How to observe Torah while traveling:
-Pay attention to the calendar. Before you buy tickets or make reservations double check when the Feast Days are and consider if you want to be out of town during those special times. If you go somewhere for Sukkot, think about planning your stay and activities around the no-work days.
-Consider where you will stay. Particularly if you are planning on celebrating a feast while away you will want to have space to do so, whether by staying at a campsite or renting a house or cottage. Will you need to have a place with at least a small kitchen for meal prep? Will you need to find a place to go on Shabbat?
-Let your hosts know. If you're staying with friend or relatives make sure they are aware that you don't eat pork or shellfish (it's also a good idea to let them know what you DO eat), and let them know that Shabbat is a set apart day for you, and what that looks like. Having expectations set up front will make things easier for everyone.
-Look ahead. Before you leave do a little research on the area you will be in. Is there a congregation you can attend on Shabbat? Are there any kosher restaurants to go to? When I spent Sukkot with Torah to the Tribes I was able to visit a Sukkah exhibit at the Oregon Jewish Museum. You might be unexpectedly surprised about what's going on at your destination.
-Pack snacks. Having food to eat when you're hungry is just about the handiest thing ever. This goes even for a day trip. You spent more time at the museum than anticipated, your flight was delayed, the place you planned on eating closed early. Odds are someone will get hungry and there won't be anything nearby. Have at least a few things to eat in case you can't find anything kosher and healthy. It will save lots of headache and frustration, not to mention money and time. Airlines will let you take solid food (sandwiches, trail mix, apples, carrots, etc), which will be considerably better quality and less expensive than what most airports have available.
-Look for vegetarian restaurants. If you aren't near a kosher restaurant (you probably won't be) vegetarian food is miraculous! No need to worry about cross contamination, and dairy products will be vegetarian as well so you don't have to hope that's not pig rennet in the cheese. If neither restaurant option is to be found look for a place that is at least vegetarian friendly. Most places have their menus online so you can see what your options are. Restaurants that accommodate special needs diets like gluten-free are typically your best bet, as the wait staffs are typically more informed about ingredients and the chefs are used to adjusting things when needed.
-Where will you be on Shabbat? If no congregation is to be found or if the service is short, will you want to spend the rest of the day in a stuffy hotel room? Look for a beach or park area or other free place to visit to spend time on Shabbat. If you are able to find a congregation to attend, call ahead and see if they have a meal after service you can attend.
-Shop ahead of time. If you are going to be out of town for Shabbat you will need to make your purchases before it starts, just as you would at home. That includes buying food to eat on the Sabbath, and getting gas if needed. You'll also want to check into your hotel before Shabbat if that's where you are staying.
-Pack a cooler. This is a must if you are staying somewhere without a fridge! Friday afternoon you can get ice and pack a Shabbat picnic for the next day.
-Think about when you will travel. Personally, I don't think there is anything wrong with driving a car on Shabbat. Without driving attending congregation wouldn't be feasible for most of our members, so I think that's a positive thing. That said, there is a big difference between driving 20 minutes to attend Shabbat service vs a fifteen hour drive to get to vacation, which isn't exactly restful. There are also the costs of toll roads and refueling, which should be avoided on a no-work day. The same for air travel, which can be physically exhausting for the passengers.
-What time is it there? If you will be switching time zones be aware of what time Shabbat or feasts start at your destination.
-Take your Bible. Being on vacation doesn't mean Torah studies should be put on hold. That might look a little different than at home but deliberately making study time part of your trip is one of the best things you can do for your time away. You will also want to be able to read appropriate passages for the Feast Days and Shabbat if that's on your trip. You can also take teachings to listen to on the flight or in the car.
-What are you packing? Besides clothes and a toothbrush of course. If you'll be gone over a Festival, take decorations. If lighting a candle helps set apart Shabbat for you, take one along. Will you be traveling in a camper? Think about putting up a mezzuzah.
Do you have any other ideas for making travel easier for those of us who observe YHWH's commands? I would love to hear them!