[Note: The following is an excerpt chapter from a book I’m publishing titled, Departing the Comfort Zone, Long-term, meaningful, solo travel, a guide and memoir. It is scheduled launch before the end of 2026.]

Finding a place to lay your head is part art, part science, and part luck. As the kids say, “don’t sleep on these tips.”

If I have a super power, it’s booking rooms. I have had a long career as a free-agent ad-biz creative fixer living on an island, which literally means every time I go to work, I need to book transportation (next chapter) and a place to stay. A conservative estimate of the number of nights in hotels, resorts and short-term rentals over the past four decades is well over 3,000. 

“Checking in, the name is Sanders.” (Hands over ID and AMEX gold card.) Repeat 2,999+ times.

On my most recent trip around the world, I booked 140 nights of stays in 23 different accommodations, which included grass huts, An overnight ferry, tents, tiny private rooms, grand private rooms but with a bathroom down the hall, a boat in a harbor that once belonged to Frank Sinatra, sleep capsules, standard hotel rooms, night buses and luxurious home stays. The process of booking involved researching hundreds of places and weighing the pros and cons of each one. And, as I said, a little luck. In this chapter, I’m going to explain my process and the things I look at to optimize my stay. 

I’ll also point out where my stays have gone horribly wrong, and how to avoid making the same mistakes. 

Sidebar: why I steer clear of Airbnb and VRBO. Please allow me to apologize in advance for waxing political. Over the past decade, I have stayed in a handful of Airbnb or VRBO accommodations. The generic term for them is short term rentals or STRs. And they are often wonderful experiences. It’s like having a little slice of home away from home. A kitchen, a living room, a big TV, Washer/dryer, a pool, better amenities than any hotel room. It’s rather addictive. Every good short term rental experience makes you want to have even more good STR experiences. But in the past five years, I have come to realize that AirBNB and VRBO, like many addictive drugs, come with harmful side effects. In communities that attract a large number of visitors, like my home Town of Nantucket Island, Massachusetts, STRshave become incredibly popular. And people with money, see an opportunity. They buy up property to be used solely for short term rental purposes. If enough speculators engage in this kind of activity, the result is fewer homes available for people who live in that community. And not just fewer homes, fewer parking spaces, fewer restaurant reservations, more trash, and a more difficult time accessing roadways, public transportation, public parks, and more. As more and more people get addicted to the convenience and luxury of STR‘s, the community wakes up with a hangover. Add to that the recent infestation of the dreaded social media influencer and you have a real problem. Because I see this happening in my own hometown, I have absolutely no desire to inflict this kind of pain on the places where I visit. As a result, what I try to look for are the kinds of accommodations that residents of the community would not choose to stay in, mainly home stays, hotels, hostels, boats, tents, and apart-hotels. I make a conscious effort to stay in places where my dollars benefit the local community and not some investor or speculator trying to make a dollar on the backs of the people who live and work in the location that I’m visiting. My intention is not to get all preachy on you, but I hope you see the difference. There’s a reason the anti-tourism movement is taking hold around the world right now. Visitors who come in and sap the resources of a community like Barcelona or Tokyo or Bangkok are not supporting the community. They are extracting from it. Or at the very least they’re doing more harm than good. In the process of experiencing other cultures, we don’t want to do anything that would serve to destroy that culture over time. Please sleep responsibly. 

(Ooh… Nice segue:)

The primary consideration: Sleep. 

I can’t overstate this. Sleep is vital. When you are on the road, moving from airports to ride-share to buses to trains having a place where you can lie down and get some rest is critically important. When I was young, I used to think that I could go several nights with one or two hours of sleep and be fine. But with age and experience comes wisdom. Sleep is one of the most important things that you can give to yourself. Sleep improves your mental health and your physical health. Your body needs it. Your brain feeds on it. So finding places where you can get some decent sleep should be one of your most important activities while traveling. 

And this, my friends, is the main criteria I use when choosing an accommodation. Can I get quaility sleep there? A beautiful room that’s inexpensive but next to a construction site where you won’t get any decent sleep is a wasted opportunity. A night bus that saves you a pile of money as you travel from point A to point B is useless if you can’t get a decent night’s sleep on it. A capsule hotel, where people are loud and the pillow is rock hard will not feel like a bargain in the morning when you are yawning and trying to pack and get to your next destination. It will feel like a massive burden that you’re carrying until you can get to a place where you can get a decent night’s sleep. 

Here are the things that I personally need in order to get a good night’s sleep, and it’s a safe assumption that these criteria will apply to you as well. But please make your own list. For example, my wife needs a completely dark room to get a good night’s sleep. I do not. 

Grant’s Sleep Priority List:

• Quiet.
• Comfort for my kind of sleep — side sleeping. 
• A good pillow (actually, two pillows). 
• Climate control. 
• No pests.
• Safety and security. 

If any of these things are missing or sorely lacking, then I pass. It doesn’t matter if it’s a good deal or in a fantastic location, or if there’s a magnificent chocolate fountain and fresh strawberries delivered to the room every hour on the hour, if I can’t get a decent night sleep, it’s a deal breaker.

The other things I look for.

Getting a good night’s sleep is the bar any room needs to clear, but whenever possible I look for some other features to make my stay more pleasant. Or fun.

Grant’s Nice-To-Have Amenities list:

• Location within walking distance of cool stuff. 
• Larger bed (queen or king)
• Free coffee
• A pool or beach
• A couch or comfy chair
• A decent bathroom with a toilet that has a seat, separate shower or tub
• A kitchenette or at least a fridge
• A convenience store or market nearby
• Something cool and quirky and different
• A chocolate fountain and free fresh strawberries

The process

In order to show you how I do this, I’m going to find a room in a place I’ve never been (Tangier, Morocco) and walk you through the process, sharing screen grabs and pictures as I do so. For the purposes of this exercise, I’m going to choose a one-week stay in mid November. All prices and listings are accurate as of this writing.

1. Tools. 

Every booking starts with choosing a tool online to find prospective stays. The table below seems like a long list; I have used every one of these tools to book rooms in the US and around the world. These days, however, nearly all of my bookings begin and end with two tools. Booking.com and Google Maps. And if I can’t find something I like using the two tools, that’s when I turn to the other options. But that only rarely happens. 

So let’s start by choosing a location.

Tangier, Morocco is a place I have wanted to visit for many years. It was a favorite of the famous American beat poets and there are plenty of great stories about the city. It will be one of my next international stops, for certain.

2. Picking the right neighborhood

First, I open up google.com to choose Tangier, Morocco and scan for the things I might want to see and do. Google supplies thousands of user-generated photos so you can see what you might see at each location. It looks like there is a nice beach within the city limits to the east of the port (where I likely will arrive by boat, but I have not decided yet) where people can go when it is hot. The hotels around this beach, according to Google, appear to be nice, but way out of my target price range of $25 a night (the ones displayed by Google were between $150 and $300 a night). Google never tries to display bargains unless you mess with the search filters, and the filters in Booking.com are more powerful, more reliable and easier to use (Google often sends you to book on another third-party site where the price is different and usually higher). 

My goal is to find something that will allow me a good location from which to explore. And the beach is just one place I might want to walk. Now let’s look for other landmarks. Cafe Hafa, which overlooks the Mediterranean to the west of the port, was a favorite hangout of William S. Burroughs and the Rolling Stones, who reportedly loved the hashish and other strong substances offered there. I am more of a mint tea kind of guy. I will definitely go there at least once. And I’d also like to find a local open air market to explore. There are food markets near the port and some more open-air markets less than an hour walk due south from the ferry terminal. So finding a room at a halfway point between those markets and the ferry seems like a good idea. Fortunately there’s an area called The Medina of Tangier, which is a walled city neighborhood that offers lots of charm and options. 

3. Have a target price before you search. 

Now on to the actual search for rooms. My target price is $25 a night, with about $5 of leeway on the higher side. Firing up booking.com on my phone, here’s what I see. I loaded the map view of the city and then tweaked the filters to only show me options in my price range and a little higher. This tool shows you the price for your entire stay, so you will need to do a little division in your head to figure out the nightly cost. This is why I have chosen a ten-night stay. Math is not my thing. But I do have ten fingers to help me. 

4. How to interpret room reviews

Next I always look at user reviews. There have been times I have ignored red flags found in reviews and regretted it afterwards. Like the time someone mentioned that the window in the room I booked was bricked up. It was. Pro tip: filter the reviews to see the latest review first. A property’s overall rating may be inflated by a bunch of 10-star reviews from three years ago. Recent reviews will tell you if the service has gone downhill or if there is a loud construction project happening on or near the property. Another tips is to check the nationality of the reviewers. A large number of reviews from people from the country you are visiting could be the room/hotel owner’s friends padding the reviews. So take those 10-star local user reviews with a grain of salt. I hope this isn’t inappropriate, but in my experience, I have found reviews from French guests to be the most candid and therefore helpful. They are good at speaking their truth, they know what luxury and hospitality should look like, and have no trouble telling everyone if the pillows are too hard or if the bathroom smells funny. Merci beaucoup, French buds! 

5. Get some clues from the pictures

Sometimes you can tell if the hotel or apartment listing is not quite telling the truth from the photos they show. If there are only a few, that’s a red flag. Obviously they are not showing everything there from every angle if there are only four pictures of the bed. Also, it pays to make sure the photos match the listing amenities. When I stayed in a small flat in São Paulo, Brazil, the listing for the place had all kinds of great art on the walls and a very cool vibe, but it was slightly different in every picture. Some had big couches. Some had larger kitchens than others. When I got there, everything was fine, but there was no cool art and it was not as nice as the places pictured. I was happy with it because it was $28 a night. But I did want a larger couch and a comfortable place to eat. I had a tiny couch and not a lot of table space. I’ve also seen listings where the photos were obviously doctored with AI and I steer clear of those. Scammy vibes. 

6. Payment Terms: Up front or on arrival? 

I sometimes prefer payments up front (This is so I don’t need to worry about finding an ATM at the last minute. But after learning the hard way, I will make sure I can cancel and get a refund if I need to when doing this. See below.), and sometimes I prefer to pay the owner in person. Paying in person means it’s more likely they will have a room for you. These payments are almost always in cash. Sometimes, paying in cash can get you a room upgrade. Once, in Vietnam, the owner said that since I was staying 10 nights, if I paid cash I could have a nicer room with a balcony on the second floor instead of the (very cheap but decent) room in the basement I had booked. I needed to cancel with booking.com however, which is one way the owner can avoid paying the listing commission fee. I was just happy to have such a lovely room. My hosts were super nice to me. 

7. Cancellation policies. 

For the most part, it’s better to book a room that can be canceled a day or less ahead of time. I booked a room in De Nang, Vietnam and paid up front (oops) with no cancellation policy (double oops) but when I arrived, they had no record of my reservation and told be to find another hotel. In the pouring rain. Of course, they kept my $70. The only reason I booked this hotel was because of its location and for some reason De Nang was so popular at the time that the best rooms were either gone or crazy expensive. I ended up in a place that was a little older and much further away than I wanted. But it was comfortable and there was a great Bahn Mi cart two doors down. On a previous occasion, I had a 10-night stay in the Philippines that I had booked but then found something that was much nicer, so I turned that 10-day stay into a one-night stay (I needed to fly out of the nearby airport the next day) because the cancellation policy made it possible. Good thing. 

So based on all of these factors, like the views of the Mediterranean Sea, the location right in the Medina walled city, free coffee, good cancellation policy, and private space, I have chosen to book at Dar Gara which technically is a hostel, but it also has private rooms with shared bathrooms. (I have no problem with a shared bathroom situation as long as the doors lock. For my friend, Tom, however, a shared bathroom is a deal breaker.) I love the idea of being surrounded by other — often younger — people who I can interact with and learn from. Plus this is the area where I am most likely to find food tours and other diversions. And the price tag of $16 a night leaves me an extra $9 each day for fun, food and tours. It even got a decent review from several French visitors. It looks like it’s a little hard to find, which can be a good thing. Or at least result in a good story.

Sidebar: Hotel Horrors. A few hotel stays that did not go as well as I would have liked. But I survived. 

• One hotel I had in Hanoi was hidden down a long, winding alleyway and if the hotel had not provided a car and sent the front desk gent to the main boulevard to lead me through the labyrinth, I might still be looking for it. It turned out to be one of the top three nicest hotels of the whole trip. And same day laundry service cost $4
• In the Galapagos, I checked into my room and rested when I awoke, I found thousands of the tiniest bugs — ants, maybe, but they were too small to tell — all over the nightstand, the wall and other parts of the room. I talked to the owner of the homestay and he assured me that this was normal for this time of year. Fortunately, they only came out when the sun was hot and went back to where they came from at night when it was time to sleep. On the upside, the room as $18 a night and was located in the best area of the island. 
• In KohSamet, Thailand, I think I found the cheapest possible room for $19.20 a night. But it was only big enough to hold a single bed. It had no AC, and just a big fan pointed at the bed. I ignored the sweaty heat and the geckos in my bathroom, happy that I was not paying $225 a night five minutes closer to the beach. The coffee was free and I made sure I got my money’s worth. 
• In HCMC I arrived to check in, groggy, at 3AM and realized too late that payment needed to be made at my cheap little hotel, up front. I had no Vietnamese Dong. It was not a lot of money. Maybe $32? I tried to pay in US dollars. No go. They wanted to hold my passport until I paid. That was not going to happen. Eventually one of the hotel workers took me on a hike to find an ATM (the danger bells were going off in my head the whole time). We never found one, but returning empty handed, the front desk clerk took pity on me and gave me my room key. The next day I found an ATM across the street and was able to pay for my safe but spartan two nights. 
• I took a tour from La Paz Bolivia to the salt flats in Uyuni. Suffering from altitude sickness, I boarded the night bus there and never got a wink of sleep because the woman in the reclining seat ahead of me had a nasty, rasping cough. On the bright side, I found out her name was Laurie because she was in my Land Rover for the tour, so we had a good laugh about her cough and I found out she was from the Netherlands. She got better and I did not hear any coughing on the night bus back to La Paz. Still, the seats were terribly uncomfortable and I found that I needed a long nap when I got back to my (awful) $11 a night hotel which had run out of coffee when I arrived.
• When in SãoPaulo Brazil, after getting only two hours of sleep the night before because I was helping my daughter re-book and catch a canceled flight, I decided to book an expensive (double my daily budget) hotel at the airport so I could get a decent night’s sleep before flying out at 11 the next morning. Unfortunately, the hotel was right at the end of the runway so every plane in and out of the GRU International airport roared, rumbled and shook the walls of my first floor room. It was like being in a war zone. I was so tired, I slept like a slab of concrete anyway and drank seven cups of espresso at the free buffet the next morning. 

You can download a copy of this travel budget spreadsheet that I created in Apple Numbers. It works in Excel. With a nod of thanks and love to Lisa and Josh for offering the one I used on my trip. I built this new one when I found that Lisa and Josh’s planner was no longer available for download. I also added an additional feature that I wish I had added on the first trip: A daily cost average by each location and for the entire trip.

A full year before I left on my 2025-2026 round-the-world trip, I started planning. (Actually, I started planning well before that, but it was not an organized process. It was like filling a paper sack with a bunch of random thoughts.) I got myself a big, laminated map of the world and some dry erase markers and I wrote all over it. I connected the dots. I made lists. I downloaded resources. And I wrote blog post on my plans, mostly so they would begin to feel real to me.

In December of 2024, I started to plan the trip for real. If you go back to the early posts in this blog you will see my first itinerary, copied and pasted below.

Countries not listed that I did visit on my trip: Brazil (which was a last-minute addition so my daughter could accompany me and visit a friend there), Spain and Portugal! The last two were late entries because going to these two places for ten days made it possible for me to fly back to the US using credit card points. And they turned out to be highlights of the trip. Also a shout out to Kenya. It fell off the itinerary early on but made a surprising comeback in the last month of travel.

As you can see, back then, I did a little research into the best times to visit each location. That turned out to be effort well spent because it allowed me to identify shoulder seasons for some locations (like Japan and Uyuni Bolivia) when going would be worthwhile, less expensive, and not crazy crowded. 

You will note that I have color-coded my first itinerary list to show the I have not gotten to half of the places I planned to see back in December of 2024, a full year before I left on my trip. Plans change and one has to be flexible. But as I look at this list today, I see a plan for the next trip starting to take shape. There is a lot of the world in red above that is still out there and ready to see.

The next trip will likely be west to east, first stop Morocco? One can dream.

It’s been a month since I returned to Nantucket to resume being a husband and a father and dog owner and (per usual) I am happy to be here, but I have to be honest.

I wish I was still out there on my trip.

I’m not depressed about it. I’m just missing it. Solo travel defined who I was for five full months not to mention the year leading up to the trip. It’s very hard to adjust to life on Nantucket. (Where I play the role of the local inhabitant and the tourists are so freaking annoying. That’s a joke. But not really.)

It’s very expensive to live on Nantucket and I have blown through all of my remaining travel money for the most part. Going to my friend’s funeral and staying in a hotel was about the same cost as two months in Vietnam. The same is true of a recent trip off island to attend my daughter’s graduation. I’m glad I went, don’t get me wrong. It’s just shocking.

In SriLanka a trip to the grocery store cost me $11. Here on Nantucket I just paid $122 for a single bag of (really amazing) groceries. Also, I filled up my truck’s gas tank with Nantucket gas last week. Our regular gasoline is very close to $6 a gallon as of this writing. That’s island life for you.

My phone continues to give me alerts that I set up months ago about some of the activities and places I should be at right now. My calendar reminds me I should be in Indonesia. And I am so obsessed with the trip that I’m writing a book about solo travel and what it has meant to me.

Maybe the book will sell well and I will be able to use the money to get back out there. I’m going to try to work my butt off and live frugally to put away some money. And my hope is that by the midterm elections I will know if travel is a good idea or not.

In the meantime, to adjust to being back I’m enjoying some of the things I really missed while traveling. Dates with my wife. Fixing stuff around the house. Cooking in my kitchen and grilling on the back patio. Spending time at the beach with my dog. Playing music on the streets of Nantucket. Visiting with friends.

I’m trying not to get too comfortable. It’s a real danger.

I’m home now. Sooner than I wanted to be, for obvious reasons, but now that I’m home I can start planning for the next trip and write about the last one. I’m actually writing a guide to solo travel, kind of a collection of stories, how-to suggestions and personal transformations. It might end up being a book and it could end up being something else. A video series or a podcast or something.

Now that I’m home and have written 140 (more, surely) daily journal entries I have some interesting statistics on the trip. Here they are.

18 countries in 140 days over 42,436 miles. I was in some countries for a few hours and others for up to a month. In countries like Japan, Vietnam and the Philippines, I moved every week to ten days.

35 Beds. The hardest part about getting regular sleep was getting used to the different pillows.

150 different modes of transport — planes, trains and automobiles. Most were a few miles but some were big hops. The biggest jump was from Mexico City to Tokyo, which took a little over 18 hours.

53 street food carts/stalls. This surprised even me. And I only got food poisoning once.*

203 Americanos. I also made my own coffee with a French press that I purchased in a Manila shopping mall.

2 days sick in bed. Altitude sickness is no joke. I almost passed out five times. *Food poisoning is to be expected.

51 blog posts (www.circlethe.world). There’s got to be a book in there?

62 Instagram posts (43 videos shot, edited) I had a good time producing those.

1 shoe stolen by monkeys. &*$%@#$%@ monkeys.

22 loads of laundry. The whites got a little dingy but overall, a success.

29 swims. I do love the ocean. a few of these swims were in pools as well.

7 sento/hotspring immersions. Best jet lag cure ever.

2 safaris. In the same week! Asian elephants on a Saturday, African elephants the next Thursday.

9 client projects completed

• 7 writing assignments
• 1 corporate messaging engagement
• 1 non-profit brand identity

Lisbon is hilly. In the city, there are signs that say “Miradouro.” These are scenic overlooks that offer up panoramic views. Especially on crisp sunny days like the ones I was fortunate enough to experience while I was there. Not too hot. Very few clouds. Perfect for seeing the sights.

On the second full day of my time in Lisbon, I created a little game for myself: Map most of the Miradouro sites on Google, connect them with walks and get to as many as I could in a day before I got too worn out. Fortunately, there were cafes and benches along the route.

As it turns out, I was able to see nine of these sites and walk a little over five miles (I actually missed a couple I wish I had added). There were a lot of uphill climbs and downhill jogs. And more than a few stairways. Check out the map and the different sites I captured below.

This was good exercise.

In Lisbon, Portugal, many of the buildings are adorned with tile. Many of the tiles are hand-glazed and unique to a particular building. Some feel manufactured or at the very least, stenciled.

Some of the buildings covered with tile feature gaping holes where people have stolen the tile. As souvenirs. To sell to tourists. And for other reasons. I’m not sure why people do this when they can walk around and get pictures of as many tiles as they like.

(Incidentally, yet importantly, there’s a very well done account on Instagram that highlights an art project drawing attention to the loss of culture and beauty when people steal these tiles called Stolen Tiles of Lisbon. Check it out!)

Here are a bunch of tiles I took photos of during my three full days in Lisbon. I could have taken many more.

I had zero expectations for Barcelona, really. It was just the place I was able to land after leaving Kenya. The least expensive option from Google Flights, and close to my final destination and jumping off point in Lisbon Portugal. So I scheduled three full days in Barcelona. Not knowing much about it except for tapas and “buenos dias.”

My whole experience in Barcelona is one I felt needed to be shared because unlike a lot of cities around the world that vaguely remind me of other cities (São Paulo reminds me of LA, Bangkok reminds me a little of Tokyo), Barcelona is its own experience. Likely because of its deep historic origins, and the fact that it has hung onto its cultural heritage with both fists.

As I walked this city, and I walked a lot of the historic old quarter (you can see my 8-mile criss-crossing route on Strava: https://www.strava.com/activities/18104114519) I kept saying to myself, “Barrie (my wife) would love this!”

So yeah, we will be back.

I’m in Barcelona staying on a nice sailboat for four days. It once belonged to Frank Sinatra. Marylin Monroe might have had coffee where I’m sitting right now.

I met a really nice couple from British Columbia who are in the cabin across from mine. They are retired. Traveling. The husband has cancer and he said this is probably the last trip they will be able to take. He can’t eat solid food. His wife told me that he is starting to decline rapidly. He can’t see out of one eye.

This is why I’m traveling now. I’ve had people in my life — friends, my parents, siblings, in-laws — whose plans have been interrupted or stopped cold by chronic illnesses or worse. I wanted to do this trip now, before I get older, before I get sick, before I die.

While I can still enjoy it. Inspire people with the stories of it.

Death is a part of life. It arrives, and often we don’t know when. My hope is that we all work to perfect the life part in the meantime.

The hardest part of the safari experience is getting up at 3 AM and then resisting the urge to take a late afternoon nap when you get back. Aside from that, wow. What an experience. Well, two experiences. I had two safaris, one in Asia and one in Africa, in the span of five days. Crazy huh?

The first safari was inside Yala National Park on the southern end of Sri Lanka. It took a couple of hours to get to the park, and once outside the park we transferred to an open Land Rover vehicle with six comfortable seats up high with great viewing angles. I was able to cross a number of must-see animals off my list, including Elephants, a bear, the briefest glimpse of a leopard, and a number of other cool species. We got to the park at sunrise when the animals are just getting moving, and the temperatures are cool. As the sun rose in the sky, it got warmer, but I was never uncomfortable until the second I got off the bus back at the guesthouse. 

The second safari was in Nairobi National Park, which is 118 square miles of wilderness within the city limits of Nairobi, the capital of Kenya. You will notice the city skyline in some of the photos I took of wild animals. That just comes with the experience. The Yala safari five days earlier was so good, I was expecting a let-down in Kenya, but that didn’t happen. Despite the fact that the single lion we saw only lifted his head above the vegetation for only a few seconds, so I could get a somewhat decent pic of him, all of the other animals were more than happy to oblige. We also got to visit an orphanage that rescues baby animals that are taken away from, or abandoned by, their mothers. Plus an area where you can feed a giraffe by hand for 1500 Kenyan Shillings. 

I have two friends, Andy Lerner and Sean Crane, who are bona fide expert wildlife photographers with multiple awards under their belts. I just have my trusty iPhone 12 Pro Max and some bayonet-mount moment lenses. I share the results with you. 

All in all, I was blown away. Great experiences, both!

Images: First batch from Sri Lanka

Next batch: Kenya.