Planning your first trip with someone you haven’t travelled with can be a bit like cooking a meal together for the first time – it could be fun, but potentially chaotic.
Whether it’s with a significant other, family members, friends or colleagues, the secret to a harmonious trip lies in a blend of proper communication, thoughtful planning and a pinch of compromise.
Here are some practical tips and expert advice to help you navigate all these different dynamics and still enjoy your vacation.
Before planning begins, establish a foundation of open communication. Discuss travel preferences, expectations and boundaries at length.
“Go in without any assumptions and listen with an open mind,” said Ruchira Raj, a registered psychotherapist with the Singapore Association for Counsellors.
Two other things to keep in mind when having these conversations are empathy and fairness. “Empathy is more than about understanding someone’s needs and wants, it is also about having empathy for oneself. Do you know what you want, and are you (holding yourself back) from expressing yourself in an attempt to be nice to everyone else?” she said.
As for fairness, it is about how to create a sense of equality in planning a vacation, as the people you’re travelling with would want to have an equal say and be part of the conversation.
A group of travellers. (Photo: iStock/bernie_photo)
While open communication sets the stage, it’s equally crucial to identify overlapping interests. Hendric Tay, co-founder of The Travel Intern, a content and social media agency from Singapore that specialises in travel marketing, suggests asking each person in the travel group to share their top three things to do, see or eat.
“Being respectful of each other’s top wants and prioritising that can help mitigate any differences in travel styles or preferences,” he said.
Money can be a sensitive topic, but it is also critical to address to align expectations especially when the travel group consists of people with differing financial backgrounds. Ruchira shared that there are two types of budget discussions to have: A big-picture discussion on larger expenses such as whether to splurge on luxurious accommodations or opt for more modest options further from the city, and a tactical-level discussion to set budgets for daily expenses such as meals.
Mingwei Chu, founding partner of Beyond Footprints Travel, a Singapore-based luxury travel agency that specialises in tailor-made private tours, highlighted that understanding whether companions prefer fast-paced sightseeing or leisurely exploration can make a significant difference in planning.
Additionally, “some crave adventure, while others prioritise relaxation. For instance, one person might thrive in the buzz of city life, while another finds joy in the serenity of nature”, he said.
Set boundaries: Figure out what is appropriate to share with your colleagues. Ruchira advised practising selective vulnerability, in which you share just enough to foster rapport but stop shy of overly intimate details that may blur professional boundaries.
Start small: Tay suggested starting with a short trip to test dynamics. “While aligning before a trip helps, nothing beats doing a trial run to a nearby destination for a couple of days,” he noted.
Define roles and responsibilities: Decide on shared duties, such as who handles logistics or budgeting, to maintain fairness and prevent misunderstandings.
Leverage team strengths: You can also delegate tasks based on individual strengths. For example, the most organised person in your group might handle flight and hotel bookings while another who has been to the destination before can take care of activity research.
A couple having an argument. (Photo: iStock/Rawpixel)
Respect individual preferences: Ruchira highlighted the importance of maintaining intimacy while respecting differences. “When sharing a space, how will you negotiate those shared spaces?” she said, stating bathroom usage and sleeping times as examples of what to discuss.
Plan together: Using collaborative itinerary planning tools like Google Sheets or Notion makes planning easier and ensures both parties feel involved.
Learn from conflicts: Conflicts on a trip, especially between couples, are inevitable. Instead of feeling defeated by them, “learn from conflicts and move forward”, said Ruchira. One way to do this is an end-of-day reflection, where you chat about how your day went and what can be done differently.
Make an activity-based itinerary: Instead of planning an itinerary around a destination, plan it around an activity you’ll both enjoy. “Hiking, diving, and snowboarding trips are great ways to experience travelling together without the pressure of catering to too many preferences," said Tay.
A family taking a selfie while on holiday in Bangkok. (Photo: iStock/gahsoon)
Prioritise accessibility: If you’re travelling with the elderly and little ones, look for robust infrastructure that caters to their needs. This includes comfortable hotels with family-friendly features, accessible restaurants with diverse dining options and convenient transportation, according to Chu.
Acknowledge power dynamics: Families often have set roles and patterns. Recognise and respect these to avoid unnecessary friction and ensure everyone feels heard.
Celebrate togetherness: Remind yourself and your family of the primary reason for such trips, which is to spend quality time together and create cherished memories. “By shifting the focus from individual preferences to collective happiness, we can foster a more enjoyable atmosphere for all,” said Chu.
Charlene Chew, a travel content creator who goes by @missuschewy online and documents trips with her husband and their two young daughters, echoed this sentiment. “Since you’re already spending money to go on (a) trip, make it a happy and memorable one for the entire family,” she said.
Integrate inclusive activities: Chu also recommended planning activities that encourage participation from all ages, as this can serve as a good starting point for creating an inclusive experience.
As for Chew, she advised that in planning an itinerary, parents should make sure it is not only child-centric but age-appropriate as well.
“If you plan to include amusement parks into your itinerary, it is advisable to consider Disneyland instead of Universal Studios Japan if your child is less than eight to 10 years old,” she said.
A group of young travellers in Kuala Lumpur. (Photo: iStock/Benjamin Tan)
Establish the non-negotiables: Communicate clearly what each friend’s must-dos on the trip are, so that everyone’s baseline requirements for the trip are met.
Identify a common interest: By focusing on shared passions, you can find activities that resonate with everyone involved, advised Chu. For instance, if everyone in the group loves animals, make it a point to include an aquarium or wildlife park visit into the itinerary.
Encourage flexibility: While having pre-trip conversations, “it’s good to discuss if (the group) should stick together for the entire trip or have room for (members of) the group to do their own thing and be flexible,” said Tay.
Remember why you’re there: Even the best-laid plans can hit bumps along the way, which is why Chu recommended approaching the trip with an open mind and collaborative attitude. Doing so, he said, helps smooth over any hiccups and keeps the focus on enjoying the experience together.
Identify early signs: According to Ruchira, this can look like a lack of engagement (for instance, short, one-worded answers to suggestions), an overly dominant trip leader or planner, and a lack of boundaries (for instance, pressuring someone to go out for drinks when they don’t feel like it). Once you identify such signs, be proactive in addressing them before they escalate.
Use ‘I’ language: When addressing an issue, using “you” and speaking in an accusatory tone may only cause the other party to be defensive. Starting your sentences with “I” highlights how much something is affecting you and makes you more assertive. For example, say “I feel stressed when we’re late” instead of “You’re always late”.
Stay focused on the issue: Ensure that the conversation focuses on the issue at hand, instead of making it about the person and dragging other grievances and personal faults into it.
Ruchira also had this to share about building stronger connections post-travel. “One thing that helps is carrying good memories in a tangible format (like a photograph),” she said.
Having a memento like this serves as a tangible reminder of shared good times.
You might need to turn to your apps to avoid any arguments while on holiday. (Photo: iStock/Deagreez)
With the right apps, you can turn your smartphone into a pocket-sized personal assistant for all your travel planning needs and focus more on having a good time.
TripIt: This app organises your travel plans in one place by syncing email confirmations for flights, hotels, and car rentals, creating a comprehensive itinerary.
Wanderlog: Ideal for collaborative planning, this app allows groups to build itineraries together, adding notes, places to visit and travel routes.
Splitwise: Keep track of shared expenses effortlessly. This app calculates who owes what and simplifies the process of settling bills.
Tricount: Similar to Splitwise, Tricount helps manage group expenses and allows for easy reconciliation at the end of the trip.
Maps.me: This app offers offline maps with detailed routes for hiking, driving, and city exploration, making it an excellent choice for travellers venturing into areas with limited connectivity.
Baidu Maps: An alternative to Google Maps in China, where the Google Suite is inaccessible without a VPN.
Komoot: A favourite among outdoor enthusiasts, Komoot provides navigation for outdoor activities like hiking and cycling, with detailed trail maps and user reviews for added guidance.
Klook: Boasts a wide range of activities, experiences, tours and tickets, particularly across Asia.
Viator: A robust platform for discovering guided tours and unique experiences in Western countries.
Continue reading...
Whether it’s with a significant other, family members, friends or colleagues, the secret to a harmonious trip lies in a blend of proper communication, thoughtful planning and a pinch of compromise.
Here are some practical tips and expert advice to help you navigate all these different dynamics and still enjoy your vacation.
START WITH OPEN CONVERSATIONS
Before planning begins, establish a foundation of open communication. Discuss travel preferences, expectations and boundaries at length.
“Go in without any assumptions and listen with an open mind,” said Ruchira Raj, a registered psychotherapist with the Singapore Association for Counsellors.
Two other things to keep in mind when having these conversations are empathy and fairness. “Empathy is more than about understanding someone’s needs and wants, it is also about having empathy for oneself. Do you know what you want, and are you (holding yourself back) from expressing yourself in an attempt to be nice to everyone else?” she said.
As for fairness, it is about how to create a sense of equality in planning a vacation, as the people you’re travelling with would want to have an equal say and be part of the conversation.
A group of travellers. (Photo: iStock/bernie_photo)
IDENTIFY SHARED GOALS
While open communication sets the stage, it’s equally crucial to identify overlapping interests. Hendric Tay, co-founder of The Travel Intern, a content and social media agency from Singapore that specialises in travel marketing, suggests asking each person in the travel group to share their top three things to do, see or eat.
“Being respectful of each other’s top wants and prioritising that can help mitigate any differences in travel styles or preferences,” he said.
DISCUSS BUDGET EARLY
Money can be a sensitive topic, but it is also critical to address to align expectations especially when the travel group consists of people with differing financial backgrounds. Ruchira shared that there are two types of budget discussions to have: A big-picture discussion on larger expenses such as whether to splurge on luxurious accommodations or opt for more modest options further from the city, and a tactical-level discussion to set budgets for daily expenses such as meals.
CONSIDER TRAVEL STYLES
Mingwei Chu, founding partner of Beyond Footprints Travel, a Singapore-based luxury travel agency that specialises in tailor-made private tours, highlighted that understanding whether companions prefer fast-paced sightseeing or leisurely exploration can make a significant difference in planning.
Additionally, “some crave adventure, while others prioritise relaxation. For instance, one person might thrive in the buzz of city life, while another finds joy in the serenity of nature”, he said.
TAILOR TIPS TO THE GROUP
1. Travelling with colleagues
Set boundaries: Figure out what is appropriate to share with your colleagues. Ruchira advised practising selective vulnerability, in which you share just enough to foster rapport but stop shy of overly intimate details that may blur professional boundaries.
Start small: Tay suggested starting with a short trip to test dynamics. “While aligning before a trip helps, nothing beats doing a trial run to a nearby destination for a couple of days,” he noted.
Define roles and responsibilities: Decide on shared duties, such as who handles logistics or budgeting, to maintain fairness and prevent misunderstandings.
Leverage team strengths: You can also delegate tasks based on individual strengths. For example, the most organised person in your group might handle flight and hotel bookings while another who has been to the destination before can take care of activity research.
A couple having an argument. (Photo: iStock/Rawpixel)
2. Travelling with a significant other
Respect individual preferences: Ruchira highlighted the importance of maintaining intimacy while respecting differences. “When sharing a space, how will you negotiate those shared spaces?” she said, stating bathroom usage and sleeping times as examples of what to discuss.
Plan together: Using collaborative itinerary planning tools like Google Sheets or Notion makes planning easier and ensures both parties feel involved.
Learn from conflicts: Conflicts on a trip, especially between couples, are inevitable. Instead of feeling defeated by them, “learn from conflicts and move forward”, said Ruchira. One way to do this is an end-of-day reflection, where you chat about how your day went and what can be done differently.
Make an activity-based itinerary: Instead of planning an itinerary around a destination, plan it around an activity you’ll both enjoy. “Hiking, diving, and snowboarding trips are great ways to experience travelling together without the pressure of catering to too many preferences," said Tay.
A family taking a selfie while on holiday in Bangkok. (Photo: iStock/gahsoon)
3. Travelling with family
Prioritise accessibility: If you’re travelling with the elderly and little ones, look for robust infrastructure that caters to their needs. This includes comfortable hotels with family-friendly features, accessible restaurants with diverse dining options and convenient transportation, according to Chu.
Acknowledge power dynamics: Families often have set roles and patterns. Recognise and respect these to avoid unnecessary friction and ensure everyone feels heard.
Celebrate togetherness: Remind yourself and your family of the primary reason for such trips, which is to spend quality time together and create cherished memories. “By shifting the focus from individual preferences to collective happiness, we can foster a more enjoyable atmosphere for all,” said Chu.
Charlene Chew, a travel content creator who goes by @missuschewy online and documents trips with her husband and their two young daughters, echoed this sentiment. “Since you’re already spending money to go on (a) trip, make it a happy and memorable one for the entire family,” she said.
Integrate inclusive activities: Chu also recommended planning activities that encourage participation from all ages, as this can serve as a good starting point for creating an inclusive experience.
As for Chew, she advised that in planning an itinerary, parents should make sure it is not only child-centric but age-appropriate as well.
“If you plan to include amusement parks into your itinerary, it is advisable to consider Disneyland instead of Universal Studios Japan if your child is less than eight to 10 years old,” she said.
A group of young travellers in Kuala Lumpur. (Photo: iStock/Benjamin Tan)
4. Travelling with friends
Establish the non-negotiables: Communicate clearly what each friend’s must-dos on the trip are, so that everyone’s baseline requirements for the trip are met.
Identify a common interest: By focusing on shared passions, you can find activities that resonate with everyone involved, advised Chu. For instance, if everyone in the group loves animals, make it a point to include an aquarium or wildlife park visit into the itinerary.
Encourage flexibility: While having pre-trip conversations, “it’s good to discuss if (the group) should stick together for the entire trip or have room for (members of) the group to do their own thing and be flexible,” said Tay.
Remember why you’re there: Even the best-laid plans can hit bumps along the way, which is why Chu recommended approaching the trip with an open mind and collaborative attitude. Doing so, he said, helps smooth over any hiccups and keeps the focus on enjoying the experience together.
TOOLS AND STRATEGIES FOR NAVIGATING CONFLICT
Identify early signs: According to Ruchira, this can look like a lack of engagement (for instance, short, one-worded answers to suggestions), an overly dominant trip leader or planner, and a lack of boundaries (for instance, pressuring someone to go out for drinks when they don’t feel like it). Once you identify such signs, be proactive in addressing them before they escalate.
Use ‘I’ language: When addressing an issue, using “you” and speaking in an accusatory tone may only cause the other party to be defensive. Starting your sentences with “I” highlights how much something is affecting you and makes you more assertive. For example, say “I feel stressed when we’re late” instead of “You’re always late”.
Stay focused on the issue: Ensure that the conversation focuses on the issue at hand, instead of making it about the person and dragging other grievances and personal faults into it.
Ruchira also had this to share about building stronger connections post-travel. “One thing that helps is carrying good memories in a tangible format (like a photograph),” she said.
Having a memento like this serves as a tangible reminder of shared good times.
You might need to turn to your apps to avoid any arguments while on holiday. (Photo: iStock/Deagreez)
EMBRACE TECHNOLOGY
With the right apps, you can turn your smartphone into a pocket-sized personal assistant for all your travel planning needs and focus more on having a good time.
1. Itinerary Management
TripIt: This app organises your travel plans in one place by syncing email confirmations for flights, hotels, and car rentals, creating a comprehensive itinerary.
Wanderlog: Ideal for collaborative planning, this app allows groups to build itineraries together, adding notes, places to visit and travel routes.
2. Budgeting
Splitwise: Keep track of shared expenses effortlessly. This app calculates who owes what and simplifies the process of settling bills.
Tricount: Similar to Splitwise, Tricount helps manage group expenses and allows for easy reconciliation at the end of the trip.
3. Navigation
Maps.me: This app offers offline maps with detailed routes for hiking, driving, and city exploration, making it an excellent choice for travellers venturing into areas with limited connectivity.
Baidu Maps: An alternative to Google Maps in China, where the Google Suite is inaccessible without a VPN.
Komoot: A favourite among outdoor enthusiasts, Komoot provides navigation for outdoor activities like hiking and cycling, with detailed trail maps and user reviews for added guidance.
4. Online Travel Agencies
Klook: Boasts a wide range of activities, experiences, tours and tickets, particularly across Asia.
Viator: A robust platform for discovering guided tours and unique experiences in Western countries.
Continue reading...