“Whatever you can do

or dream you can

begin it.

Boldness has genius, magic

and power in it.

Begin it now.”

Helen, Athens, Greece: “I’ve never thought about what I want. I’ve spent my life giving to others and fulfilling their needs. When I sit and think about what I want, I get uncomfortable–that same uncomfortable feeling I get when I dream about going to church in a slip. I don’t think anyone has ever asked me what I want. Good question. What do I want?”

Helen, like many women, overlooked her own needs to fulfill the needs of the people in her life – it’s part of what makes us women. But to truly have a rewarding life, we need to honestly ask ourselves what we want. No where is this question more apparent than in solo travel. After all, it’s only you out there! And because your solo trip is all about your needs, you have a chance to be self-centered for a change! With travel, there are two things that get overlooked quite often. The first is what your expectations are for this trip—what do you really want to get out this adventure? Failing to define your expectations is akin to going to dinner and letting your waiter order his favorite meal for you, then disliking your dinner and blaming him for his poor choice in epicurean delights. Had you given your waiter clues—that you wanted to eat something light, that you love fresh vegetables and fish, but don’t like pasta or tomatoes—you would have been far more likely to enjoy your meal.

The second overlooked element is which destinations are able to fulfill your expectations. Once you have a clearer idea about what type of trip will satisfy your needs, you can focus on finding a location that is well-suited to you. The situation is a lot like dating: you already know what kind of men you like, and if you like tall blond men with fabulous physiques, it is unlikely that Mr. Right will be short, dark-haired, and beer-bellied. Destinations are much the same. You either want to be there, or you don’t.

The first mistake that many new solo travelers make is relying on the recommendations of others, while not considering what they personally want from their vacation. This was the case when Bethany from Portland asked friends for advice on destinations for her first solo voyage. Bethany is twenty-eight, works in marketing, and is happily single. She didn’t think about what she wanted from this trip, so when she asked a few married friends where they enjoyed going, many of them said Maui. She excitedly booked her trip to Maui, with a hotel in the coastal city of Waialua, where her friends had stayed. Bethany had never been to Hawaii, nor did she think about what to expect there. She’d heard some fabulous stories of beach parties in Waikiki, but because none of her friend had ever stayed in Waikiki, she decided to stick with their recommendations. So, Maui it was. When she got there she was shocked. She had expected to meet fun singles, hang out on the beach, and go on adventure tours with others. What she found was the complete antithesis of her expectations; the coastal town was brimming with newlyweds and families. Everywhere she went, she was met with roomfulls of happily married couples or families with obnoxious kids. Bethany is an outgoing, friendly person, but she found it very difficult to meet others. She didn’t find many who wanted to hang out with an attractive single. (Well, a few guys did, but their wives didn’t think too much of that idea.)

Although this trip was not Bethany’s ideal vacation, she did learn from her experience. Now, she defines her expectations before traveling. Of course, being alone in a beautiful setting might be your ideal vacation; you might not care if the place is littered with couples because you plan on spending time alone with a few good books. Whatever the case, the goal of this article is to help you decide what you truly want from your vacation through answering a series of simple questions. Once you complete them, you’ll have a clearer idea about what will make you happy on your exciting solo adventure. And that is what flying solo is all about—your happiness.

First, you’ll learn how your personality influences your destination and travel style. Then we’ll discuss how to research the most appropriate locations based on your expectations. You’ll also learn how to review the reviewer when researching locations via books, online resources, magazine articles, and newspapers. Once you’ve completed this, you’ll have designed the kind of experience that you really crave and found a few suitable destinations that will satisfy your desires.

“Go confidently

In the direction of your dreams!

Live the life you’ve imagined.”

—Henry David Thoreau

Amanda from Carmel, CA shares her journey: “I’ve spent my life organizing family vacations. Once the kids left for college and my husband and I divorced, I found myself alone, but still wanting to explore. All the trips I planned in the past were focused on the desires of the rest of my family- I was just the travel agent, planner, and luggage shlepper. Then, I had the chance to travel and I had no idea what I wanted! I had to sit down and think about my self – someone I forgot about for the past 30 years. At first the conversations I had with myself were painful, but I was able to find out what I needed. I needed to go somewhere warm where I could rest and enjoy new faces.”

Based on my extensive travel history, I have found four key components that can make or break a trip:

Cultural interests: how much culture and art do you want to experience?

Activity level: how active do you want to be on this vacation?

Weather expectations: how important is the weather for you?

Social interaction: how social do you want to be?

We’ll dive into these separately, and you’ll have an opportunity to think about yourself and what’s important to you on this trip. Remember that all vacations differ, so what is true for this trip will not necessarily be true for your next one. As you move through the four decisive components, rate each based on a one-to-five scale, one being LOW on your list and five being HIGH. I call this four-component score the CAWS rating. Once you know what you want, you can review destinations more easily.

Cultural Interests

Lori lives in Santa Fe and loves world history. “Some people think that I am a bit weird because I don’t care to take normal vacations to places like the Bahamas or Hawaii,” she says. “I just love ancient civilizations, so when I plan my trips, I plan them around some great place I haven’t been. So far I have seen Stonehenge in England, the Mayan ruins in Mexico, Rome and Athens. My next trip I’m going to Macchu Pichu. Don’t get me wrong, I like sleeping in fine hotels and ordering room service, but I also enjoy learning about the world we live in.” Lori is someone who would rate culture high on her expectation list. Other popular cultural activities include going to museums and the theater, exploring historic locations, enjoying wine-tasting or epicurean tours, taking educational trips, and visiting archeological sites. Individuals who don’t really care about culture tend to take pleasure in other aspects of travel such as sports, weather, and social life. Whatever is true for you, honor that on this next trip.

Think about your desires for this vacation. Do you want to stroll through museums during the day, or are there other things you’d rather be doing? Take a moment to think about your expectations for you trip and rate the cultural importance of this trip.

Rate your Cultural interest level by choosing the one statement below that best describes your attitude towards culture on this journey:

1. The last thing I want to do is see a museum. Weather and Activity level are more important to me.

2. I really am not interested in art or education. I want to rest and relax on this trip.

3. I would like to go to a big city, but it’s not to visit museums and theater. I want to shop.

4. Yes, I plan on visiting museums and learning about my destination’s culture and history, but I want to do other things as well.

5. Yes! This trip is all about the cultural significance of the locations I want to visit.

Activity Level

Many times we don’t consider our activity level an important factor in planning a trip. I didn’t think about it until I was stuck on a small but beautiful island in the Great Barrier Reef off Australia. It was a place where couples went away to honeymoon, and hiking, biking, and water sports were not on its list of activities—the island was too small to support them. Sharp coral surrounded the island and the only way to get there was by boat. It lacked a wide, sandy beach with lovely half-naked tanned gentlemen giving windsurfing lessons. Although the hotel had a workout room (two stationary bikes and a set of dumbbells), there was little opportunity for outdoor exercise. I went crazy there, and it was then that I realized how important activity was to me. Even just a brisk walk outside or an hour of aerobic training—I need to move!

How important is activity to you during this trip? Do you need to be running around all the time to enjoy yourself, or are you more laid back and relaxed? Do you find darting around exhausting, or does sitting on a beach all day sound like torture? Is this trip about getting into shape, or is it about resting after a few months of stressful work? Do you plan on working out every day, or is this trip about reclining with a good book and a cocktail?

Based on your expectations, rate your Activity level now by choosing the one statement below that best describes your attitude toward activity on this trip:

1. I really want to rest on this vacation and I don’t plan on moving from my beach chair or cozy recliner for a week.

2. I can handle a short walk to the bar or beach for a cocktail, but that’s about it.

3. I would like the option of working out, hiking, biking, or walking, but if it does not happen, that’s OK. There are more important things to keep me busy.

4. Yes, I want to get my heart rate up, and I would like to get a few days of exercise into my schedule. I plan to walk everywhere.

5. Definitely! I need to move and get my heart racing; this trip is about getting fit, staying active, and exercising.

“The indispensable first step to getting the things you want out of life is this:

decide what you want.”

-Ben Stein

Weather Expectations

I’m planning a trip right now and my top priority is the weather. A warm breeze, a nice hint of sunshine on my shoulders, and a cool cocktail resting on the sand by my stacks of must-read magazines sounds like heaven. It’s winter where I live, and I’m getting a bit bored with chapped lips and pale skin, so I’m looking for destinations that can guarantee me temperatures in the high 70s during the day. In the past, this hasn’t been the case. I usually look for places that are high in culture, where I can stroll through museums during the day, enjoy lovely meals, and scoot off to the theater at night—without regard for the temperature. But this trip is different, and I’m determined to find a destination where I can recline on a white, sandy beach, get a lovely bronze tan, and wear cute, revealing dresses at night.

Of all the variables that can affect your vacation, climate is the one that can dampen your trip the most, if you are not prepared. When Judy from Baltimore planned her trip to the Bahamas, her goal was to get out of the harsh Maryland winter. Unfortunately, she did not check the weather before she booked her trip, as she assumed it was always warm and sunny in the Caribbean. It’s usually very lovely there, except during hurricane season!

When deciding how important the weather is to your trip, consider what time of year you plan to travel. Don’t expect the sun to be out just because you’re going on vacation. Check out www.weather.com. There you can find the average temperatures for the month you plan to visit. I found this very helpful when choosing a warm destination for my Christmas holiday. For the destinations I was considering, I looked up the past’s year’s average temperature for the same weeks I was going to be there. Cancun and the Mayan Riviera won, with an average daily temperature of 81 degrees. It tends to rain for an hour or so every few days, in the afternoon, so I’ll make sure to pack a light jacket. Research and thoughtful planning can ensure that you have the kind of vacation you’re craving and that you’ve packed the appropriate clothing.

Now, rate your Weather expectations by choosing the one statement that best describes your attitude towards weather and climate for this trip:

1. I want to go somewhere rich in history (or whatever component is most important to you) and I don’t care about the weather.

2. The weather is not going to affect the destination I choose. If it’s pouring rain or blistering hot, I don’t mind.

3. Nice weather can be a plus, but if I find out the weather is less than perfect during my planned trip, I won’t change my itinerary.

4. Yes, weather is a big factor for me. I want to be somewhere (warm, cold, hot, etc) and I will choose a location that will fit my expectations.

5. Definitely! I need (warm, cold, hot, etc.) and I am choosing my destination based on the weather. If the weather is not what I expect, I will be very disappointed.

“He never is alone that is accompanied with noble thoughts.”


Social Level

When you travel alone, you decide how many people you want to meet—or not meet. Very often, we want to get away and spend time with our own thoughts, while resting our bodies. But other times we want to get dressed up and meet new friends and live like our spirited selves. Janet, who lives in Kansas City, is considered by her friends to be a shy and conservative intellectual. However, her trip to Greece in 2000 revealed a different side to her personality. She recalls: “After I finished my graduate degree, I decided to take some time off before starting my new career as a researcher for a consulting firm. I sat down in my airplane seat and something changed in me: instead of being scared or self-conscious, I became this outgoing, fun girl from the Midwest. By the time I got off the plane in Athens, I’d met three boisterous blondes from Canada who were staying in the hotel down the street from me and we planned to meet for dinner that evening. I went out every night, bought sunny little dresses, and danced the nights away. I even met a guy from Italy who spent a semester at the University of Kansas and didn’t understand why KU’s football mascot looks like a chicken. We spent a day taking a bus tour to the Parthenon and sharing stories of the Midwest. Now, when I take my vacations, I tend to go places where I know I can meet a ton of people and where there’s a social nightlife.”

Although Janet enjoys high social interaction on her trips, many women are looking for a bit of peace and alone time on their vacations. Diane from Houston is one of these women. “I am a high school teacher with two daughters who are about to enter middle school,” she explains. “When I get a chance to retreat from the world for a few days, I want to be left alone. I let others know where I am, but I just want some time to regroup and spend time thinking in silence. During the year, I collect books and magazines I want to read when I go away. I have this little pile in the corner of my office and I smile every time I see it, because it’s my reminder that I’ll be getting away one day to read it all—and I do!”

Do you want to meet new people, or do you want to spend time alone? Are you interested in taking tours, or do you want to do things completely on your own? Or would a combination of both make you happy? Can you see yourself spending time alone in a museum, but looking forward to a group tour a bit later on? Take time to play each scenario out in your mind.

Rate your social expectations by choosing the one statement below that best describes your attitude about Social activity for this journey:

1. No, I don’t want to meet a soul. This trip is about spending time alone with a few good books.

2. I really don’t want to meet anyone, and I am not choosing this destination based on my need for social interaction.

3. If I meet people fine, if not, no big deal. And I won’t write off a location if it’s buzzing with people either.

4. Yes, I would like to meet new people. I want to go someplace where I can spend some time with new friends.

5. Yes! I need people around me all the time. I want to make new friends and do things with others.

“Desire creates the power.”

—Raymond Holliwell

Putting It All Together

Take a look at your ratings of Cultural Importance, Activity Level, Weather Conditions, and Social Level. By now, you’ve envisioned yourself walking barefoot, wrapped in a floral sarong on a warm beach, or strolling through the streets of Europe with a latté in one hand and a museum guide in the other. Or are you looking forward to hiking through the rain forest, or sipping coffee at a sidewalk café?

With this in mind, brainstorm your answers to the following questions:

Where do you want to go? (Beach, city, village, island, small town)

What are you going to do there? (Rest, read, relax, walk, hike, run, work out, stroll, sail, eat, learn)

How social do you want to be? (Meet lots of people, meditate alone, meet a few like-minded friends)

What kind of weather do you want? (I don’t care, wonderfully warm, nice and chilly, windy, calm, hot)

This part of your trip planning becomes a process of elimination as well as an exploration of your desires. Perhaps you know that you don’t want to go to a big city, and you know you want to be somewhere warm, so you focus on small towns in warm areas. Or you know you want to work out, so you plan to find a place with a gym, or close to outdoor activities. Finally, you would like to meet new people, so you want to go somewhere social. Quickly looking at these sets of desires, you know you won’t be going to Toronto in winter or Jamaica during spring break!

When I asked my friend Carolyn these questions before she took her annual Christmas vacation, this is what she said: “Perhaps a city for a few days, then off to the beach — I want to walk around a city and then learn how to scuba dive at the beach. I’m not too interested in seeing anything cultural; I did the museums thing last year when I went to Venice (Culture rating: 1). In the city I would like to meet a few people, but no big deal (Social rating: 3); when I’m at the beach, I would like to take scuba lessons (Activity rating: 4), so I’ll get to meet a few people there; and the weather, I want it to be warm, warm, warm! The most important thing to me is the weather (Weather rating: 5). I’d love to see a new city, but I really want to learn to scuba dive, so the rest is frosting.” Where would you advise Carolyn to go? I told her to go to Australia. And this is why: she wanted warm weather, which is hard to guarantee in the northern hemisphere during December; she wanted both city (Sydney) and beach (Port Douglas); she wanted to learn to scuba dive, and what better place to do that than the Great Barrier Reef? She had the time and the money, and she had a fabulous vacation in the Land Down Under!

This is the time you can call on travel agents, friends, and family. Instead of asking them, “Where do you like going on vacation?” say, “I’m interested in taking a trip alone where I can meet interesting, new people (Social), check out museums (Cultural), stay in a hotel where I can work out in the morning (Activity), and I don’t care what the weather will be like (Weather).” The responses you get will be much more specific to your needs, because you have made your requests very clear. Travel agents love to talk to clients who have a good sense of what they want to experience. You’ll find that once you have a basic list of expectations for your trip, it will be much easier to determine which locations can fulfill your desires.

Reviewing the Reviews

The easiest way to find the perfect locations is to read what others are saying about various destinations around the world. But be forewarned- you need to review the reviews to ensure quality control. Dorothy from Chicago writes: “I learned this lesson after my second bite of a horribly fattening cookie in Hana, Maui. It occurred to me that I needed to take more time reviewing the reviews I read before going on a trip. I remember reading an in-depth review written by a woman who raved about all the wonderful things to experience in Hana. She wrote about the hair-raising yet beautifully lush drive to the town, the quiet nights, and the fabulous cookies one can buy at the corner store. I should have suspected the reviewer when she wrote a whole paragraph on her beloved to-die-for macadamia nut cookies. My taste buds prefer robust wine and soft cheese, so I don’t know why I was so impressed by her cookie review. When I reread the review, I began to develop an image of the person who wrote the article. Not once did she mention any activities that I enjoy, such as snorkeling or horseback riding. She did mention a small, secluded beach that was hiking distance from the hotel, but the path was too treacherous for her to hike. She said nothing about the hotel service, or the lack thereof (there is only one real hotel in Hana and I would advise you to keep on driving); she said nothing about the grounds or the rooms.

“When I look back on her review, I can see that it was written by someone I would not take advice from. Her information was about the cute corner store, the fabulous cookies, relaxing by the pool all day long, eating at one of the only two restaurants in town, and the treacherous hikes. When I found the ‘dreaded’ trail she’d written about, I was more likely to get hurt from the bellyaching laughing I was doing than the ‘difficult’ hike. Based on her review, I’d decided to wear my hiking boots to the aforementioned location, and I looked more like a ridiculous, over-reactive tourist than a savvy, world-class traveler. It was a lovely trail that laced around the side of a rigid, wind-blown hill. The trail was a wide, forgiving path that was as flat as a table and smooth with thick black sand. As an active person, this was not a ‘hike’; it was a short walk to a secluded beach. I should have done more research into the activities I enjoy before choosing Hana as a destination.”

Because reviews can sometimes be a bit one-sided, or not focused on your personal interests or desires, you should review your destinations using a large selection of sources. Books are a great place to get pragmatic facts and statistics on a destination and country. My favorite city and country guides are published by Knopf and Dorling Kindersley, I love their high-style appeal and in-depth historical backgrounds. In these guides, you will find passionate details about the historical relevance of the country and its locations. Other guides I rely on are Time Out, for their social and cultural sections; Michelin Guides, for their basic pragmatic information; Frommer’s, for their detailed listings of hotels and restaurants; and Lonely Planet, for their sense of adventure (albeit more adventurous than I ever plan to be; you’ll never catch me in a hostel or sleeping bag!).

I recommend that you go to a large bookstore, see what they have to offer and see what resonates with you and your style. Also, visit your local library to find books on different destinations, and see what the history and general-interest books have to say about your chosen places. Online, www.amazon.com has a great selection of travel books, destination topics, and subject guides, so you can search a very large selection quite easily. Make sure to get a few magazines as well. The magazines I rely on are Condé Nast’s Traveler, Travel and Leisure, Budget Travel, American Express Platinum’s Departures, magazine, and the travel sections in my favorite fashion and lifestyle magazines. For website reviews, I first try Google by typing in key terms like the destination, type of hotel I want, and the time of year I want to go. I’m given a random selection of hits that all have one thing in common: my search request. This can be overwhelming, so schedule some time to search online for nuggets of useful information. To weed out places you want to avoid, try inputting negative terms like “bad experience” or “don’t go there,” and see if anything comes up. Check out newspapers such as the New York Times’ Sunday travel section, or any metropolitan newspaper’s Sunday edition. Visit a travel agent to discuss your expectations for your trip, and see what locations he or she recommends. If any sound like winners, ask for a brochure or two on each location. By this time, you’ll be forming an idea about the locations that will be right for you.

Exploration Exercises:

1. Take a moment to rate your Culture, Activity, Weather and Social expectations for this vacation. Which are the most important?

2. Start researching locations based on your desires. What destinations seem to resonate with you?

3. Keep a record of the reviews you find. Which ones inspire you and which disappoint you?