How to solo travel intentionally, sustainably, and meaningfully

If someone were to ask you, “Where in the world would you go if you could right now?,” would you have an answer?

I was one of the people who had an immediate answer. Though I do dream about what it would be like to travel all around the globe to foreign countries and remote, untouched areas, the place I had deeply rooted in my mind was actually right here in the United States.

Hawaii.

I’m sure we’ve all seen beautiful photos of this collection of islands online or on instagram tourist or influencer feeds. But, something about this far away state from my home in New York drew me in beyond just its beauty.

I believe that one’s environment shapes who you are and subsequently who you will become. Though I had never visited the state before, I had a feeling that being surrounded by surf, sand, sun, farmland, and a diverse mix of people would create a community tied together in a spirit of connection to the land, the waves, and to each other.

Hawaii comprises eight major islands: Hawaii (“The Big Island”), Kahoolawe (smallest and prohibited to the public), Kauai, Lanai, Maui, Molokai, Niihau (population of only roughly 200 people), and Oahu. The insight I share is based on my personal solo travel experience living and farming for two weeks on the North Shore of Oahu. The negative impact an over influx of tourists and visitors can have on a place/community of people (especially in Hawaii) cannot be ignored. This makes it that much more important to be mindful and practice ethical ways to travel. Read on for my advice on this.

If you’re nervous about solo traveling, especially as a solo female… trust me, I feel you. I faced my own anxieties and resistance from my family to go someplace new and unfamiliar without any real certainty of knowing who I would be surrounded by or if I’d even like it. But, without a bit of risk, there is no reward. And now that I’ve completed my first solo trip, I can confirm that it is possible to travel smart and meaningfully despite the unknown.

Here’s how I did it:

Save money and integrate into the community through a work-exchange or volunteer program

People travel for all different reasons: destination weddings, work trips, weekend getaways, family vacation, to get to a hike in a neighboring town, etc. And good news: there are ways to harness meaning and intentionality in all the above! With that said, from my own personal life experiences thus far in my 24 years, some of my more meaningful travel experiences have been ones that allowed me to more fully immerse myself in the local community and connect to the land.

All inclusive resort trips can be wonderful for rest, relaxation, and convenience– there’s nothing wrong with pampering yourself! On the flip side, challenging yourself to be hands-on, get a little dirty and sweaty, and find a job whether temporary or for an extended period of time can be an uncomfortable, yet extremely rewarding life experience. It forces you to integrate deeper into the community by taking part in the workforce, often allowing you to meet more locals, learn about the history and development of the area, navigate transportation, and uncover gaps/challenges within the community, regardless of how perfect and shiny it may appear from an outsider’s perspective.

Finding a job at a local cafe, market, hotel, or boutique can be one way to go. But a potentially even cheaper way to travel is to participate in a volunteer or work-exchange program, which typically provides housing and some food items free of cost (depending on your host) in exchange for some hours of work throughout the week. I was WWOOFing (Worldwide Opportunities on Organic Farms) on the North Shore of Oahu. I found a WWOOF host on the wwoofing website and arranged a two week stay, working roughly 4-5 hours a day tending to the land (i.e. mulching, weeding, landscaping, feeding chickens, harvesting fruit, watering the greenhouse herbs, pruning, planting, etc.) Monday-Friday. I stayed in a tree house up high on a hill in a tropical jungle setting with views of the waves from Sunset Beach below.

Each host is different, so you’ll need to be diligent about researching the host/reading reviews/contacting former wwoofers to determine if you’d be a good fit. Fortunately, for my first solo travel experience, I couldn’t be more grateful for my host and the location I ended up in! Sometimes you get really lucky, but be smart and do your share of preparation in advance.

Ask questions about the land

Since I was working on an organic farm, I was set up well to learn about the aina (the Hawaiian word for “land”). Aina demonstrates the Hawaiian core value that there is a reciprocal and even familial relationship between people and the land. To many native Hawaiians, connection to land is critical to one’s physical, emotional, and spiritual wellbeing.

When most people think about the word, “conservation,” within the context of the environment, the thought of protecting and preserving the land free from human intervention usually comes to mind. Native Hawaiians, on the other hand, believe that there is meant to be a symbiotic relationship between people and land, meaning that the two go hand in hand. There is a duty to be good stewards. I learned this from someone I met during my travels who has lived on Oahu for several years now.

I need to acknowledge that I also worked with an incredible farm manager who taught me about the land and permaculture (ecosystem intended to be sustainable and self-sufficient) daily. This made information about the environment more convenient and easily accessible to me. But there are certainly other ways to learn about the land should you intentionally choose to do so. Download inaturalist on your phone, a plant identification app where you can snap a photo of a plant you want to learn about. Perhaps even better, however, is to seek out information by simply talking to people in the community. You never know what a conversation might teach you.

Get your hands dirty, give something back

For me, this looked like filling buckets of mulch to deposit around fruit trees, cleaning out a chicken coop, weeding, harvesting, pruning, watering a greenhouse, re-planting, and other small landscaping tasks. I worked on a small-scale family farm with tropical fruits, herbs, and chickens, which differs from a large-scale production farm. Keep in mind that your responsibilities may vary depending on the type of farm you choose if you decide to do this type of work-exchange.

But taking active initiative and “getting your hands dirty” doesn’t exclusively mean farming. There are plenty of other ways you can get involved and give back to the community while visiting a new place.

Volunteer at a local food bank. Support or donate to a local initiative you care about (i.e. disaster relief, marine health, local school system, etc.). Attend community events at a church or other worship group. Participate in an organized or self-initiated beach clean up. Give someone a ride. The list of ways to help a community whether big or small goes on.

Get curious about culture

I don’t just mean the large scale cultural/traditional differences found in remote faraway places. You might be surprised to discover significant cultural/societal differences in places all around the US or even in a neighborhood an hour or so away from where you live. Each town has its own unique community of people and vibe.

Are you in a place where people tend to have a special connection to land/sea and native traditions, like where I was on the North Shore of Oahu? An outdoor enthusiast’s paradise? A foodie capital? A quaint coffee shop and bookstore lovers’ dream village?

Look around you and notice how locals live– how they spend their time, what they wear, the kind of vehicle they drive, and who they are with. You can learn a lot through quiet observation, but if you make an effort to talk to people who live in the area, you are highly likely to enrich your visit and maybe even learn a thing or two about yourself.

Pass along useful knowledge

Think about a time you arrived somewhere new and felt a bit out of place or nervous uncertainty. As fun as travel can be, it can also be stressful and uncomfortable, especially if the place you visit is unlike home. This is the reality!

But you get by because you do research in preparation for your trip. You ask your uber driver questions. You meet locals who give you suggestions for places to eat or beaches to check out or cultural practices to respect or tourist traps to avoid.

Once you’ve accumulated these useful tidbits of knowledge, share your wealth with others! They will appreciate it greatly and your advice may make the difference between a good and great stay! YOU might be the one to open someone else’s eyes– whether it be to take good care of the land, support local businesses, or participate in an upcoming community event. And you just might also open the door to a potential new connection or friend or adventure buddy!

While living on the farm, I met two visitors who were staying at an airbnb, working remotely on the same property as me. I introduced myself and gave some suggestions for things to do nearby. We ended up exchanging phone numbers, became friendly, and even spent some time together one afternoon. Though the connection was fleeting as they departed a week later, meeting those new nice people undoubtedly contributed to the joys of my overall experience. They became part of my plot!

Walk, bike, bus

Perhaps you’re on a budget and renting a car for multiple days isn’t part of your plan. Or maybe you just want a more active experience, slowly appreciating your surroundings without needing to be in any major rush.

Walking, biking, or taking the long route on the bus is an amazing way to see any area from a fun new perspective– much slower than zipping down the highway in an SUV. Enjoy and savor the sights. You’ll probably get the chance to see things you normally wouldn’t by taking your time. You’ll also be saving non-renewable resources and reducing your environmental footprint.

Luckily, there were bikes on the farm I could use free of cost, so biking around the North Shore was my primary mode of transportation and I LOVED IT. Each time I hopped on my rickety, rusty beach bike (yes, I did have to learn how to put the chain back on when it fell off multiple times), I felt like a kid again, gripping the handlebars and letting the wind blow through my hair while blazing down a hill. And because I was constantly biking or walking, I felt myself getting stronger– no worries about hitting the gym ever crossing my mind! Moreover, the trip from the Honolulu airport to the North Shore required one bus transfer and about three hours of my time. But in taking the long way, I saved money and got to really enjoy the view outside my window, appreciating the lush green mountains and ocean vistas much more than I would have, as if watching a cinematic masterpiece.

Reduce your environmental footprint

In addition to the above (walking, biking, taking public transport), there are plenty of other ways to travel consciously with regard for the environment.

On a farm, I ate from the land (i.e. herbs, tropical fruit, farm fresh eggs), took cold showers, carpooled when possible, reused plastic containers from my takeout food, and fed safe food waste to the chickens.

But regardless of whether or not you’re living on a farm, you too can take shorter showers, use reusable products, compost, and limit fuel consumption from transportation. Don’t discount even the smallest of adjustments.

Support local businesses

Traveling, especially solo, can feel lonely at times. It’s not always a glamorous thing. It can make you think more about the people in your life you appreciate deeply and miss whether that’s family, friends, neighbors, etc. If you’re someone who likes bringing back souvenirs or mementos of your travels to your loved ones, support local businesses and artisans. Not only will you be helping out their business and the community as a whole by consciously choosing where to spend your money, it’s likely that you’ll find more unique and authentic treasures compared to your typical airport gift shop. It’s fun to browse around and speak with the talented artists, craftspeople, and entrepreneurs of the community. And don’t forget to pick something up for yourself too!

My favorite encounter with a local artist occurred when I was biking with my new friend, Erynn, along the bike path in our neighborhood. Erynn spotted a red surfboard painted with “Clothes for Sale!”. We spontaneously decided to stop and check it out. We found a girl sitting on the beach with her boyfriend (who happened to be a pro surfer!) by a tent. Under the tent, she was selling her own handmade jewelry with shells she dove for herself along with a few racks of thrifted clothes. I bought a crochet cardigan (second-hand) and a couple of her beautiful handmade necklaces. Not only was I very happy with my purchases, but speaking with her about how she ended up on the North Shore with this business was so inspiring! I love hearing about people’s stories and how they got into their craft. Now when I wear the necklace, I am reminded of this nice memory and feel happy I had the chance to support her efforts.

Make conversation with locals

Assess the situation and be smart about who you strike up a conversation with, especially if you are riding solo. You definitely want to be cautious of strangers who might not have the best intentions.

With that said, some of the very best moments stem from conversations with the people who you might normally pass by. You never know where a conversation could lead you or how it could positively affect others involved.

During my time spent on the North Shore, I spoke to a wide range of local people, most notably:

• Sunset Beach lifeguards
• Big wave surfers
• Yoga instructor
• Food truck/shop employees
• Jewelry-making entrepreneur and pro surfer boyfriend
• Girl I met at a yoga class who works at a local acai bowl cafe and shares an interest in surf and film photography with me
• World-traveled 93-year-old woman formerly married to a well-known linguist and the mother of a famous artist (Ashely Bickerton) based in Bali who recently passed, but whose work will be exhibited this Fall 2023 in a renowned NYC museum
• Jack Johnson and his wife, Kim!
• Local swimwear company owner
• A young guy in the military currently stationed on the North Shore
• Woodworking artist and surfer from Europe
• And others!!

Cultivate connections (whether fleeting or long term)

While vacationing or traveling, we usually have a return date in mind (unless you plan to travel around indefinitely). Whether you’re somewhere new for a couple of days or a couple of months, it might feel strange to seek out friends in a place you know you’ll be leaving. But cultivating connections with others is what life is all about!

You may be lucky enough to make a lifelong friend from your trip or simply have a really nice conversation with a farmer or server at a restaurant. These moments can be mutually beneficial, memorable, and fun!

You probably won’t remember what your room looked like or what the names of the shops you browsed were called years down the road, but you’ll likely remember the conversations with people who touched your heart, inspired you, or taught you something new.

Open your mind: it’s your greatest super power

Humans are resistant to change. Change is uncomfortable. Change is scary. And we all want to feel settled and safe to a certain extent anywhere we go.

If you choose to solo travel to a new place, you’ll probably feel some discomfort among all the newness. But instead of closing in on yourself and defaulting to the thoughts, routines, and behaviors you are accustomed to at home, use what could be our greatest power if properly unleashed… an open mind!

Lean into the discomfort and uncertainty. Don’t immediately yuck someone else’s yum. Ask questions or simply just listen to someone else’s opinion on a topic. Smile and say hello to people who don’t resemble those in your tight knit friend group at home. Shamelessly try out the big local sport or style of dance. Sure, you might feel silly or a bit embarrassed at first, but being open to different people and experiences can teach you the greatest lessons and feel the most rewarding or transformational.

Do things with love and intention

It’s easy to do things because other people recommended it, you read a blog or good reviews online, or because it’s on your personal bucket list. We all do this. But, it’s important to take a bit of time to reflect on why you want to do something and approach the experience with intention rather than indifference. There’s no need to stress yourself out by adding way too many items on your to-do list if you don’t feel like you’ll enjoy or properly respect the site you plan to visit.

Your intentions can be as simple as:

I want to do this hike because it would feel good to move my body and appreciate the natural landscape.

I want to spend 20 minutes picking up trash on the beach because I want to protect marine wildlife and preserve the beauty of the park for the public to enjoy.

I want to attend this concert because I feel like dancing with my friends.

You don’t need to go into every experience with the intention of saving the world! But you should go into each situation with a sense of goodness and respect for others, so you can fully appreciate the moment and consciously honor other people and the land you are a visitor on.

Attend community events even if it's outside your comfort zone

There are plenty of places to gather if you take the time to look into it!

Craft fairs, concerts, free workout classes, food trucks, church, food banks, garden/farm volunteer days, cultural center events, etc. There’s likely something that will interest you. And if you’re not usually one to attend events on your own, let this be a challenge! You can build confidence in knowing you are capable of going to things solo. And furthermore, just like the name suggests, community events bring the community together (mind-blowing, right?)! You may find yourself surrounded by locals and visitors alike and have the opportunity to chat with a wide range of new people.

Though I didn’t expect or plan this at all, I met and made friends with some pretty amazing people through attending church, a free community sound bowl session in the park, and a yoga class! Had I not gone to these things, I would have missed out on connecting with some extraordinary people who contributed to making my time so special. And something as simple as an initial meeting led to exchanging numbers/instagram accounts followed by a spontaneous group dinner. Unplanned, but totally worth it.

Bring a journal or write in your notes app

If you looked at my notes app, you’d probably think it was taken over by a hundred random people with a multitude of even more random thoughts. I whip out the notes app on my iPhone when spontaneous inspiration hits, to write down quotes I like, to create lists/reminders, etc. From baby/dog names I like to grocery lists to places I want to travel to, the notes app is probably the truest reflection of my inner mind.

Bringing a notebook/journal or simply typing on your notes app to write down things you want to reflect on or remember so that you can re-read it in the future and see how you’ve evolved or to re-experience the emotions you had at that point in time is so precious. It’s the closest thing we have to bottling up a moment in addition to photographs/videos.

Set some time aside during your day or night to sit and write– could be 5 minutes or an hour. You get to choose! And you don’t need to be a “writer” to do this. It doesn’t need to be for anyone else but you. Writing your thoughts down from the day can be a special treat for you to re-read down the road, but can also help you feel more grounded, intentional, and appreciative of the present moment.

Write letters of gratitude to those who made an impact on you

This is not something I’ve ever done before, but I felt so touched and inspired by many of the people I met during my work-exchange experience. I could not have known or imagined I would encounter the cool, kind, and fascinating people that I did over the span of two weeks.

I am extremely lucky to have formed friendships/connections with different people and felt the desire to pass along my gratitude for them through handwritten notes. When saying goodbye, it can feel sad and a bit awkward to begin expressing everything that you’re thinking, but writing it in a letter– whether a short and sweet thank you or a longer, more personalized note– is a great way to say what you want and to brighten someone’s day.

Before leaving Hawaii, I wrote letters to the other farm worker I got quite close with and another new friend, the property owners, my farm manager, and the lifeguards I got to know and receive advice from. It felt good to leave something as simple as a handwritten note behind– something small in comparison to the vast happy moments I was lucky to experience on my first solo travel trip.

It’s always a good idea to say thank you (Mahalo!). If there’s a chance of a positive domino effect, it’s safe to say you’ve traveled meaningfully and with good intention no matter where you are in the world.

Safe and happy travels to you as you find your next adventure! And just know that if no one else is coming along for the ride, you can do it yourself! I believe in you!

Feel free to write me a letter about your solo travel experiences at jessica@theoutbound.com. I'd love to hear about it!