You’re so excited because you have selected a destination for your next vacation… but… now how do you plan the best trip ever that aligns with what you want out of it? I often get asked about my itineraries for various locations, which of course I am happy to share! But if you don’t have a personal travel consultant and want to plan a dream vacation on your own, and one that is perfect for YOU, here are some tips. I happen to be planning a trip right now for my husband’s birthday, so let me walk you through my example! On a side note, if I am ever NOT planning a trip, please check my pulse, as something is seriously wrong.
STEP 1: Think about how you want to feel on your vacation.
In other words, do you want an adventure trip, a relaxing trip, a cultural trip, a foodie trip (shouldn’t all trips be foodie trips?), or a mix of a few of those? This will guide the activities you will eventually choose.
- MY EXAMPLE: My husband has been so sick this year and hasn’t been able to eat cheese or drink beer, hasn’t had a fancy foodie meal in a while due to his diet restraints, hasn’t been able to socialize (aka hasn’t been around other humans much) due to high COVID and co-infection risk, and hasn’t been able to enjoy many cultural activities as a result either. Those are all things he loves! So naturally, he wants to feel HUMAN on his birthday and he wants a mix of mostly cultural and foodie experiences. Specifically, he wants to celebrate his birthday by eating a deep-dish pizza, drinking a cold beer, having a fancy foodie meal with wine pairings, and exploring museums within a city buzzing with people. Where better to do that than in Chicago?!?!
STEP 2: Create a personalized Google map
On Google you can create a map of wherever you want to go and then save locations that you are interested in on that map. That way, you get a sense of whether many of your activities are within certain neighborhoods (and if so, perhaps you want to stay in that neighborhood so you can walk between activities). Or if you are visiting a museum in a certain neighborhood, for example, then you can pull up your map afterwards when you are starving to remember that there’s a bakery nearby that you had researched.
- MY EXAMPLE: I went to this link and started making a map of Chicago. I then searched for activities I wanted to do (see Step 3 below) and saved these activities to the map. For example, he really wants to go to Alinea restaurant, so I am saving that in the map (by clicking “Add to Map”) and color coding it to represent restaurant (I color code restaurants, hotels, and activities differently).
A start to a personalized map to Chicago—
STEP 3: Research whether there are any nice hotel groups where you’re going.
Specifically, I always research Relais & Chateaux hotels, which is a network of luxury retreats and gourmet restaurants around the world—I trust the quality of those hotels. Even if I don’t end up staying in the Relais & Chateaux hotel, I add it to my Google map, because in general they are usually in nice locations. If there isn’t a Relais & Chateaux where I’m going, I also look up hotels on trivago.com, which aggregates reviews from many websites, and I put the top 5-10 hotels on the map, again to get a sense of where nice locations may be.
- MY EXAMPLE: There aren’t Relais & Chateaux hotels in Chicago, so I looked up the top 5 hotels on Trivago and added them to my map: The Langham, Thompson, Four Seasons, Loews, Park Hyatt, Viceroy, and The Peninsula. What I found was that Alinea (the restaurant my husband wants to go to) was far north of those hotels, so I’m glad I did this because I won’t stay near Alinea now—I’m already assuming, based on this exercise, that most of the activities are near those nice hotels.
STEP 4: Find activities you want to do and save them to your map.
For finding the right activities, here are my secret tips: (a) I access a few sites, always. I do trust TripAdvisor, in general, to help me with major “can’t miss” tourist attractions in places. I also tend to find smaller private tour companies that way. (b) I also do a Google search and see if there is a blog (like mine for you, I hope!) that I vibe with. (c) I check if there’s a NYTimes article about the location (often they do neat “72 hours in XYZ” articles). (d) Another tip is that I go to websites of those nice hotels (I do this always!!! Don’t miss this step!!!) and see what activities they recommend in the area. Sometimes hotels also recommend events or festivals, which is helpful. (e) I always search whether there are good festivals or big events whenever I’m in a spot. (f) And of course, once I book a hotel I reach out to the concierge to share what I’m thinking and see what I’m missing.
- MY EXAMPLE: My husband knew he wanted to go to the Chicago Shedd Aquarium, and I listed out (in a Google doc) a few other activities that seemed fun for us—the Art Institute, Chicago Theatre, Goose Island Beer Company, just to name a few. I almost always book a tour when visiting new cities, to appreciate its history. There are often free walking tours of big cities (but always tip well!), and sometimes I splurge on private ones so that my husband can ask his many (haha) questions. There are lots of options in Chicago! I will ultimately book a private vs public tour, walking vs biking vs boat, based on the rest of our itinerary, to get a balance of activities and budget. The Four Seasons proposed private boat tours on their website, and bloggers have recommended Candlelit concerts or even ghost tours in October (something I never want to do but my husband always wants to do… and it’s his birthday after all!)… it all sounds fun! For now, I’m listing inspiration, and in a week or so, after reflecting, I will put it together and book!
STEP 5: Book your hotel!
Now that you know what activities you are interested in, and where your food, go to Trivago.com, RelaisandChateaux.com or MrandMrsSmith.com (good for boutique hotels and perks like cocktails on arrival), and figure out hotels that may be a good fit for you!
- MY EXAMPLE: The Publishing House gets 9.4 on Trivago and is on MrandMrsSmith.com for a decent price, so I may book that—if I book on MrandMrsSmith, I get welcome drinks on arrival. 🙂 And who wouldn’t want a welcome drink?! I’m still deciding on hotel though… stay tuned!
STEP 6: Book any activities that have to be booked in advance.
That way you aren’t disappointed if you show up and the activity isn’t available. If you can’t get the booking at XY or Z activity that you want to do, you can always reach out to your hotel to help.
- MY EXAMPLE: Alinea is a fancy restaurant that requires you to book two months in a row on the 15th of the month at 11am… my alarm clock to make the reservation is already set!
Don’t forget, this process should always be FUN!
So if you’re ever overwhelmed, stop what you’re doing and come back to your process another time with a glass of wine in hand. I could talk about this forever, I love planning trips that much. Hope your next trip planning is a whopping success! Let me know how it goes! xx
