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True Travel Stories and Advice from Wise Women

If It's October, We Must be in San Francisco

Karen Stinson

My husband, Lee, tears up when he hears the opening strains of "I Left My Heart in San Francisco". It's his favorite place to visit, so we have been there at least 10 times and I know we'll go there on a yearly basis as long as we can get onto a plane. In fact, a few years ago, we accepted this fact and bought a timeshare in a building a block from the wharf with an incredible view of the bay from the roof deck.

I don't mind Lee's desire to return to San Francisco over and over because I am the same way about Key West. We skipped our Key West trip last year and, by February first I was urgently surfing the net for any Key West deal. If you're wondering, nowhere else in Florida can be substituted. Don't get me wrong. I'll willingly go to many places in Florida in addition to Key West but not instead of Key West. So, Lee goes willingly to Key West over and over again and I go to San Francisco over and over again.

Although Lee and I can go on forever about the benefits of each location I thought I'd share what I've learned about getting the most enjoyment out of repeat trips to favorite destinations. Some of the four ideas below are from conversations with friends who are repeat visitors to San Diego, Dublin, Las Vegas, New York, Paris and Seattle.

1. One of the reasons people like to return over and over is because it's comfortable, so acknowledge that comfort factor and relish it. Travel can be stressful but revisiting takes the stress out. You know where things are and the best place to stay. You know how things work. You are greeted by name at your condo or favorite restaurant. You know where to go to see the best sunset. You know where they make the best martinis or ice cream sundaes. One thing Lee and I enjoy about having made multiple trips to San Francisco is that we don't need to take any pictures. We've got plenty of them already and we look younger and thinner in the old ones.

2. Be clear about why you like to return. What do you enjoy about the place? Is it the weather? The restaurants? Shopping? The outdoor activities and sports? Relaxing by the sea? Cultural events? Make sure you devote enough time to those things that make the city special to you. For example, in San Francisco, we spend hours walking through the diverse neighborhoods and visiting art galleries. We always book ahead to make sure we get into a couple of favorite restaurants (like the fabulous Gary Denko). Every trip to Key West includes a couple of snorkeling trips and going out at night to enjoy all of the live music.

3. Every city has surprises and experiences you haven't taken advantage of. Last year, Lee and I took a guided bus tour of San Francisco and learned all sorts of history we weren't aware of. We took note of unexplored neighborhoods and parks to visit later. Next year we plan on taking a 20 mile bike trip we just heard about. It goes from San Francisco to Tiberon back to San Francisco by ferry. I also recommend that you check on-line ahead of time (possibly before you even book your travel) to find out what events or celebrations or shows are coming up. Plan your trip around one that appeals to you.

4. Ask a friend or another couple or a grandchild to join you. You will take on the role of guide and you'll get to share your love for the city with people who matter to you. Seeing the other person's excitement and being a guide can bring you renewed enjoyment of the city. Just be sure you are open to ideas of your guests that you haven't tried. Go for it! You may end up in some vineyard sipping champagne or kayaking around a mangrove.

A really nice benefit of repeated visits to a vacation spot is that each morning when you get up in the morning and pack your WisePack™ travel purse for the day, you know what to put in it.

For example, the temperature in San Francisco can vary greatly during the day based on the sun and your proximity to the water. Each day we're going to be traveling around the city or taking a ferry somewhere, I dress in a sleeveless tee with a sweater over it. Then I throw our lightweight jackets, some sunglasses and an umbrella for each of us into my WisePack™ and we can stay out until after dinner. Of course it has my mini-tote inside for those unexpected purchases.

If you go to San Francisco, I advise you to buy passes (one day, three days or a week) to get around the city. You can buy them at the cable stations and they give you unlimited access to all cable cars and buses. I keep ours handy in the front of my WisePack™. On days we're hitting museums or galleries, I just carry the small day bag with lipstick, a compact, a brush, our cable passes, a credit card and my license.


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