Travel Hacks from a Nomad Investor Living in the Caribbean

Travel hacks are 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 became a full-time traveller in 2019 and was "stuck" in Bali during the onset of the global pandemic.

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

1. Extend Stopovers

Booking a flight with a long layover is often cheaper than a direct flight, allowing you 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.

2. 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.

3. 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 smart travel hacks. Depending on where I am travelling to, Airolo and Gigsky offer good value.

4. 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.

5. 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.

6. 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.

7. 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.

8. 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.

9. 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. This is one of my favourite travel hacks. Additionally, travelling during off-peak times can provide a less crowded experience.

By implementing these top travel hacking tips, you can save money and have a more enjoyable travel experience. Travel hacks are 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 new travel hacks that is better than the last. With the right approach, travel hacks can help you explore new destinations, experience new cultures, and create memories that will last a lifetime.

Bio

International Real Estate Investor and Entrepreneur — Founder & CEO @Offshore Freedom. Helping successful investors and entrepreneurs live and invest tax-free in the Caribbean and abroad.

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

Writer on Medium in Tax Reduction, International Tax Planning, Citizenship by Investment, Second Residence, Real Estate Investing, Asset Management, Lifestyle Planning, Travel Hacks, 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.