Zacharius

Always insure a higher dollar trip, and always insure it with a third party. Those are my rules. And don't forget travel medical insurance.

I think the flight attendant gave bad info. For example, American Airlines has a 40 minute MCT for DOM-DOM flights at DFW, but I think it might be as low as 25 minutes DOM-DOM at AUS.

Couple things: 1. Pricing fluctuates from day one, not just at six months. 2. Air2Sea just sticks to minimum connection times (MCTs), which are a bit different for each airline and airport. But these are the minimum connection times an airline will let you book. That being said, they're not always ideal. A 1-hour connection DOM-INTL in whatever airport Roselo is going through may be perfectly "legal" (as is common phrasing with MCTs), but may not be enjoyable (or even realistic sometimes). I'll do whatever I can to avoid a MCT, especially on a DOM-INTL or INTL-DOM connection.

That's all great, but have you ever had an 8x8 animal style?!?!

I would include Southwest on this. They are, I believe, the third largest in the US, and while they don't have a hub/spoke system, they do have plenty of flights out of most of their airports that they do have a pretty good chance of re-routing you if nothing else. I'm not the biggest Southwest fine, but they've always done a good job of accommodating me on other flights (even if it's through a different connection point) when needed.

Damn, as someone who books trips a few weeks out, I can't wrap my head around June being "last minute" haha

One other thing to think about (and, again, I am 100% Team "One Day Ahead" on flying) - if you're flying domestically in the US, for example, try to avoid airlines that only have one flight per day (or less). Airlines like Frontier, Spirit, Allegiant, and Avelo often fly a route only once a day, or maybe even once/twice a week. If something happens, you're really in big trouble. Sure, they're going to try to find another plane, but even that can be tricky on those carriers. And their ability to re-route you is much smaller, or even non-existent. My vote in these cases is to always stick to the big guns - United, Delta, American, Southwest...airlines with multiple flights per day (usually), more capabilities to re-route, and bigger fleets with a better ability to sub aircraft in/out when needed. I would put Easyjet somewhere in between. I have had really good experiences with them, and am a big fan, but irregular operations do sometimes put them in a tougher situation than an airline like BA.

In-N-Out is definitely overrated, but it's worth checking out if you've never been. Takes a few visits to figure out the right order, though! (Proven Fact* - best order is a double double, protein style, mustard grilled, which grilled onions and chopped chilies, fries light well). * - proven by me, for me

That's a bit unfair. I practically live on planes, both domestic and international, and most flights are on time (at least, in the developed world) and the statistics are there to back it up. I would never, ever fly in the day of a cruise, but to say you "usually" won't arrive on time is a bit of a stretch. You usually will...but the implications if you don't can be huge.

From my understanding, that's the case. I'm not really a "dress up" kind of guy so I don't know if I would, but I would love to see people dressed up as:

I'm a Star Trek geek and this is definitely on my bucket list. I just forget about it every year, including this one. My wife has already told me "go for it, loser"...maybe one of these days.

In my opinion, not worth it in your case. I don't see you getting to Jersey City before 5:45ish if your flight is on time (picking up luggage, waiting for a ride, getting the ride in traffic). Yes it opens up food/drink options, but grabbing a room at Newark Airport that has a restaurant would probably be the way I would go. Maybe even just the Marriott right at EWR Airport.

Good call...I always forget about Jersey City but it's a great area.

You might wish you had just spent the money when you try to get from LGA to Cape Liberty! I only slightly kid, but it can be a bit of a pain. Are you against staying in the city, either Brooklyn or Manhattan? That's one option of a mid-way point if you're up for it, and offers the fun/excitement and meal options that the city has to offer.

American pepperoni should be blasphemous to Americans. Nothing ruins a perfectly good pizza like a quart of grease and oil per slice.

Honestly this sounds like the perfect Naples stop to me...I would definitely recommend this combo.

You will encounter very few people who aren't at least conversational, if not fully fluent, in English. There are plenty of people in Quebec who do only speak French, but you're unlikely to encounter many or any in your relatively short visit to the two largest cities in the province. If you make stops in between the two, it's possible but it won't be a big deal. Road signs will all be in French, but they'll be pretty self-explanatory (for example, the stop sign won't say "Stop", but you'll know it's a stop sign).

Meh, my French is not great but it's really not hard to just brush up on the (fairly minimal) differences in Montreal and/or Quebec driving laws. I wouldn't say that alone is a reason to not drive.

If you don't absolutely need to leave the same day you arrive, do also consider spending a night in Montreal. It's always a good time and would cut back on the stress of needing to "rush" to YUL for your flight.

I have a lot of experience in some of these locations, but not on a cruise. Here's my thoughts: Sydney - if it's your first time there, don't do an excursion. Just walk around, hit the highlights (Opera House, Harbour Bridge, Botanic Garden, The Rocks, food and drink). Picton - if you're in to wine, find a half-day wine tour in the nearby Marlborough region. Lots of good wineries there. You may not have enough time, but the Mail Boat tours in Picton are fantastic (https://www.beachcombercruises.co.nz/scenic-cruises/mailboat-cruises/Mail-Boat-Cruise/). Wellington - you mention something already, but Wellington is another one of those "just walk around" places. Botanic Garden, Mount Victoria Lookout, Cable Car, Parliament, Te Papa Museum, Cuba Street, food and drink.

Renting a car may work best. As far as YQB airport - United flies year-round from Newark; American flies seasonally from Chicago and Philly. Not sure where you live, but you can also get via Toronto or Montreal on Air Canada.

Driving is about three hours. You can google "Montreal car service" and there are plenty of options to take you even as far as Quebec (or, in this case, a pickup in Quebec), but since it is a three hour drive, expect it to me...expensive. No idea what exactly, but I imagine several hundred dollars each way. There is a bus that can get you from Quebec city center to Montreal airport with a change of bus in Montreal city center. Much cheaper, but of course it's a bus so...not as comfortable. I have no experience with it personally. Also no personal experience with the train between those two cities. I think this is a case where you need to analyze which is more important - loyalty to Delta, or ease of flying out of Quebec. No right or wrong answer, but only you can determine. I have a massive loyalty to American Airlines/OneWorld, but there are some times where I just need to suck it up and fly someone else once in a while for ease.

Train schedules are pretty easily available either through the Trenitalia website, or through Google Maps where you can type in your origin and destination and it'll give you a good list of transit options with times/connections.

Smokeybandit is spot on - Israel is not the place to try and cut it short, because security can be fast or it can be painstakingly slow. And even "fast" isn't the same as Heathrow or JFK or somewhere else's "fast".

That is a good point. There are countries that are very much "have you passport with you at all times, by law" kinds of places. Definitely good to know which ones those are and follow the laws as needed.