We’ve traveled to more than ninety countries over the years. Mark is the mastermind; he does all of our travel planning and has acquired a great deal of expertise about the following topics.
🌎 Itinerary Selection
Deciding where to go, when to go, how long to stay and how to get there isn’t so simple when you travel continuously. Choosing your next destination sounds easy, but involves many considerations, such as how to get there, cost of living, safety, lifestyle, internet, walkability, public transport, co-working and remote work, English and climate. While we go to places we are interested in, we try to offset higher-cost destinations by adding in lower-cost ones.
Repositioning Cruises
We love repositioning cruises and you can get amazing deals that include your accommodations, food, entertainment, AND transportation, so we grab them when we can. Then we are tasked with filling in the rest of the itinerary around these cruises, so they influence where we go and when.
Visa Considerations
Also a key consideration is length of stay, especially as it applies to visas. For example, a tourist visa in the EU’s 27 Schengen countries is only good for 90 days. At that point (and not an hour later), you must be out of that bloc or risk not being permitted to come back. After another 90 days, you can re-enter. If you enter and exit repeatedly within the 90-day period, there are online calculators that allow you to track your days more easily. We nomads call the process of departing and returning the “Schengen Shuffle;” countries like Albania, Montenegro, the UK (thank you, Brexit!) and Ireland (EU but NOT Schengen) are popular destinations when you need to duck out.
Where to Go Next? How To Choose From 4,116 Cities
Your Personal AI Travel Planner: Design Your Next Epic Adventure
🧳 Packing
How do we pack for months and months of travel? What luggage do we use? What gear do we bring? How does everything stay charged, with long flights, multiple voltages and myriad outlet plugs? Here is a guide to our favorite travel gear, including e-sim cards to keep your phone working:
Indispensable Companions: Our Favorite Travel Gear
We have been traveling with Away’s medium suitcases plus backpacks, but many nomads go with carry-ons or even just backpacks! We’re not there yet but we just started doing carry-on only this year.
✈️ Flights
Which routing should we take? Which airline has the best price? Where do we search for the flights we need? How do we book with points or miles? How do we upgrade to Business Class? If you’re new to credit card travel rewards, check out our posts about earning points to get you started.
Chase Sapphire Preferred: The Ultimate Starter Card for Travel Rewards
New Year, New Cards, New Adventures: Unlocking Travel Riches in 2024
Fund Your Digital Nomad Journey: The Credit Card Arbitrage Hack (Earn up to $1,200 or more)
🚖 Transfers
How do we get from the airport to our accommodations? Is there Uber? Or do we need the Grab app… or InDrive? How do we get from city to city – plane, train or bus? Finding answers to these questions takes a little research… and preferably before you’re standing at the airport curb. We suggest downloading and setting up Uber, Grab, Bolt and InDrive apps before you leave the U.S., so you’ll have them when you need them.
🛳️ Cruises
How do we pick a cruise? There are loads of cruises out there, all over the world, and the prices fluctuate all the time. There are websites that help us find the best deals. In addition to offering “low daily rates” when we find an amazing deal, repositioning cruises are a fun way to get from one place to another without taking a flight.
Choosing a Cruise: Finding the Right One for You
Cruise Deals: How We Get the Best Price
Repositioning Cruises: Discover the Ultimate Slow Travel Hack
Virgin Cruises 2024: Adult All-Inclusive Luxury Voyages
Work From Paradise: Virgin Voyages’ Scarlet Summer Season Pass Announced (Limited Time)
🚩 Tours and Excursions
In most places, we are confronted with a vast array of tour and activity options. Which should we choose? How do we know if it’s a good tour?
Choosing cruise excursions is another challenge. Typically, ships offer their own excursions or we are free to book a local tour on our own. Often it’s less expensive but it comes with risks. For example, if the tour gets back late, you could miss the ship’s departure. How do we decide? Here’s how to navigate the world of cruise shore excursions:
Cruise Shore Excursions vs. DIY Adventures: Navigating the Seas of Choice
How to Save Money on Cruise Excursions: A Personal Guide
🏨 Accommodations
Should we stay in a hotel or an Airbnb? Does this city even allow Airbnb? If not, are there serviced apartments? How do we know if an area is safe? Which amenities do we look for? Is high-speed internet really high speed and how can we tell? Here are some tricks we use to choose the best Airbnb for our stay and to find the best rate.
Best Airbnb: Crack the Review Code and Book the Best Airbnb
Airbnb Hacks for Best Rates: Save Big on Your Next Stay
Best Hacks for Saving Money on Hotels: Airbnb & Booking.com Exposed
Another great strategy for saving on accommodations is to join a hotel network and earn points and status. The best way to get started is to get a hotel-branded credit card (generally issued by Amex or Chase) that lets you earn points for stays. The best hotel networks are Hilton, Hyatt, IHG and Marriott. Look for status matching offers like this one that Hilton is currently offering:
Status matching accelerates your status and fast tracks you to perks like free nights. Sometimes they let you buy points at a favorable rate so once you sign up, watch your in-box for special offers.
💳 Credit Cards
And speaking of credit cards, we highly recommend getting cards that offer travel rewards – points or miles – that can be converted into business class flights and hotel stays. If you’re overwhelmed by multiple cards, consider defaulting to a good general-purpose travel card like the Capital One Venture X, which offers 2X points on every purchase. That way, you’ll always be earning rewards without overthinking it.
➡️ See all the top travel credit cards and their current offers here.
🥗 Dining
Eating while traveling is a mix of dining at local restaurants, picking up something cheap at a food hall, market, or grocery store, or buying groceries and making something in our kitchen. How do we choose? There’s definitely a strategy to this. We always start with a food tour or two to be introduced to local restaurants and markets we might not find on our own.
A lot of cities use OpenTable for reservations. However, it’s a great idea to download a couple of other reservations apps as well. Resy and TheFork are two others we run into.
🏥 Travel Insurance
Before you head out on your overseas adventure, you definitely want to consider your travel insurance options. It’s essential to be covered should any emergencies arise.
SafetyWing offers global travel medical insurance for nomads and travelers. They have built a global social safety net tailored to the needs of online freelancers, entrepreneurs, and remote companies.
Staying Connected with Family and Friends
One of the challenges of traveling the world is staying connected. We are on the T-Mobile Magenta MAX plan that provides 5GB of high-speed data in over 215 countries and destinations. It works great when we travel. However, it’s a U.S. plan, and when we use too much overseas data relative to U.S. data, T-Mobile gets annoyed and sends us nasty messages. This plan will not work for traveling more than a month or two – and we cannot risk losing access to our phones – so we had to find another solution.
Airalo to the rescue! Airalo is the world’s first eSIM store that solves the pain of high roaming bills by giving you access to 200+ eSIMs (digital SIM cards) globally at affordable prices.
We stay in touch with family and friends with WhatsApp rather than using text since it uses Wi-Fi or eSIM rather than cellular data. One annoying aspect of modern life is two-factor authentication when logging into websites or apps. We’ve always preferred to get these by text, but we’ve changed them over to email where possible to avoid getting extra texts.
Recent Posts on Travel Resources
