How I Decide Where To Travel: Picking the Right Destination for the Perfect Trip

Choosing a vacation destination is never easy. Do you just tag along on ski trips with friends just because you don’t know where else to go? Begrudgingly head to that annual family Florida spot?

Discovering memorable and special vacation destinations takes a lot of time and energy, both of which many of us don’t have. Plus, vacation styles and goals can change as life evolves, so it can be difficult to figure out how to adapt to family-style vacations with new babies or get used to taking couples trips when you’re used to traveling alone.

After COVID-19 paused travel in 2020 and I had a child in 2021, I found my vacations, which used to be exotic, far-flung, and exciting solo trips or vacations with my partner or friends, changed. I stuck more to easy destinations closer to home and all-inclusive resorts in sunny spots that gave me the rest and energy reset I needed with a new baby.

In 2024, though, I decided I was ready to ramp things up again and created a system for myself to figure out where I wanted to go. With renewed energy and dedication, here’s what I did to plan my family’s upcoming summer 2025 vacation.

Evaluate Interest, Budget, and Travel Style

I’ve always loved wellness travel (way before it started trending), and I’ve always been a fan of warm, sunnier spots, urban hubs, and natural landscapes. I also love exploring, adventures, and safaris. However, with a 4-year-old in tow, I need to be selective about the types of vacations we can have where everyone has an enjoyable experience. I’ll leave a wellness-inspired trip for my next solo vacation and put a safari on the back burner (until my son is 7 or 8), but add some adventure back into our travel in ways that feel feasible, safe, and not too far off the beaten path.

So I made a list of exactly what I wanted to do on vacation, considering my partner and my son (and what they would enjoy), what we could spend on a trip in cash, and how we wanted to travel. For example, I wanted to rest but also have an adventure in a place that felt exciting but not too far-flung or complicated to get to, and an affordable destination where I could stay in decent hotels without overspending (now that my son is older, I enjoy hotels more than rental properties because I don’t desperately need access to a kitchen or laundry facilities).

Once I had clarity on the type of trip I wanted, it was time to think about actual places.

Find the Right Destinations

I brainstormed a short list of spots that I’d like to visit — here’s how:

Start With a General Bucket List

I pulled out my lifelong bucket list to start. I had to discount some destinations right off the bat for various reasons (war, distance, cost, general difficulty of the trip and activities), like the Galapagos Islands, Beirut, Nepal, Raja Ampat (in Indonesia), and Rishikesh (in India).

However, I was able to maintain several on my original list. I’ve had a bucket list since I was 12 (though it’s evolved greatly from its original 2 entries: Universal Studios and Paris). It’s never too late to create a bucket list or amend an existing one.

Look at a Map

One of the best ways to get inspired is to take out a globe or map. I often forget about certain destinations, while others have piqued my interest when I’m looking at different countries and places. For example, after consulting my map, I added the Azores and Cape Verde to my main bucket list.

Consult Friends, Blogs, and Social Media

I also spoke to friends, considered a few trusted travel blogs, and scanned the profiles of a few travel influencers I like. I used heavy curation for this, only consulting people, profiles, and websites where the travel style really resonated with mine. Social media was also a great resource for destinations I realized I wanted to skip or that were over-visited.

Finalize the Shortlist

After doing all the above, my list for summer 2025 included the following destinations:

• Croatia and Montenegro
• Malta
• Egypt
• Thailand
• Oman
• Hawaii
• Georgia (the country)
• Cyprus
• Puerto Rico
• Dominica
• Corfu and Albania

Narrow Down the List

I knew I would keep my shortlist of destinations lying around for future family trips, but I needed to start narrowing things down to find my perfect spot. Here’s how I did it.

Compare Destinations to Budget and Travel Goals

I compared my shortlist of destinations to my budget, travel style, and goals. Thailand and Hawaii felt too far away, and Georgia felt too far-flung of an adventure. Cyprus I wanted to do in combination with wine-tasting in Lebanon, which didn’t feel feasible given the current sociopolitical context. With expensive car rentals and pricier hotels, Puerto Rico felt a bit out of my budget, and many of the activities I’d like to do there would be better suited to a couples trip (like salsa lessons and nightlife in Old San Juan and Santurce). Corfu and Albania felt a bit too wild, and I didn’t feel like dealing with a ferry in addition to rental cars and planes.

This put my list at the following:

• Croatia and Montenegro
• Malta
• Egypt
• Oman
• Dominica

Take Key Factors Into Account: Seasons and Climate

Next, I ran through seasons. My travel would be in August, so I needed to consider things like crowds, heat, and hurricanes. It would be hurricane season in Dominica, and I was concerned about the island’s infrastructure in major storms, so I took that off the list. Egypt and Oman would be extremely hot, plus I had minor safety concerns about Egypt, so those destinations were coming off. This left me with Malta and Croatia and Montenegro.

Think About Overtourism

I knew Malta would be very crowded in summer, and I didn’t want to visit historic landmarks like Valletta with hordes of people. I’d also been to Dubrovnik in the summer before, and it was mobbed. So, I nixed Malta and chose Croatia and Montenegro, but without spending time in Dubrovnik.

Organize Points and Miles, Then Book

Now that I had my general destination in mind, I needed to figure out exactly where I wanted to go and how to structure the trip and start booking. I took count of all of my points balances, including credit card rewards, hotel points, airline miles, and even my Hotels.com balance.

Flight

I started researching airfare and routes. Although I wanted to go to Istria, getting to Montenegro from there was harder. Instead, I could fly between Madrid (MAD) and Dubrovnik (DBV) using Iberia Avios. But I didn’t want to stay in the center of Dubrovnik. That said, the Dubrovnik Riviera felt feasible, including cute towns along the 1-hour drive from the airport to Montenegro. So I decided on a road trip.

Car Rental

Then I needed to think about car rental and what it would be like to take the car over the border (and out of the EU). I’d done this before between Croatia and Bosnia without issue, so it felt doable to me, even with my toddler. I’d have to pay additional fees, but it fit into my budget as the rental cars were fairly affordable. The drive was short, so even if we got held up at the border, it shouldn’t take more than a couple of hours.

Hotels

The Hyatt Regency Kotor Bay looked positively dreamy. The images were stunning, and I knew I wanted to stay there for a few nights. It was on the outskirts of Kotor, but we could easily drive into the town center or reach it via taxi. I had some Hyatt points to burn and figured I could move some over from Chase. I also had IHG points to use for a stay at the Iberostar Herceg Novi.

Then I’d stay for 4 nights in Cavtat, a cute seaside village that felt less intense than Dubrovnik. There were plenty of affordable hotels that fit into my cash budget. The points and miles would cover our 3 plane tickets between Madrid and Dubrovnik, 4 nights at the Iberostar, and 3 nights at the Hyatt Regency Kotor. I’d pay cash for the car rental and a few additional nights at a hotel in Cavtat. For the Cavtat hotel, I applied my OneKey Rewards on 2 nights booked via Hotels.com, and also used my $300 travel credit for 2 nights booked via the Capital One Travel portal, plus I would get 10 points per $1 spent on the additional hotel cost since I’m a Capital One Venture X Rewards Credit Card holder.

Final Thoughts

I didn’t have to dig into my second choice, Malta, because I was able to make my first-choice trip work with my budget and travel goals. I had enough points and miles to cover a significant portion of the trip, and the rest fit into my cash budget. A short but stunning road trip felt exciting but feasible to do with a preschooler, and I organized a great mix of seaside and pool moments combined with exploring cute villages and checking out some of the stunning natural landscapes, all without having to face the cruise ship crowds that plague and exhaust Dubrovnik’s historic medieval center each summer. I booked cancelable rates for everything, just in case — a consequence of living in a post-COVID travel world, where you never know what might happen.

This is just 1 easy example of how my travel process planning works. I use this system to plan most of my trips. It helps me uncover exciting travel destinations (and define where I don’t want to go), keep my go-to, tried-and-true bucket list alive, and make sure that my travel companions (read: a cranky preschooler and my husband) and I will have a great time.