Crafting Your Dream Trip: Insights from Context Travel's Client Experience Team

Here at Context Travel, we're passionate about helping you craft the perfect itinerary, one that helps you reach the heart of a destination. Think local tapas joints you can’t find on your own, a tour guide who becomes a friend, or an eye-opening revelation about an artwork you’ve seen in history books but never really understood. 

It all starts with great planning, so we’ve rounded up a few of our top tips from two of our Client Experience managers, Corrie and Brittany. It’s like having a travel advisor’s best insights right in the palm of your hand! 

Of course, if you have other questions or would like assistance, you can contact us here. 

Let’s begin, shall we?

Finding Your Perfect Destination

The first step on this adventure is identifying your ideal destination. Consider your interests – are you a history buff drawn to ancient ruins, or a gourmand seeking a culinary adventure? Aligning your destination with your passions is key to a fulfilling experience.

Joo Chiat Road, Singapore

Budget and timing are also crucial factors. 

"If you are just looking to get away on a budget, a fun way to pick a destination is using the “Anywhere” feature on Google Flights. Set your travel dates, and select “Anywhere” as your destination–you’ll see flight options pop up all over the world and can filter by the price." - Corrie

If you can travel in the off season, you’ll likely have a much quieter and intimate experience in the venues and destinations you choose to visit.

“It’s great to travel in the off or shoulder season, when crowds aren’t as intense. I traveled to Venice–notorious for its summer crowds–in January, and it was just me and my Context guide in the Doge’s Palace.” - Corrie

Doge's Palace, Venice

If your only time to travel is during the busy season, be sure to research local holidays and events to avoid unforeseen closures or inflated prices.

“Are you choosing dates that overlap with country or city events or holidays? For example, Italians typically vacation in August and many shops will be closed.” - Brittany

Building a Memorable Itinerary

Now comes the exciting part: crafting your itinerary. List all the must-see sights, activities, and local experiences you want to explore. 

“Create a list of some of your must-sees and must-dos in your destination so you aren’t forgetting anything important. Put together a soft itinerary so you can make sure you have scheduled time for each of these activities.” - Corrie

This will help structure your trip and avoid feeling overwhelmed. However, leave room for spontaneity! Some of the most unforgettable moments occur when you least expect them.

Context travelers stop for a beer in London

For popular venues and restaurants, especially during peak season, research and book reservations in advance. 

“Once you have a plan, secure tickets or tours as soon as possible! Venues have become very strict with their ticket limits, and they do sell out.” - Brittany

Pre-Trip Planning

For a smooth and enriching experience, some pre-trip planning is essential. Research cultural norms so you understand what to wear and how to remain respectful in important venues or in interactions with locals. 

“You can prepare with a pre-trip talk from Context. Led by a Context expert, these shorter videos help answer your questions so you can focus on deeper connections once you arrive.” Brittany 

It’s also important to consider any specific mobility needs and the city's infrastructure. Researching transportation options beforehand ensures a smooth travel experience.

“Look into how established the public transport network is in your destination. It’s super easy to hop onto the Metro in Paris, but you may want to add car service if you are exploring the Tuscan countryside.” Corrie

The London Underground

Finding the Ideal Tour

Once you've chosen your destination, explore tours that bring it to life. Context Travel offers a variety of options to suit diverse needs. Opt for shorter introductions, usually around two and half hours, for a quick highlight of the city. These tours are great for familiarizing yourself with the layout of your destination and can help orient you for the rest of your trip.

If you want to go deeper, consider half-day explorations or in-depth full-day tours depending on your time constraints and interests.

“If you have more time available, a half or full-day tour with an expert makes sense to add to your itinerary. If you are interested in art history, choose an in-depth half-day art tour with an expert guide for a deep dive into the topics you care about. 

On the flip side, if you don’t know much about ancient history but are itching to learn more, it makes sense to take a tour with an expert guide who can point out the significance of the sites and really help you relate more deeply to the culture and history of your destination.” - Corrie

Teotihuacan, Mexico

Let us know your group size and interests and we'll find the ideal tour for you. Solo travelers or families and groups who seek more flexibility should consider audio guides for added freedom without losing the value of expert guidance.

“An audio guide is a great way to see a bit more of the city with a Context expert in your ear. Pop your headphones in and explore at your own pace. I love our audio guides because you can start, pause, or stop at any time and then resume when it fits your schedule.” - Corrie 

Full-Day Immersions

Let’s talk a little more about full-day tours. While this might conjure images of tired families fanning themselves in the heat of the day while slowly trodding behind a bright colored flag sticking out above the crowds, our full-day tours offer an alternative. 

Yes, you will do plenty of walking, but it will be alongside-not behind–one of our passionate expert guides. 

“Our tours are structured but not scripted, and experts are happy to tailor or adapt the tour based on your needs and interests, as long as it is along the tour route.” - Brittany

Plus, a full-day experience allows you to connect with a local while also visiting additional venues that aren’t normally included in shorter tours.

“Some of our full-day tours include venues that we normally don’t include on our half-day tours, so this is an added value if these destinations are on your bucket list. For example, we visit Park Güell in our Barcelona in a Day tour and are able to offer a visit to St. Patrick’s Cathedral on our Dublin in a Day tour.” - Corrie. 

Park Güell, Barcelona

We recommend scheduling full-day tours earlier in your trip when your energy is high. Lunch breaks are factored in, and there's flexibility for restroom and snack breaks along the way. 

Full-day tours also often offer optional add-on car services for an additional fee, perfect if you prefer a break from walking or have specific mobility needs.

Going Beyond the Expected

Context Travel's knowledgeable guides are your key to unlocking a destination's hidden treasures. They'll navigate you away from the crowds and introduce you to unique experiences and cultural nuances you might otherwise miss.

After you’ve seen the major sites, go deeper into your destination with an expert leading the way. From Fashion in Milan to Artisan Workshops in Florence to our Night Food Tour in Shibuya, there are so many ways to see your destination in a different, unique, and more personable way. These experiences are your ticket behind the curtain, letting you in on life as a local.

Fashion in Milan tour with Context

“Feel free to provide notes about you and/or your group so we can share them with the expert before your tour. Why are you traveling? Have you been to this city before? Is your child into ancient history or a specific artist from the area? What inspired you to travel to this place?

Knowing more about you helps us create a personalized experience that allows you to connect and engage far more deeply than other tours. This leads to strong, vivid memories for our travelers that influence them for the rest of their lives.” - Brittany

Accessibility Matters

At Context Travel, we believe that everyone deserves an enriching travel experience. No matter who you’re booking with, be sure to share any accessibility issues you or your party may have. 

If traveling with Context, we’ll contact the local experts and our portfolio team in that region to figure out how to make the tour work for you and ensure you have a great experience.

“For those with mobility aids, know what you will be bringing and if the places you’d like to visit are accessible. Consider narrow sidewalks, stairs, or cobblestone streets, or if the venues allow your specific mobility aid. Sage Traveling is a valuable resource that offers information on accessible travel in Europe.” Brittany 

For guests with serious mobility concerns, we also offer private tours and car service. If you have accessibility concerns, do not hesitate to reach out to our team to learn more.

Traveling with Young Explorers

Traveling with children can be a great bonding and learning experience for families. But we all know that younger travelers often have shorter attention spans and need more interaction. 

National Gallery Kids Tour, London

Or family tours are designed for younger travelers, with shorter durations and engaging storytelling to keep young minds captivated.

If traveling with newborns or toddlers, it’s helpful to know what you can and should bring on a tour. 

“If you're able, you may want to use a baby carrier instead of a stroller in the Vatican Museums as you will be going up lots of steps. We can help you determine what will work best in various venues.” - Brittany

Final Tips

Remember that you are traveling to experience life through a different lens, connecting across cultures over the things that bind us: a love of art, a passion for history, a connection with agriculture, or a fascination with architecture. Your travels should be fun, engaging, and open your eyes to the numerous ways we are all different, but the even greater number of ways in which we are similar. 

Try something new. Talk with a local. Explore side street shops or learn how to order a special item at a neighborhood cafe. These are the things that you’ll remember for years to come.

Nishiki Market, Kyoto

Travel Authentically, Connect Deeply

We hope that these tips help you craft an unforgettable adventure. Remember, the most treasured souvenirs aren't trinkets, but the memories you create and the knowledge you gain. So, pack your bags, unleash your curiosity, and join Context Travel on a journey that surpasses the ordinary.

Need assistance planning your trip? Reach out to our Client Experience team here.

About Corrie, Pre-Booking Manager: We help support our customers with tour selection, checking availability, confirming pricing, and assisting with bookings as needed. The pre-booking team is also your go to resource for all things Context Pre-Trip Talks and Audio Guides.

About Brittany, Consult Manager: The Client Experience Consult team helps with larger multi-day and multi-city tour planning, with a focus on regions to ensure product specialization.