I've never been interested in cruises before, as I like to go places fast. This is why I like to fly. But, then, I realized that there are cruises that are priced very nicely (less than the cost of staying in a hotel and I get transportation on top of that!) so now I'm interested! So, I have a few questions:

1. What are some things I should look out for when booking a cruise?
2. Are cruises like hotels and airlines where it's best to book direct? Or should I take advantage of all the offers and rewards that a package seller would offer me (ie United Cruises)?
3. How does dining and drinks work? Are the packages worth it, or are the included meals (if any) decent enough if I'm not looking to get fancy?
4. Are there any fees that I should be aware of that aren't included in the price shown? (Internet? Food? Entertainment?)

I will likely not book any sort of excursions through the cruise operator unless I see something that I am really interested in. Otherwise, I am a pretty savvy traveler who will research things to do ahead of time so that when I arrive anywhere (whether it's by plane or the cruise ship port) I'll already have a plan for things to do on my own.

Oh, I guess I should mention that I intend to cruise alone, and I know that there's a few cruise lines (ie Norwegian) that don't charge a single supplement.

Some of the best deals are on the so-called repositioning cruises where cruise lines move ships from one continent to another with the change of seasons. Examples are some trans-Atlantic, trans-Pacific, and Panama Canal cruises. (Use your frequent-flyer miles for one-way flights to or from the other continent.)

I typically have purchased my cruises through vacationstogo.com, which often shares part of their commission with the passenger in the form of shipboard credits. I find their website very easy to use, but you do have to "register" on their website with an email address in order to see their offerings.

If you are flexible about your travel dates and are willing to play a game of chicken, some of the best deals appear anywhere from a couple of weeks to a couple of months before sailing date.

1. There is a huge range of experiences available, from low-end party ships to high-end luxury cruises. Most (but not all) cruise lines will also allow you to take advantage of price drops.
2. There's no advantage to booking directly. Some travel agents give onboard credit, some give cash back. You can also put up a request for quotes on cruisecompete.com.
3. It depends on the cruise line. If you drink a lot, the packages can be worth it. We rarely book specialty dining because most of them aren't worth the cost and we're generally really happy with the including dining options.
4. It depends on the line. Most of the lower tiers charge extra for internet and gratuities. Also watch out for refundable vs. non-refundable deposits.

Also, some lines will match status from hotel and airline programs, so that can be nice to get started.

Thank you everyone for the insight so far!

Do the repositioning cruises visit many ports or are they primarily days at sea? Part of the appeal of cruises to me, is the ability to visit many places. For example, there is a 4-day cruise out of Florida on Norwegian that only has one port stop in the Bahamas. It's not as interesting to me, although the price tag at $339 is very appealing.

I am somewhat flexible as far as my employer being ok with me taking PTO with at least a week of advance notice. I initially became interested in cruising when I read about Holland America's standby cruises (and I live near a port; not a particularly popular one, but cruise ships do start trips here!). (Holland America now charges a single supplement for standby cruises, making it less appealing than just booking a cheap cruise outright.

While I'm excited to see what a cruise ship is like onboard, the thing that appeals to me the most is being able to get off the ship in places where it would cost more than the cruise to fly to (ie caribbean destinations)

Trans-Atlantic repositioning cruises typically take about two weeks, and visit a few ports during the crossing. Here's an example of an upcoming Celebrity repositioning cruise from Tampa:

Take a look at Virgin Voyages. They have a very diverse crowd and do a lot for single cruisers. They do not have a main dining room nor a buffet. There is the Galley which is like an food court where everything is made fresh to order. There are several restaurants which are all included in the price. Virgin works different but skews a very diverse crowd and is very laid back. You can dress up, or not. You're choice.

There are a few different ways to think about it and then you need to go from there.

Where are you located? If you are in FL you have a ton of flexibility in dates, if you live in Michigan, you need to fly to any cruise anyway. Personally I live in NYC area, so if its a shorter trip I look for dates that work and dont care about destination. We typically cruise without our 4 kids, so its about getting away while Grandma watches the little ones, destination does not matter to us at all. We would do 5 days to Canada or Bermuda, we almost never get off the ship so it doesn't matter. If its a longer trip, we will likely fly to Orlando where we can get more options of days, and then look for the dates that work for us (we are much more restricted in timing than it sounds like you are).

Do you care about number of ports or do you want to minimize days at sea, those are not always the same. We have done cruises from NY that do 3 days at a single port, and thats the only place it stops. You can also find 5 ports in 7 days, depending on from where and what ports.

Personally I like they layout of https://www.cruisetimetables.com/ I find it very user friendly. Since I normally say "I can only go on December 9 from Orlando, show me all the options" its very quick and easy to find what I want. I always book using chase points, so I cant speak for their booking ease.

I started cruising about 15 years ago with my late wife and still love it. Welcome to the club!

I don't think a repositioning cruise is what you want. You're basically looking for a hotel with good food that moves with you. Many cruises are like that. I'd start by asking yourself two basic questions:

1. What part of the world do you want to see? (This is related to the season when you go. Ships visit different regions at different seasons. That's why repositioning cruises exist.)
2. Do you think you'd prefer a mega-ship (4,000 passengers, plus or minus) with all sorts of facilities, casinos to rock climbing walls and water slides, and Broadway-style entertainment nightly? Or are you leaning toward something smaller, say 700-900 passengers, with a quieter atmosphere and a more intimate feel?

Then, if you know (or know of) a travel agent who focuses on individual leisure travel, talk to him/her, Cruise lines depend on TAs for most of their bookings. They pay good commissions and offer their best fares. As posted above, TAs often pass some of this along in the form of shipboard credits or direct discounts. A good one will also have sailed on several lines and will be able to offer meaningful suggestions. You can also get a lot of useful information from YouTube videos. Watching people tour ships with their video camera running may help you decide your ship size preference.

My travel companions and I have never found drink packages worth it, but that has a lot to do with our habits and the lines we cruise on (which offer free wine and basic mixed drinks). YMMV. Once you pick a cruise, look at the packages and pick one that works for you (or none). We've also never gone in for specialty restaurants, but we might this year. The need for one depends a lot on what other options your ship has, The cost of drinks and dining isn't a big enough deal to determine which cruise you want.

Ditto for Internet: pick a cruise first, then look at your choices. I use my cell phone as a wi-fi hotspot while in port or near land, which makes ship wi-fi unnecessary; see if that's possible with your phone plan in the region where you'll sail. In general, focus on the big picture and work out the details after. Don't let the tail wag the dog.

You'll have to choose a cabin type. I don't like interior cabins, though they're inexpensive and might be fine if you'll just use them for sleeping. I've also found suites too expensive; I'd rather spend the money taking another cruise or flying to/from in greater comfort. That leaves outside and balcony cabins, One decision factor is the weather you expect where you'll go. However, another advantage of a balcony is that it gives you a full-wall window. I had a balcony cabin on an Antarctica expedition. Never sat on it to bask in the "balmy" weather (daily highs were around 30�F/-1C), but the view was priceless,

Finally, don't dismiss cruise-operated shore excursions out of hand. Some offer good value for money and might show you things you wouldn't see on your own. At least look at what's available. If nothing else, the process might give you some ideas. And, if your booking comes with substantial shipboard credits, this might be a good way to use them up!

I've never booked on vacationstogo (my in-laws had a not-great experience about a decade ago - I know everyone has blips, but subjectively I'm no longer interested in them as an agent) BUT they have the best schedule/database I've found online. They also have a newsletter for singles - cruises with small or no single supplement. I do all my own planning but typically book with a travel agent for the perks.

For us - we cruise to see where we might want to visit more on land in the future, and also to see things best/only seen by ship. I want a small ship (<1000 passengers, preferably closer to 600) because I don't care about nightlife or being entertained, and I don't like people. Though we started out cruising old/smaller HAL ships, then R-class on Princess, these days the small ships are all luxury brands. So when we do cruise, drinks & tips & internet are included in the fare. So choose among all the variables, and when you are comparing fares- make sure to compare inclusions/exclusions as best you can.

I book with a travel agent. Not for onboard credit or discounted pricing, but for one other important reason. If something goes wrong, I have someone on my side to help me out, someone who has probably encountered the same issue before. It can be minor or major. I have listened to her instruct a cruise line agent how to book my cruise using a future cruise deposit (which covers a deposit with a smaller down payment and comes with onboard credit). And her number would be the first one I called if I needed to cancel a cruise after final payment or missed the ship somewhere or any of a number of screwups on my part or the cruise lines. She also helps me select the best cabins and dates, but that can be done with multiple Internet resources if you have the time.

As far as packages, they differ from line to line. We sail Princess exclusively for now and their Plus package fits us nicely. We are not heavy drinkers, but are ahead with as few as 2 daily adult beverages because the package includes internet (necessary for us and expensive) and �crew appreciation� (tips). You need to do your own math to determine whether it makes financial sense.

Boston! I know Norwegian and Princess stop here, and Holland America has cruises originating from here for cruises that end in Canada, and cruises that cross the Atlantic.

I care more about number of ports! I know I'll probably have to fly to Florida or Galveston to get on a decent cruise.

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1. No preference for part of the world. I'm ideally looking for best cost advantage while starting out. I guess I would also prefer cruises that go to places that I haven't been before over ones that visit places that I have been before. I guess also for now, I'm not looking for really long trips (ie over a week) or trips that start outside of North America.
2. No preference, as I haven't taken a cruise yet to have a preference yet!

You might want to check out/ join Cruise Critic. I had lots of questions answered by them.

We decide which cruise based on its itinerary, whether it is going to places we'd like to see and if going by boat make sense as opposed to land travel. A Caribbean cruise where all the ports look the same holds no appeal but Tahiti and Alaska were cruises we enjoyed.

Unless you really enjoy being on the boat sea days are wasted days filled with mind-numbing monotony. You may find the short time in ports frustrating as you only have a few hours there. Also a few thousand of people on your boat and perhaps others in port are also going to be disgorging at the same time so popular attractions may be crowded.

Cruising isn't for everyone and if you are a spontaneous traveler who prefers to set their own agenda the more rigid schedule of cruises may not be to your liking.

That's one person's opinion. We love sea days.

Two ways around this. Don't sail on large ships, and don't go to the "popular attractions". Both these strategies work well for us.

I would imagine that I wouldn't like sea days as much, but also as someone who has gone on international trips where the weather was so bad that I've stayed in my hotel room all day getting work done in a comfortable environment, I might not dislike the sea days because on top of being able to do the same, there would be things to do on the ship, and I can probably go eat almost whenever I want.

I'm someone who likes to find unpopular attractions as a hobby, and often will want to do off-the-beaten path activities before I actually go do the cliche every-tourist-does-this activities. I've ended up traveling to places before where a cruise ship happened to be in port and had to "deal with it" with the crowds (ie. I was in Sint Maarten for an aviation related event, and decided to go see Phillipsburg and two cruise ships happened to be at port when I was there. Heck, it was the final flight of the KLM 747 to SXM and Maho Beach was packed to the gills with cruise passengers who had no idea the event was going on! They were lucky that KLM had enough swag to give out! I have a photo of the 747 landing, and a beach full of people with cruise layards and blue KLM hats), and I think I am experienced enough to be able to handle it despite being part of that crowd!

I have an additional question. I vaguely remember some cruise lines allowing people to join/board a cruise at one of the port stops instead of starting from the origin of the trip, and/or that people who missed the boat at an intermediate port stop were allowed to rejoin the cruise at the next port provided that they could get there at their own expense. Is this still something that cruise lines do?

For example, Holland America's Canadian cruises (either to Quebec City or to the Maritimes) may start in Boston, and then either stop at Portland, ME or Bar Harbor, ME (and if there's a port availability issue they would sometimes go to Bar Harbor first and backtrack to Portland). As someone who has already been to those two places and might want to work the extra day or two and can get myself to Portland, would the cruise line let me join the cruise there instead?