Sibling Trip Destinations: Experience a New Adventure

What is a sibling trip?

Our idea for sibling trip destinations came up in a very unusual way. A few years back, my sister, brother, and I all flew to Pennsylvania for a family emergency. We hadn’t all three been together in several years, busy with jobs and family, so we decided to go to dinner by ourselves at Nick’s Fish House over in Baltimore, Maryland, about a ninety-minute drive each way from where we were staying. Our brother, Jeremy, had been wanting to try it, and it was so worth the drive! We don’t get authentic crab meals like this in the south!

We sat out on the patio, watching the sun set over the bay, and had the most unique meal experience. Add in a few Grapefruit Crush cocktails, and this hits as one of the best casual meals ever! We ordered a bucket of jumbo steamed crabs and started smashing away to dig out those tiny morsels of succulent meat. We had so much fun hanging out, something we have rarely done, that the idea was born to attempt to do a siblings-only weekend trip every other year. Jeremy lives up north, and Christina and I live in the south. Between us, there are nine children and spouses, so we had to be realistic about how often we could pull this off.

A Little About My Siblings

One thing my sister, brother, and I all have in common is a love of travel. Maybe being Air Force brats, living in England and around the US, created an interest in exploring the world. Christina and I have actually been traveling together on sister trips for many years, as we live in the same town. It seemed a natural extension to finally include all three of us. We’ve all traveled at different times for family trips to see each other and extended family, but those can get chaotic with so many kids. So the sibling trip destinations plan was born!

Traveling with siblings without extended family has intrigued the people we meet. We have now been on two additional trips. The first was to Park City, Utah, to ski (turns out Jeremy doesn’t ski anymore, but I didn’t know that until we were in Utah). Our second was this past March to Old San Juan, Puerto Rico. Every time we venture out, people ask us if we are related (maybe it’s the curly hair?), and they are curious why we are traveling together. It seems unusual to people that we have no purpose other than hanging out and experiencing life together for a few short days.

What makes a good midlife siblings-only trip?

If you are intrigued by the idea of trying a sibling trip, here are some considerations to help make it a success:

• Pick somewhere no one has visited! We have mixed it up; Christina and I had skied at Park City once, but it was new to Jeremy. On the next trip, we decided to go somewhere none of us had been. Staying at El Convento in Old San Juan and exploring Puerto Rico together for the first time was an amazing experience!
• Consider how much time you can realistically take off for a sibling getaway: We all have super busy lives with kids in high school, college, young adults, pets, jobs, businesses to run, and so much more. All of this can make it a real challenge to find a common time to get away. We start planning about six months out, looking at calendars and realistic travel locations. We’ve learned that a long weekend, four or five days, is the perfect amount of time for us.
• Plan at least one activity that each person will enjoy! It can be tricky to develop an itinerary that everyone likes. It’s also important to speak up, so your sister doesn’t plan a ski trip when you had ACL surgery and didn’t really want to ski! We adapted and had a blast, especially the shoe shopping for Jeremy. He showed up walking in the snow wearing boots that were literally in pieces (check out the before-and-after pics below). I have to say, his wife did tell him he needed a new pair before he came! In Puerto Rico, we all wanted to do the cooking class with Traveling Spoon. Jeremy and I wanted to hike, which Christina was willing to do with a mileage limit. Everyone wins!
• Plan some downtime: Everyone needs a little time away, whether to catch up with family at home, check in on work, or just take a quick nap. It will help keep the peace and let you enjoy the time you spend together with your siblings!
• Mix up your meal options: Some of your group may not want to dress up every night. Try including casual meals along with at least one elevated dinner or brunch. Consider letting each of your siblings pick one meal, so everyone gets to try something that appeals to them. I usually have a list of restaurants I’ve researched beforehand, mixing casual and high-end options for each area we will visit. Sometimes, a last-minute pivot, like the meal Jeremy found at Verde Mesa in Old San Juan, a farm-to-table restaurant, ends up one of our best meals! We spent our last night in Park City at Grappa Restaurant, enjoying a rustic Italian dinner in a charming house. It was the perfect ending to our Park City weekend!

Sibling Trip Destination Ideas

What works for us may not work for everyone, but if the idea has you wondering, it’s worth throwing it out there to your siblings! We have enjoyed it so much, we’re already tossing out ideas for 2028. We love the idea of Central or South America, as there are so many islands and fascinating spots that none of us have explored.

Other ideas for long weekend adventures:

• Belize – Hidden Valley Wilderness Lodge is a destination that has intrigued me lately. Tucked into the Mountain Pine Ridge Reserve, this 7,000-acre property has hiking trails, waterfalls, unique dining experiences, excursions, and more to offer!
• St. Maartin (Kingdom of the Netherlands)/St. Martin (France) – You get to experience two cultures on one island! We spent a day here on a Royal Caribbean Cruise several years ago. My husband took a cab and explored the French side while my daughter and I explored the beaches on the Netherlands’ side. Best of both worlds!
• St. Thomas – Another great relaxing destination spot with beaches, snorkeling, boating, and so much more to explore. Our favorite activity was taking a catamaran out to snorkel with the sea turtles.
• Costa Rica – Christina and I took a sister trip to Secrets Papagayo resort last summer. An adult-only destination with amazing restaurants, daily excursions available, and a relaxing spa experience (look for a detailed post soon).
• San Juan, Puerto Rico – Puerto Rico is a United States territory that isn’t too far away. You can go without a passport, and they use American currency. We stayed at El Convento, a former convent remodeled into a hotel. Check out my post about our authentic Puerto Rican cooking class we took while in San Juan!
• Mexico – We love Unico 20º87º, Riviera Maya! We’ve been twice with my sister and her husband. An all-inclusive adult-only resort (notice a theme?) is the best way to relax! I’ve also been seeing a lot of buzz about Mexico City over the past year, so it’s on my possible sibling travel list.

Are you inspired yet to take your own sibling destination trip?

I can say only good things about our experiences on our three sibling trip destinations so far. It is a chance to get away, reconnect with those important to you, and create lasting memories. Our children also hear all the stories when we return, and it will hopefully inspire them to keep connected with their brothers, sisters, and cousins. If you’ve done something similar, share your experiences and where you went! I love getting new ideas!