Street scene in Key West, Florida. (Michael S. Williamson/The Washington Post)

As an aunt, daughter and sister (by birth and by law), I carry certain responsibilities on family vacations. For example, I usually drive the rental car to the supermarket for provisions. Take the bed that is farthest from the floor and the bathroom. And play several rounds of dolphin in the pool with my young niece and nephew. However, during spring break in Key West, an unprecedented situation tested my role in the clan.

“Why is that man wearing a tutu?” Jamie asked during an evening parade on rowdy Duval Street.

I wondered: Is it my auntly duty to explain drag queens to my 5 1/2 -year-old nephew? I didn’t know the answer, so I instead redirected his attention to the woman dressed like a jellyfish — a much safer subject.

Family travel is a tricky endeavor that requires the mediating skills of a diplomat and the rallying cries of a camp counselor. You have to balance the needs of many generations and, depending on your branch of the tree, bend to the oldest and youngest travelers.

Snorkelers in Key West. (Michael S. Williamson/The Washington Post)

You must also know when to employ diversionary tactics.

Chickens roam the streets of Key West, they are considered a part of history and add character to the area. (Michael S. Williamson/The Washington Post)

Key West wasn’t our first holiday as a roving circus of seven. In 2014, we rendezvoused on Amelia Island, on Florida’s east coast. The kids were transfixed by two shiny objects: the resort’s pool and mini-golf course. Several years before, on Longboat Key, the family learned that you can get freezer burn on Florida’s Gulf Coast in February.

For this April’s getaway, we chose Key West by a vote. Andrew, my brother-in-law, booked a pair of cottages with a private pool and rented an SUV large enough to fit our party of people and luggage. Lisa, my sister, printed out coupons for attractions and packed cheesy snacks. My parents brought an iPad stocked with games; I contributed animal stickers.

Despite the well-executed planning, I harbored a secret concern about the trip: the under-tween’s inevitable encounters with the randier side of town. The bare-chested men and barely clothed women strolling the main drag. The raucous drinking at open-air bars. The drag queen bingo joints and Jimmy Buffett’s Parrotheads.

“A lot of what you do in Key West is bars and nightlife,” Lisa said, when I asked about her own worries. “If we didn’t have a pool, we’d be struggling.”

Amid the craziness of Key West, the pool became our oasis and our “safe room.”

During our week away, most mornings would begin with a splish-splash in the back yard. While my mother worked on her first cup of coffee, Kate and Jamie would be halfway through their first aquatic session of the day. Andrew would float on a raft to nowhere. My dad would relax in the skinny arms of a buoyant noodle. I would usually join the kids during their third or fourth dip. We would practice underwater acrobatics and execute Operation Dolphin, coming to the aid of mermaids, princesses, shipwrecked captains and an armless octopus.

“I think I am going to like this place,” Kate, who turned 7 in January, declared. (She seemingly forgot her initial reaction: “This place is too hot!”)

On occasion, we would rouse ourselves from our over-chlorinated state and seek a change of environment. The most popular pre-lunch activities included searching for six-toed cats at the Ernest Hemingway House, visiting the small beach on the southern end of Duval Street and watching the Key West chickens cluck about (aloof father, heli-hen mom, impish chicks). Lisa and Jamie also ventured over to Kermit’s Key West Key Lime Shoppe as part of our ongoing study of the signature pie. Eventually, though, our default modes would kick in and we would be back at the house floating, swimming and channeling marine animals.

After lunch, we would grow more serious about excursions. We would check the hours (usually open till 5 or 6 p.m.), special events (shark feedings, turtle talks) and admission fees (quite pricey) of the most kid-friendly attractions (aquarium, turtle museum, butterfly conservatory). Then we would discuss the transportation options. The majority of the voices called for driving; my lone wolf howled for walking. I made sure to buckle my seat belt as instructed.

A blue morpho butterfly in Key West. (Michael S. Williamson/The Washington Post)

We held our first outing at the Key West Butterfly and Nature Conservatory. Before entering, an employee reminded Kate and Jamie to not reach, touch or grab the insects. I asked the staff member whether she only gave the speech to younger visitors. She said adults receive the same warnings because they often crush the delicate creatures in their hands.

“Butterflies only live for 10 days,” she added, “so we need to be careful and give them a chance.”

Inside the sealed flight chamber, hundreds of butterflies fluttered around us like falling petals. Dozens of residents sidled up to the flower bar to drink up the sweet nectar. Platters of tropical fruit attracted blue morphos, the sapphire color peeking out from brown outer coats.

I had purchased an identification guide at the gift shop, and Kate and I knelt close to the butterflies to match their markings to the pictures. We recognized the insomniac eye of the owl butterfly and the tiger stripes of the longwing, the saturated Rothko hues of the cattle heart and the stained-glass design of the atlas moth. Around us, we heard a persistent honking. In a small pool of water, we discovered the source of the ruckus: Rhett the Caribbean flamingo was courting Scarlett with his Barry White moves.

Kate read the sign explaining the birds’ behavior and asked the obvious first-grader question: “What is mating?”

In my head, I was thinking, “Too soon, too soon.” But in a soft teacher tone, my sister answered, “Mating is like having babies,” Kate’s eyes widened. Lisa quickly added, “But not right now.” (The lesson didn’t stick too well. Later, Kate explained how the birds were “dating.”)

A flamingo. (Michael S. Williamson/The Washington Post)

On the way out, a worker presented us all with blue morpho stickers. We slapped them on our shirts, hats and bags, proof that we had finally exited the pool.

Not surprisingly, we made mistakes in Key West. They weren’t so big that the kids were destined for years of psychoanalysis, but they forced us to reevaluate our approach to certain necessities.

The evening meal, for one. The kids eat early (about 6 or so); I dine late (9 or so). My parents are more easygoing about the hour. Say anytime between lunch and breakfast the following day.

The first night we improvised, reviewing menus door-to-door. We discovered the enchanting al fresco garden of BlackFin Bistro and toasted the start of vacation with water in plastic cups and beer. The following evening, we didn’t plan, and the pre-dinner scene fractured. We ended up with a divided meal of hot dogs and beans and takeout from a Mediterranean-Uzbekistani cafe.

We eventually figured out the algorithm of dinner. Research a place in the morning, make a reservation for early evening and don’t forget the take-away.

The other sticky topic involved walking. When setting out to explore town, we had to consider the wild variety of leg lengths and tolerance of heat. However, we sometimes made incorrect calculations. The March for Sprinkles is a textbook example.

My parents and I had planned an ice cream sundae bash at our cottage and needed toppings. Five of us headed up Duval to find a grocery store, but we had no sense of distance. (Duval, from the Atlantic to the Gulf of Mexico, is just over a mile long. Our rental was about two blocks from the southernmost tip.) At one point, my sister disappeared into a pizza place to make a reservation while the rest of us feigned interest in sunken treasures at Mel Fisher’s store. (Our true passion was air conditioning.)

During the second half of the trek, we passed tattoo shops and loitering men with burnt-toast tans. Lisa declared this part of Duval “seedy.” A woman yelled, “Goddammit, David,” and I overheard my sister telling the kids that #$%& was a very bad word.

By the time we reached the market, we were puddles. We bought rainbow sprinkles and considered our return options. I was game for walking back — alone. The rest of the group cruised by me in bicycle rickshaws. We arrived minutes apart but in different moods. I was hot but happy; my sister and mother were cooler but clearly upset. The drivers had charged them $50 for the short sprint up the street. From then on, we took the rental car.

The tame location of our cottages and the kids’ early-evening bedtime insulated us from the more unsavory aspects of the party town. However, several times I was caught off-guard and had to quickly resort to my look-over-there skills.

One afternoon, we embarked on a scavenger hunt to gather materials for an arts-and-crafts project. We were building tiny turtle beaches and successfully collected empty jewelry boxes, a bag of sand and two small pails (actually sample beverage cups from Kermit’s). We needed cocktail drink umbrellas to complete the tropical scene, which meant hitting the bars with a pair of milk-drinkers. We stopped by several watering holes but struck out. A hostess told us to try the coconut vendor around the corner.

A vendor in Key West. (Michael S. Williamson/The Washington Post)

The man didn’t have any umbrellas but, as a consolation prize, he demonstrated the art of coconut mining for us. He drilled two holes in the hard shell and stuck two straws inside. To extract the meat, he told us to slam its bottom four times against the ground. I paid him $3 for the lesson and beverage. He bid us farewell, calling out, “Enjoy nature’s Ga­tor­ade.” After several sips, Kate asked what “Gatorade” meant.

The coco-man kept our trail hot with another tip: the smoothie shop. As we approached the store, I noticed a gentleman’s club next door and a parked car featuring the image of a scantily clad woman. Neither belonged on my syllabus. To avoid innocent inquiries, I quickly herded the kids forward with promises of cracking a coconut.

At sunset, droves of visitors convene in Mallory Square to join the nightly gathering of magicians, jugglers, clowns, fortune-tellers, musicians, artists and food carts. Our family never made it to the event because the kids went down before the sun. Also, my sister was unsure of its age-appropriateness.

As an alternative, Lisa suggested that we swing by Higgs Beach, a white strand with a playground, grilling stations and diving pelicans. To the west, the sun doused the sky in Valentine’s Day colors.

For our final evening, we ignored tuck-in time and celebrated the close of the day — and the end of our family vacation — with hugs and cartwheels.

If you go

Rent KeyWest

505/507 Luisa St.

305-294-0990 (rental company)

The neighboring cottages each have two bedrooms and a kitchen, plus a shared pool. They can be rented individually or as a pair. From $270 a night or $1,750 a week.

Where to eat

BlackFin Bistro

918 Duval St.


Serves local seafood (conch, shrimp), pasta, burgers and more inside or out in a lovely garden. Main entrees from $23.

Blue Heaven

729 Thomas St.


A heavenly setting with towering trees, roaming chickens, live music and a hearty menu including a sky-high wedge of key lime pie. Lunch plates from $10; dinner from $25.

Santiago’s Bodega

207 Petronia St. #101


The tapas menu and rustic decor suit diners of all ages. From $7.

What to do

Key West Aquarium

1 Whitehead St.


Kid-size aquarium with shark feedings and petting opps, a touch tank and sea turtle talks. Open daily 10 a.m.-6 p.m. $15; $8.60 ages 4-12.

Key West Butterfly
and Nature Conservatory

1316 Duval St.


A learning center, gallery and conservatory with hundreds of winged creatures. Open daily 9 a.m.-5 p.m. $12; $8.50 ages 4-12.


— A.S.