These are the tools and resources I personally use — or have thoroughly vetted — while planning a 13-month, 21-country sabbatical. Some links are affiliate links, which means I earn a small commission at no extra cost to you. I only recommend things I’d use myself.

🗺️ Trip Planning

Rome2Rio — My first stop when figuring out how to get between any two places on earth. It covers flights, trains, buses, ferries, and driving — and shows every option with rough costs. Indispensable for multi-country trips.

Google Flights — Best for flexible date searches and price calendars. The “Explore” map feature is great when you’re open to where you go next.

Skyscanner — Search flights to “Everywhere” from your city and let the deals guide your itinerary. Also great for finding cheap regional hops while already abroad.

Going (formerly Scott’s Cheap Flights) — Set up alerts for your home airport and get notified when mistake fares and deep discounts appear. Worth it for long-haul international flights.

TripIt — Forward your booking confirmation emails and TripIt automatically builds a master itinerary. Great for keeping flights, hotels, and transfers in one organized timeline.

Kiwi.com — A powerful flight search engine that’s great for finding creative routing and multi-city itineraries. I use it to compare prices across airlines and find deals for my longer legs between regions.

🎟️ Tours & Activities

Klook — Book tours, attractions, and experiences across Asia and beyond. I use Klook for things like temple tours, cooking classes, and day trips. Prices are often better than booking at the gate.

Tiqets — Skip-the-line tickets for museums, landmarks, and attractions — especially strong in Europe. Great for places like the Acropolis, Sagrada Familia, or any popular site where lines get brutal.

🏨 Where to Stay

Booking.com — My go-to for hotels and apartments, especially across Europe and Southeast Asia. The free cancellation filters are essential when your plans are still flexible.

Airbnb — Best for monthly stays, which get 20–40% discounts. Essential for slow travel when you want a kitchen and a proper “home base” feeling.

Agoda — Often beats Booking.com on prices across Asia. Always compare here if you’re traveling through Thailand, Cambodia, Vietnam, Indonesia, or Japan.

Hostelworld — For budget stays and meeting other travelers. Private rooms at nicer hostels are often a steal and the social vibe is unmatched for solo travelers.

💳 Banking & Money

Charles Schwab High Yield Investor Checking — The single best bank account for international travel. Zero foreign transaction fees, and they reimburse 100% of ATM fees worldwide at the end of each month. This is what I use as my primary account abroad.

Wise (formerly TransferWise) — Best exchange rates available, period. Hold multiple currencies, pay international bills, or send money home. The Wise debit card is a solid backup to Schwab.

Revolut — A strong alternative to Wise with excellent budgeting tools and a clean app. The free tier works well for occasional currency conversions.

🛡️ Travel Insurance

SafetyWing Nomad Insurance — The most popular choice for long-term travelers. Subscription-based (~$56/month), you can buy it while already traveling, and there’s no trip duration limit. Great value for anyone on an extended sabbatical.

World Nomads — Better if your trip includes serious adventure activities (trekking, diving, extreme sports). Covers 150+ activities that most basic policies exclude.

IMG Global — What I’m using for my sabbatical. Their Patriot International plan provides solid medical coverage for extended international trips. A good option when you need real health insurance abroad, not just emergency evacuation coverage.

📶 Staying Connected

Airalo — My top recommendation for data while traveling. Airalo is an eSIM marketplace with plans in 190+ countries starting around $4.50 for 1GB. Download the eSIM before you land — no more hunting for SIM card shops at airports.

Holafly — If you’re a heavy data user, Holafly’s unlimited data eSIMs are worth the higher price. Especially good for Southeast Asia and Europe where you’re streaming maps constantly.

Saily — Built by the team behind NordVPN. Clean app, competitive prices, and reliable speeds. A great alternative to Airalo if you want a second eSIM option or better coverage in certain regions.

🛂 Visas & Entry Requirements

Sherpa — Enter your passport and destination and Sherpa tells you exactly what you need: visa requirements, health rules, transit visas, and how to apply. One of the most accurate and current tools available.

iVisa — Apply for e-visas online with a clean interface and solid customer support. Particularly useful for countries like Egypt, Turkey, Indonesia, and India where e-visas are available.

US STEP Program — The Smart Traveler Enrollment Program lets you register your trip with US Embassies in each country. Free, takes 5 minutes, and can be critical in an emergency. Every American traveling long-term should use this.

US Travel Advisories — The State Department’s official safety ratings for every country on earth. Check these before booking and monitor them while you’re abroad.

💉 Health & Vaccines

CDC Traveler’s Health — The most authoritative source for destination-specific vaccine recommendations, health advisories, and disease outbreaks. Check every country on your itinerary, not just the obvious ones.

IAMAT (International Association for Medical Assistance to Travelers) — Free membership. Access to a worldwide directory of English-speaking, vetted physicians. Invaluable if you need real medical care in a country where you don’t speak the language.

Find a Travel Clinic — Get your vaccines from a certified travel medicine clinic before you go. They know what’s actually required (vs. just recommended) for your specific itinerary. Use the CDC clinic finder to locate one near you.

🎒 Gear & Packing

Osprey Farpoint 40 — The gold standard carry-on backpack for long-term travel. Airline carry-on compliant, comfortable to wear all day, opens like a suitcase. If you want to live out of one bag, this is the one.

Eagle Creek Packing Cubes — A total game-changer for staying organized in a backpack. I use a set of three: tops, bottoms, and misc. You’ll never go back to stuffing everything in loose.

Universal Travel Adapter — Get one that covers all plug types (A, B, C, G, I) with built-in USB-A and USB-C ports. Europe, Asia, the UK, and Australia all use different standards. One good adapter saves you every time.

📚 Books Worth Reading

Vagabonding by Rolf Potts — The sabbatical travel bible. Written in 2002 but more relevant than ever. It’s less about logistics and more about the mindset shift required to actually leave, not just fantasize about it.

The 4-Hour Workweek by Tim Ferriss — The book that started a million sabbaticals. Most useful for the sections on “mini-retirements” and redesigning your lifestyle before you optimize for income.

The Year of Living Danishly by Helen Russell — One of the best first-person accounts of someone who pressed pause, moved abroad, and let the experience genuinely change them. Funny, honest, and surprisingly moving.

🎙️ Podcasts & Community

The Sabbatical Project — Run by DJ DiDonna, a Harvard researcher who studies sabbaticals for non-academics. His podcast and research are the most data-driven look at what extended breaks actually do for people. Featured in TIME, Fast Company, and the Wall Street Journal.

Sabbatical Stories — Real people, real career breaks. Each episode explores what motivated someone to leave, what surprised them on the road, and what they’d do differently. Great listening for the planning phase.

r/solotravel — One of the most active and genuinely helpful travel communities online. Great for destination-specific questions, safety intel, and connecting with people who’ve done exactly what you’re planning.

Nomad List — A database of cities ranked by cost of living, internet speed, weather, safety, and quality of life. Useful for deciding where to slow travel and for how long.

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This page is updated regularly as I discover new tools on the road. Got something you swear by? Send it my way.