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"Look! There's one right next to the engines! There are two near the front."

I obediently followed the directions of several grade school kids and scurried back and forth on the deck of the Vagabond tour boat. I struggled to capture photos of bottlenose dolphins, surfacing randomly like Pop Goes the Weasel.

Launching right next to the Harbor Town Lighthouse in Hilton Head, S.C., the 90-minute excursion delivered dozens of dolphin sightings, but an unexpected reward was the natural beauty of Calibogue Sound. The tidal marsh entertained with the graceful dive-bombing of brown pelicans and the melodic hubbub of sandpipers, clapper rails and herons.

Was Hilton Head Island a long-awaited vacation for this retired Minnesota native? Not at all. And I'm not a "digital nomad," either. Instead, Hilton Head was one of my recurring extended-stay adventures, living like a resident in some of the most retiree-friendly destinations in the world. Why invest hundreds of thousands of dollars in a single vacation condo when you can immerse yourself in enviable locales worldwide?

I am not alone. Over the past year, the number of older adult Airbnb guests in the United States has grown by nearly 20%. From 2019 to 2021, senior bookings increasingly turned traveling into living. At the same time, Airbnb CEO Brian Chesky told CNBC that 20% of the platform's 2022 stays were for more than a month.

How to plan your own extended stay

I have used an economical, repeatable process to live like a retired expat in places like Hilton Head, Portugal, Iceland, Colombia and Singapore. Let's trace the steps to help you build your own memorable, extended stay.

1. Getting there. Use Kayak or Google Flights to assess flight convenience and airfare levels. Both services enable fare alerts so that you can receive updates when your chosen destination goes on sale. According to the travel analysis company Hopper, finding cheaper flights requires booking domestic flights one to two months in advance and international trips three to five months ahead.

2. Lodging. Download the Airbnb or VRBO apps and get a feel for your destination by searching homes or apartments 90 days in the future. I use the map feature to display the lodging supply.

3. Unbiased advice about where to stay. TripAdvisor forums are my go-to resource to determine the best neighborhood of a city to stay in. Google can also be helpful, but I favor authors who are not selling something.

4. Public transportation can make the trip affordable. Rental car prices have exploded in recent years. Unlike in the past when the car might be the last item you booked, today that is a major cost to be reckoned with. Public transport in Portugal, Colombia and Singapore and rental bikes in Hilton Head helped facilitate extended stays.

5. Why not fly for free? When I have a longer planning window, I follow the Points Guy ( and View From the Wing (, to find the best travel credit card bonus offers. The current hot pick is the Capital One Venture Rewards card, with a 75,000-mile bonus — worth approximately $1,275 — after you spend $4,000 in the first three months. Rewards can be transferred to at least 15 travel partners, or redeemed for a statement credit on any airline or hotel purchase. The card also earns 2 miles per dollar spent and has a $95 annual fee. (To assess if a credit card's bonus mileage offer is attractive, I query NerdWallet [] to determine the dollar value of its points or miles currency — for example, Capital One miles are valued at up to 1.7 cents per mile.)

6. Slow down and enjoy. There is something liberating about an extended stay. Everything seems to slow down a bit. The rush to do daily tourist activities fades away. It's fun to get into a routine of enjoying the next-door patisserie or coffee shop — or just whiling away the hours on the balcony, absorbing ocean views and the sound of waves rolling nearby.

Now it's your turn. Where will your dreams take you?

Where to be a retiree nomad

Sunset in Hilton Head, S.C.
Sunset in Hilton Head, S.C.

Discover South Carolina

Head to Hilton Head

During two COVID extended stays, I was mesmerized by Hilton Head, S.C. The vast, stunning beach was hard-packed and perfect for jogging or biking. I'm embarrassed to reveal how cheaply I was able to stay in Airbnbs during the pandemic, but you can still find beach-area apartments sleeping three or more for a reasonable $100-$150 a night. My condo was two blocks from the beach and you definitely want to be close to Coligny Plaza, a chic area with more than 60 shops, restaurants and bars.

Moreover, Hilton Head Island is a cyclist's paradise, offering 64 miles of dedicated trails. There were many days when my rental car never moved. Other required outings include touring the historic Harbor Town Lighthouse and kayaking from Shelter Island.

Porto’s iconic rabelo boats in the Douro River, flanked by the Old Town skyline.
Porto’s iconic rabelo boats in the Douro River, flanked by the Old Town skyline.

Getty Images/iStockphoto

Porto perfect

I arrived at my Airbnb in Porto, Portugal, after dark and only had a vague notion that I was close to the crest of the Douro River valley. The next morning broke crisp and clear and my immediate mission was to get coffee, so I headed up a mild incline.

Within 200 yards I was stunned. The summit of the river valley revealed a spectacular panorama of the river dotted with cruise ships, ferries and the ancient, iconic rabelo boats. The valley was painted with the brilliant pastels of Portuguese architecture: a Monet-like tapestry of pink, azul, magenta and yellow buildings capped with the signature Porto red-tiled roofs. My path led over the striking Dom Luis I steel suspension bridge — designed by Gustave Eiffel.

An Airbnb apartment in Porto can be had for $50 to $80 a night in September or March. Stay near the Sao Bento metro stop to walk one of the world's most beautiful cities. It's nestled close to bus line 500 ($2.50) for easy access to its gorgeous beaches.

Hallgrímskirkja church in Reykjavík, Iceland.
Hallgrímskirkja church in Reykjavík, Iceland.

James Lileks/Star Tribune

Fast track to Iceland

Delta Air Lines and Icelandair are again flying nonstop from Minneapolis-St. Paul to Reykjavik this summer. Icelandair's presence makes for a competitive airfare. Even better, on connecting flights to Europe, Icelandair offers a free stopover of up to seven days in Iceland. So, if Rome, Prague or dozens of other onward destinations are on your wish list, use the free stopover on the way there or back. Expenses within Iceland are higher than average, but that is no excuse to ignore the country's wealth of volcanoes, geysers, waterfalls, aurora borealis and the amazing Blue Lagoon.

I recommend an Airbnb or VRBO rental near Reykjavik's very walkable city center. Use the soaring Hallgrimskirkja Church as a centering landmark. The church's 73-meter tower provides an amazing 360-degree view of Reykjavik, the surrounding mountains and the ocean. Score an apartment in the city center for $140-$220 per night in September.

Cafe culture is alive and well in Cartagena, Colombia.
Cafe culture is alive and well in Cartagena, Colombia.

File photo

Colombia for every budget

Colombia is a staple in rankings of top retirement locations. I had heard that the exchange rate was favorable for Americans, and that was an understatement. My Cartagena apartment on the beach was $50 a night with breathtaking views of the Caribbean.

When I checked my daily expense log, I found that it was nearly impossible to spend more than $33 a day on groceries, restaurants, beers and taxis. Just about any taxi within the city is $2. It is easy to secure an apartment for $45-$90 per night in October or March.

Colombia is under a Level 3 travel advisory, meaning "Reconsider Travel," from the U.S. State Department. While I found Cartagena to be very safe, I recommend staying near El Cabrero or in the Bocagrande neighborhood.

The Cartagena Walled City is a historic 17th-century treasure, replete with excellent restaurants, bars, retail shops and cafes that can keep you occupied for days on end. You can walk atop the soaring walls built to protect the city's gold stash from pirate attacks. The dazzling Plaza La Serrezuela is unlike any other in the world — a rebuilt 1893 bullfighting stadium seamlessly melded into the stone walls and cobblestones around it. The Castillo (Castle) de San Felipe de Barajas is worth the climb, delivering magnificent views of the city and harbor.

Tony Randgaard of Minneapolis is retired after more than 20 years in airline marketing.