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

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.
- 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.
- If the destination is Europe, buy the Rick Steves book. His guide books are the hands-down best.
- Look for an NY Times “36-Hours In” article on the destination. These are great sources for inspiration about the destination.
- 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.
- 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.
- 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.
- 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.
- Consult “1,000 Places to See Before I Die.“
- Read any articles from Condé Nast Traveler about the destination.
- 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.
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