Travel Hacking Tips from a Nomad Entrepreneur and Investor

Travel Hacking - Hotels at a Discount — Fairmont Royal York, Toronto, Canada

Travel hacking is a popular strategy used by many successful entrepreneurs and investors to save money and travel better. I’ve always loved hunting for deals and finding new ways to travel smart, but I didn’t realize how resourceful I was until I was stuck in Bali in 2020 during the onset of the global pandemic.

Here are 9 top travel hacking tips that I regularly use while working remotely and exploring far-off places:

Travel Hacking - Extended Stopovers for Cheap

1. Extend Stopovers

Booking a flight with a long layover is often cheaper than a direct flight, and it gives you the opportunity to explore a new destination for as long as you want. I’ve done 24-hour quick stopovers and often book a return flight months later when travelling Asia or Europe. This can be a great way to add a new destination to your itinerary without paying extra.

Travel Hacking - eSIM Apps like Airolo or Gigsky

2. Use eSIM Apps

When I severed ties with Canada and became a non-resident, I had to get rid of my personal cell phone plan in Canada. While travelling and working remotely, data is like oxygen. You need it. An eSIM is a virtual SIM card that can be activated on your smartphone without needing a physical SIM card. You just load a new virtual SIM on your phone, and immediately where ever you travel, you can get a data plan. By using an eSIM carrier, you can save money on international roaming charges and have a convenient way to stay connected while travelling. This is a great example of travel hacking. Depending on where I am travelling to, Airolo and Gigsky offer good value.

3. Avoid Checked Bags

Checking a bag can often add a significant cost to your flight and slow you down at the airport. Consider packing everything you need in a carry-on bag to avoid these fees and hassles. This will also give you more control over your belongings and avoid the possibility of lost or delayed luggage. I carry around the classic LL. Bean Duffle Bag that is light and often gets overlooked as an oversized carry-on.

Travel Hacking - Advance Air Bnb Bookings — Air Bnb in Barrio Alto, Lisbon, Portugal

4. Book Airbnbs in Advance

Booking an Airbnb in advance can often save you money compared to booking a hotel, especially if you’re travelling during peak season. It’s really simple. Unlike hotel inventory, with Air Bnb, the best accommodations for the best prices sell first. Pretty simple, really, when you think about it. Too many people book Air Bnbs late and get stuck with the bottom of the barrel.

Travel Hacking - Points from Credit Cards — RBC Visa Infinite Privilege for Private Banking

5. Credit Card Rewards

There are a variety of credit cards that offer different travel rewards, and lounge access, such as that can be redeemed for flights, rental cars, hotels, and other expenses. Generally, the more premium the card, the higher the percentage of points offered. Cash-based rewards are generally simple and easy, but often travel rewards offer a greater return, specifically when booking flights. Use these travel rewards and use it to book your personal flights that cannot be deducted as a business expense. For example, I use the RBC Avion Infinite Privilege card that provides several perks, including concierge service, 6 lounge visits per year, and 1.25 Avion points for every dollar spent.

6. Bid on First Class Seats

Some airlines offer the opportunity to bid on first and business-class seats, allowing you to upgrade your flight experience for a fraction of the cost. Usually, the cost is 1/4 or less of the regular ticket price when booking. You can also find a discounted business class and other premium flights by booking with Avion or AMEX points.

Travel Hacking - Last Min Cruise Ship Deals — Barbados Cruise Port, Bridgetown, Barbados

7. Cruise Ships Deals to Travel

Cruises can be a great way to travel to multiple destinations in one trip, and they often offer great deals. This is one of my favourite examples of travel hacking. While working remotely in Saint Martin/St Maarten during the pandemic, I was looking for a way to get back to Antigua. I noticed a 7-day cruise with the last stop on day six being Antigua. This specific cruise line also allows for single occupancy. It was such a great way to travel and an incredible deal (US $550 per week) that I ended up living on the ship for a month.

8. Book Off-Peak

Travelling during off-peak times can save you money compared to peak times, such as holidays and weekends. Most investors and entrepreneurs have a flexible schedule which allows them to fly on days that most business and vacation travellers can’t. Travel hacking at its best. Additionally, travelling during off-peak times can provide a less crowded experience.

9. Budget Airlines

Budget airlines offer low-cost flights that save money compared to traditional airlines. As much as I enjoy a first-class experience, there is something satisfying about paying a $100 round trip from Toronto to Vancouver or booking a whole multi-flight trip from Thailand — Singapore — Moscow — Berlin — Vancouver for under US $800…CAD! (Inside joke with Joshua Fairbairn). It’s important to note that budget airlines often have strict baggage policies, so be sure to review their policies before booking.

Travel Hacking with Dan Merriam — Lester B. Pearson Airport, Toronto, Canada

In conclusion, by implementing these top travel hacking tips, you can save money and have a more enjoyable travel experience. Travel hacking is not just about finding the cheapest flights or hotels but finding the best value for your money. Be creative, flexible, and willing to try new things, and you’ll find that travel hacking can save you money and allow you to see more of the world. Travelling is a game, and I’m always trying to find a new travel hack that is better than the last. With the right approach, travel hacking can help you explore new destinations, experience new cultures, and create memories that will last a lifetime.

Dan Merriam Real Estate — **Bio**
International Real Estate Investor and Entrepreneur — Founder **@Offshore Freedom** | Host of the **@CaribbeanRealEstatePodcast**

We help successful investors and entrepreneurs live and invest in the Caribbean and buy real estate internationally.

Schedule a consultation with Dan Merriam, and let him help you design the life of your dreams and achieve Offshore Freedom™. Ask questions and get answers about lifestyle design, tax planning, banking, international real estate, second residencies, or citizenship by investment.

Writer in Tax Reduction, International Tax Planning, Travel Hacking, Citizenship by Investment, Second Residence, Real Estate Investing, Asset Management, Lifestyle Planning, Company Formation, Offshore Banking, Asset Protection, Technology, Entrepreneurship

This article is for informational purposes only; it should not be considered financial, tax planning or legal advice. Consult a financial or investment professional before making any major financial decisions.