Narrowing down my top 5 favorite vacation spots was a challenge. I love to travel and experience new cities and cultures. I don’t think I’ve ever been on a vacation that I didn’t enjoy … honestly, that’s a bit counterintuitive, right? But, as I’ve been thinking about my top 5 favorite vacation spots, it dawned on me that so much of what makes a trip special are the people you share it with.

1. Italy
If forced to choose a favorite of my top 5 favorite vacation spots, I’d say Italy. Italy is a country I have returned to time and time again over the course of my adult life. I went to Italy for the first time in 1996 as part of my bar trip (lots of American law school grads travel for at least a few weeks after taking the bar exam and before starting their “real lives” as lawyers). I met up with a good friend of mine who had been studying in Spain that Summer. We started in Nice and trained our way to Italy where we spent time in Venice, Florence and Rome.
I returned in 2005 to Milan to visit my good friend Barbara, who’s become like a sister. I went back in 2008 with my then boyfriend, now husband, and we toured the Amalfi Coast where I fell in love with the Isle of Capri. And then our families joined us for a tour of Tuscany. The next trip was in 2012 when my Italian friend got married in her hometown outside of Venice. Spending time in the Italian countryside was an experience of its own, but the wedding was beautiful and my best friend who’d never been to Italy came as my plus one. I’m not sure what I enjoyed more, celebrating my friend’s nuptials or watching my bestie fall in love with Italy and international travel.

And, when it came time to decide what I wanted to do for my BIG BIRTHDAY, all I wanted to do was to return to Capri. And return we did! My husband planned the most amazing 6 week trip – we started in Sardena with Barbara and her family and worked our way around the country. Stay tuned, there will be a post on that trip soon!

2. St. Barth’s
I love a beautiful beach and a beautiful beach with full service? I’m smitten. There’s so much more to St. Barth’s though. The more I think about what makes St. Barth’s special to me, the more I realize it’s got a special je ne sais quois, that both my husband and I dig. We spent our 5th wedding anniversary in St. Barth’s and have been going back regularly ever since. It’s chic, it’s a bit secluded and it’s totally Euro; if these are pleasure points for you, St. Barth’s might be an island to check out.

3. Paris
I took French from the second grade all the way through high school. My obsession with all things French started early and apparently there’s no end in sight if my love of St. Barth’s is anything to measure it by. I went to Paris for the first time with my 9th grad French teacher, Mrs. Kontry. We went to the Louve and saw the Mona Lisa, Versailles, Notre Dame, the Folles Berger, the Eiffel Tower and all of the other must-see sights for a first time visit. Traveling abroad at the age of 14 was an amazing gift from my parents, I have no doubt it’s what sparked my wanderlust.
It took me awhile to get back to France, but I took my sister to Paris as a graduation gift when she finished her MBA program. She had never been, so we did lots of touristy things … but my sissy is very chill, so we also did lots of café sitting accompanied by lattes and good wine. We did, however, make it to Clingancourt, the BEST flea market in Paris. O.M.G. THE BEST. If you have not been, the next time you go to Paris, you must go. To read about my adventures in Clingancourt, click here.
It’s been 10 years since I’ve been to Paris. But that trip 10 years ago this June, was the most memorable. My husband had been planning it for months unbeknownst to me. He surprised me with the news about 48 hours before we were supposed to leave. We’ve had many great adventures together since then, but I still remember, walking around the cobblestone streets hand-in-hand late at night like it was yesterday. If you’re lucky enough to go to the city of love with the one you love, GO! It’s magical.
4. Hong Kong
I’d say next on the list of my top 5 favorite vacation spots is Hong Kong. If you don’t know me personally, you may not know that in my next life I plan to come back as a CRA. Crazy Rich Asian for the uninitiated. Yes, CRA does in fact come from the title of Kevin Kwan’s book and the resulting block buster movie. I had high expectations for Hong Kong and it did not disappoint! The food, the shopping, the hotels, the bars … I couldn’t get enough of it.
You can have anything made in Hong Kong. Literally, anything. We had clothes made, bags made and shoes – all custom made. It was such good value for money, but it all felt so gloriously decadent! Like I said, I’m coming back as a CRA in my next lifetime.
I cannot wait to go back!
5. Martha’s Vineyard
I do travel in the US! I know, it may seem like I have no interest in traveling around our great 50 states, but I do. My top 5 favorite vacation spots list would be incomplete if I didn’t include Martha’s Vineyard. Martha’s Vineyard is a Massachusetts island that sits in the Atlantic just south of Cape Cod.
To be honest, Martha’s Vineyard is one of the most relaxing places I’ve ever been too. Just as Willow Springs, the island in Gloria Naylor’s book Mama Day, plays a vital role in the lives of its inhabitants, Martha’s Vineyard is a special place that holds a very dear spot in the hearts of those who return to it annually. Time stands still when you’re on the island. Eating good food, catching up with friends, going to the beach, lazing around – there’s time for all of this and more in just one day. However, getting there is no joke! It is literally planes, trains, automobiles and ferries for just about all who travel to Martha’s Vineyard. Is it worth it? ABSOLUTELY! But, getting there is more than a notion. And I’ll be honest, packing can be a bit overwhelming because you never know exactly what you might need (i.e., want) while on the island. At this point, I’ve pretty much gotten it down to a science, but it took a great deal of practice.
What makes each of these places special to me are my memories and those I share them with. They say people don’t take trips, trips take people. There’s definitely some truth to that!
Stylishly yours, Kalyn
P.S. If you love to travel, but have yet to figure out the carry-on suitcase game the airlines have forced us to play, you might find this post helpful.
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