Where do I go?
What is my budget?
Where should we stay?
What should we do?
What should we eat?
The longer, the more comfortable the trip is, the more these questions may overwhelm you. At the start of our relationship, Rob and I were lucky to fall into a bit of a travel routine; a routine that takes some of the stress out of planning, but a routine that still allows us plenty of spontaneity in our travel.
Where Do I Go?
For us, we sat down to decide what our travel priorities were. Rob and I both had extensive travel bucket lists, so focusing these lists allowed us to set shorter term goals for our travel experiences. Our final travel schedule filled in something like this:
Spring: Off on a tropical jaunt to relax, catch up on some sun, sit on a beach, and rejuvenate ourselves.
Summer Big Trip: An exploration of the U.S. With 50 states, there is SO much to explore in our own country, that we want to take advantage of it.
Summer Weekend Road Trip: Living in the North East, there are an almost never ending list of places for us to explore within a short drive, so we try to take 1-2 short road trips a year.
What is my Budget?
Setting a budget for a trip can be a very difficult thing to do; a weekend road trip is not going to need the budget a two-week long trip to Hawaii or Europe will. However, I suggest you break your budget down when you're researching your trip into the following components:
Transportation to Destination
Transportation at Destination
Food & Beverages
Activities & Tours
Regardless of what you establish for your budget, be sure to shop around! Check different websites, call different tour providers, and utilize forums such as Trip Advisor. The more knowledgeable you are, the more likely you are to get the most experience for your dollar.
Where Should We Stay?
When trying to determine where to stay, we tend to look at a few options. For our tropical vacations, we tend to choose All-Inclusive Resorts; they provide us with everything we need for a relaxing vacation (you can see our review of Cancun here and here). For big cities (Chicago, DC, Boston), we tend to use sites like Priceline.com or Hotels.com. You're able to plug in your price limit, your wishes for the hotel, and your ideal location. Once you book, you're sent which hotel you'll be staying at; and after using it multiple times we've always been pleased with the results (doing this has resulted in BIG savings).
What Should We Do?
What we decide to do in any given location is highly dependent upon what type of trip we're taking. That being said, we do have a general idea of what we like to do in different locations.
For tropical vacations, we usually like to do one unique activity that neither of us have done. In Cancun, it was seeing Chitchen Itza, in Costa Rica it was watching a turtle hatching. Other than that, our tropical vacations are meant for relaxing. We often make a visit to the spa, and enjoy sitting on the beach for hours at a time.
When it comes to large city trips, there are two activities we always try to take part in; watching a baseball game (at somewhere like Fenway), and visiting a brewery (like Sam Adams). Once these two activities are established, we fill in the rest of our vacation with things like museums, parks, historical locations, and exhibits.
When deciding where to eat, scouring chat boards for suggestions is a favorite hobby of mine. I love looking at food magazines for ideas, and talking to people who live in the area. Rob and I tend to eat a late lunch/early dinner as our big meal out, and supplement with snacks and light food throughout the remainder of the day.