6 trips we want to do again
There are people who take trips and then there are people who travel. Those of us who travel, we want to really experience a place. Explore. It’s not just about checking a box.
And that means that there are times when you have done the walking, the people watching at the cafes, the rambling museum exploration or historical site and you still don’t feel done. It’s that feeling of having only scratched the surface of a destination that makes you want to immediately book a flight to come back.
Today, we’re diving into six trips that our founder Samantha has been dying to do again. These are the places that she’s visited but is dreaming of going back for another round of exploration.
The trips we’d revisit in a heartbeat
Hi, it’s Samantha here, Eldest & Co founder and CEO. I’m so excited to dive into this topic. Obviously this is not going to be an comprehensive list of trips worth going multiple times because I can’t recommend places I haven’t been yet. So just keep that in mind, this is my personal experience slash wish list. With that caveat done, let’s dive in!
The Greek islands
I first visited the Greek islands in my mid-20s, single, with a girlfriend. We’ve all seen those dreamy photos of whitewashed buildings against a backdrop of azure skies. We made our way through Santorini, Mykonos, and Ios. This trip definitely involved some adventures, some late nights and some flirting ;)
Part of why I want to go back is because there’s an entirely different energy that I know can be had in an islands trip. We were feisty this trip and the islands blew us AWAY with the stunning sunsets, the vistas and the environment but I only scratched the surface because we were out having a good time, if you know what I mean? We left feeling like we had so much more to see.
The vibes in the Greek islands are impeccable, and I’ve since heard amazing things about Milos and Paros, plus a smattering of smaller islands worth exploring for more laid back vibes. Santorini, while stunning, felt more suited for a romantic couples trip so that’d be the only way I’d really want to go back there. Also definitely recommend this one not during high tourist season as the crowds were crazy.
A ski trip out west
I love summer but there is something magical about a winter vacay to ski towns. Picture this: cozy lodges, the scent of pine, and the thrill of fresh powder. I grew up skiing out west and have also done group trips with friends in my 20s. I love a day on the slopes followed by cozy apres ski, hot tubs and big cooked dinners at home. Places like Park City, Jackson Hole, Big Sky, and Telluride are stunning.
This stays on my list for repeats because it’s such a fun combo of activity and beautiful landscapes and there’s something for everybody. Not a skiier? Go snowshoeing and join in for apres. Go to the spa. Stay at the house with a cozy book and a fire and be ready to join the skiiers in the hot tub when they get home.
Not to mention each town has its own unique vibe, and I can’t help but feel that I’ve only just begun to explore the charm of the various mountains. Definitely staying on my list for future travel
Savoring the Loire Valley
I spent time in the Loire Valley during my digital nomad adventure year so I was traveling solo. Those memories are something I’ll always cherish. The beautiful châteaux, lush vineyards, and quaint little towns made for a picturesque backdrop as I drove through through this enchanting part of France. But let’s be honest—one visit just isn’t enough, especially when you’re solo and have to be “on” all the time.
Let’s also be honest - I’m a wine lover and this region has some unbelievable vineyards that I didn’t get to experience on this trip (Sancerre is a region in the Loire Valley, if you weren’t aware!). I’m eager to return to the beautiful, quaint hotels and plan a little more actively for some days of diving deeper into the wine tasting experiences that this region is famous for.
What I did get to do in my adventuring was exploring some of the historic chateaux in the region. The architecture is stunning and I wish I’d had more time to take longer tours. This might be niche, but if you watched and loved the show Reign like I did, the castle pictured above was literally a battle between Catherine de Medici and the king’s mistress Diane de Poitier - they had battling gardens on the premises trying to one up each other!
Discovering Bordeaux
My time in Bordeaux was a whirlwind, and I barely scratched the surface of this wine lover’s paradise. It felt like a charming, low key Paris in the city itself and with its stunning architecture and rich history, Bordeaux has so many more places to explore and stories to uncover.
Not to mention this is one of the wine meccas of the world in terms of sophistication. There were so many tastings that I wish I could have taken advantage of and didn’t have time.
Unsurprisingly for a big wine area, the food here was also exceptional. All in all, this is one of those places that I was asking myself “why am I not hearing more about this place?” and was immediately thinking about coming back!
The magic of Paris, London, and Rome
I can’t talk about trips we want to do again without mentioning the classics: Paris, London, and Rome. These cities are like old friends that I never tire of visiting - if I add up my visits to all three, I’ve probably been to these cities at least twenty times and each time, there’s something new to discover and explore. I won’t spend too much space here because you can check out the full Paris Guide, London Guide and Rome Guide individually but have to make sure these spots are getting the shout out they deserve as places I will happily return to.
Upstate New York in the fall
Oh, the beauty of Upstate New York in the fall! The foliage is simply breathtaking, and the cozy small towns have a charm that makes you feel right at home. I have only done day trips from New York, back when I lived in the city and always wanted to have more time and overnights to explore places like Kingston and Hudson, which I didn’t get to delve into as much as I wanted.
I did get to explore Storm King when I was in this region and either as a part of a longer visit or just a day trip, this property turned art museum was absolutely worth the trip and a return!
Frequently Asked Questions
Q: How do you get to the Greek Islands?
A: Bigger islands can be reached via small flights and all islands are connected by a series of ferries. It’s something to consider when planning your trip to determine whether you need to fly into Athens to be able to connect to your first island stop or if you have options from more European airports! And then of course planning transit between the islands throughout your trip.
Q: How long do you need in each island?
A: This depends on the pace of travel you want to do. More sightseeing oriented could keep you moving faster but you also don’t want to spend half your trip going to and from ferries. Craving more relaxing? Might make sense to just pick one or two. I’d say minimum 2 days in each spot would be my starting point, keeping travel timing oriented on not chopping days in half if you can!
Q: Do you have to ski to enjoy a ski town?
A: Absolutely not. There have been many ski trips over the years where I didn’t even rent skis! As long as you have a good cozy book and maybe a buddy to go explore the village with, non skiiers can absolutely enjoy.
Q: How do you get to the Loire Valley from Paris?
A: I rented a car and drove from Paris, which was easier than I expected and made the logistics of popping from a hotel to a chateau and back much more convenient. There are trains available from Paris but connections are often required and then you’ll be investing in car services to get you where you want to go!
Q: How do you get to Bordeaux from Paris?
A: Regionally there are flights in but it was a super convenient 2 hour express train from Paris that would be my recommendation. I expected much longer travel so this would be a no brainer for me!
Q: How do you get to Upstate New York?
A: There’s different definitions of upstate (because New York isn’t just the city, even though us city girls might sometimes act like it). So if you’re heading to Kingston, Hudson, etc. from the city, it’s just a simple train. If you want to go truly upstate, like up closer to Canada, it might be worth taking a quick flight to one of the smaller cities nearby or renting a car!
