Best of Sicily 11 day tour - when to purchase travel insurance?

Are you going to buy the Travel Guard insurance that you are offered when you book the tour, or some third party? We bought the Travel Guard option at the same time we booked the tour, because they were familiar with the RS tour process and had access to that information. But if you want to include the airfare, you will have to call them back after you book your tickets to tell them what the airfare cost, which means additional cost for the insurance. I don't know if cost goes up or down, but read the fine print carefully.

We get the insurance not necessarily for refunds on cancellations (since RS offers credit if you have to cancel) but rather for trip assistance and medical expenses. Sorry if this does not help.

To cover pre existing conditions , you need to purchase insurance within ten days of making your trip deposit. We insure the deposit and then add other expenses as they occur including airline change fees. It is very easy to do online.
We don't insure all the airfare if it’s a US based airline but do if it’s based in another country. If it is a US airline we can easily use up the amount it cost in a year booking domestic flights as we travel frequently.
We have had three large claims paid promptly in full by Travel Guard; cancellation of trips were due to unexpected surgery.

Many insurance companies say to get the insurance within 14 days of booking, especially for pre-existing medical coverage. You'll really have to check with a few companies to see what they require and what type of coverage they provide. You decide how much $$ coverage you want and they charge accordingly. To me, the medical coverage is one of the main reasons to get the insurance.
It also depends if you want coverage to cancel for any reason, rather than a covered reason like medical reasons or death in the family. Being able to cancel the trip for any reason is usually more expensive. Hope this helps.

I always buy trip insurance immediately after the first pre-paid fee, typically for me the airfare. If you pay for the insurance within a certain number of days of that initial trip payment (14 days for some companies, could be as generous as 21 for others), pre-existing conditions are waived. Even though I don't have any pre-existing conditions, I always believe the waiver would make it far easier to process a claim in the future if we have to cancel a trip due to medical reasons. (There would be no paperwork burden to prove to the company that it's not a pre-existing condition.) Whenever I buy trip insurance, I do it through tripinsurancestore.com. They are a broker for lots of companies, rather than an insurer. You can use the chart on their website to compare different policies side-by-side but for me it's easier to just call rather than do it online. It's one of the best customer-service companies I know! The company owner or one of his employees actually picks up the phone instead of letting their calls be answered by a menu of voice mail options! I am always pleased to talk to Steve, Becky, Kim or Deanne and they have records on me (date of birth, email address, etc.) and the transaction is so quick and easy! I typically have lots of questions and the person I talk to is always so knowledgeable and patient. When I describe the type of trip we're taking, they point me to the best policy to cover the risks I'm most concerned about. For example, travel in winter, I'm concerned about a weather delay or cancellation. We always pay for our trip insurance on a pay-as-you-go basis. I only buy insurance in an amount sufficient to cover the first pre-paid cost. It's available in tiers. For example, you can't buy $200 worth of coverage, because the minimum is probably $500. Don't try to figure out what your final costs will be and buy the coverage all at once. Just insure what you've already paid for, knowing you can keep adding to the policy and you only pay the incremental difference in premium. That is, the initial premium is the most expensive, and then each time you add to the policy, you pay just a little bit more. So if you've incurred $200 per person in initial pre-paid fees and buy insurance at the $500 per person level, then you book something else and your total pre-paid costs have risen to $700 per person, you call and increase the coverage to the $500 to $1,000 level. If you later add a pre-paid hotel or tour that's less than $300 each, you're still okay. Then, when you add the next non-refundable expense that takes your total pre-paid costs over $1000 pp, you contact the folks at tripinsurancestore.com and add to the policy again, so you're now in the $1,000 to $1,500 tier. For us, the increase to the next level usually requires (I believe) another $17 per person in premium. Doing it this way requires you to be diligent about keeping track of your costs and continuing to increase the policy as needed, because if you don't insure all of your pre-paid costs, within a certain number of days of incurring them, it gets risky. The cost of the insurance doesn't go up as you get closer to the trip. I believe the biggest variable in cost is your age at the time you take the insurance. And of course, what type of coverage you're getting. Sometimes we've purchased cancel-for-any-reason insurance, which would allow us to get back 75% of our pre-paid costs if we can't go on the trip but the reason for that is not a covered one. That's a lot pricier than regular trip insurance but sometimes the circumstances merit the extra expense.

Thank you for the information. It has been very helpful. I can see that because I paid the deposit and didn't purchase insurance immediately, I'm already in trouble. It feels like I need insurance for 2 reasons. The first is a father that is elderly and I'm a bit nervous that he could run into serious medical issues that could affect our trip. The second reason is that we're going to fly Alitalia from Ohare to Palermo (stopping in Rome) and my recent experiences with flights this winter have not been good. My flight to Ft Myers was cancelled by SWA on the morning of the flight. A flight 2 weeks ago on American to Mexico kept us sitting on the tarmac for 4 hours. I want to be sure that if something happens to our trip, we haven't lost all of money paid.

It feels like I need insurance for 2 reasons.

Only your father's health would be worthwhile reason for the insurance, but first read Rick Steves' Trip Cancellation insurance language to see if it applies to you (also, the company is quite liberal about switching dates or tours, if need be). The airlines themselves would have to "make you whole" for delays and cancellations - I don't think insurance would be very helpful as the airline is on the hook to get you to your destination even if not at the initially scheduled time/date. If you bought a flight ticket, you've entered into a contract to get to a certain destination, and the airline has to deliver (even through weather and other constraints). You're not expected to lose money unless you willingly buy another flight flight ticket totally unrelated to the initial one.

I'd go ahead and start researching all of your options. If you booked Alitalia through their US partner, Delta, you may still be able to purchase insurance for the flight portion of the trip. I have seen the 'purchase trip insurance' option on my Delta webpage for flights still in the future.