RESOURCES
Book a Flight!
Skyscanner
My go-to for comparing prices across airlines fast. I use it to scan a whole month at once and catch the cheapest days to fly, especially for routes into the Caribbean and Latin America where prices swing a lot.
Google Flights
Great for tracking price history and setting alerts. I check this alongside Skyscanner before booking anything, especially for flexible-date trips.
Here’s a Tip!
Set a price alert on Google Flights 4–6 weeks before you fly — fares into the Caribbean and Latin America can swing by $100+ in a single week, and an alert catches the drop before it’s gone.
Transportation
Welcome Pickups
Pre-book a vetted local driver to meet you at the airport, so you’re not negotiating a taxi fare at midnight in a country where you don’t speak the language. Highly recommend for first-time visits to Santo Domingo.
DiscoverCars
My pick for comparing rental car prices across multiple companies in one search, with clear cancellation policies so you’re not stuck if plans change.
Travel Insurance
SafetyWing
My go-to recommendation for digital nomads and long trips — flexible monthly coverage you can buy even after you’ve already left home.
World Nomads
Solid pick for adventure-heavy trips (diving, hiking, watersports) that some basic policies exclude.
Here’s a Tip!
Buy travel insurance within 14–21 days of your first trip deposit — that’s the window most policies require to unlock “cancel for any reason” and pre-existing condition coverage.
eSIM & Connectivity
Airalo
My default for short trips — install before you fly and land with data already working, no airport SIM-shop hunting. Use code VAUGHN2847 at checkout for a discount.
Holafly
Unlimited-data plans, which are worth it if you’ll be posting a lot of video/photos on a longer trip.
Start packing!
packing Tips
Check out my FREE packing guides!
Whether you’re headed to a beach town or a colonial city center, packing right makes the trip. Here’s what I bring every time:
What’s In My Bag?
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Bags
Tech
Gear
Booking Accommodations
Agoda
Especially useful for hotel deals in Southeast Asia and the Caribbean — I check here first for smaller boutique properties that don’t always show up elsewhere.
Booking.com
My default for free cancellation flexibility and the widest inventory, from apartments to resorts.
Expedia
Handy for bundling flights and hotels together, and their rewards program stacks well if you already book flights there.
Here’s where I book my tours!
Viator
Reliable for skip-the-line tickets and day tours with real reviews, especially in bigger cities.
Get Your Guide
Good alternative when Viator doesn’t have a specific local experience — I compare both before booking.