If you’re a Rolex owner planning to travel, chances are you’ve asked yourself at least one of these questions: Should I wear my Rolex at the airport? What if I lose it? Will customs stop me? Is it covered by insurance abroad?
You’re not alone. Whether you’re flying to New York for a quick business trip or heading to Europe for the summer, bringing a luxury watch like a Rolex isn’t as simple as just slipping it on and going through security. There’s a lot that can go wrong, confiscation, theft, or losing coverage from your insurance, unless you’re properly prepared.
At Toronto Watch Exchange, we’ve helped countless collectors and Canadians who own a Rolex understand what’s safe, legal, and protected when travelling. This guide walks you through everything Canadians need to know about how to travel with a Rolex, covering airport security, CBSA rules, international watch insurance, and real tips for flying smarter with your watch.
Can You Travel With a Rolex Through Airport Security?
If you’re flying from Toronto to the U.S. or internationally, your first concern is probably about airport security checkpoints. Can you wear your Rolex through the TSA scanners or CATSA (Canadian Air Transport Security Authority)? Or will you be asked to remove it and risk losing it in a security bin?
Good news: You can absolutely wear your Rolex through security, and you should.
The TSA officially allows jewelry and watches through screening, and most of the time, you won’t be asked to take them off. If security agents do ask you to remove it, it’s completely acceptable to request a manual inspection rather than placing your watch in a tray where it could be stolen or damaged.
It’s not just a matter of theft; bins have been known to cause scratches or minor impacts, especially if other items like keys or laptops are dropped on top. If you’re travelling with a high-value piece, avoid letting it out of sight even for a second. Keep it on your wrist, under a sleeve or jacket if you’d rather not attract attention.
And remember: the TSA’s official guidelines make it clear that watches are allowed in both carry-ons and on your person, so you can confidently decline if you’re asked to toss your Rolex in a bin.
Do You Need to Declare Your Rolex at the Canadian Border?
This is where things get a little more complicated, and where a lot of Canadians make mistakes. If you’re travelling with a Rolex you already own, purchased in Canada or previously declared and taxed, you do not need to declare it again. That said, CBSA officers can question luxury items on re-entry, especially if the watch looks brand new.
To avoid confusion or unwanted delays, always carry proof that the watch wasn’t purchased on your trip. This could be:
- The original sales receipt or invoice
- A copy of your insurance policy
- An appraisal document
- Photos of you wearing it before departure, time-stamped
If you’re buying a Rolex while abroad and bringing it back to Canada, you must declare it when returning. The CBSA’s duty-free exemption limits vary depending on the length of your trip (typically $800 CAD for trips over 48 hours), and anything above that may be subject to HST and import duties. Watch purchases are often flagged due to their value, so don’t take chances, it’s not worth having it seized.
You can review the official CBSA guidelines on returning with goods to understand exactly what you’re allowed to bring back and how to avoid penalties.
CBSA Rolex Re-Entry Scenarios
Situation |
Declaration Needed |
Risk Level |
| You bought a Rolex abroad and returning with it | Yes | High |
| You’re travelling with your Canadian-purchased Rolex | Not required (but proof helps) | Low |
| Inherited Rolex from outside Canada | Yes | Medium |
| Selling your Rolex abroad and returning without it | May trigger income/tax scrutiny | Medium |
How to Safely Travel With a Rolex Watch
This is the part that makes most Rolex owners nervous, and rightfully so. Travelling with a $10,000 to $100,000 timepiece comes with real risks, but they’re manageable if you take the right steps.
Wear It, Don’t Pack It
The most important rule? Never, ever check your Rolex in luggage. Checked bags go missing, get handled roughly, and are a common target for theft. Always wear your watch or, if absolutely necessary, carry it in a protective case in your carry-on. Even then, the watch should never leave your direct supervision.
For owners with multiple watches, we recommend using a compact, padded travel roll that fits securely in your carry-on. If you’re just bringing one timepiece, wearing it is always the safest option.
Take Photos, Record the Serial Number, and Store Documentation
Before you leave, create a digital record of your Rolex. This is vital in case of loss, theft, or insurance claims.
Here’s what to document:
- Photos of the watch from multiple angles (with time/date metadata)
- The reference and serial number
- Any original warranty card or certification
- Your proof of purchase
- A copy of your insurance certificate
Email these documents to yourself or save them in secure cloud storage. If your watch is ever stolen or damaged, you’ll need this information to file police reports or insurance claims.
We also advise registering your Rolex with a third-party watch registry or contacting the manufacturer with your ownership details, it can help authorities verify your claim if the piece is recovered.
Make Sure Your Luxury Watch Is Properly Insured Abroad
This is where most Canadians are caught off guard. Standard home or condo insurance usually does not cover luxury items while travelling internationally, unless you’ve added a specific rider or floater.
To make sure your Rolex is protected while abroad, look for:
- Worldwide coverage
- Full-value reimbursement for theft, loss, or accidental damage
- No location exclusions
- Zero or low deductible policies
Specialty providers like Jewelers Mutual, Lavalier, or BFL Canada offer coverage tailored to luxury watches. We recommend checking your current plan before any trip, many people assume they’re covered, only to find out their protection ends at the border.
We go into more detail about this in our post on how to insure your watch properly, including how to get an accurate appraisal and the types of questions to ask your broker.
Don’t Broadcast Your Watch on Social Media or in Public
Luxury watch theft is on the rise worldwide. In major cities like Barcelona, Paris, or even Toronto, criminals have started targeting tourists wearing high-end watches, often at cafes, hotels, or while walking in public. Travel smart:
- Avoid sharing real-time photos of your location with your watch
- Use discretion in crowded or unfamiliar places
- Store your Rolex in the hotel safe if you feel uneasy
Sometimes it’s worth considering a less conspicuous watch for travel, especially if you’re heading somewhere with high pickpocketing or robbery rates. For high-stakes trips, some collectors even travel with a decoy watch that resembles their daily wear but isn’t worth nearly as much.
What to Do If Your Rolex Is Lost or Stolen While Travelling
If the worst happens and your Rolex is stolen or lost while abroad, staying calm and acting quickly will make a big difference.
- Report the theft or loss to local police and request a copy of the report
- Notify your hotel, airline, or tour operator if they were involved
- Contact your insurance provider immediately
- Provide all your documentation and photos
- Let Rolex or the watch registry know using the serial number, it could help recover it later
If you’re unsure what steps to take, our full guide on what to do when your Rolex is stolen is a must-read. It walks you through exactly what to do in Canada or abroad if your timepiece disappears.
Should You Travel With Your Rolex or Leave It at Home?
There’s no universal answer. If you’re attending a wedding, business meeting, or milestone event, wearing your Rolex can be the perfect touch. But if you’re island-hopping, backpacking, or heading to a city with known theft concerns, it might be better to leave it in the safe at home.
Ask yourself:
- Will I be in secure environments most of the time?
- Do I have proper travel insurance for my watch?
- Can I avoid drawing attention to it in public?
If you’re ever unsure, we can help you weigh the risk. Our team at Toronto Watch Exchange often provides clients with appraisals, advice, and even pre-travel evaluations to help them decide what to bring.
Before You Travel with a Rolex: What to Remember and Why It Matters
Travelling with a Rolex isn’t just about showing up in style, it’s about moving through the world confidently, knowing your watch is safe, insured, and fully accounted for. For Canadian owners, the key isn’t just having a Rolex, it’s knowing how to travel with it smartly.
When your documentation is in order, your insurance covers you globally, and you know how to handle TSA or CBSA questions without hesitation, you’ve removed the biggest risks. You’re not leaving anything to chance, and that’s exactly how a Rolex owner should travel.
So whether you’re heading to a business meeting in New York or a summer getaway in the South of France, you now know what it takes to protect your investment. Carry proof of ownership, avoid packing it in luggage, keep it on your wrist through airport security, and double-check your insurance before boarding that plane.
At Toronto Watch Exchange, we want every client to feel not just proud to own a Rolex, but prepared. Because when you’re equipped with the right knowledge, your Rolex becomes part of the journey, not a worry that holds you back.