Your destination, trip length, and planned activities help determine the protection you need overseas. Choosing travel insurance means matching those details to a policy’s benefits, limits, and conditions.
For travellers departing from Singapore, the process starts with identifying who needs cover and reviewing existing protection. Once these requirements are clear, assess medical benefits, cancellation terms, and baggage limits alongside the premium.
DBS distributes TravellerShield Plus, underwritten by Chubb, with options for different travel needs. Reviewing the policy wording and clarifying any conditions before purchasing can help you decide whether the selected cover suits your itinerary, health needs, and travel budget.
Quick Steps on How to Choose Travel Insurance
Use the following sequence to organise your checks and resolve any coverage questions before you purchase.
- Confirm your itinerary and travelling party.
- Choose single-trip or annual cover.
- Assess medical and evacuation protection.
- Check cancellation, delay, and baggage benefits.
- Review exclusions and optional cover.
- Check emergency assistance and claims requirements.
- Confirm the policy details before purchasing.
What You’ll Need Before Comparing Policies
Have these details ready before comparing travel insurance policies:
- Destinations, transit stops, travel dates, and planned activities
- Each traveller’s age and residency status
- Relevant medical history and current medication
- Booking costs and refund terms
- Estimated values of luggage, electronics, and other belongings
- Existing employer, health insurance, or credit card benefits
- Policy wording, benefit schedules, and quotations for identical dates and destinations
Step-by-Step: Choosing a Suitable Travel Insurance
1. Map Your Trip and Travelling Party
Match each destination to the policy’s geographical cover, including any stopovers where you plan to leave the airport. For a family policy, check which relationships qualify and whether everyone must travel together. Reviewing destination advisories alongside these conditions helps establish eligibility for the journey and each person you intend to insure.
2. Choose Single-Trip or Annual Cover
When choosing between single-trip and annual travel insurance, compare the cost and suitability of each option using the same expected itinerary.
| Decision factor | Single-trip cover | Annual multi-trip cover |
| Journeys | One specified journey | Multiple journeys during the policy year |
| Cost comparison | Combined premiums for planned trips | Annual premium for comparable benefits |
| Duration | Maximum length of the chosen trip | Maximum length of each journey |
| Destinations | Cover matching that itinerary | Selected region covering all expected trips |
For example, Chubb’s April 2026 TravellerShield Plus policy specifies “a maximum of ninety (90) consecutive days for any one (1) Journey” under Annual Multi-Trip cover. Its Single Trip policy allows up to 180 consecutive days, subject to the selected insurance period and applicable conditions.
3. Assess Medical and Evacuation Protection
Assess overseas medical expenses separately from emergency evacuation, which addresses transport for necessary care. According to the CDC’s 2026 Yellow Book, the decision to medically evacuate is “at the discretion of the insurance company.” Ask how medical necessity is assessed and which assistance provider arranges the transfer.
Government travel advice updated in July 2026 describes a Singaporean traveller whose family paid S$74,000 upfront for hospital care and an air ambulance. This individual example illustrates the potential cost of treatment and transport. Review both benefits and establish whether direct hospital payment can be arranged or reimbursement applies.
4. Check Cancellation, Delay, and Baggage Benefits
Calculate the prepaid costs you would lose after available refunds, then compare that amount with cancellation benefits and covered reasons. For delays, establish the qualifying duration and payment basis.
SITA’s 2026 report records 24 million mishandled bags worldwide in 2025. When assessing baggage protection, distinguish delayed baggage from loss or damage, and check the maximum payable for each item.
An excess is the amount you contribute towards a covered claim, while a sub-limit caps payment within a benefit category. A high overall baggage limit can still leave an expensive item partly covered.
5. Review Exclusions and Optional Cover
Read the policy exclusions against your medical history and booked activities. If you plan to dive or ski, look for requirements concerning qualifications, operators, permitted locations, and activity limits.
Singapore’s Ministry of Foreign Affairs advises, “Ensure your policy covers your planned activities, especially if they are high-risk.” Where additional protection is needed, check the relevant add-on’s scope, eligibility, and separate limits.
Obtain clarification from the insurer so you understand which circumstances remain outside the selected cover. Include any additional premium in your overall cost comparison.
6. Check Emergency Assistance and Claims Requirements
Locate the emergency assistance number and establish when insurer approval is required for treatment or transport. Reviewing the documents required for a travel insurance claim also helps you assess the practical requirements. Identify reporting deadlines and whether receipts, medical reports, or carrier confirmations are needed, then save these instructions for the trip.
7. Confirm the Policy Details Before Purchasing
Check when each benefit becomes effective before paying. Under TravellerShield Plus’s April 2026 policy terms, conditions, and exclusions, journey cancellation cover starts upon policy issuance or 30 days before departure, whichever is later, subject to covered reasons. Once the policy is issued, review your certificate to confirm that the selected travellers, dates, destinations, and add-ons are recorded correctly.
Addressing Common Travel Insurance Issues
Resolve these comparison problems with targeted questions and a simple record of the answers.
- Similar premiums, different benefits: Create a comparison sheet with one column per policy. Mark which benefits meet your priorities, then compare the remaining options by total cost.
- Unclear activity or medical terms: Describe your circumstances in writing and ask the insurer to identify the applicable clause. Keep its response with your quotation.
- Overlapping existing cover: Ask your employer or card issuer how to activate the benefits and how claims involving another policy would be handled.
Frequently Asked Questions
When should I buy travel insurance?
Arrange cover when you commit to your bookings. Check purchase deadlines and when pre-departure benefits begin, particularly if departure is several months away.
Is annual travel insurance always cheaper?
No. An annual premium may exceed the cost of covering one short trip. Savings depend on actual quotations and how often you travel.
How much overseas medical coverage should I choose?
Choose a limit that reflects potential treatment costs at your destination. Check whether hospitalisation, outpatient care, and follow-up treatment share that limit.
Can I get travel insurance with a pre-existing medical condition?
Yes. TravellerShield Plus’s optional pre-existing condition benefit is available for eligible Single Trip policies of up to 30 days and travellers aged up to 75, subject to additional premiums and policy terms.
Does credit card travel insurance cover everything I need?
No. Card benefits cover specified events and eligible travellers. Check whether paying for the trip with that card is required to qualify.
Does a family policy cover relatives travelling separately?
Yes, some policies allow this. TravellerShield Plus Annual Multi-Trip family cover permits separate journeys, while children under 12 must be accompanied by an adult.
Make Informed Choices Before You Travel
Choose travel insurance that addresses your priorities and fits the journey you have planned. Once you understand the benefits and conditions, you can make a considered decision about the protection you are paying for.
Explore TravellerShield Plus through DBS and review the available plans against your itinerary, budget, and individual coverage needs before applying.
Reference and Source Links
- https://gia.org.sg/consumers/travel.html
- https://www.cdc.gov/yellow-book/hcp/health-care-abroad/travel-insurance.html
- https://www.mfa.gov.sg/travelling-overseas/general-travel-advice-for-singaporeans/
- https://www.sita.aero/about-us/pressroom/news-releases/tech-drove-down-mishandled-bag-rates-by-23-in-2025-but-mishandling-still-costs-the-industry-%246.3-billion-a-year
