Conduct research on your destination. This gives you a clear idea of what's available in terms of activities and amenities. It also points you in the right direction when considering activity type. For example, you would be hard-pressed to plan water-based activities in a city environment. Moreover, it helps to know what's available so that you can pare down your choices. After all, there is generally not a way to see everything you want to in the span of one trip.
Poll your travel companions. Find out what kind of vacation they are anticipating and what kinds of activities they are interested in doing while there. For example, perhaps some of your companions want to walk around and sight-see, while others want to shop in local stores. Families might be split between doing things for kids -- such as visiting amusement parks -- and getting in some adult time at a local nightclub. Couples have to balance between romantic interludes and adventure. Ask everyone where their interests lie so that you can strike a good balance on the trip.
Determine special needs of anyone traveling with you. This could apply to someone with a disability or a pregnant traveling companion. An individual with exceptional needs may require special consideration in terms of access to activities or accommodations. Moreover, you may eliminate items from the itinerary to ensure they don't feel left out. For example, you likely would not plan a challenging group ski excursion down a mountain if one or more of your traveling companions are physically compromised due to injury, disability or pregnancy.
Consider personal budgets. Even if you are just traveling with your significant other, you don't want to break the bank with a jam-packed itinerary. Consider what you -- and anyone traveling with you -- has to spend on the trip. Mix it up with big-ticket activities -- such as a Broadway show in New York City or a diving excursion in a tropical locale -- with free or low-cost adventures, such as a walk through a large area park or a visit to a local museum.
Create daily itineraries instead of one big one. It doesn't necessarily help to come up with one long list of things to do if there is no determination or balance to when you engage in various activities. For example, if you are in NYC, plan a visit to the Rockettes show on a different day than a jaunt to the theatre and save museum visits for their own day. If you are vacationing in the tropics, deep dive trips and snorkeling adventures should be on separate days, so you don't overdo it.
Plan locally as much as possible. Part of what makes for a great itinerary is ingratiating yourselves into the local scene. Eat at restaurants specific to your destination instead of chains. Visit places that are unique to that city instead of places that can be found in cities across the country. Encourage anyone traveling with you to soak up the scenery and try activities specific to your destination.
