In 1998, “Nathan” was 33 years old. He was the sole breadwinner for his family of four. Both he and his wife, “Lisa” each could contribute $2,000 to the newly created Roth IRA, but they did not have cash to spare. After reading about this account type in the Wall Street Journal, Nathan’s father, “Jack” called up his son and offered to gift him the money. “Think of it as a retirement gift,” he said, even noting that in the memo line of the check.

 

Fast forward twenty-eight years to 2026 and Nathan now plans to retire next spring. His father, Jack, has since passed away, but Nathan fondly remembers his dad’s words that accompanied the present: “This gift will fund your first trip in retirement. Where do you think you might like to go?”

 

At the time, Nathan shrugged it off, realizing he had neither the time nor the money to plan a vacation. “The only trips we seem to take these days are to see family,” Nathan admitted. “I think the last time we went anywhere special was for our honeymoon, and you planned that for us,” he recalled telling his dad.

 

That evening, so many decades ago, Nathan and his retired father planned for the future. “We first need to determine how much $2,000 will grow to in 30 years.” Jack helped his son imagine retiring at age 65 in 2028. Let’s say you invest aggressively in stocks for 30 years, achieving an average annual return of 9%. Using a financial calculator, they entered the initial deposit (present value) of $2,000, the number of years he planned to save (30), and the estimated annual interest rate (9%), assuming annual compounding.  

 

The results showed that in 30 years, he would have $26,535.36 available from his father’s $2,000 gift to take his first trip in retirement.

This month, Nathan and Lisa started planning their retirement trip. With the help of their financial advisors, Nathan feels confident to retire at age 64 and spend approximately $25,000 for this once-in-a-lifetime adventure, honoring his father’s wishes. Before eliminating any options, Nathan and Lisa wanted to lay out all the possibilities. Below is their list of vacation types (with some of their notes in parentheses). See if you can guess which one they decided before you get to the end.

Vacations Types:

Cruise

• Caribbean/Island hopping cruise (They went on one in 2000 as a babymoon, and 2010 for Lisa’s 40th birthday)
• Expedition Cruises – Alaska, Antarctica, Galapagos, Norway (Alaska was the 20th anniversary trip, Galapagos was the twins’ high school graduation trip, not sure about going to Antarctica, but the fjords in Norway look amazing).
• River Cruises (Lisa’s parents went on the Nile River trip; Nathan said if he’s going on a river in the U.S., he is going to be the captain of the boat. Lisa found the National Geographic website about the Danube, Rhine, Amazon, and more. She really likes the idea of Amsterdam and the Netherlands, to Brussels, Belgium, in the spring to see the flowers most of all, but it has historical sites for Nathan too; she saved her thoughts about this one until the end of the list-making).
• Family Cruise (They had a Disney trip in 2023 with twenty-two family members (aunts, uncles, cousins. Good memories, maybe when they have grandkids?)

City Tour

• United States (They’ve seen so many cities in the U.S.; good ones still left, though. They’ve hit the highlights: NYC, Chicago, Washington, D.C., Boston, San Francisco, and many minor cities).
• European (They checked off, London, Dublin, Paris, Madrid, Pamplona, Rome, Florence, Berlin. Many more to go, but not sure how much extra walking they want to do. Nathan was still recovering from knee replacement surgery)

Beaches and Relaxation

• North America: (They’ve been to beaches in Cancun, Costa del Sol, Virginia Beach, and the Outer Banks, lots in Florida, and Hawaii for their honeymoon). (Lisa has always dreamed of going to Bali, the Maldives, or Bora Bora, some far-off place. Would $25,000 cover that amount?)  
• Best beaches in the world:. According to TripAdvisor, the top ten best beaches in the world in 2026 are:

1. 1. Isla Pasion, Cozumel, Mexico (quite close)
   2. Elafonissi Beach, Crete, Greece (would like to add Athens and the Acropolis; perhaps combine with a cruise, although it might feel too touristy).
   3. Balos Lagoon, Crete, Greece (same as note above).
   4. Eagle Beach, Palm – Eagle Beach, Aruba (they both have always wanted to go scuba diving in Aruba; relatively easy trip to plan).
   5. Praia da Falésia, Olhos de Agua, Portugal (Combine with Lisbon or save for Camino de Santiago)?
   6. Banana Beach, Phuket, Thailand (popular)
   7. La Jolla Cove, La Jolla, San Diego, California (seals)!
   8. La Pelosa Beach, Sardinia, Italy (Italy is beautiful, but not this trip)
   9. Manly Beach, Sydney, Australia (prefer to avoid crocodiles and great white sharks on this vacation)
   10. Boulders Beach Penguin Colony, Simon’s Town, South Africa (consider combining with an African Safari)?

Sporting Vacation

• Skiing (all-inclusive resort in the Alps)?
• Hunting and camping (Nathan goes every few years with his buddies; Lisa has no interest).
• Fishing (stay on the boat for a few days? Lisa would be ok with it, maybe combine with scuba)?

African Safari

• Bucket list item for both Nathan and Lisa. 

RV Camping

• Rent (1 month travel the west)
• Buy (sell the house and live in an RV for a year. Should they start there)?

Collection Theme 

They could start a new retirement tradition. Every year, they visit something in a set, like:

• Baseball stadiums
• State capitals
• Civil War battlefields
• National Parks

(Although neither Nathan nor Lisa collects souvenirs, maybe they could start)?

Road Trip in a Sports Car

Drive up the Pacific Coast Highway in a rented Porsche 911 convertible (or driver’s car of choice).

Volunteer Vacation 

Lisa and Nathan recalled the Sloth & Wildlife Rescue Sanctuary, where they took all three kids the summer after their youngest graduated high school in 2018. The volunteer organization planned their family’s entire trip to Ecuador. Now, the same organization offers trips to more than 20 different countries. They could do some good while exploring a new place.

Surprise Vacation

Let someone else plan it for you, and you just show up at the airport. “Is there a travel agent that does this?” Nathan wondered. He guessed he could give this list to someone else, circle his top five, and have them plan everything for $25,000, but would have a hard time delegate full control. 

The Decision

After much debate, Nathan and Lisa settled on a beach vacation, but the options seemed too vast. So, they asked for a little help from Claude.ai. They gave this prompt: “We want to go on a remote island beach vacation in April 2027. We don’t want to see very many humans; we don’t want to cook any meals for ourselves. Look for an all-inclusive. We want to spend a full week there, so it’s ok to add a few days on the end for extra travel. We want to walk out of our hut and right into the water. Can you make some suggestions for places where it will be warm enough, with a perfect temperature for swimming, sailing, snorkeling, and day hikes?”

 

The first result was The Brando, a remote resort on Tetiaroa Atoll, French Polynesia, but it was a little too far from everything. Instead, Nathan and Lisa chose the Likuliku Lagoon Resort on Malolo Island, Fiji. The adults-only resort in Fiji features authentic over-water bures (bungalow-style huts) in a natural ocean lagoon, surrounded by a protected marine sanctuary.

 

The all-inclusive rate includes all their meals and complimentary use of various non-motorized watersports equipment such as catamarans, windsurfers, stand-up paddleboards, kayaks, and snorkeling gear. The resort also offers hiking trails to explore scenic spots, including Jona’s Lookout, the Ridge Track to Naroba Point, and the trek to the summit of Malolo Island.

 

Since flying to the island required a stop in a nearby major airport, Nathan and Lisa chose to connect through Auckland, allowing them to combine their trip with a week in New Zealand. After all, if they’re going that far and have the budget for it, why not enjoy the extra destination?

The Budget

So here is how Lisa and Nathan plan to spend their time and money during the last week of April 2027,

• Fly to Auckland in upgraded premium select seats at a cost of ($4,000 round-trip per person).
• Tour New Zealand for six days during the peak autumn season. (budget $6,000)
• Fly to Nadi, Fiji, on May 1 or 2, just past the rainy season ($450 round-trip per person)
• Catamaran to Malolo Island ($140 round-trip per person)
• Stay six nights at Likuliku Lagoon Resort $8,311-12,377 depending on the room type (budget $10,000).

In total, their planned expenses amount to $25,180. With this budget in place, Nathan and Lisa felt really good about Nathan’s retirement decision and this vacation. They couldn’t wait to tell their financial advisors at Hurlow Wealth Management Group!

Where Will You Go When You Retire?

While Nathan and Lisa’s story is fictional, the feelings expressed represent those of real retirees. For over two decades, the financial advisors at the Hurlow Wealth Management Group have helped Midwest Millionaires in 26 states find clarity, make decisions with confidence, and achieve comfort in retirement. If you’re unsure if you can retire and would like the confidence to spend $25,000 on a dream vacation, call 812-333-4726 or click here to schedule your complimentary introductory call with an advisor today.