Travel Insurance- Is it worth and when to buy? What are the best?

Yes, it is worth to buy travel insurance, because travel plans can get disrupted so easily. It may be some minor inconvenience like delay of flight for 6 hours or lost luggage, or it can be major problems like accidents or health conditions that require emergency care in the destination.
It may be extremely disruptive not just to your travels but your productive work life scheduled after your holidays. There are times where airports and flights schedule does not follow through. An example of natural disasters like the Bali volcanic eruption and dark skies that canceled all air flights. Or political protests in Phuket that blockade the international airport.
If you have friends who are in general insurance or life insurance, they will let you know a common open secret- travel insurance is one of the easiest claim policies in Singapore. This is mostly because of all the features and benefits that make is convenient to protect your travel scheme.
Lost luggage, delayed flights, medical illness during your holidays. All these make travel insurance worth getting it.
Do Not blindly buy any travel insurance from airlines, hotel booking sites. You can probably get a better deal, or a greater coverage annual plan from insurance brokers or agents.
There are many great travel insurance companies in Singapore, and many of the best deals depend on seasons and promotion. So if I write in here that Axa travel insurance or DirectAsia plans are the best travel promotion in 2019, it may not be true by the time you read it. For the best price, it may depend on seasonal promotion
Having said that, with the value and reputation of the travel insurers, most of the large general insurers provide great value and features for vacationers like us! The popular ones are HL Assurance, FWD Travel insurance, Chubb travel insurance, Allianz Singapore, Etiqa, Sompa etc.
You may not simply want the cheapest. It is all about value. For example, AIG travel insurance may be more expensive than NTUC Income, but they offer more. In the Phuket airport shutdown, AIG policyholders got shuttled to Bangkok for a flight home. NTUC Income policyholders got a bus ride all the way back to Singapore
AIG travel insurance buyers may have paid a higher premium but when claims come, they get a better, comfortable resolution.
Travel insurance covers cancelled or delayed flights

Travel insurance covers cancelled or delayed flights

Every insurer offers its own value, some like HL Assurance or FWD is rocking the competition with low costs, great value, some like AIG is sticking to premium pricing, with great premium coverage.
We can safely say that with great competition, every insurer is giving great value. It is not the cheapest plan you are aiming to get, nor is it the most comprehensive plan you may love it. You could get any one of the current promoted travel insurance and you will get great value because Singapore travel industry is so competitive.
Get any, as long as you are protected, it is better than forgetting!
The best travel insurance is one that covers all the major event that can cause a huge hole in your pocket, such as medical coverage and repatriation in case of emergency.
It is also one that you do not spend too much time pondering about. (Your time can be spent more productive for work, or for leisure).
Which is one of the reasons why annual plans covering all trips (or all trips in a specific region) is the best, you do not need to think and buy insurance every time you plan for a vacation or business trip.
If you are buying single trip insurance, you should do it immediately after you booked your flight or travel package from the agency.
This is because buying it immediately after you book or buying travel insurance at the last minute before you board your plane (or train, ship, car) cost exactly the same, but buying it sooner gets extra benefits at no cost.
For example, if someone meets with an emergency medical situation and has to forgo the air ticket, the travel insurance may cover that. Or if the travel agency or airline goes bankrupt and unable to honour the deal, your travel insurance may take care of the losses. If you wait till the last minute to buy insurance just on the day of departure, you will not enjoy these benefits and it is too late to seek coverage.
All these are great benefits that are stacked on with no additional fees, insurers like to encourage you to buy early. Go ahead and buy early, you never know what urgency matters occur even before your trip starts.
This is also why annual plans are great. You are covered the day you bought any flights, travel package or hotel accomodation (check your travel insurance policy for AirBnb coverage too).
Go for annual plans for any insurers, it is worth the time saved.

Is it too late to buy travel insurance? Can you buy travel insurance the day you leave?

Yes, It is not too late to buy insurance on the day you leave, in fact, you trigger most of the benefits of travel policies to start protecting you the minute you leave Singapore. The key is you have to buy BEFORE you leave Singapore/
If you landed at your destination country, or in the middle of the trip, no, you are unable to buy coverage for the trip since you left Singapore.
Do note that incidents that occurred before you bought the travel policies would not be covered. For example, if there is a travel agency bankruptcy, buying the plan later will not get you the benefits that should have been paid out.

What is travel insurance used for? Do I need travel insurance?

The biggest event that you are worried during travel is the occurrence of accidents or medical emergencies that may cost a huge bill for emergency medical treatment, and emergency repatriation back to Singapore. You want these to be covered as these are huge out-of-pocket expenses if it happens.
In the event of accidental death, a lump sum is payable to family members back home.
Travel peacefully with insurance

Travel peacefully with insurance

Other simple expenses that most package will cover are luggage losses, flights delay, thefts and loss of valuables.
You may also get covered by travel agencies closure, flight cancellation due to airline closures etc. Some package will even cover burglary or problems at your home when you are enjoying your trip at overseas.

How much does travel insurance cost? What is the cheapest travel insurance?

Basic travel insurance will cost only a few dollars per day while overseas. Even if you opt for a premium comprehensive package, it may only cost ten dollars or so per day.