Travel slowly, staying in vacation rentals (villas, farms, cottages, apartments)
Travel insurance gives you extra "peace of mind" for a trip. If you have a medical emergency, you are covered. If you get sick just before the trip and have to cancel, you are covered.
Do You Really Need Travel Insurance?
Many things on your trip are refundable, so you do not need to insure for canceling them. Check your agreements for all your trip bookings to see the policies.
Flights: Some flights are non-refundable, so if you cancel or have to come home early, you lose the amount you paid. Many airlines have a "change fee" (sometimes not available on the cheaper tickets) which allows you to change your return date once you have started your trip. We have done this several times and paid the $100 - $200 per person to change our return flights.
Lost Baggage: Check your credit card, many have some type of coverage for lost bags. If you get travel insurance, find out how much they reimburse for this.
Car Rental: Most car rentals agreements can be canceled at the last minute. If you book with AutoEurope, you may prepay the whole amount, but if you cancel it is refunded. We had to come home early once and just dropped off the car, then called AutoEurope when we got home and got a refund for unused days. Check the details on your rental contract. Sometimes the refund is not as much as you expect; if you booked during a sale they may change the booking to the regular rates, then refund the unused portion from that amount.
Hotels: Most hotels allow you to cancel 24 hours ahead. Once you arrive, you may have to sign saying you will stay for the complete booking, so if you left early you would still pay for unused days. Check the cancellation agreement with your hotel. Many B&Bs now ask for full payment a week or two ahead and do not issue refunds.
Vacation Rentals: This is where you need travel insurance. Most vacation rentals ask for a 25% - 50% deposit on booking, with full payment made 30 - 60 days ahead of arrival. If you have to cancel at the last minute, you lose the whole amount.
Medical Emergencies: Check with your health insurance to see if you are covered when traveling. Our US medical insurance covers us when in Europe, but it would not pay for evacuation back to the US (which some travel insurance covers). In many European countries, emergency care at a hospital is free for tourists.
AIG Travel Guard offers various plans. Some allow you to buy insurance any time before the trip, others require you buy right after you make your first booking.
I looked at Travel Guard for a two week trip, two months from now, costing $2000 per person. Two people traveling, each in their early 50s. Travel insurance cost from $166 to $292 (total for two people). If you buy insurance within 15 days of your initial deposit, it covers you for more things (default of airline, pre-existing medical conditions, etc.). They have free 24-hour assistance to help with emergencies, tracking lost bags, travel advisories. They have a PDF file of their policy which tells you exactly what is covered.
How to Decide
It is a personal decision. Can you afford to lose some of the money you paid for the trip if you have to cancel? Or do you want the extra security of travel insurance?
If you decide to get insurance, read the policy carefully so you know exactly what is covered. Also know the cancellation policies for all your bookings.
To read stories of how people used their travel insurance, go to the Slow Travel Talk message board and search on "insurance". There have been many interesting stories over the years, from someone who got very ill in Florence and had to be hospitalized, to someone who hurt her back a few days before the trip and had to cancel it. Their travel insurance covered them. You can also post any questions there.
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