With most cruises leaving roughly 4/5pm would you recommend catching an early flight into the departure city or play it safe and get a hotel the night prior?

Anytime I absolutely, positively, need to be somewhere by a specific time, I always plan to arrive the day before. I have never been on a cruise, but considering the downside of missing the cruise departure, I think this guideline also applies.

If the cruise departs from a place you've never been to (or would like to visit again), it makes sense to fly in even earlier, enjoy a few days in the departure city, and have absolutely no worries about missing your cruise. At least, that's what I would do!

thank you. very logical answer. I'll do just that. I was trying to cut cost but I have over a year to pay for it so I'll be fine.

Flying in a day before usually gives you more choices of flights, more leeway to find deals, etc. If you fly in day of, then you are limited to flights that arrive before a specific time (remember you must be checked in and onboard the ship no later than 60 minutes before sailaway, some lines it's even 90 minutes), reducing your opportunity to look for deals. Many people are able to find less expensive flights+hotel combinations than flying in day of, so keep searching for deals.

If you must fly in day of (sometimes you have to), here are some good guidelines:

1. Make your planned arrival at port no later than 4 hours before departure - this gives you leeway for delays with flight, baggage, and transport from airport to port. So count back, departure at 5 for example means onboard at 1pm. If airport is 30 minutes away from port (for example MIA to Port of Miami), then that's back to 12:30. Depending on the airport give yourself 30 minutes to an hour (for MIA at least an hour), to get off the plane, collect bags, and get ground transportation, so that's back to 11:30. So you're back to a flight that must arrive no later than 11:30 (flying into MIA sailing from Port of Miami).

2. A non-stop is typically better than a connection. The more flights, the more opportunities for delays, lost bags, etc. Notice I said typically because:

3. The earlier the arrival the better. Gives you more room to work if something goes wrong. A connecting flight that gets you in at 9am and has several later alternates (on the same airline) if something goes wrong, might be better than the non-stop that doesn't get there until noon, depending on your situation.

4. Be aware of typical weather when choosing your flight route. In winter beware of snowstorms in northern airports, but in the spring/summer DFW, ORD, ATL, etc can be nightmares for thunderstorms for example.

5. Know your options if you miss sailaway. Do you have a passport so you can fly and join the cruise at an intermediate point? Is the first stop the next day or 3 days away where you've missed half the cruise if you join it at that point? Are there obstacles preventing you joining the ship at the first stop? For example, many lines have stops at private islands (frequently the first stop) that don't have airports. Another example is a cruise from Miami that has a first stop in Key West. You would think you could just drive down and join the ship in Key West, but unfortunately there is a law (PVSA) that prevents that. How would you pay to join the cruise at the next point - travel insurance, credit card etc? Know the day of cruise contact number for your cruiseline.

Several years ago, we flew from SF to Seattle to take a same-day Alaskan cruise. My mother and aunt got to the busy airport too late, and missed the flight, and were fortunate enough to get seats on a later flight! I had to stay at the Seattle airport to accompany them to the boat. Very stressful! Not a good way to start.
This past summer, we were booked on a very expensive bus tour in Alaska. Having learned our lesson from the cruise, we arrived a day early to make sure that we would not miss it. It turns out that another party in the tour was very late and held up 3 busloads of eager tourists! It caused our tour that day to be very hurried.

We always fly a day early, for all the reasons mentioned above. Plus, since we typically cruise in winter, we like to just get away a day earlier. Our first cruise was part of a group and the flight was early the morning of departure. 7am flight meant 5am at the airport, which meant 4am wakeup call at the hotel. Nothing went wrong, but man, was I tired by the evening, and being a first cruise, who wants to nap or go to bed early?

Very valid points. I plan on using miles to fly into Singapore, only downside is all flights to my knowledge arrive at midnight which is not ideal. I will have to keep an eye on the schedules to see if anything opens up for a better situation.

With a very late arrival, an airport hotel is always very nice.

If you find a flight that arrives earlier in the day, picking something close to the ship pier area would also work well.

Romelle

It's only a half hour or less drive to lots of hotels in Singapore. Then you'd be in shopping areas where you can get a taste of Singapore before leaving.

Name hotels in Singapore are expensive, but several hotel credit cards offer certificates for free nights for signing up and meeting spend requirements. And book hotels in Singapore early. I've found the least expensive rooms go and you might have to book a more expensive hotel.

Some cruise lines offer an air package that if your flight makes you miss the cruise, they will get you to the next stop.

I don't usually recommend travel insurance, but if this is a one-time, expensive trip you might want to consider that, too. But read the fine print so you know what is covered. And some travel insurance companies are very difficult to get reimbursement from.

Definitely at least a day before embarkation, preferably a couple of days if possible, to explore the city and rest up before the cruise. On an Alaskan cruise, it was funny to watch all these people dozing off during the muster drill (it was held in one of the lounges). Bet they just arrived after a long journey.

Even better. That gives you a year to do a bit of research on lodging, watch for sales, and possibly find something interesting to see/do in the port where your cruise starts.

I always try to arrive a day or two ahead of time. Not only do I like having the cushion just in case something goes wrong with my flights, if I am ever unfortunate enough to have my bag not arrive, I'll want the extra cushion - either so my bag does turn up or so that I have a bit of time to shop for new gear for my holiday.

I always try to get in the day before, and it saved me once when IROPS delayed me a full day - only one flight per day to the island from which the boat was leaving.

Out of sheer curiosity BTW which island?

Add me to the chorus suggesting arrival a day prior as I've have weather trouble almost delay my arrival and had I been arriving same day would've missed the boat. The only time I might suggest it would be if the cities were relatively close, such as ATL & FLL/MIA.

St. Maarten. It was a small boat traveling around the islands.

I could have hopped a ferry over to Anguilla to catch up, but who needs the hassle?

I almost always try to fly in the day before. Way to stressful with a day of arrival, for me at least. I have flown in day of when the flight was short, and the cruise was inexpensive enough that my feelings wouldn't be hurt too badly if I missed it.