Annual Multi-Trip Travel Insurance – Smart Coverage for Frequent Travelers

Traveling often for work, holidays, or family visits? An annual multi-trip travel insurance plan offers year-round protection for an unlimited number of trips, so you can travel with confidence — without the hassle of buying a new policy each time.
Annual plans are designed for travelers who take multiple journeys a year, whether domestic or international. Each trip is covered up to a maximum trip length (usually 30, 45, or 60 days depending on the plan).

Why Choose an Annual Travel Insurance Plan?

Annual plans are ideal for:

  • Frequent flyers and business travelers
  • Digital nomads or remote workers
  • Retirees or expats visiting multiple countries
  • Couples or families who travel several times a year
  • Anyone looking to save time and money compared to multiple single trip policies

These plans provide reliable protection and peace of mind all year long.

Key Benefits of Annual Travel Insurance

Most annual plans include comprehensive travel protections similar to single trip plans:

Trip Cancellation & Interruption

Coverage for prepaid expenses if you need to cancel or end a trip early due to illness, weather, or emergencies.

Emergency Medical & Evacuation

Essential for international travel — covers hospital visits, physician services, and medical evacuation.

Baggage & Personal Effects

Protects your belongings if they’re lost, stolen, or delayed in transit.

Travel Delays & Missed Connections

Compensation for meals, lodging, or rebooking fees if your travel plans are delayed.

COVID-19 and Quarantine Support

Includes coverage for COVID-related cancellations, treatment abroad, or required quarantine.

24/7 Emergency Assistance

Get help anywhere in the world with medical coordination, translation services, or travel support.

Who Should Consider Annual Coverage?

Annual plans are particularly cost-effective for those who would otherwise purchase three or more single trip plans in a year.

An annual policy is a great fit for:

Frequent business travelers who need coverage for multiple trips year-round
Families and couples taking several vacations per year
Adventure travelers or surfers attending seasonal events or international competitions
Frequent cruisers who join multiple sailings each year
Snowbirds or retirees who split time between two countries
Remote professionals and digital nomads who blend work with international travel

Choosing the Right Level of Coverage

Annual plans are usually available in tiered options based on the maximum number of days allowed per trip:

  • 30-Day Trip Limit – Ideal for business travelers and short holidays
  • 45-Day Trip Limit – A balanced option for longer holidays or flexible schedules
  • 60 or 90-Day Trip Limit – Perfect for retirees, extended family visits, or nomadic lifestyles

Premiums may vary based on your trip limit, destination region, age, and optional add-ons such as:

  • Pre-existing condition waivers
  • Adventure or high-risk activity coverage
  • CFAR (Cancel For Any Reason) options

Our widget makes it easy to compare these options and find the plan that fits your travel profile.

Choosing the Right Level of Coverage

At Surf Travel Insurance, we currently offer annual plans from:

  • IMG Global – Offers 30, 60, and 90-day trip limit options for both U.S. and non-U.S. residents with high medical and evacuation limits

  • Auras – Flexible plans with competitive rates and coverage for U.S. and international travelers, including professional athletes and high-risk destinations

Note: Generali does not offer annual travel insurance plans.

Our quote tool helps you compare the best annual options available based on your residence and trip needs.

Ready to Find the Right Plan?

Heading to the mountains? Make sure you’re covered for all your winter sports adventures.

Compare Plans Now

Main Plan Comparison

You’ll instantly see plans that match your profile — filtered by eligibility, insurer, and activity type. Compare benefits at a glance, then proceed securely to complete your purchase directly with the insurer.

Have questions or a complex itinerary? Contact our team at [email protected] — we’re happy to help you find the best coverage for your journey.