Nitemare

No. $988 is NOT "down the middle" price for Boston at any time, other than maybe a last minute booking on Marathon Monday

The airport is across the harbor from the cruise terminal and from most of Boston. There isn't really anything "near" the airport to hang out that is going to be particularly easier to get to the airport from than elsewhere in Boston, so I'd pick a place in town, like Copley Square, as suggested, or near Fanueil Hall or along the waterfront, depending on the weather. If you want to stay close to the Cruise terminal and only "transfer" once, you could probably walk to the Institute of Contemporary Art along the waterfront, which has tons of seating and great people watching, plus options for a quick meal.

They've been discussing pre-clearance there for at least 6-7 years. FWIW, clearing Customs in Boston isn't hard if you are arriving in off hours. We landed mid day from Toronto on Porter and were landside in under 20 minutes, without Global Entry

We went to Westmann via ferry on our last land trip to Iceland, we were staying overnight and had a reservation on the 10AM ferry back to the mainland. Due to high winds we didn't get off the island until 5PM, and they somehow squoze all (most?) of the cars planning to return onto that 1 ship. Literally door handle to door handle.

Chickadee is excellent, and is basically next door. Yankee Lobster for a sort of "shack" experience My Diner is our favorite diner in Boston, the Galley Diner is good, too. Both great b'fast options Row 34 is our favorite seafood restaurant in Boston, we think it's better than Legals and more affordable 75 Liberty is good Bar Volpe is excellent

We've been to Jokulsarlon on 4 separate days. Some cloudy, some sunny. Never seen it foggy, always been able to see from the ocean to the glacier. We love it! The price you quoted seems very high but it is likely your cruiseline has booked up all the local operators, but it might be worth seeing if you can do this independently for much less $

Lots of great alternatives for breakfast near the Aloft, which is also much closer to traditional Boston Siteseeing locations.

It also matters what is included in each tour. There are lots of options on a South Coast tour, fewer on a GC visit

We've done both multiple times, once with a guide, once on our own. Both are magnificent and you'll be happy with either one assuming you like incredible natural sights

10PM on a weekend is PEAK time for Ubers. Fares will be high, and drivers who don't want to deal with drunks won't be working

If you do walk it, and we've done that walk many times, aim for the water and take the HarborWalk. It's not always well marked but it's much prettier to go via the ICA (Institute of Contemporary Art) and past the piers and behind the Courthouse and walk along the harbor than taking one of the main streets, which would be slightly quicker

taxi makes sense with 3 or more people. Otherwise "Flybus" is what most folks take. Yes, you do need to reserve going from city to airport, and yes, you will have to make a change at the central bus station.

Rome2Rio is ok to get a general idea of options but ALWAYS double check to see if they still work. I have yet to review a R2R suggestion without seeing something that hasn't been in place since Covid or whatever. I find Google Maps is more uptoday on bus lines and air options and ferry choices than R2R is, but their lists also need to be double checked for accuracy

Taxi should be on a meter from the airport or to the airport or anywhere else in Boston. When you ask for a quote you are putting yourself at risk for the driver making something up.

Unless there was dreadful traffic, and that can happen, I agree. Way out of line

The site is "famous" because Justin Bieber filmed a video there. It has been thoroughly scavanged, so honestly, unless you are a Bieber fan or a military jet fan (so technically, not a DC3), I don't think it's worth the lengthy hike out and back instead of doing a glacier walk or snowmobiling or ice cave visit. And if it's raining . . . Have you looked into the Into the Volcano excursion? Of all the things we've done with 31 nights in Iceland, it is by far the most memorable and unique

No one has reported that on this forum that I have seen

Cancellations due to weather are always possible in Iceland. My concern with third parties is if there are delays or changes, how much harder might it be to communicate from the provider to the traveler (or the other way around) if time is of the essence? We like knowing we can email the provider directly at the last minute to let them know we hit a closed road and are going to be 15 minutes late and expect there is a better chance they will get that message than if we have to go thru a third party.

September is wicked expensive in the Boston area. Coming from the south, I expect they will arrive via the Mass Turnpike, it is almost always faster than I-95. Since they aren't picking you up first thing in the morning, I'd look for lodging between Hartford, CT and Sturbridge Mass to get the best combo of rates and convenience

Sure, it will work out. A hotel nearer the tourist areas might be more convenient for this purpose and won't take much longer getting to the dock on monday. I'd ask your hotel if you can leave bags with them for a few hours upon your return. I doubt they'd say no. Most places will hold bags for a small tip ($5/bag or so).

It's too early to see prices for next year, but we can come up with some ideas. Take a look at a map to see what you want to be near. I don't think you want to be near the airport since you have 24 hours or so to see the city, and the HOHO doesn't go to the airport. The cruise port is on another edge of the city, the Seaport District. There are a few hotels near the port, but again, that's not near the touristy areas of the city. If you could take 10 minutes to figure out what YOU want to see in Boston, and come up with a few neighborhoods, we can help suggest nearby properties that might work. $300 shouldn't be hard, $200 probably won't work that time of year.

Budget? Any thoughts of what you'd like to be near and see? One bed or two?

It is recommended to arrive at KEF Airport 3 hours prior to international flights. I have had it take close to 2 hours to get checked in and start walking to the gates (which are a long walk) so I would not suggest getting picked up in the city just 3 hours prior to flight time

Always wear waterPROOF outer layers in Iceland, and expect wind and rain. Leave the umbrella behind, they don't work there Last time we were in Isafjordur, there was a tour office near the dock that the tenders use that I would have thought you could have taken shelter in. And there are nice shops in town, which is about a 10 minute walk away.

I used to work down the block from there and it seemed to be fun for the kids, maybe up to 12 or so? But perhaps less so for adults. There are some good exhibits about the history around the Tea Party Patriots, but the reenactment of throwing the boxes into the water is the Big Deal which gets the kids smiling