Amakhala Reserve, South Africa

How I Plan My Trips

The best trips rarely happen by accident. Behind every unhurried afternoon and perfect cup of coffee is a little planning.

After planning a variety of trips over the years, from solo international adventures to group travel for more than 10 people, I’ve developed a method that works for every kind of trip. Whether the goal is to explore a new city or relax on a beach, the framework is similar.

Long Island, Bahamas
Long Island, Bahamas

Decide on the Type of Trip

Do you want to explore a part of the world you haven’t seen? Are you looking for a city where you can stroll the streets, or for nature where you can hike to waterfalls and overlooks? Or do you need a beach vacation where you can read a book by the ocean or pool? Once you’ve decided, you can move on to the next step.

Create a Shortlist of Destinations

Once you know what type of trip you want, create a shortlist of destinations that fit your criteria. I try to keep this shortlist to 3-5 destinations.

Porto, Portugal
Porto, Portugal

Decide When You’re Going

You might already have a time frame in mind, but if you don’t, this step matters. Some destinations are best during certain seasons, and maybe there’s a festival you want to catch. Researching each location at different times of the year can help you decide where to go and when.

Choose a Destination and Start Researching

Once I’ve picked a destination, I learn everything I can about it. I want to understand the key things I can’t miss and what the area is known for. I research where to stay, what to see, what to do, and where to eat.

Manhattan Bridge, New York City
Manhattan Bridge, New York City

Use Google Maps

Whenever I find something of interest, I save it in Google Maps. The more pins, the better. For each city, I have a variety of saved spots, so as I wander, I have plenty of options for a bite to eat or simply directions to the next point of interest. This saves me so much time because I never have to look up a coffee shop or lunch spot on the fly.

I also always download the map offline before I leave, so I have directions even if I lose cell service. This is critical if you’re headed somewhere like a national park or a remote destination where service can be spotty.

Amakhala Reserve, South Africa
Amakhala Reserve, South Africa

Book Tickets and Tours

No matter the type of trip, I book tickets to popular sites and tours ahead of time. Things fill up quickly, especially during peak season, and I don’t want to miss something simply because I didn’t plan ahead. It also gives me something to look forward to throughout the trip. I do this even on beach vacations, because it’s nice to have a few activities planned between relaxing days.

Amakhala Reserve, South Africa
Amakhala Reserve, South Africa

Planning for a Group

When I’m traveling with a larger group, I share my saved map and the plan in advance so everyone knows what to expect. I also build in free time, so people can explore what interests them most.

Final Thoughts

A little planning doesn’t take the spontaneity out of travel. It creates room for it. When the logistics are handled, you’re free to wander, linger, and enjoy the moment. If you would like help booking a trip, I’m here to support you. Fill out this form to get started.

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