up with the actual provider before you fully rely on them

I would ask on the Princess board here where they have more info about Princess's historical additions. You may find this board to be more helpful for cruises that do landings instead of Sail Bys, like Princess and the other larger ships do

You might want to reach out to a luxury travel agency who has a cruise specialist to get the best fit for you

Any uber driver who accepts your request for a ride will take you to your destination. That is how it works, the 'message' goes out of your need, and whoever is closest who says "Yes" gets the gig. Same thing going back. Plenty of Uber drivers in Manhattan who would like a fare like this

Oops. Misread the wall of text. In my defense, I did suggest an Off Broadway show, too. 😁

LOTS of Broadway shows to consider. You can usually sit in the nosebleeds for under $99 for most shows (not Hamilton), but for good seats expect to pay near $200/seat or more. With other options priced in between. Go to a site like Show Score to read up on your options and see what other folks and professional reviewers have said about the shows. They also have Off Broadway options, which usually are lower cost. There are also many legit Broadway discount sites you can buy tix from (again, not Hamilton). TripAdvisor has a great Broadway discount question on the right side of the NYC forum page

I'd search the Internet and US Customs sites instead of relying on random input from strangers on the internet. It is likely your question here is too vague to answer, anyway, as I expect Polar Bears might be treated differently than seals.

What's your budget per night? How many beds? Exact dates? What do you want to be close to?