15 of History’s Most Memorable Family Vacations

Ah, the family summer vacation — that time when Mom, Dad and the kids road trip to the nearest beach, fly to Florida to hit the lines at a certain amusement park or ... attempt to sail around the world? As it turns out, not all family vacations are created equal. Check out these 15 impactful and impressive trips.

1. THE CIVILIZATION THAT STARTED IT ALL

Due to Alexander the Great’s conquest, Greek culture and language was spread across the Mediterranean—making it relatively easy for people to see the sights, thanks to similar cultures and (relative) peace. This legacy of travel is best summed up by the Seven Wonders of the Ancient World. The Ancient Greeks didn’t call them wonders, they called them theamata, or "sights to be seen." Think of it as the OG bucket list.

2. THE TRIPS THAT SERVED AS PUBLICITY TOURS.

In the UK’s Tudor period, travel was mainly reserved for monarchs. Twice a year, the King, Queen and other royals would head off on a sojourn called a “royal progress.” Once they reached their intended spot, they would ride around the town on horseback allowing commoners to catch a glimpse of their regal faces. In 1535, King Henry VIII took such a trip to show off his new wife, Anne Boleyn.

3. THE GETAWAY THAT SPAWNED A GREAT NOVEL.

A year after marrying poet Percy Bysshe Shelley in 1816, writer and avid traveler Mary signed up for a one-year getaway at Marlow, England’s Albion House along the River Thames. There in the charming spread—inspired by previous trips she’d taken to Germany and Switzerland—she wrote her great horror novel, Frankenstein. 

4. THE PRESIDENT WHO TOOK SEVEN MONTHS OFF.

In 1799—the third year of President John Adams’ term—he vacated the capital (then in Philadelphia) for his farm in Massachusetts to be with ailing wife Abigail. His vacation lasted a whopping seven months—longer than any other U.S. president's.

5. THE TRIPS THAT COINED THE TERM.

By the late 1800s, the concept of summer travel was gaining steam in the United States as new stagecoach services began operating in the Northeast and some 200 hotels and camps sprung up near the Adirondack Mountains in upstate New York. The scions of New York City—families such as the Vanderbilts, Rockefellers and Carnegies—were enticed by the outdoorsy areas but repelled by crowds of commoners, so they built their own luxurious resorts called “great camps.” (The Vanderbilts favored Camp Sagamore, a 1526-acre wilderness estate.) The wealthy crowds took to describing their travels as the time in which they would “vacate” their homes in the city for their lakeside spreads. The term eventually replaced the British word, “holiday.”

6. THE FAMILY THAT BUILT ITS OWN SUMMER COMPOUND.

Sailing on Nantucket Sound, posing in matching sundresses, football on the expansive lawn—one famous family is synonymous with New England summering. Starting in 1929, the notable clan slowly began building their compound in Hyannis Port, Massachusetts. Eventually the six-acre Cape Cod spread would consist of three separate properties—including a 21-room main house—and would be the site of countless iconic photos and one successful presidential election.

7. THE VACATION INTENDED TO HEAL THE SICK.

One U.S. president, suffering from a serious disease, choose his vacation spot in Warm Springs, Georgia, because he heard that the warm spring water there could soothe his ailments. While the site—where he eventually built a six-room, Georgia pine property dubbed the Little White House—didn’t cure his sickness, it was the spot where he came up with several successful policies.

8. THE TRIPS INTENDED TO GAIL POLITICAL CLOUT.

For presidents even selecting a vacation spot is a critical decision. According to a historian, one recent president would poll the population to see where they wanted him to go. (The result had him and his family skipping seemingly elitist Martha’s Vineyard in favor of riding horses and wearing cowboy hats in Jackson Hole, Wyoming.) Another presidential hopeful eschewed a family trip to the beach, instead flying off to the mountains, because tanning looks less American than hitting the slopes.

9. THE FAMILY THAT SAILED AROUND THE WORLD.

In a sailboat they dubbed NuevaVida (translation: New Life) one family of five took to the sea in 2003. Over the course of seven years, they boated from destination to destination, calling places such as New Zealand, Papua New Guinea, Vanuatu, and the Solomon Islands home.

10. THE FAMILY THAT JUST KEPT RUNNING.

Hoping to transform the way people view health, a Canadian family of eight embarked on a 9300-mile run in 2011. Though six of the family members hadn’t completed more than a 5-kilometer race, they each took turns logging miles while the rest of their relatives recharged in an RV stocked with 65 pairs or running shoes, 120 pairs of socks, and a 10-pound tub of organic peanut butter. As they jogged from Vancouver to Newfoundland to Washington, D.C. to California, they visited schools to share their message of health. Explained one teen, “I like to be an example for kids my age.”

11. THE FAMILY THAT TOOK ROAD TRIPPING TO A NEW LEVEL.

In 2014, one family of four set off to travel via electric bike from Montana to Maine and then down to Florida in attempts to break the Guinness World Record for the longest electric bike trip across America. The brood—wanting to promote sustainable travel and healthier family lifestyles—turned their six-month adventure into a yet-to-be released documentary.

12. THE FAMILY VACATION THAT NEVER ENDS.

Twenty-four/seven family time and an opportunity to see the world was the goal when one family of six (plus two dogs) decided to sell their 3000-square-foot Wisconsin home, pile into a 400-square-foot RV and drive. In the two years since embarking on their travels in 2014, the group has hit up Florida, Tennessee, Kentucky, West Virginia, Wyoming and countless other spots.

13. THE 13,000-MILE PLANE-FREE ROUND-THE-WORLD JOURNEY.

When one family of four piled into canoes and paddled away from their home in the Canadian Rockies in 2014 they had one mission: see the world without ever boarding an airplane. Over the course of 96 days they traveled 13,000 miles—even enduring a harrowing 16-day ride on a cargo ship to cross the Pacific Ocean to get to a monastery in India. By the end of their travels—filmed for a TV docu-series—they had visited seven countries, hiked India’s Shingo La Pass, walked the Great Wall of China and meditated with a Tibetan monk.

14. THE ADVENTURE THAT WAS CUT SHORT.

Two weeks after a San Diego couple and their two young daughters set off toward the South Pacific in their 36-foot yacht, they had to be rescued by the Coast Guard when one of their tykes fell ill. While their journey was ultimately unsuccessful, it did spawn a vigorous online debate about parenting.

15. THE CROSS-COUNTRY TRIP THAT CHANGED LIVES.

One New York-based ultramarathoner ran from Washington to New York all while pushing his son in an adaptive racing wheelchair. The 60-day, 3205-mile 2015 trip was charted to raise awareness for cerebral palsy, a condition his son suffers from. (His wife and other son followed along in an RV.) Running 55 to 60 miles a day, the athlete raised $100,000 for a special needs charity and donated 20 racing wheelchairs to those in need.