When Three Days is Not Enough Time

street cars in san franciscoFor years, I’ve been able to explore destinations at my own pace. Two days, two weeks, two months; it didn’t matter – I had as much time as I needed. In my view (still unchanged), when you travel, less is more. It’s better to see fewer attractions and go deeper than cast a wide net and go shallow. You get to know the people and places better, and you won’t rush, stress, or spend a lot of money on transportation.

I understand the desire to overload your itinerary when you only have a couple of weeks per year available to travel. Who knows when you might be around that way again? But I’ve always counseled against it, both on this site and in e-mail. You’ll spend too much time running around, traveling, packing, and unpacking. Heck, I once tried to see most of Dublin in 24 hours and that was just insane.

In March, I made my first visit to San Francisco as part of my book tour. I spent only 3.5 days in the city and, unlike most trips where I can stay as long as I want, I had to cram everything into a very short period of time. I knew I’d only scratch the surface, but something would be better than nothing.

What did I learn from this experience?

Three days is not nearly enough.

I found myself running around to see the big sights, fitting in the best restaurants, getting exhausted walking up all those hills, fitting in meet-ups, and overall, just being tired of always feeling like I had to race around a city.

the golden gate bridge in San Francisco

Having to sightsee in just a couple of days was my own personal hell. Places become such a blur that you feel like you end up with only photos instead of memories.

I walked away from San Francisco with two realizations: (a) I need to go back because what I saw of San Francisco was amazing and (b) there has to be a better way to experience short-term travel than running round like a chicken with its head cut off.

My trip to Lisbon in May gave me an opportunity to find a better way. I only had three days and I was determined not to repeat my experience in San Francisco.

This time I did it differently.

This time I came with a plan.

No, I didn’t regiment every second of every day. Travel is about letting things unfold and happen to you naturally, not rigidly planning your journey. But I wanted to walk away from Lisbon without feeling exhausted or that I hadn’t seen anything.

Having a general idea of what I wanted to see and do before I went allowed me to better prepare, organize my visit, and pace myself so I could have some downtime and opportunities to just go with the flow. I missed a lot of stuff the first time I was in the city last year.

lisbon portugal houses

I decided that on the first day I would wander the city center, visit the history museum, and see Se Cathedral and Saint Jorje Castle. On the second, I would go to the beach outside of town, and on the third, I would take a city walking tour offered by the hostel, visit the lookout tower, and explore a few other churches.

I figured this rough outline would give me enough to fill each day — but not enough to make it too packed.

So how did it work out?
lisbon portugal beach on a nice day
Despite being super jetlagged and sleeping through much of the first day, I found that creating a framework allowed me to check off most of my list without feeling I was running around like crazy. I was able to see what I wanted to see while still finding time to add in local recommendations.

And while I rearranged the order of everything when I got into town, by breaking up the days into “bite-sized portions” I found I could explore at a relaxed pace.

I applied the same strategy when I was in Madrid a few days later to the same effect. I had four days in the city and I started with a plan. I made a list of everything I wanted to see and then each day went through that list: botanical gardens, food tour, walking tour, art museums, nightlife, cathedral, and the royal palace. I didn’t get to everything but I found creating a list helped set a pace that made exploring a giant and sprawling city in a few days seem less overwhelming.

So the takeaway? If you are trying to explore somewhere new and have only a short period of time to see it, it’s best to go in with a rough itinerary to maximize your limited time. By doing some preliminary planning, you can avoid feeling overwhelmed and instead focus on actually enjoying your trip, seeing what you want, and still finding time to let the road take you interesting places.

I get many e-mails asking for help with itineraries and hour-by hour planning for trips, and I see many people trying to cram too much into a short period of time. In my experience, however, creating a framework for your trip instead — and filling in the little details along the way — is a much more relaxing way to not only plan a trip but also see your destination.

  1. If I know I will only be in a city for a short amount of time, I will make a rough itinerary with the aid of tripadvisor.com (and your site, of course). I’ll see what the top attractions are and prioritize them for myself. Sometimes, if I know a little about a city, I’ll skip several of the top 10-15 items just to do something that appeals to me, but may show up in the list at 20+.

  2. I hate feeling rushed in a place. Even a month in each country I’ve visited in Southeast Asia hasn’t felt like enough. I’m still running around from town to town after a max of a week! Three months in Thailand and I know I barely scratched the surface. Goes to show, only living somewhere and getting totally immersed will reveal a place’s true colors.

  3. You must go back to San Francisco!
    I definitely agree that creating a framework for your trip rather than a strict itinerary is the way to go. Nobody wants to be stressed while on a holiday! I am a total list maker so this post was right up my alley.
    Thanks :)

      • Peter Francis

        As others have noted, there is so much to see in San Francisco that three days is much to short a time to enjoy the city and it environs. On your next visit see the city but get out to the EastBay, Saulsalito, the peninsula and Silicone Valley as well as Santa Cruz and Monterey!! You owe it to yourself to soak all of Northern California in!!

  4. Shinelle

    Reading your post made me realise that I have been planning my trips the right way. I always choose just a few attractions that I REALLY want to see, and just go there. This is exactly how I plant to spend my time when I go to Atlanta GA

  5. I do a lot of off-the-beaten-path cruise travel and find myself with 2-3 days on either end to cram in all I can see about a city. Think Barcelona in 3 days! I did it, and saw all I wanted, but my best planning tool has been Google Maps. I find all the things I want to see and create a custom map for my destination and plan a rough route through the highlights I want to hit. At each stop, I reference my map for what’s around, check out my saved details about a place and adjust my route along the way. A short detour off my main plan often rewards me with a greater experience and a feeling of not being stuck to a schedule.

    This has proved amazingly effective in quelling my fears of missing anything by having an exhaustive list and choosing things moment by moment based on my interest and energy level at the time.

  6. Kaleb

    I just recently began to travel for week long periods! Before it was 3 days max I visit Chicago and NYC in 3 days! Is just about the planing for me!

  7. I feel the same way. I looove just taking my time and walking around just sucking it all in. Slowly. It’s the best way to travel in my opinion.

    I’m currently on a three months biking trip around Europe with my boyfriend and we really had the same experience as you did in SF when we were in Berlin last week. I really like this advice about creating a rough framework! We’ll be trying that out for when we reach Amsterdam next week!

    Thank you for the advice! :)

    • Marilynn

      I traveled for a month with a carry on and a rail pass, with my spouse. (no plans except a place at the atart and the end to sleep)When we arrived a a new place, we found a hotel and than just wandered. When in Paris we did take the hop on hop off bus tour, saw the main sites. I also live in Los Cabos, Mexico where I see a lot of cruise ship passengers wander by. One afternoon while eating pizza on the wharf area a coupe from the cruise ship popped in for a beer and relaxation. Their comment was right on, we can’t see it all so we decided to just stroll along and take in whatever seemed interesting. SOOO much better. And guess what they ran into a “local” couple who could give them a few fun tips. Relax and enjoy the places you visit you can’t see it all.
      I will be taking my second trip, now a widow, in Sept and Oct. I have the beginning and the end planned and will just wing it with a rail pass for a month! Can’t wait, I turned 65 in March, so i wil have one wheelie and a personal bag.

      • Gwen

        I’m so sorry that you are now a widow. I am inspired that you are planning to travel as a Baby Boomer! My husband and I are also about your age and want to get moving as we both retire!

        Thanks so much for your comments!

  8. Hi Matt

    Great post! My entire travel life was restricted by limited corp vacation time so I got good at cramming a lot in a little time. Since you’re so helpful and inspiring, feel free to use my trip planning and itinerizing techniques dfor our shorter trips in rerurn
    Best, Eva

  9. I always used to think that if I were to visit some countries, I had to make plans in advance and draw up some places of interests I would like to visit before hand to make full use of my time there (even if it’s just a 2-3 days trip). My trips will usually turn out organized, but tiring as well since I will be moving from places to places endlessly.

    Now I tried to decide what my travel purpose was. If it was a short getaway, I will not try to plan too much ahead and just let things unfold when I arrive. If I really want to experience visit some places, I would add into my list to get a rough outline so that I will not miss out as well!

  10. Matt,
    Couldn’t agree more. I wanted to get out of the USA and explore the world, but instead of simply backpacking, I decided I’d live and work in different countries. So far, I’ve been Living in Thailand for 3 months and it’s been the greatest experience of my life. It’s not about seeing X amount of temples, or visiting X tourist attraction. It’s about absorbing the culture, the language, the country itself! 3 days to see a destination? Hah, after 3 months I’ve hardly seen any of Thailand.

  11. Totally agree with your great post. I used to travel trying to cram things in, but these days prefer to take my time. I’ve seen more of the real culture and local life that way and am already going back to places that I’ve been before to change my crammed experiences of the past :).

    • NomadicMatt

      My friend Matt has a rule that he only tries to see three things a day. Anything more than that is just icing on the cake.

  12. Amen! Great you touched on this subject Matt because people can certainly leave a destination with an opinion of it (good or bad) when they truly haven’t discovered it entirely. I did Petra, Jordan in such a short amount of time i literally ran majority of the day. This is one place i wish I never did that and know I need to head back there again. People please don’t do this learn from our mistakes!

  13. I completely agree with the idea of setting up a loose plan for short trips – they seem to work really well for city breaks. I’m often only able to visit a city for three or four days at a time as I’m still at university, so I try to work out the things that I absolutely cannot miss and put aside the things that I’m less crazy about. I always feel a bit disappointed when I can’t do everything I want (I also recently visited Lisbon and missed out on riding Tram 28 and St Jorje Castle – but instead I got to spend a full day in Sintra and the next exploring Belem)
    but it’s the best way of spending time.

  14. Geri

    San Francisco: Ferry Building and it’s Farmers Market. One of the best foodie havens on the West Coast. Asian Arts Museum and Japanese Tea Garden in Golden Gate Park are special. Giant baseball at AT&T Park. Along Market Street,the F streetcar line runs historic cars — very cool. Lived there for ten years and barely scratched the surface. Dress warm — August can be chilly (or warm), who knows.

  15. Just Jan

    When I had a just a few days in Lisbon I bought one of those open top bus tickets and did 3 different circuits on the first afternoon. It gave me a feel for the layout of the city and helped me choose what areas I wanted to see close up.

  16. sc

    I only had 4 days in madrid and google maps really helped. picked key spots and saw how close they were to each other. set up an rough plan per day and freestyled the rest if things went awry or took a stroll on my own just for a break. i moved a few things when i realized they were closer than i thought and also so that i wasn’t rushing to do something day of my leaving flight.

  17. Colin

    Great post. Personally I’d prefer to be in a city for 1 or 2 weeks (shortly I’ll be in London for 15 days) but sadly that is not always possible. If I am only going to be in a city for a couple of days I’ll do the research as you suggest, but then I’ll also do some research for a decent tour that lasts for 3 to 6 hours that will give me a good overview of the area I’m visiting. I’ll try and take the tour as early as possible during my visit.

    Based on this tour I can either decided to go back to certain areas for a more detailed visit or move along to other things on my list, but which were not covered by the tour. When investing an upcoming tour to San Francisco I came across a great 4 hour hour walking tour of Muir Woods with a picnic thrown in. Sounds like a great way to get to know the city and surrounds

  18. Larisa

    I like to arrange a 3.5 to 4.00 hour bicycle tour of the city on my first day to get a lay of the land and then select places that I’ll visit again later on during my stay. I find this works well but I try not to book less than 5 days in any major city as things seem to become a blur otherwise. I do agree that less is more.

  19. Terri

    Great post thanks Matt. Totally agree combo of freestyle and planned. I like to do a lot of research before I go somewhere (never understand people who say they just turn up and float, I’d think I was missing out and I want to make the most of any trip). Once I know what’s there I’ll plan using map and when I get there I’ll go with the don’t want to miss eg a trip that only runs one day I’m there. And the rest I’ll do according to what I’m feeling on the day.

  20. Linh

    Hi Matt,

    Thanks for the post. I’ve found it reassuring to know that having a rough framework of places to go and things to do is not a bad idea rather than to plan everything down to the last minute.

    We’ve recently booked our trip to San Fran in October with another couple and I’m thinking that it might have been a mistake to stay for only 3 days instead of 5. They would like to include a day in the amusement park when we’d rather spend a day exploring private beaches and visit some winieries. With that being said, mapping out a flow of things to do will allow us to enjoy each others company in a new city as well as to experience the things that we each want to see in the short time that we’re there.

    If you know of any hidden gems in the city then please share a few of your favourite places.

    Thanks so much!

  21. Seeing places quickly can be so debilitating! Long term travel is so nice because you can just RELAX. You get the real feeling of a place that way!

  22. Robyn

    Sometimes, talking to the right people and a little bit of luck can shape how you see a city. While traveling through Europe several years ago, a friend and I had less than 24 hours in Rome before flying to Greece. I had seen the city once before, but for my friend Jon, this was his first visit.

    We arrived late into the city due to train delays and didn’t get into our hotel until the early afternoon. After talking to the hotel manager (who offered us delicious cappuccinos in the hotel terrace garden) he gave us a map with scribbles all over it. In 6 hours we were able to travel from our hotel to see several of the major sights (the Trevi Fountain, the Colosseum, the Vatican, St Peters Square, the Spanish Steps), eat Gelato, stumble through open markets and a few public protests (George Bush was in the city, which was the cause for our train delay). We finished off our evening with an authentic Italian dinner at a restaurant tucked away in alley recommended by the hotel manager before we wandered home to bed before our early morning flight. It was the best experience to see the highlights of the city in such a short amount of time.

  23. You’re right its always good to have a short and a sweet trip. I know that we miss out on a lot a of things, but you’ll at least have a brief look at the place. Something is better than nothing.

  24. Spock

    I think I’m going to have a similar experience soon enough…I’ve planned on a max of 3-4 days in my trip each place I visit. I hope to see the ‘Big ones’ first and then move on to the smaller things….dunno if it’ll work!

  25. I was brought up in different countries and had the “chance” to experience travellers from various parts of the world. Their preparations for their trips varied quite a bit.
    When communicating with them after their return I found their “travel satisfaction” biggest when they had tried to plan and prepare their journey and their “learning to get to know other peoples and other cultures” before travelling.

  26. Agree.

    I was lucky enough to spend not 3 days, but 3 years in San Francisco.
    Yes, the city is insanely beautiful and there are many famous spots to check out. I mean, the Golden Gate Bridge only is amazing and I could never have had enough of it.
    But traveling is also about experiencing what’s in the air. Coming from classy Paris, it was amazing to me to experience that HiTech and …Hippy atmosphere. The same way someone coming to Paris should not limit himself to the Louvre and la Tour Eiffel but also go to cafés, and have a picnic with a glass of Rosé by the Seine… My favorite:-)

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