10 Travelers Share Why They Take the Same Annual Vacation, Year After Year

Photo: W+G Creative
Each year growing up, my parents, my two siblings, and I made the two-hour drive from our home in Pennsylvania to Ocean City, New Jersey—a quiet beach haven on the south end of the Garden State's coast. As a dry town, it had everything you wouldn't see on a raucous episode of Jersey Shore. Meaning, it was perfect for wholesome days complete with strolls on the boardwalk, refreshing ice cream cones, and playing in the waves. The blissful week of togetherness and fun became a family tradition, and the annual vacations were always the highlight of my summer.

As I got older, I still loved our yearly beach week, but I simultaneously started to envy my classmates who traveled differently, getting to explore new places. Whether skiing in Switzerland, surfing in Hawaii, or snorkeling in the Virgin Islands, the stories my classmates shared following summer or winter break made my nights on the Ocean City boardwalk seem boring. It led me to wonder, with all the places in the world to visit, why did we have to return to the same shore town every year?

I'm 29 now, and in the years since graduating high school and college, my parents have bought a house in Ocean City, fulfilling their dream of owning a place to make even more memories in our special spot. Now, even though my siblings and I have spread out, every Fourth of July, we all make the pilgrimage to Ocean City to lay in the sun, lick ice cream cones, and spend the week together. Quite frankly, it's become one of my favorite weeks of the year.

Be it due to nostalgia and tradition or in pursuit solace, many of us are creatures of habit.

And—despite my high school naïveté—I'm not the only one who returns to a special place every year. Be it due to nostalgia and tradition or in pursuit solace, many of us are creatures of habit. Below, 10 readers share what their annual vacations to the same spots mean to them.

Westport, MA

We’ve been going to the same house in Westport now for over seven years. My brother and I share a room that’s always a little damp from the ocean. It's hard for me to describe why Westport is so special… It feels like stepping into another life: It's comfortable, I know what to expect and where to go, and it's entirely devoid from the complications of daily life. Westport serves as an annual reminder that as things change and the world evolves, some facets of life will remain constant.

Time on the ocean also reminds you of how small you are, how inconsequential work is, and how much in life is truly out of your control. I simply cannot be expected to carry the weight of life and its expectations while in salty water.

Olivia L., 30, Potsdam, NY

Bella Vista, AR

When I was growing up in Los Angeles, my family and would go back to Arkansas [where our extended family lives] every summer for two weeks, like clockwork. I went every year until I was 17.

I didn't get to see my grandparents much during the school year while growing up, and both my parents worked demanding corporate jobs, so Arkansas equaled pure family time. It's one spot that holds so many memories and emotions. And as a kid, Arkansas was fascinating because it was the antithesis of Los Angeles: rolling green hills and a distinct smell of humidity (sweet humidity, not NYC humidity). Looking back, it was my first introduction to travel. More importantly, it taught me that people and places weren't all the same.

Alexis B., 31, New York, NY

Monte Velho Equo-Resort, Arraiolos, Portugal

I've been riding horses since I was 10 and am currently competing in first-level dressage. I've been going to the Monte Velho Equo-Resort in Portugal for the past four years now. It's this 12-room resort where you get to ride and watch professionals train gorgeous Lusitano horses.

Each year, I ride there for about a week. The lessons are world-class, but there's also comfort in knowing what to expect when I return. When I'm there, I get to meet people from all over the world who share my love of horses. We get to explore 700 acres of vineyards dotted with cork trees, eat wonderful meals together, and learn something new every day.

Cindy H., 73, Lake Placid, NY

Walt Disney World, Bay Lake, FL

Disney adult jokes aside, my mom and I enjoy going to Disney World every year because it's comfortable, familiar, genuinely fun, and a place where we have a lot of great memories. We've been going together for 25 years, sometimes multiple times a year.

"It's comfortable, familiar, genuinely fun, and a place where we have a lot of great memories."

There's always something new to do or some new treat to taste, making it exciting to go back. It's a nice, safe break from reality with excellent hospitality, cool hotels, and great food. Plus, flights to Florida are fairly easy.

Alaina W., 30, Pittsburgh, PA

Long Beach Island, NJ

In the '70s, my grandparents bought a duplex with their best friends in Barnegat Light, Long Beach Island. My grandmother loved the beach. My grandfather hated it and would read on the porch [while she went to the beach] before eventually making his daily pilgrimage every day at 4 p.m. with a pitcher of something to share with my grandma—that's love!

We vacationed there as a family every summer. I grew up in Maryland, so as a teenager, I resented LBI and just wanted to go to the Ocean City, Maryland, boardwalk with my friends. I was the worst! My grandmother died unexpectedly and young, and that beach house is still so comforting; all of our happy memories of her are there, and it keeps all of us—my aunts, uncles, and cousins—coming back, year after year. It's the only house I've come to every year of my life, and now we're bringing my kids along, too.

Katie B. D., 38, Maryland

Napa Valley, CA

For me, it's more of a staycation—I love returning to Napa Valley, where I grew up. I moved away when I was 14, but didn't realize at the time how wonderful it was to grow up around such earthy beauty, as I was too young to appreciate it. Now, at 37 and two kids later, I'm in awe every time I return!

"I feel like I'm back home, but also in a new place at the same time because there's always somewhere new to stay or explore."

And while heading to wine country always feels like a luxurious vacation when we meet friends there, it's also a homecoming for me that's full of comfort and nostalgia that I get to share with my children. I feel like I'm back home, but also in a new place at the same time because there's always somewhere new to stay or explore. San Diego has the same feel for me, as I met my husband there, and every time we go back, it awakens so many wonderful memories while we're simultaneously making new ones.

Heather L., 37, Yorba Linda, CA

Charlestown, RI

It's a quaint beach town where time literally feels like it stops as soon as I arrive. New England coastal vibes are a 10/10. — Ambria P., 24, Connecticut

Hilton Head Island, SC

Since I was 5, my family has been making an annual 13-hour car ride (now three-hour flight) down to Hilton Head Island to get away for the week. When I was younger, vacation was filled with pool time, beach time, and lots of special activities and adventures: horseback riding along trails with my dad, overpriced sand art by the pool, dolphin-watching boat tours, and very long walks along the beach where we'd find sea critters in large conch shells and our parents demanded we'd put them back because we couldn't take them home.

As I have gotten older, each trip back to this island offers a time to bond with my family and a nostalgic reminder of how much we have been through. Of course, it is lovely to go lay on a beach and have delicious food every night. Hilton Head also offers my family and me an all-encompassing comfort that other places don’t: The spot knew us when we were little and still welcomes us back with its cozy, familiar, and consistent open arms. As long as it keeps showing up for us, we will continue to show up there.

—Elizabeth K., 31, Michigan

Lake George, NY

Lake George holds a very special place in not only my heart, but in all of my family members' and now friends' hearts, too. My dad grew up going to the lake for family vacations and then, when he met my mom, she and her family would also go.

When I was 2 years old, my decided to purchase a home there. It has been very special to do the same activities and create similar memories to the ones my dad created growing up with his parents. My son is only 1 year old, but even now, it's been so special to share the lake with yet another generation.

— Kerry H., 30, Long Island, NY 

Emerald Isle, NC

We haven't been going as much lately, but for many years, my family went to Emerald Isle, North Carolina, every year, usually in late August. It was just a super-relaxing week of going to the beach and beach shops, eating seafood, mini golfing, and eating ice cream at night. The beaches there are super quiet (and dog friendly!).

We still try and go every once in a while when we can, and it's always a really nice week that we all look forward to; it still feels like a home away from home. I have a lot of travel anxiety that starts from when I have to pack, so it feels nice to go to a place that feels like home and I have a good idea of what to pack and expect, too. — Lydia C., 33, New York 

Our editors independently select these products. Making a purchase through our links may earn Well+Good a commission.

Loading More Posts...