Taking (and surviving) your first trip together as a couple is an important relationship milestone. It may seem daunting at first, but it’s also a precious opportunity to build a core memory in years to come! Follow our overseas holiday tips and ideas for couples to have a thoroughly enjoyable first vacation!
1. Choose a destination together based on common interests
The world is your oyster! You might be overwhelmed trying to decide on one travel destination from so many choices. Narrow down your options by discussing with your partner what you both want from this holiday – relaxation or adventure? Nature or city views? – and seeing what are some common goals and interests that draw you to a travel destination.
Here are our recommendations for the best couple places to travel to, categorised based on various interests, with some cities appealing to many interests at once. These are great for couples making your first trip together from Singapore as they consider accessibility, reasonable budgets and safety.
- For beautiful nature views: Bali, Indonesia; Krabi, Thailand; Langkawi, Malaysia; Maldives; Cinque Terre, Italy; Amalfi Coast, Italy; Santorini, Greece
- For rich culture immersion: Kyoto, Japan; Hokkaido, Japan; Seoul, Korea; Chiang Mai, Thailand; Shanghai, China; Melbourne, Australia; Nice, France; Venice, Italy
- For great food and distinct cuisines: Bangkok, Thailand; Osaka, Japan; Taipei, Taiwan; Hong Kong; Shanghai, China; Lyon, France; Florence, Italy; Athens, Greece
- For outdoor adventures and adrenaline: Perth, Australia; Sydney, Australia; Bali, Indonesia, Raja Ampat, Indonesia; Krabi, Thailand; Phuket, Thailand
- For a relaxing wellness retreat: Bali, Indonesia; Krabi, Thailand; Chiang Mai, Thailand; Maldives; Bintan, Indonesia
- For exciting shopping sprees: Bali, Indonesia; Bangkok. Thailand; Seoul, Korea; Osaka, Japan; Hanoi, Vietnam
2. Agree on a budget or estimated expenditure beforehand
Money can be a sensitive issue, and the means and willingness to spend on leisure travel can vary greatly, depending on your ages, salaries, savings – or even stage in your relationship. Communicate with your partner to understand each others’ needs, and help agree on a joint budget. Deciding beforehand on how to settle personal expenses overseas, if any, can be beneficial, too.
Some major considerations for planning your travel expenditure include flights and accommodations (which a quick search on airline or travel aggregator websites can help estimate) as well as any big-ticket items you think of spending on there, for example tickets to a famous tourist attraction, a full-day tour package, or a special anticipated activity that may be costly.
Pro-tip: Many prefer to go budget-friendly on their first trip to test the waters, so countries in Southeast Asia and East Asia are ideal. Keep on the lookout for overseas travel packages via social media or online sites to help save costs, and subscribe to airlines to be notified of cheap flight deals.
3. Timing is everything
Ideally, you’ll want an itinerary that allows plenty of time to enjoy each other’s company while exploring the country, and also sufficient down time, so as not to tire yourselves out.
We recommend three to five full days, short and sweet for a first holiday together without overstaying each other’s welcome. This will, of course, depend on your planned activities and travel style or goals.
Make sure to account for flight schedules as well. Landing too late at night might pose challenges safely getting to your accommodations, not to mention spending on an extra hotel night.
Landing in the afternoon might see you needing to recharge with a nap and a meal, especially if you’re flying with a low cost carrier and unwilling to pay for overpriced, unsatisfying meals.
Morning flights are the best in theory, but may only work for people who are able to sleep while on board. You will also need to stow your luggage – challenging if your accommodations are out of the way – or else you’ll need to lug them around with you until check-in time (3pm or 4pm at most accommodations).
4. Pick accommodations thoughtfully for optimal comfort
You and your partner will be staying together for the first time in a foreign country, so it’s crucial to ensure both parties are comfortable with the facilities and environment. First, discuss rooming arrangements: are you two comfortable with sharing a room, and with sharing a bed? Sharing the room is great for a romantic holiday and likely saves costs, but some may prefer more private arrangements to recharge in between packed travel days.
Browse your options carefully and look out for small, but important details – what are each other’s needs and wants when choosing where to stay? Are you or your partner okay with open or see-through bathrooms or would something more private be appropriate at this stage of the relationship? Would you two need soundproofed walls for better relaxation and privacy? Is it important to have facilities such as gyms or wellness facilities at your accommodations, or breakfast included so the day doesn’t need to start hunting down food?
Location-wise, do you two prefer a quiet and cosy stay? Or would you want somewhere close to where the action happens? And when it comes to transport, it could be beneficial to stay somewhere near a public transport stop, or with a parking space if you are renting a vehicle. Cabbing everywhere is an option too for more remote accommodations, but ensure you and your partner are aligned on what main transportation modes you two would want to take. (You’ll be surprised how many travelling couples end up fighting over something as seemingly minor as this!)
5. Communicate travel styles, responsibilities and dynamics
Holiday planning can certainly get stressful when you’re striving for the perfect first-ever trip as a couple. Discuss and figure out with your partner if your preferred travel style would be more:
- Type A – planning and scheduling ahead your days with lots of attention to detail and clear objectives.
- Type B – going with the flow and having flexibility to roam or make impromptu choices.
Make sure both sides agree on much travelling and rest is done in a day as well, lest one of you end up overly exhausted or feeling bored.
It’s natural to tend towards one style over the other, and you might find differences between each other’s preferences. Work out a compromise beforehand to avoid conflict later on; you can meet in the middle by planning ahead and reserving major activities and areas of interest, then scheduling dedicated time for free-and-easy exploration for other activities.
Play to you and your partner’s respective strengths as well when it comes to different roles and responsibilities as a travel partner. Who is detail-oriented and adaptable in planning and adjusting itineraries from a wide range of resources? Who is a natural at navigating maps and transport systems even in foreign countries? Who has tons of food recommendations up their sleeve? Be ready to look out for each other in your own ways, and be willing to ask for help when the going gets tough.
6. Make time for meaningful connections
While you’re engaged in new sights and adventures overseas, don’t neglect to appreciate the partner experiencing it together with you. Carve out some time in your itinerary for some quality couple bonding time during the trip.
This could be an intimate and romantic meal somewhere nice, a sunset cruise with gorgeous views, drinks at a rooftop bar overseeing the night sky, or some wellness therapy with a relaxing couple’s spa or massage. You could go even simpler, by just having time together back at your accommodation space to play card and board games over an inexpensive supper trying local snacks.
The aim is to make time for both of you to chat and reflect together on your holiday, talk about your favourite moments, have straightforward conversations on any issues faced – you know, just bond and look forward to the next trip together!
7. Be open to new experiences
While planning for your couple’s holiday, or in the middle of it, you may find differing interests and preferences in your partner’s travelling style. Discovering these new experiences may come as a surprise, but remember to stay open-minded and be ready to to explore new experiences together; doing so will allow you to discover more about the person you’re dating – maybe even a whole new side you never knew existed!
Daring to explore something new together could surprise both of you with a newfound interest or a lasting shared memory. Even if you found the experience wasn’t quite for you, it’ll still prove to be an interesting bonding moment.
In a similar vein, be prepared that things can go wrong. Delayed flights or an unexpected closure can throw your plans into disarray, but stay flexible and work with your partner to adapt your plans to turn a mishap into a new adventure.
8. When tensions arise, work together to resolve conflicts
Arguments can occur even when travelling with friends or family; with a relatively new person, the risk is likely higher.
But don’t let that discourage you from taking that trip with your partner; getting to spend a few days literally in each other’s space is a great litmus test for compatibility, and learning how each other approaches and solves issues.
Should tensions rise, be willing to express your emotions and thoughts, give each other space to cool down, and talk things out. Listen to each other’s perspectives and respond with empathy, before sorting out the root cause of the conflict to work together towards a resolution, for this trip as well as future ones.
Be magnanimous and try not to pinpoint blame on any party for these issues – after all, it’s your first time travelling as a couple, and it takes time to figure out the right dynamics that suit you both. Remember to communicate and cooperate as a team, not fight like enemies, and you’ll likely come out the other end with a deeper appreciation and understanding of each other.
Tips on how to plan an overseas holiday as a couple
- Choose a destination based on common interests, whether it be scenic nature, rich culture, delicious food, adventurous activities, relaxing retreats, and/or shopping hotspots. Some great options that cover a range of interests include Indonesia, Thailand, Japan and Italy.
- Agree on a budget first, estimating your expenditure based off big-ticket items, and look out for budget-friendly overseas travel packages to save costs.
- Plan a trip of three to five full days for enough quality travel time without overly tiring yourselves.
- Pick accommodations carefully for the right amount of privacy and comfort, and discuss whether a tucked away or busy location suits you both.
- Communicate travel styles and responsibilities together to work out a dynamic that works to your strengths and makes the trip enjoyable for both partners.
- Make time for meaningful connections during dedicated couple time, over a romantic meal or a shared relaxation activity.
- Be open to new experiences with your partner, and stay flexible in case of unexpected changes or mishaps.
- When tensions arise, work together to resolve conflicts and listen to each other’s needs, as travelling together for the first time can be a process.
Happy travelling, and keep the spark alive!
with Love,
The Dateideas Team
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