When it comes to big surprises, it's hard to top gifting someone with a surprise vacation. Whether it's a long weekend in Paris to celebrate a milestone birthday or a bucket-list adventure like seeing Machu Picchu, there's a lot of planning and thought that goes into giving travel as a gift. Luckily, Oyster's editors have been on the giving and receiving end of these kinds of surprises. With that in mind, we've put together a list to help you out. So, how do you plan a surprise trip? Where should you consider going? And how should you break the news? Read on for the ultimate guide to giving someone the gift of travel.
How to Begin Planning a Surprise Trip
If the person you’re gifting wants to go on a trip, you’ve likely heard them talk about where they want to go in conversation. Perhaps your wife has mentioned wanting to go back to Paris after more than a decade, or your parent often reminds you of the one place they’ve never seen. Or, maybe your kids are obsessed with a particular amusement park. In any case, the yearned-for getaway will have been on their lips — frequently. With that in mind, there may not be any mystery to the destination.
You’ll want to get a sense of how flexible their schedule is first. In some cases, reaching out to their boss at work (if they have a good relationship with them) can help you get a handle on whether the person has vacation days and can use them when you’d like to escape. You can also organically weave this into conversation. For instance, if it’s a parent or grandparent, tell them that you’re planning a trip home for the time you’re taking them away to make sure they don’t make other plans.
Things to Keep in Mind When Booking the Trip
Depending on the kind of trip, consider how much of it you should schedule ahead of time. Chances are, if it’s a trip the giftee has been talking about for some time, they have very specific ideas about what they’d like to see and do. With that in mind, your best bet is to purchase the plane tickets well in advance, but hold off on any expensive tours, excursions, or nonrefundable hotels. This allows them have some input when you do reveal that you’re taking them somewhere.
However, when booking the plane tickets, you must have certain pieces of information. If you’re booking an international trip, you’ll need to make sure the person either has their passport, or there’s enough time for them to get one (allow at least three months for this). On top of that, you’ll need to know how their name appears on their government-issued ID or passport. The best way around this is to use their first name and last name — leaving out the middle name. TSA agents will let you through if that’s present on the ticket, but if you’ve gotten the middle name wrong, misspelled it, or the government-issued ID doesn’t include it, you might have to pay extra to have the ticket changed at the airport desk.
Our Favorite Destinations for a Surprise Trip
For a Long Weekend From the East Coast: Paris
Paris is easily one of the world’s greatest cities. And the weight it holds in the collective consciousness as a place that must be visited before you die is hard to understate. Whether you’re a foodie, a history lover, an art enthusiast, a night owl, or just someone who loves long walks amid breathtaking urban scenes, Paris is for you. It also happens to be reachable by a relatively painless nonstop flight from most major East Coast and certain Midwest cities in the U.S. Even better, these flights often aren’t too expensive compared to other continental European destinations.
Most travelers want to visit Paris during the summer, but keep in mind that you won’t be alone. Hotel rates and flight prices skyrocket at this time of year, and lately, the city has been enduring sweltering summer temperatures. You should also take note that August is prime vacation time for the French, and many things are simply closed for the majority of the month. You’ll score incredible flight and hotel bargains by visiting Paris in the winter months, though you’ll have to contend with cold and often damp conditions. With that in mind, April, May, and October can be pretty as a picture in Paris — crowds won’t be at their peak, and hotel and flight prices are still generally low.
Of course, you can just tell your loved one that they’re going to Paris by putting their plane tickets inside of a cute card with an Eiffel Tower on the front. But if you want to go the extra mile, give them their tickets along with a box of Laduree macarons (and then sample them at Laduree when you’re on the ground in Paris as well).
Hotel des Grands Boulevards was one of our favorite boutique properties during a 2018 visit to Paris. With just the right blend of classy Parisian history and luxe contemporary amenities, the hotel strikes the perfect balance of form and fashion. Its location in the 2nd Arrondissement — surrounded by brasseries, cafes, and bars — is hard to beat. It’s only a 15-minute walk to the Opera Garnier and an incredibly quick ride from the trendy Le Marais neighborhood or the Louvre.
For a Long Weekend From the West Coast: Mexico City
Like Paris, Mexico City quite literally has something for every type of traveler: history buffs, art lovers, aspiring chefs, street-food enthusiasts, architecture nerds, shoppers, and even club kids. It also enjoys spring-like weather year-round, making a visit here especially welcome for those living in colder areas of the U.S. Central neighborhoods like Roma, Condesa, and Juarez are packed with boutiques, cafes, restaurants, and bars that buzz every day and night. Small jazz clubs and underground raves can also be found here. The culture of the city stretches back millennia, and today, you can explore everything from ancient ruins to La Casa Azul — the former home of Frida Kahlo and Diego Rivera. If you’re looking for a taste of how modern-day Mexico City goes about its weekends, head to the neighborhood tianguis and mercados.
What’s the Best Time to Visit Mexico City?
Temperatures in Mexico City are fairly constant. You’ll rarely find daytime temperatures outside of the 70s and low 80s, though at night, it’s often chilly enough to require a sweater or light jacket. However, Mexico City is subject to wet and dry seasons. The former runs concurrent with the late spring to early fall months in the U.S. (May through October), while the latter generally lasts from November through April. In any case, even on rainy days, the showers are limited to late afternoon and early evening downpours and rarely wash out an entire day. Just note that you should reserve tickets for La Casa Azul well in advance.
If you’re taking someone to Mexico City for the first (or fifth) time, you’ll likely have La Casa Azul (or The Blue House) on your itinerary. This Coyoacan compound was the home of Diego Rivera and Frida Kahlo, and offers a cool glimpse into their lives together (for better and worse). Give your travel companion (and maybe yourself) a little context on the iconic Mexican painter by gifting them “The Diary of Frida Kahlo: An Intimate Self-Portrait.”
Year after year, Las Alcobas proves to be one of the finest boutique hotels in Mexico City. It’s located in the safe Polanco neighborhood, which is home to all manner of luxury retailers, cool boutiques, and amazing upscale dining. Chapultepec Park is essentially next door, and trendy districts like Roma and Condesa are a quick taxi ride away. Rooms here are chic, stylish, and spacious — plus, you’re guaranteed peace and quiet (which isn’t always a given in busy Mexico City).
Spain is home to a plenty of cool cities and towns. You could easily spend weeks here and not get bored, but it also happens to be a great place to tackle in bite-size nuggets. That’s especially true since the cost of everything — food, drinks, hotels, and entertainment — is far lower than other major European destinations. Madrid and Barcelona make a great pair for a surprise trip to Spain. This gives you several days in each city, which is the perfect amount of time to hit up major cultural spots, like the Prado and Reina Sofia in Madrid and Gaudi’s masterpieces in Barcelona. You’ll also be able to indulge in amazing Spanish and Catalan cuisine, epic nightlife, and an easy pace of life. Both cities are easy to navigate, with reliable links to the airports, as well as efficient and extensive metro networks that make getting around a breeze.
Like Paris, it’s hard to top the summer months in Madrid and Barcelona. However, you’ll be contending with large crowds (particularly in Barcelona) that can make being a tourist unpleasant. Additionally, Madrid tends to roast in the summer, and it can be brutal to walk its picture-perfect streets in the sweltering heat. Winters are relatively mild in both cities, so an off-season discount shouldn’t be off the table (just expect some rainy days and potentially cold nights). Your best bet is during shoulder season (May and October). While you’ll miss prime beach season in Barcelona, the weather is beautiful at this time of year and likely still warm enough for catching some sun if that’s what you’re after.
There’s no better way to celebrate a surprise trip than by clinking glasses and making a toast. With that in mind, tell your loved one they’re going to Spain with a bottle of Spanish cava. Segura Viudas Reserva Heredad Cava Brut is highly rated by Wine & Spirits magazine, and makes the perfect sparkling salute to an amazing vacation.
As a cutting-edge design city, it’s perhaps no surprise that Barcelona is home to the chic and stylish Mercer Hotel. This intimate boutique hotel puts most other Gothic Quarter options to shame, with its blend of sleek, contemporary interiors and historic details. It has a small rooftop pool that’s great for cooling off on hot summer days, as well as excellent dining, tapas, and cocktails at the rooftop lounge.
For a Two-Week Vacation: Japan
Japan is a country that really has it all: dazzling cities, amazing cuisine, serene mountain landscapes, indulgent hot springs, and a culture that stretches back millennia. Whether you’re visiting to stuff yourself with ramen and sushi, marvel at the stunning temples, or experience the buzz of cities like Tokyo and Kyoto, it’s hard to argue with a visit here. Two weeks gives you plenty of time to balance Japan’s frenetic urban pace with forays into more tranquil destinations like Hakone, where hot springs bubble amid the beautiful mountain scenery. You’ll also get plenty of use out of your JR Pass, which allow you to zip around the country on an incredibly efficient and extensive network of trains.
Depending on your travel style, you can visit Japan any time of year. The climate is fairly similar to the U.S. East Coast — four seasons in the central and northern Japanese islands (similar to the Northeast or Mid-Atlantic depending on your destination), and sub-tropical temperatures in the far southern islands (like Florida). If you’re hoping to visit Japan’s most famous cities — Tokyo, Kyoto, and Osaka — and maybe some hot springs and a few more outdoor destinations, time your visit from late March to October. Late March and early April coincide with Japan’s cherry blossom season, and you’ll find hotels in Tokyo and Kyoto booked up far in advance. Likewise, October is fall foliage time, which again tends to draw domestic and foreign tourists. Visiting in the late fall and winter months may score you cheaper flights and hotels, though you’ll have to deal with cool and sometimes rainy weather.
If you know someone who has been to Japan, you may have heard about the fascinating world of Japanese sweets. These range from cartoon-like pastries to mochi and — most famous of all — Kit Kat bars. But we aren’t talking about your run-of-the-mill chocolate flavor here. Japanese Kit Kats come in flavors like matcha, wasasbi, sweet potato, and banana (and those are the most straightforward ones). This sampler pack of Kit Kat minis is the perfect primer for a trip to Japan.
Tokyo is packed with amazing attractions, but the best might be seeing the city’s skyline from high above. There are plenty of places to do this throughout the city, from the Mori Art Museum to the Tokyo SkyTree, but we recommend soaking up those views right from your hotel room. The luxurious Prince Gallery Tokyo Kioicho is hard to top. With excellent dining, a swish bar, a full gym, an excellent pool, and polished rooms, this is Tokyo done right.
For the Ultimate Bucket-List Adventure: Machu Picchu and the Sacred Valley
There is nowhere else on earth quite like Machu Picchu. This ancient Inca site was unknown to everyone but the local communities until the beginning of the 20th century, evading even the marauding Spanish invaders during the colonial era. Today, it’s one of the Seven Wonders of the World, and a must-see for anyone interested in history and beauty. But Machu Picchu isn’t the only fascinating thing to see in this part of Peru. The Sacred Valley is home to the incredible Andes Mountains, its own network of archaeological ruins, and some of the most awe-inspiring treks in the world (the Inca Trail being first among them). You’ll also want to spend some time exploring nearby Cusco, a stunningly preserved colonial relic with its own buzz and fascinating history to explore.
Like most countries that straddle the equator, Peru is subject to wet and dry seasons, despite generally having constant temperatures year-round. To make sure you get the clearest views of Machu Picchu and the surrounding mountains, visit from April through October. Skies are clearest during North America’s peak summer months (though you’ll be contending with higher hotel prices and airfares). November through March bring low clouds and rain, which can put a damper on hiking and scenery. Keep in mind that you’ll need permits for the Inca Trail and Machu Picchu — both are subject to strict caps to preserve the sites.
When you’re in Peru, you’ll see plenty of clothing and accessories crafted from the super-soft coat of the alpaca (you’ll also spot your fair share of alpaca in the Andes region). Go luxe and give your loved one these cozy Lunya alpaca loungers to tell them they’re going to Peru. Trust us when we say they’ll make lounging in your beautiful suite at the JW Marriott Cusco feel all the more awesome (and keep you warm on chilly nights).
If you’re heading on a bucket-list adventure, make sure you’re relaxing in style. The JW Marriott El Convento Cusco is one of the most stunning hotels in the region. Set inside a colonial-era convent, this property balances pampering contemporary amenities with striking historical decor and design. It’s location — right in the center of lively Cusco — is hard to beat. A few nights here is well worth the splurge, whether you’re gearing up for your Machu Picchu visit or recharging after it.
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