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The clueless guy’s guide to planning a romantic getaway

Deb Finkel thought she was spending the weekend in the Hamptons with her boyfriend, Ron. Little did she suspect he’d actually booked a romantic weekend at a small luxury hotel in Bermuda, complete with beach time, the best table at a highly rated restaurant, and a marriage proposal. He’d even managed to smuggle her passport and a fancy black dress out of her apartment to take on the trip, and sneak a diamond ring through security so she wouldn’t notice.

Think a romantic getaway of this quality is out of your league? Think again. Whether you’re a beginner at couples travel or a Casanova stuck with a tight budget, we can teach you how to plan a trip that’ll make your lover swoon. With the right tips and tools, you won’t be as clueless as you might think you are.

Practicality is sexy

Before you indulge in dreams of rose petals and candlelit dinners, you must first take care of the practicalities of plannng your trip.

  • Time: First, think about how much time you can take for your romantic getaway. Kate Chynoweth, author of Best Place to Kiss: Pacific Northwest and Best Place to Kiss: Northern California, recommends three days (for a nearby getaway) to a week (for somewhere farther). But, even one night can be enough if you’re not going too far from home. What you don’t want to do is squeeze a trip to a far-off destination into two nights—you’ll be exhausted the whole time and not in the mood for romance.
  • Destination: Your first decision is whether you want to plan a trip in your home city, in a nearby region, or in another country. As noted above, the amount of time you have may determine the distance you travel. You will also want to factor in things like time changes, travel time, and the stress factor of foreign travel into your decision. Whether you choose to go near or far, your trip can still be equally romantic.
  • Budget: When Ron planned his Bermuda trip for Deb, his attitude was “whatever it costs, I’ll pay it” because he wanted a luxurious and exclusive experience. However, when Joe Conaty took his girlfriend Jennifer to Washington, D.C., to propose to her, he said, “I tried to shoestring it because I was a graduate student. I wanted to do everything as nice as I could without going bankrupt.” Both of these men planned successful getaways on widely different budgets. Empty pockets are stressful, not romantic, so decide what you can afford and work within that price range.

Your trip should be special to you both

When Joe planned out his proposal trip, he chose locations that were meaningful in his relationship with Jennifer. He chose to stay at the Key Bridge Marriott in Georgetown because he’d “stayed there earlier and knew it was inexpensive with a great view,” and made dinner reservations at Geranio’s in Alexandria because “we’d been there before and it has history. Jennifer likes it, they have nice wine, and the setting is romantic.”

One way to find surefire romance is to choose a destination that’s special to you as a couple. This could be a city where you spent a lot of time, a location that played a key role in the evolution of your relationship, or even a place you’ve talked about for years but have never been. The benefit of choosing a place you’ve been to is you know what you’re getting. You might not want to risk staying at a mediocre hotel or eating at a restaurant with bad service during your special trip.

But whether you choose a familiar place or someplace new, the key is to create an experience that will be enjoyed equally by you both. Paris Permenter, co-editor of, says to “make sure you plan things you both like to do,” whether that’s learning a new sport or exploring a new city. If you love golf and your partner couldn’t think of anything more boring, your romantic getaway is not the time to hit the greens. Instead, think about the kind of trip your loved one would enjoy, whether it be indulgent, active, adventurous, or relaxing—and plan a getaway that will keep you both happy.

Romance lies in little details, not high prices

When Josh Weinberg took his wife Sharon to Costa Noa, a luxury camping destination in northern California, he wanted to surprise her with an extra touch of romance. He waited for her by the outdoor fireplace with a bottle of champagne, real glasses, and a box of fig newtons. The two of them sipped bubbly and nibbled on cookies… at 9 o’clock in the morning. “I knew she loved champagne,” Josh explained. “And I wanted to do something that was a little bit decadent, a little bit unexpected. It really shined the spotlight on us.”

Plus, a bottle of champagne and a box of cookies is well within the budget of most travelers. While five-star dining is certainly romantic, thoughtful touches that don’t cost a lot can be equally meaningful. Chynoweth believes “unexpected small gifts can go a long way. Even a little key chain that’s related to the trip can make it feel like a special moment.”

Permenter agrees bringing your own is the way to go. “If you can’t afford a luxury hotel room, buy nice items like wine, fancy soaps, and chocolate, and bring them with you.” Hotels may overcharge for turndown service with rose petals, but you can create an intimate atmosphere yourself for much less.

Or, seek out your own romantic spots. Cheap yet intimitate moments can be found in jacuzzi tubs under the stars, on a ferry boat, or during a stroll along the beach or quaint shopping street.

Plan for romance

While you can create special moments out of little details, it doesn’t mean you shouldn’t plan for romance. When choosing accommodations, look for a property where kids aren’t allowed. Chynoweth puts it best: “Other people’s crying kids is the least romantic thing in the world.” You should also tell the hotel manager your stay is part of a romantic vacation, and you might be surprised with an upgrade or other special service. “In big places it’s harder to get that special treatment,” warns Chynoweth. “The one place I’ve found it really changes things is bed and breakfasts. If you tell the owners, they will often go really far out of their way to make your time there special.”

Restaurants can also add to a romantic atmosphere… or quickly kill it. If your partner loves wine or a certain type of food, try to find a restaurant that’s highly rated in that category. An intimate corner table that seems worlds away from the other patrons will allow you to have quiet moments together, so ask the maitre d’ to seat you accordingly. Poor service can ruin a special dinner, so you should find out about your restaurant’s reputation for service before you book.

Permenter also recommends outdoor dining, candlelit dinners, and intimate breakfasts for instant romance.

Don Juan knows when to ask for help

If you’ve begun to panic because you don’t know where to find quaint B&Bs or intimate cafes, relax. No one expects you to come up with all of these ideas on your own. The savviest romantics know that help is only a phone call or mouse click away.

Ron chose Bermuda for his proposal destination because a friend of his had been there. When his friend heard that Ron was looking for an exclusive destination that wasn’t too far from New York, he raved, “Dude, you gotta go to Bermuda!” To find the perfect hotel, Ron went online and did several Internet searches looking for highly rated resorts and restaurants. He also discussed his trip with his friend’s mother who was a travel agent; she recommended that he rent a moped for a day and explore the island by bike.

The Internet is full of sites that rate restaurants and hotels, as well as bulletin boards where you can post questions about travel destinations. You can also use the Web to find flights or discounted rates on accommodations and car rentals. If you’re feeling clueless, let your fellow travelers clue you in. And, don’t hesitate to call up trusted friends or even a travel agent, and ask for advice. The more information you have, the better decision you’ll make.

Don’t try to do too much

“Sleeping in is the most romantic thing in the world,” declares Chynoweth, and her words are ones to live by. While it’s tempting to jampack a trip with sightseeing, active pursuits, and nightlife, you mustn’t forget the purpose of the trip is to reconnect with your partner, to spend time just being with each other as a couple. You can easily lose sight of that goal between the parasailing, mansion tours, scuba diving, mountain climbing, and pottery sculpting.

Permenter recommends you plan together time. “Leave time to take long walks or linger over a meal,” she advises. “You don’t want to feel like you’re on a schedule.” Many experienced romantic travelers said they booked the flights, accommodations, and car rental, but left the daily activities unplanned. This approach lets you take care of the essentials while leaving time for spontaneity and relaxation.

To surprise or not to surprise

There are many ways to surprise your significant other with a romantic getaway. Deb knew she was going on a weekend trip, but Ron surprised her by taking her to an unexpected destination. Josh told Sharon about their romantic getaway, but didn’t let her in on all the details. A surprise can be as large as an unanticipated trip or as small as a secret gift.

While you’re figuring out how much of a surprise you want your trip to be, here are some things to take into consideration:

  • How well does your significant other handle surprises? If she likes to be well prepared for a trip, perhaps you’d better tell her about your plans a week or two ahead of time, or stick to small surprises along the way. But if your partner loves spontaneity, an unexpected trip could be the best present possible.
  • Can you handle the planning? If you plan a secret getaway, you’ll be responsible for collecting passports, packing clothes for the two of you, and arranging for your partner to have time off and an empty social schedule for the duration of the trip. If all of those details makes you crazy, you might not want to go for a total surprise.
  • Can you keep a secret? Some of the best surprises are ruined by a slip of a tongue, either by you, a friend, or a travel vendor leaving your confirmation number on your shared answering machine. If you’re a master of deception, go for a surprise, but if you think you’ll have trouble keeping your plans under wraps, opt for a more open approach.

Attitude is everything

Ultimately, you create your own romance. You can make the diviest dive bar romantic with the right attitude. As Permenter points out, “Travel can be frustrating, so you need to stay in a romantic frame of mind. It helps to laugh at things along the way.” No matter where you go, what you plan, or how much you spend, you can make your getaway romantic by embracing the spirit of the occasion. If you can focus on your partner and spend as much time together as you can, you’ll find that you’ve become a clued-in expert at the art of planning a romantic getaway.

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