Planning a Trip

So you’ve decided where to go. Now what? How many days? What is the best time of year? What sights to see?


I’ve already given you my tips for picking a hotel so here’s the process I use to actually plan the trip.

The first thing to decide is if I can plan the trip myself or if I need some professional help. I prefer to plan myself but if the destination is complicated then I will hire a professional.
When hiring a professional, I prefer a group which will design a bespoke private vacation for me as opposed to a large group. A group can be fun and you have the chance to meet some interesting people but you also run the risk of having your vacation ruined by miserable people. I highly recommend Jacada Travel to arrange trips for me. I also like travel experiences like cycling trips. I highly recommend Duvine Cycling and Adventure for cycling trips.

Regardless of whether or not I hire a professional, I always do the following things.
  1. Start a Google Doc for notes on the destination. Google Docs are stored in the cloud so can be accessed everywhere and are easily shared with others. 
  2. If the destination is Europe, buy the Rick Steves book. His guide books are the hands-down best.
  3. Look for an NY Times “36-Hours In” article on the destination. These are great sources for inspiration about the destination. 
  4. I’m a foodie so I always want to eat at the hot restaurants. Eater and Zagat are good places to find the exciting restaurants for an area. With Zagat, I like the “Best Of” or “Exciting new” articles. The concierge at your hotel is another great source for restaurants. 
  5. Arrange for tours. If I’m not using a trip planner, I’ll contact the hotel for tours or hire someone from “Tours By Locals.” Again, I prefer private tours over group tours. 
  6. Make a list of the attractions I absolutely don’t want to miss. Using Google maps, I create a plan for which attractions I’ll see on which days. I don’t like to overly plan the day and want to leave plenty of time for exploring so I pick just 1 or 2 attractions per day. 
  7. Research if I need to buy tickets ahead of time. For example, the Anne Frank house only allows a limited number of visitors per day and the tickets sell out quickly. 
  8. Consult “1,000 Places to See Before I Die.“ 
  9. Read any articles from Condé Nast Traveler about the destination. 
  10. General Googling about the destination. 

The best advice I can give you is to not plan every minute of the day and allow for plenty of time to explore.

Comments