What is the best way to plan a trip to a destination you have never been? With all the information out there it is obviously very easy to research any destination and you could spend 100's of hours doing that. We narrow things down and follow a few of the same steps for most trips so we spend less time getting ready for our trip and arrive ready to use our time there to our advantage.
1. Ask your friends. Anytime we are thinking of going somewhere, we post it on Facebook and ask for feedback. This works great for us because we have friends who have travelled a lot and have been to more amazing places than we have or they know someone who has and will connect us. As with all research, you need to consider the source. When a friend says, "My wife is Thai and we have been there 20 times and have been to most countries around there." We consider him a great source. The, "We loved Ireland because we drank all day at a different bar each day" is not so great of a source for a family trip. I gather information from as many people as possible and start compiling it. Once we have a general plan it's time to start hunting for deals.
2. Depending on what type of trip we are taking, looking for airfare looks different. Spring break, with a set of dates that have little flexibility offers less possible deals than summer when you can really play around with pricing. A longer trip where we have flexible entry and departure points also offers a lot of possibilities. We pow wow on a couple computers, hitting many sites until we find a price that works. Many airlines offer a 24 hour refund so if it looks good, book it. You can always cancel after thinking about it for a few hours or overnight. We have lost good flight prices because we waited to do more research or talk about it and then the price went up. We've recently been talking a lot about taking an extended family trip to Asia. Our dates are flexible because we planned to go over the kids' summer vacation. One day Per got wind of flight deals to Tokyo and sure enough, he scored 6 tickets on United for $400 RT. He booked on the spot knowing that United had a 24 hour free cancellation penalty. (Actually, he booked 3 separate itineraries with different dates until we were able to talk and select the best one, and then he cancelled the other two.) Booking fast matters. As you can see from the google flight chart below, there are a few key dates where flights were available for around $440 RT per ticket (highlighted in red), whereby other dates close to that were more than double that rate (highlighted in blue). For our family of 6, that's a over a $3,000 savings in airfare alone, just by booking airfare on one of the "right" days. Lucky enough, when we went to book, the google-listed $437 RT airfare actually priced out for less at $400 even! (Coming soon we're posting an in-depth article about flight deals and how we'll parlay this screaming deal to Tokyo to make it even better!)
3. Once you have your dates planned it's time to find a place to stay. Again, this varies greatly for us. Depending on number of days in a place, we will either do a hotel (usually for short stays or great location in a city) or we will rent a condo or apartment. Hotels are a very safe bet because you usually get what is advertised. Make sure you know exactly what you are booking if you are doing VRBO or AirBnB. We have found that houses can be very far away from where you actually want to be if you are not careful or the pictures aren't really photos of the house you will end up getting. Google maps is a great way to check this. We almost rented a house on Long Island that looked amazing, until we google mapped the address and realized that there was no way that the house in the pictures was the house at the address. We would have ended up in a shack, not on the beach despite the photos showing a gorgeous ocean side property. We also had this happen on Expedia in NYC when several apartments were listed together under one address. We booked an apartment on the Upper West Side and then got a confirmation for the lower East Side. Reviews on these sites can be very suspect as well because you never know how many "friends" have left them for the owners. If you go the VRBO/Air BnB route, over-research.
If we are taking a long trip with multiple destinations and fluid schedule we book our arrival night and departure night and keep the rest open for planning as we go. With sites like booking.com this is really easy to do now (unlike when we used to do it when tourist bureaus or train stations were the places to get rooms). This provides the most flexibility but can add a bit of stress when you can't find a place where you want to be (on the bright side, that can also lead you to great places near where you thought you wanted to stay). On our last trip through Europe we were leaving Ljubljana (the capital of Slovenia) by car and wanted to stay close to the Italian border on the Slovenian side to visit some cool looking caves. We couldn't find a hotel anywhere near that area and ended up booking a place much farther out in a town we never heard of along the Italian coast. We thought it would just be a crash pad used as a brief overnight stop on the way to our next major destination. It turned out to be an awesome resort in a hopping, adorable Italian port town packed with Italians and Germans on their vacations, but a town we've never heard about from the American tour guide books. It was a local gem that we absolutely loved for an unexpected day of leisure.
We take the same approach on road trips and use sites to book hotels as we go. Instead of planning in advance where/when we want to stop, we drive until we can no longer make it. Be warned that after 11:59 you can not use these type of booking sources because they will flip to the next day. At that point, you need to make phone calls or stop in to ask at the hotels you want. Luckily on road trips, hotels seem to be grouped together right off the highway so it is doable.
4. Once you have your airfare and a place to stay go back to all those friends' ideas, get a few travel books and start planning your itinerary. I love Frommer's and still get real books, rather than do on-line research. I absolutely hate Trip Advisor because the reviews people leave are way to picky for us. I do not want to go to a place knowing every single thing that people were dissatisfied with that we would likely never notice. A cheater way to find great itineraries is to look at travel companies pre-arranged tours. We never actually take them but I'm happy to borrow their itineraries and travel plans!
I use what we call "the three bears" method for our planning. By this I mean do not plan too much that you don't enjoy anything, or too little that you waste time and miss things, but plan just the right amount so you see the things you want to see and have flexibility for exploring and finding the magic in a place. When I look in a travel book and they have listed what to do in a day, we can cover about a third of it with our crew. We take into account everyone's interests. For example, in Europe we hit soccer stadiums for our son, art museums for our daughter, some shops for another and add in parks, renting bikes, boating or something active. Our general rule is one activity in a category, unless a place is really noted for something (how could you only go to one museum in Paris). If we have gone to a fortress in one city, we do not go to one in the next city. We pick the one church that is the must see on the trip and skip the rest. If we go kayaking, we don't paddle board.
When we have chosen our top sites, we study the area they are located in and find the other stuff around it, like parks, sites worth seeing, walking streets, etc... Most times, these other things are a bigger hit for our kids than the tourist attraction. A sample of this for San Francisco could be----Alcatraz as the big activity for the day followed by meandering around Fisherman's Wharf where we would get food, shop a little, watch some street performers, pop into the Wax museum for a second smaller activity and take lots of photos. The next day we may do the area around Chinatown where we would go into the fortune cookie "factory", play at a park, get food........ By tackling the area around an activity when we are there we do not waste time going back an forth. The flexibility in the schedule is on purposes so we can go back somewhere we like or move on when we have seen everything we want to see. If we have had a huge sightseeing day one day we try to have a lower key day the next.
We also like to try to find things that our unique to our family and do them, even if they are not a top priority in a tourist book. When we found out there was a Rue Berger in Paris we set out to find it and take photos. Our daughter wants to own a bakery someday, so we will always make a stop at a place that has been on Cupcake Wars. When our son was into Harry Potter we made a point of visiting spots from the movie in London (we did the same with sights from Notting Hill before we travelled with 4 kids). These little things often turn out to be just as great as the sights from the tour books.
The one time we skip #4 is if we are taking a beach vacation (different from a trip). Besides pools, beaches and the possible water sport, it is very rare for us to get our kids to leave the resort. Instead of spending a chunk of money and having them complain, we skip the sightseeing and enjoy the outdoor, usually perfect weather. In this case the "activity" may be watching turtles hatch on the beach or body surfing or playing tennis.
5. Arrive and be willing to change all of your previous plans for something that is going on when you are there. Some of our most fun activities have been things that the locals are doing that do not appear in tourist books. For example, last summer as we were heading to Stuttgart our German friend told us that the LeMans race was going on and the Porsche museum had set up fan seating to watch its team compete on big screen set up all over the grounds. After a quick check to see what that even was, we realized that this would be the perfect day to visit the museum. It was open all 24 hours of the race, offered free admission, and drew thousands of spectators to their outdoor viewing area. We not only saw the museum that was on our list of sites but we were able to witness Germans go crazy when the Porsche car won the event. Our kids loved the kid activities they had on site as much as seeing the cars. In Iceland we stumbled upon a town's summer festival where the four quadrants of the town were all decorated with a different color and all the people from each section marched in a parade with all of their clothes and "floats" boasting the same colors. While on a ski trip in Vail we found out the x-games were going on in Aspen. A quick day trip and we were standing under the half pipe watching some of the World's best snowboarders. These are the type of things that connect you with an area more than just site seeing.
Also, get advice from locals. When I say this, I do not mean the concierge at your hotel. Remember they are paid to get you to go to certain places. I'm talking about real people who probably know the area and know where to get the deals. If you are at a hiking destination, there is no better place to find out about good hikes than a store like Patagonia or Marmot. The people working the cash register know the non-tourists places to go. If they are in their 20's you may be able to get some good food recommendations that won't break the bank too. In a hotel we chat with the person that cleans the club lounge about food spots, not the guy working the desk. When we stay at a condo or house, we ask questions at the nearest grocery store or a neighbor we see. All of our best Broadway lessons like which shows are good and how to score deals have come from talking to people who wait in line for discount tickets.