Margo Weinstein

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Family Travel: How to Have a Great Family Vacation, Not a Great Family Vacation Story.

16, 24, 24, 25, 26, 26, 28, 28, 29, 30, 31, 56, 57, 59, 60, 61, 77, 81, 84, and 90. No, this is not an ACT math question or a riddle. These are the ages of the family members (including two girlfriends and a boyfriend) I traveled with on a family vacation in Southern California. What activities could we all participate in together and enjoy? Hike in Los Padres National Forest near Ojai? Ride the Santa Barbara Trolley? Some relatives wanted to do each, but no one wanted to do both.

What about food? Finding great restaurants to try is part of the fun of traveling. Our family has vegetarians, carnivores, people who keep kosher, someone allergic to fish, those who enjoy ethnic food and spices, those who only eat “American” food. Where could we all dine, outdoors, every night for a week, with food for everyone and tables for 20?

As the self-proclaimed travel expert, I was assigned the task of figuring it out.

The best family vacation stories, the ones that become part of family lore, are the vacations that go awry. Like the time in the south of France when we did not know that the French don’t bump into each other on the bumper car ride, and we became victims of a mass retaliation that left my six-year-old sister in tears. Or the time on a driving vacation through the Smoky Mountains when the hotel was booked in a town with the same name, in a different state. Or the time we went to a dude ranch in Montana and my mom thought it would be fun to take the train from Chicago to Whitefish Bay and the entire state of South Dakota was flooded (or so it seemed), slowing the train’s progress to a crawl, so it rolled through Glacier National Park in the dead of night. Yes, we tell these stories over and over, in shorthand form. But I wanted to enjoy the best family vacation, not create the best family vacation story.

I love planning vacations for my son and me—so many exciting options. But planning a vacation for twenty family members is taxing. It is frustrating to try and balance different interests and abilities, and it is impossible to stay within a reasonable budget—nothing you do with twenty people is inexpensive. This is probably why you see so many extended families on cruises where everyone can do their own thing during the day and get together for dinner. (This was not an option for this family vacation due to COVID-19.) Eventually, I came up with a plan that I hoped would work for everyone.

Our itinerary allowed for every other day “off.”  Off from a planned family activity for twenty. Off on your own (or in smaller family groups) to amp up, or slow down, to suit your age and interest. Off to the Ojai Valley Inn’s golf course or one of its four pools to relax. Then back together again for a family dinner and then back “on” the next day.

For the “on” days, when we would all be together, I booked activities I thought we would enjoy and hoped for the best. On day one, we headed to the Channel Islands to sea kayak. The kayaks were sit-on-top doubles. Before leaving home, I asked (required) the 20 somethings to paddle with a relative over 75, not with their respective girlfriends or siblings. With limited pushback, they agreed. I was not sure my 90-year-old father would kayak, but I signed him up. After a chilly ferry ride with Island Packers from Ventura to Scorpion Anchorage on Santa Cruz Island, we headed over to the staging area for the kayaking. My dad gamely geared up. He put on a farmer john wetsuit, paddle jacket, and helmet and grabbed a paddle. He had decided to kayak—not because he thought it would be fun, but for his family. Seeing our dad geared up and ready to go, my brother decided he was the most capable and responsible one to keep our dad upright and in the kayak. This was a good call. Capsizing, especially when navigating through caves, was a possibility, and my brother is strong enough to paddle alone or to compensate for unhelpful paddling by our dad.

I had the most kayaking experience in our family. I had done multi-week kayaking trips in Palau, and Papua New Guinea, a week-long kayaking trip in Baja on the Sea of Cortez, and many kayaking day trips around the world. I also owned a serious kayak. In the Channel Islands, I paddled with my sixteen-year-old son, who is strong and whom I have taken paddling in Nicaragua, Monterey Bay, and elsewhere. We were the most experienced duo. We were the only ones to flip. Riding the surging surf through a cave, we crashed into a wall and capsized.

For the most part, my vacation plan worked. Most of the time, most of us were on our best behavior—how you act with friends or work colleagues, not your family. As a result, everyone got along and had a great time. Still, we also added at least one more story that could become part of the lore: Remember the time when we sweated under black umbrellas in the blazing sun at the worst winery in the world, instead of sitting on the other side of the building, under a roof, with fans and misters. Not bad for a family vacation during a resurging pandemic.

Planning a trip to Southern California?

We stayed at the lovely Ojai Valley Inn:

Island Packers runs the ferry to the Channel Islands:

Santa Barbara Adventures lead our kayaking trip:

E-Bikery in Santa Barbara rents zippy e-bikes to explore the beaches and town:

Sama Sama Kitchen in Santa Barbara was the favorite restaurant of most of us:

Rumfish y Vino in Ventura offered something for every palate and preference:

Jalan-Jalan Chapters and Travels

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