How to Plan The Most Amazing Vacation Ever

If you’ve been following along for awhile now or if you know me personally, you already understand that I’m pretty Type A. When we plan a vacation, this personality type becomes extremely apparent. Thankfully, this works for Sasha, and some people like to wander lackadaisically around new cities with no itinerary – I honestly cannot wrap my head around that, as I land with a printed agenda and have plans down to the minute as to what we’ll do and see. The most important thing for me (and others like me) to remember is that if something goes awry, just let it be. If we have ten things planned, but end up spending lots of time at one museum, it’s okay to let the other things not happen. But I do need plans just in case!

When we went to Turkey, Athens and Paris, I printed a book out that had our flight confirmations, passport info, and day-by-day itinerary. I’ve wiped out personal information, but you can get a good idea of the plans we had by reading it here. I created a very similar document/folder when we went to Bali last year for our honeymoon (see the custom map here). I think it’s very important to be well-prepared before you travel to a new city in order to absorb as much culture, sightseeing and delicious food as possible.

Praying in the Tirta Empul Temple in Bali

We’re currently planning our trip to Paris and St. Petersburg in May. I spent almost four months living in Paris in 2009 and have been back twice since then, so planning that portion requires much less research. St. Petersburg is an exciting challenge, as we’ve both never been, don’t speak any Russian, and don’t have any friends who have visited before. Fortunately, my best friend’s boss is from St. Petersburg, so I’m going to ask her for advice once I’ve done more research, as well as use Tripply (more on that below).

Picking your destination(s) is the most important step early on in the travel discussion. Perhaps you’ve got a bucket list of places that you’re dying to see (like me!), or maybe you’re open to any country. If you fall into the latter group, then it’s best to do some researching. Are you looking for a cultural experience? Or a relaxing beach getaway? Once you know what kind of vacation you’re interested in and have decided on a budget, I recommend scouring the following sites for city inspiration.

• Entouriste: This travel photography site features jaw-dropping pictures from cities all around the world (all of the photos on this post are from Entouriste except the header and second photo!).
• Atlas Obscura: This travel blog has an inspiring section called Places, which highlights cities and sites from all around the world and includes a bit of background and some photographs.
• Conde Nast Traveller: I am obsessed with this site. You can browse destinations or get inspired by ‘Types of Trips’ – whatever you’re looking for, you’ll find on this site (to be referenced later on in the process too). Their travel guides are phenomenal too.
• Trip Advisor: I am a huge Trip Advisor nerd. Like huge. I swear that you can plan the most incredible vacation by reading other people’s reviews. When you’re trying to pick a city or cities, I highly recommend looking at their Top Destinations in the World listings.

Once you’ve narrowed down the destination location(s), it’s time to look into flights. I absolutely love the Kayak iPhone app (much more than the site). I spend far too much time seeing how much it’ll cost me to go from IAH to just about anywhere in the world. You can set alerts so that if a flight path gets to a certain price, you’ll receive an email notification from Kayak. That’s genius. Step two is definitely booking your travel (flights or trains, depending on where you live or where you’re going), but hold off on accommodation for now.

Okay, so the destination(s) is decided upon, and travel is booked. What’s next? Deciding what you’ll be doing when you arrive. The first step is to create a custom Google map, which you can do here. I cannot stress enough how important this is when planning a trip to a foreign city.

I create maps for all trips that I take – whether they be international or not. This is one example of a map I made, which is part of my San Francisco tour guide.

You can create multiple layers in Google maps, which is helpful if you want to divide your icons between food, activities, accommodations, etc. I typically just use one layer and make sure to use different icons or different colors for my distinctions.

As you do your research, search adding things that interest you to your map – it’s very easy to delete them later on. I start by using the top recommendations on Trip Advisor. I suggest you think outside your comfort zone too. Sasha is not a big ‘cooking class guy,’ but his favorite activity we did on our trip to Bali was take a Balinese cooking course. Trust people’s ratings on Trip Advisor!

When you find interesting places to visit, type them into the Google Maps search bar, and then when they appear, add them – and I like to add little notes to the names before cleaning them up later. It’s helpful to save places to your map as “L’Orangerie – tons and tons of Monet” vs. just saving it as “L’Orangerie” and forgetting why you wanted to go. You can also add notes in the section below, which is helpful (make sure to note if the museum, restaurant, etc. is closed on certain days!). I definitely recommend tagging places as breakfast, lunch or dinner (either by color or by text). This helps when you create your daily itinerary.

Reference the four above mentioned sites for places and restaurants. I tend to load my map up with things to do!

Once your Google map is populated (not final version, but full of sites, activities and restaurants that interest you), see where most of the activities are clustered. It’s always good to pick a place to stay that is central to these places versus picking a hotel that is just in a safe area and has good reviews, but is far from good restaurants and sites. An example of this is the business district of San Francisco – hotels in the area will have great reviews, but I wouldn’t recommend someone stay there if they’re in the city for sightseeing.

After you narrow down the areas, do further research to make sure that it is safe for tourists. Search on Trip Advisor for hotels in that specific area (you can normally see area names in Google maps). You can also rent an apartment on sites like airbnb or VRBO. We’re using one of these sites for our trip to Paris and St. Petersburg, as we want to have a kitchen and a more homey place to stay than a hotel.

Before booking anything, I recommend signing up for Trippy.com. This site is so smart. You are able to ask questions to local experts (and get asked questions too!) – you can save responses and search other forums. It’s free, so what do you have to lose, right?

Here comes the most time consuming part (but I think the most fun activity): create your detailed itinerary.

If you’ve been diligent labeling restaurants as breakfast/lunch/dinner in your Google map and have included all of the sites you’d like to see, creating your itinerary won’t be tough.

I recommend creating a Google doc if you want to share this with fellow travellers. You can paste it into a Word or PowerPoint document later to make it prettier – if desired (what I’ve done in the past). Create sections for each day you’ll be gone, and begin with breakfast. Will you be eating at the hotel? Or do you like to try cafes? What time does your day normally start? I always allocate rough times, just so that I know how many activities I can fit into a day.

Take for example, one of our days I’m working on in Paris:

MONDAY

• 8:00am Walk to get breakfast at Les Deux Magots (or St. Germain des Pres metro stop)
• 9:00am Go to Laduree for macaroons
• 9:45am Walk across the Seine to L’Orangerie for a brief stroll through some of Monet’s most beautiful pieces
• 10:30am Stroll through the Jardins des Tuileries and down the Champs-Elysees to the Arc de Triomphe
• 12:00pm Take the metro to lunch at Cafe Beaubourg from Georges V to Hotel de Ville (Line 1)
• 1:30pm Walk around the Centre Pompidou
• 3:00pm Stroll through antique shops in the Marais (on the rue de Sévigné)
• 4:00pm Go to see Notre Dame on the Ile de la Cite
• 5:30pm Go to the apartment to prepare picnic dinner
• 6:30pm Early dinner in front of the Eiffel Tower (sparkling lights!)

If we didn’t end up at L’Orangerie at 9:45am (which we realistically won’t), then that’s fine. Times are just guiding points. Your Google map should help you be able to define your day – breakfast, activity, lunch, activity, dinner and potentially another activity, if you’re looking for shows, bars, etc.

I tend to have one entire day be a ‘rainy day’ plan – or make sure you know which activities you could do if it rained. When we went to Athens, we encountered lots and lots of rain, so it was good to know we could switch around our spa day with our climbing Mt. Lycabettus day.

Once you’ve got a first draft of the itinerary, share with any friends who have travelled to the destination before. If you don’t have any friends who have visited the city, ask around, and you’re likely to find a friend’s friend who has been there before. Vetting your itinerary with someone who is familiar with the city is extremely helpful. They can tell you if getting from A to B in the time you’ve allotted is possible. You can also share your itinerary on Trip Advisor and Tripply forums, but I would recommend you don’t share specific dates for safety reasons. You don’t want strangers knowing where you’ll be on a certain day.

For organization purposes, I create a page that includes all reservation numbers – for flights, hotels, etc. Include numbers to call if something goes awry (like the airline number!). I also tend to have a page dedicated to scanned copies of our passport. If they get lost, it’s good to have a backup! In addition, I tend to copy and paste common phrases that are helpful to know, which is typically: “Thank you,” “Please,” “Do you speak English?,” “I would like…” and “Where is the bathroom?” People really appreciate it when you attempt their language (even if you butcher it).

Lastly, as you can see with my Turkey/Athens/Paris itinerary, I added a little background (normally just copied and pasted from Wikipedia) about each of the sites. I think this is very, very helpful when traveling, as a blue house in Mexico has less meaning when you don’t know that the blue tiles were chosen by the Countess Del Valle de Orizaba in the 18th century to show off her family’s wealth (referencing the Casa de los Azulejos in Mexico City).

Final tip – add blank pages at the back to take notes!

I always print and bind my itinerary, as it serves as a one-stop-shop for travel guidance.  In one bound book, you’ll have your passport, flight and accommodation information, as well as maps and day-by-day plans. I have always just taken my document on a USB memory stick to Kinkos and have them print and bind it (normally around $15). Worth every penny!

So now it’s my turn to ask you – how do you plan your trips? I love hearing other people’s tips and tricks. If you are totally overwhelmed by the whole trip planning process, I have a solution: hire me. I would absolutely love to plan your trip (down to the minute!). No, seriously. Send me an email, and we can chat.

See all of my travel guides here, or click on any of the cities below!

Athens, Corinth, Olympia and Nafplio, Greece

Bali, Indonesia

Istanbul, Turkey

Mexico City, Mexico

Paris, France

Austin, Texas

Durango, Colorado

Chicago, Illinois

Houston, Texas

New York City, New York

San Francisco, California

California Wine Country (Napa, Sonoma, Calistoga, St-Helena, Yountville)

Washington, DC

 All photos except for the header and second photo (taken last year in Bali!) are from Entouriste. As I said earlier, you need to check the site out.