Jessica’s Top 5 Insider Travel Tips

From many years traveling myself and in the travel business, I have learned a thing or two to make your travel more stress-free. 

Here are my top 5 travel tips for a seamless travel experience as you are preparing for that next big getaway! 

1. Optimize your Carry-On Bag

I always recommend bringing a good book for long-haul flights!

The first steps of your trip start at home - set yourself up for success by packing your bags with intention! Think of what items you want to be accessible to you during the flight, versus what can be safely stowed away in your checked bag or overhead bin.

For my own carry on, beyond essential travel documents I always bring my eye mask, Kindle (or library book), Liquid IV, and travel toiletries including a hydrating face mist and lip balm.   

These little things can make a long-haul flight much more comfortable. I also make sure to have all of my devices and chargers in an easy to reach spot in my bag.  

A carry-on bag with different compartments helps keep everything organized and easy to find during the flight. My favorite is the Tumi Voyager backpack. 

Avoid leaving things in your checked bag that you can’t easily replace if there is any delay in getting your bags back from the airline. Unfortunately, this does happen from time to time! Important travel documents, medication, and electronics should stay with you in your carry-on or personal item.  

Those who know me well know I almost never check a bag. If you really want to make your travel more seamless, I always recommend just bringing a carry-on plus a backpack or tote to save time checking bags and waiting at baggage claim. I recommend a high-quality hard-cover carry-on with a brand like Tumi, Paravel, Away or Monos.  

2. Streamline your Airport Experience

Some easy preparation can help make your time in the airport stress-free.

Navigating a busy airport can be frustrating, so it’s important to be prepared! Make sure to arrive at least two hours early with all your required documents.

Real IDs will be required for traveling around the U.S. starting May 7, 2025. Without one, you’ll need to bring your passport to pass through airport security, even if you are only traveling domestically.

Consider applying for Global Entry or TSA Precheck to make passing through security and customs a smoother process with dedicated, and usually shorter, lines. This is an absolute must for frequent travelers and only costs $75-$120 for a year of privileges. If you don’t have Global Entry, for returning to the US, I highly recommend downloading the Mobile Passport Control app to streamline customs and immigration.

Once you’ve passed security, kick back and relax in an airport lounge. Most airlines will offer free access to their lounges for first and business class ticket holders. Also credit cards like the Amex Platinum or Chase Reserve can include lounge access. And let’s face it, the lounge couches are a lot more comfortable than seating at the gate!

3. Consider Travel During Shoulder Seasons

Traveling in Italy during March shoulder season with fewer crowds and crisper weather.

Picking the right time to travel is one my biggest travel tips, since it sets the stage for the style trip you will have. Traveling during the spring and fall can be a great way to enjoy all a destination has to offer with fewer crowds and a lower price tag.  

Spring and fall offer pleasant weather in many countries. Italy, Spain, France, and Portugal are especially nice these times of year, being not too hot or too cold. They also showcase beautiful landscapes with blooming flowers in the spring or vibrant foliage in the fall.  

Shoulder season travel is also a great way to visit popular locations without the buzz of crowds and potential peak-season price markups. Tropical destinations like the islands of the Maldives and Thailand still have beautiful weather almost year-round, but it is easier to find reduced rates in off-peak seasons. 

4. Go Beyond Sightseeing

Creating stained glass at Primland Resort in Virginia.

There is so much more to travel than just checking out the main tourist attractions! Take a step off the beaten path and spend the day as the locals do.

After you’ve seen the Eiffel Tower, why not learn to bake your own pain au chocolat? Or while in the Caribbean, spend the afternoon with a local fisherman and cook up your fresh catch for dinner. You can make your own leather gloves in Lisbon, train a sheepdog in the Scottish Highlands, and create mosaic art in Marrakech.

As a travel advisor, it’s my goal to help my clients have the most meaningful and memorable experiences as they travel the globe! No two trips are exactly alike, and I love recommending clients try something a bit different to immerse yourself in the local culture.

5. Consider Travel Insurance

Travel insurance is one of the most important things you can pack for your trip, and it doesn't take up any room in your suitcase!

Anyone who has planned a trip with me knows I’m a huge advocate for purchasing travel insurance! You just never know what can happen and there are many variables out of your control while traveling.

As an advisor with Brownell Travel, I’m able to offer my clients some of the best coverage for their trips. Read more about why I think travel insurance is so important in my blog post here.

At JWT we are always here to make your travel experience as seamless as possible!

Travel can be a huge investment of your time and money. Careful planning ahead of time will allow you to enjoy all the best parts of traveling, without getting caught up in logistics.

As always, I am honored to be your travel planning partner and let you focus on what's most important – enjoying your trip!