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3 Ways Your Travel Bucket List May Be Holding You Back

Do you dream of visiting the great pyramids of Egypt? Eating your way through Tuscany? Exploring the Serengeti by Land Cruiser? I get it. Just imagining what things will be like at your ideal destination is half the fun. That said, sometimes I think we get so caught up in these big, grandiose adventures that it keeps us from going anywhere.

Here’s how your travel bucket list may be holding you back (and what to do about it).


The Problem: The trip feels too overwhelming to plan.

Is your travel bucket list holding you back?

I know a couple who dreamed of road tripping New Zealand for their honeymoon. They discussed whether to explore Middle Earth on the North Island, go skydiving on the South Island, or both. Christchurch seemed like a fun city stop, and what about Marlborough wine country? And since they would have traveled so far already, wouldn’t it be incredible to SCUBA dive at the Great Barrier reef?

Okay… now how do you cram all that into 12 days?

What started out as an exciting idea ended up becoming incredibly stressful. This couple did end up honeymooning in New Zealand, and only because they gave up and had a travel agent book everything. Though the trip was incredible, it left both wondering if they should’ve opted for something less involved. Maybe planning a wedding and a bucket list honeymoon (along with both working demanding jobs) was a wee bit too much.

The Fix: Ask for help.

Yes, I know you can book everything online all by yourself. But working with a travel agent saves you tons of time and money. You can still be involved in the process, but these experts have a wealth of knowledge about your dream destination, as well as access to exclusive deals. You may have analysis paralysis, but it’s their job to keep the process moving. With their help, you’ll be paragliding above Queenstown in no time!


The Problem: You discredit less spectacular trips.

bucket list vacation

Renting a private villa with your besties for a Cabo-extravaganza couldn’t sound more perfect. And a less budget-busting version would’ve been exactly what you would’ve planned back before everyone had so many responsibilities. You know, things like kids and pets and jobs and aging parents and a mortgage and car payment and, and, and!

Because you can’t figure out how to coordinate everyone’s schedules and needs, you scrap the trip all together. Oh well, maybe you next year. Sigh.

The Fix: Think smaller.

Is your travel bucket list holding you back?

Sometimes it’s less about the destination than it is about the people. There are years (hey, maybe decades) where taking an epic trip is just too hard. I encourage you to shrink your thinking. When you make travel easy, people will do it. Plan a getaway within driving distance, or book a long weekend in a mid-sized city with lots of direct flights.

I like to treat travel as a habit. It’s muscle you can strengthen, and the more you do it, the more you want to do it. This year, it may be the exotic Wisconsin Dells or enchanting Mystic, Connecticut. You can always book that Cabo trip later, when things settle down.

The Problem: Traveling for the wrong reasons.

is your bucket list holding you back?

Instagram is lovely for inspiring #wanderlust. I get lost scrolling through @DameTraveler’s feed of women in exotic locales. From sunset camel rides on Australia’s Camel Beach to soaking up the kaleidoscope-colored light in Iran’s Nasir ol Molk Mosque—I’m instantly transported to far flung destinations, scheming how I will one day get there myself. It’s lovely.

And yet…

Sometimes I wonder if access to so many beautiful images creates a warped sense of what we’re trying to get out of travel. Are we visiting Phuket for the experience, or are we looking to snap the perfect photo? Do we go to Iceland because it’s captured our imagination, or are we experiencing a fear of missing out— “everyone else seems to be going, so maybe I need to as well.” Is it good enough to set foot in a country just so you can check it off your list, even if you didn’t truly experience the local culture?

The Fix: Tune out the noise.

travel bucket list

It irks me when I see lists like “Top 10 Places you HAVE to Visit Right Now!” Travel is a deeply personal experience, and who cares what’s “cool” if in your heart, you really want to go somewhere else?

Close your eyes right now and think about what you want to get out of your next vacation. Do you see a beach? Are you enjoying seafood freshly plucked from the ocean, paired with an icy cold sparkling wine? Is your partner there? The kids? Maybe your best friends form college? Destinations like Mallorca, Sydney, or Cape Town would fit the bill. However, Boston, Charleston and Portland, Maine could also work—for a fraction of the price, and in mere hours.

In baseball, the crowd goes wild over home runs. However, it’s the smaller plays—singles, doubles, stealing bases and quick fielding—that makes the game fun to watch. Travel is a lot like that. Infusing trips into your life in smaller, more achievable ways, leads to a more fulfilling travel life.

So, where are you heading next?

Is your travel bucket list holding you back?

This Post Has 14 Comments

  1. This article is perfect. I have girlfriends I travel with all the time. As of right nowthe big trips are on hold due to a few health problems that have cropped up in our group. We look at places that we can either fly to within a day or drive to in a day. Our next trip in the Spring of 20 is Hot Springs Arkansas. I already have my eye on a nice house rental and then we can figure out the rest. Europe is on the radar probably in 2 or 3 years.

  2. Thank you, Samantha! When my husband and I travel, we visit places that mean something to us and not always the top tourists sights. Sometimes I reject places just because everybody says “you have to go there”! In Ireland, we skipped the Cliffs of Moher (gasp!), and instead drove out of the way to see Mizen Head in West Cork. I loved it! So I agree, go somewhere because it moves you, not because you wrote it down on paper years ago. I’ve learned that flexibility in travel makes all the difference!

  3. So true. I love planning the big trips, that’s part of the travel experience for me. But, they require lots of money. Also, the time gap in between is too long. Smaller trips, one single destination to explore is also exciting, more frequent and more affordable.

  4. Hi Sam ,
    Recently returned from a 3,000 mile trip in my Prius bringing my Pedego Ebike , from Raleigh NC to Ontario Canada , through Montreal to Manchester NH ( your birthplace) and to Norway Maine. Maine was so overbooked, and expensive but fortunately I had a cousin with a lakeside summer cottage and simple , uncrowded pleasures were just to swim in a clean lake , canoe and socialize-meet the locals, attend a church community Sunday breakfast to experience what I remember as a kid. My goal was to ride in Acadia NP only two hours from Georgetown Maine but hotels were booked solid and way overpriced I gave up . Memories of Maine in the 60’s were sweeter because of this when ten days for 4 adults with MAP was $350. As long as people pay the gouging rates inflation will ruin vacations for we Boomers!
    But wait what is wrong with being a tourist in ones own town? When working in Victoria BC they came up with the idea! Looking at their own town as if tourists !
    I seek out mountain villages, live with local people “Zimmer” and avoid bustours and an increasingly overcrowded popular European destinations. Its called survival and I appreciate home more now and my own bed ! The last day on my 21 day self drive saga I drove 715 miles for that reason there is no place like home!
    Oh Im a flyfisherman Sam and Ive a neat , spotless log cabin in the TN mountains at $100 a night, I book it a year ahead . Not trying to upstage you, love you and your programs but enough is enough.
    I did a motorcycle tour thru 15 countries in 1966 living with a family in Norway age 18 – total cost for 6 months $400 when hostels werent backpacker hostels and a spotless room was 3 Kroner. Ever want to chat call me at 919-622-1761. Always fun to write you!

  5. Samantha, this article came at a good time. I am thinking about a trip to Krakow, Prague and Vienna which would total app. 13 or 14 days. I have just returned from a trip to Quebec City which was lovely and all this may sound a bit greedy on my part. I had to give up a couple of trips due to a bout with cancer so Im trying to make up for lost time. Therein lies the reason, right or wrong. Now if I don’t go to Europe, (my kids don’t like the idea or so Im feeling that) I would like a trip to St. Augustine Fla, Savannah Ga, and finish at Myrtle Beach, SC.
    So Im torn between Europe and the good old USA, lol . Your thoughts. I thank you, Rick

  6. You hit the nail on the head with very single point you stated!! The mortgage, the aging parents, the work schedule, etc. I look forward to going to Italy & Greece one fine day. For now, my travel is just through Google and through you. Thank you for your excellent article. You’re so inspiring & down to earth, humble & grounded. Hugs from Texas!

  7. Just returned from my first and longest vacation in several years. I included a long cruise and a rail segment. I went to a travel agent for help with coordinating everything. I could not believe the shabby job done. I went to meet the agent to show that the people involved had ambulation issues. A walker and a scooter were involved. Not a bit of this was taken into consideration with the travel arrangements. If a so called professional can’t handle it what chance do I have.?

  8. Thank you! I’m traveling to Italy solo in September and I found exactly the same thing. It was overwhelming! I called a travel agent, mostly because since I’m 58, I didn’t want to be stuck in an airport with no flight for some reason and not know how to fix it. I can now call my travel agent. Not only did she schedule the flight, but hotels and transportation between cities; all things I could’ve done on my own, but now I can concentrate on not concentrating!

  9. Thanks Sam. I’m 100 miles from St. Louis and 200 from Chicago. I’m saving up to take my eldest and his girlfriend on Amtrack to the Windy City . I’m a foodie, and Chicago is full of great places to eat.

  10. Excellent advice. I visited Ireland last spring and it was wonderful. However I just returned from Boise Idaho visiting my niece and her family and didn’t want to leave. The mountains, hiking, family, small town vibe and beautiful weather gave me the inspiration I needed.

  11. My sister and I are going to Rochester, New York in a couple weeks because I wanted to see the Museum of Play. That’s all I had. Then my sister found the Eastman Kodak museum and the Warner Bros exhibit, so we’re doing that. Then it’s on to Niagara Falls and we’ll hit up the Corning Glass museum on the way home. It’s shaping up to be so much fun and I couldn’t be more excited if I tried. Cool things can be found all over. You just have to look.

  12. I am feeling a little overwhelmed at the moment trying to plan a cruise down the Nile. There are so many cruise operators on the market. I know that I want to travel in luxury but also I want a guide who is extremely knowledgeable. Reviews differ, great ship not so good a guide and vv. Uggh!

  13. How true! I always dreamed about a trip to Dublin but was overwhelmed with all the planning and not having enough money, so I put it off. One day my daughter helped me plan a four-day trip and that’s what we did! I didn’t need a whole week or more! I’ll tell you…it was the best trip I’ve ever taken!!

  14. This article hit home with me on several counts, especially as regards my #1 travel bucket list destination: Bora Bora.

    The island has topped my list all of my adult life, ever since I saw the 1979 remake of the film Hurricane. The film credits revealed that the film was shot on loction in Bora Bora. When I was 21 the attraction was as much for the hottie Polynesian men as for the pristine beaches and the marine life swimming in the lagoon! But the jobs I held in my twenties did not provide the budget for a French Polynesian adventure.

    After decades of saving, I began making plans to celebrate my 50th birthday on Bora Bora. But five months out, I suffered a bout of pneumonia that incapacitated me long enough to blow through all of my accrued leave time and much of my savings. The Bora Bora dream was put on hold yet again. But my 50th did not go uncelebrated. I managed to put together, partnering my own research with booking assistance from AAA and the 4-diamond resort’s concierge desk, a very scaled back but ultimately satisfying long weekend in Cancun. While there I took day trips to Chichen Itza and Isla Mujeres, swam with dolphins, and indulged myself with a spa morning between check out and my shuttle to the airport.

    In recent years, advancing age, disability retirement, a pair of personal injury settlements, and the sudden loss of several close family members made “unfinished business” more of a priority in my life. After receiving my settlement from the first accident, I finally had the budget for Bora Bora. While recovering from the second accident, I had the time to do the research and to talk to the tour companies at the AAA Travel Expo. My AAA agent partnered with a French Polynesia expert at Travel Impressions to coordinate accessible hotel stays, transfers, ground transportation and airline flights that would have easily overwhelmed me working independently. The only portions of the trip I booked myself were the USA layover lodgings and excursions (four nights in LA snd 4 nights in Honolulu).

    After over 40 years of dreams deferred, I finally realized my #1 bucket list destination–in February 2020. My timing couldn’t have been more perfect. I left my home on February 7 and returned on February 28, just two weeks ahead of the pandemic lockdown. The fresh memories of my Snowbird Paradise vacation have sustained me through the many long months of isolation. It’s a comfort that would have been lost to me had I accomplished the trip in my youth.

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