Packing Tips + How To Travel Alone

Venice, CA

I’m half introverted and half extroverted.  I took a personality test in 3rd grade that confirmed this LOL (the person running the test actually called me back because they were shocked that I scored EXACTLY 50/50 down the middle!)  Anyone who meets me doesn’t believe it because I’m super outgoing and friendly when you first meet me, but it’s true.  I was a total nerd/shy/artsy kid in middle school and had to force myself to come out of my shell when I went to a prep school in Connecticut for high school.  I could no longer be shy so far from home with zero friends as a freshman! Also, I had to learn how to connect with complete strangers in a very foreign setting.

It was the best experience and I’m so glad I overcame that fear.  Now, I love throwing myself into unknown territory and navigating my way through a foreign place.  Some of my fondest memories and experiences have come from solo trips. So I wanted to share a few tips on how to make the best of them!

How To Travel Alone

1. If it’s your first solo trip, pick a city that speaks your language and that you feel relatively comfortable in.

In high school, I lived in NYC by myself for a summer and did the Parsons Interior Design summer program which was a great way to “dip my toes in the water.”  They offer this program for adults as well (in various topics including photography, graphic design, fashion design, etc) and you can live in the NYU dorms for a relatively affordable price.  I made a ton of like-minded friends and learned SO much from the 4 week course.  In college, I lived with family friends in Germany for a summer, which was ideal because I had a safe, home base to come back to every night.  It was so fun to live like a local!  While I didn’t speak German, having the host family helped immensely.  There are so many wonderful short term exchange programs out there!

2. If it’s not your first solo trip, but you’re stumped on where to go…I have loved traveling to LA, NYC, Miami, Paris, Florence, Costa Rica, Palm Springs and London alone.

I have always felt very safe in each city and they are super accommodating to tourists.  Rent an airbnb in the heart of West Village and go to all of my favorite local cafes like Bluestone Lane and Ralph’s (more spots like this are on my app.)  Enjoy a long weekend by the pool with good magazines and plenty of spa treatments at the Parker Palm Springs.  Get lost in the incredible museums and charming shops in Paris and take in the beauty of South Beach with long runs and delicious, fresh seafood (Soho House Miami always feels like a home away from home – they leave milk and cookies by your door – the best!)

3. Book a fitness or wellness retreat.

I LOVE retreats.  I highly recommend Anamaya which is a yoga and surf retreat in Costa Rica (I went by myself last July and connected with such amazing women), The Ranch in  Malibu for a fitness retreat that involves vegan meals and lots of hiking (I did the 4 day program), or We Care Spa for a detoxing/relaxing retreat.  It’s a celebrity favorite for a reason – and I always come back feeling so refreshed and calm.

4. Bring a journal (I love journaling almost everyday on a solo trip.)

Traveling alone is such a great time to stop and reflect on our relationships, goals, hopes, and dreams, without all of the distractions and constant social interaction back at home.  It’s nice to look back on your journal entries a few months after a trip and see how far you’ve come or what you’ve accomplished.

5. Don’t be afraid to eat alone at a restaurant!

No one is watching you and no one thinks you’re weird I swear.  That being said, I personally don’t opt to eat dinner at a “hot spot” on a Friday night by myself because it’s crowded and loud and those places are more fun with a group of girlfriends anyway.  I go for a for more cozy, charming, solo friendly cafe when I travel and sometimes I’ll bring a book, magazine or journal, but often I end up just chatting with the waiters, making friends at the bar or enjoying the scenery and the food!

6. Reach out to friends or family who live in that city to meet up one night or one morning for breakfast or dinner (but also don’t feel obligated to if you don’t want to!)

I always play this by ear…sometimes when I really need a break I’ll go incognito and fly into a city like Miami where I know someone and not let them know (shhh don’t tell!)  But, other times I love seeing familiar faces half way through a trip and breaking up so much alone time.  Do what YOU want to do on your solo trip and surround yourself with GOOD VIBES ONLY!

7. Do a bit of research beforehand on fun places to eat, play, shop, and see so you’re not completely overwhelmed with your newfound freedom.

I know this sounds silly because who doesn’t love freedom and zero schedule, but it’s definitely nice to have some sort of familiar element when you’re in a new place.  Seriously though, sometimes too much freedom can be overwhelming!  For example, I love booking a Soul Cycle class with my favorite instructor the second I land in NYC, or I’ll stop by Good Life Eatery in London for a yummy green juice and avocado toast that gives me just the right taste of home as I embark on my trip.

8. Have an open mind and open heart, but at the same time be smart and remember you’re in foreign territory.

It may sound contradictory, but there’s a way to balance this excitement and fear of being alone.  Be open to making new friends, learning more about a different culture, and doing something outside your comfort zone (like zip lining through the jungle in Costa Rica – which was the highlight of my trip for sure!) but also be aware of your surroundings, always have your cell phone charged or an extra battery with you, and let friends or the concierge know where you’re going (I always send a simple text like “So excited to be heading to x for dinner – will check in with you tomorrow – love you!) to my sister or dad.  Basically, just use the same street smarts you have at home.

9. Pack a few self love/comfort items to remind you of home and pamper yourself on the road.

I always bring a face mask, my silk eye mask, a baggie of cacao nibs + coconut flakes, packets of coconut butter in case I’m starving and can’t find food, an electrolytes packet to rehydrate after the plane, and lavender essential oil to dab on my wrists if I’m feeling anxious or can’t fall asleep.

10. Pack LIGHT!

I really should take my own advice here!  But no seriously, when I travel alone and not for work or with friends, I leave my camera at home. Also, I leave anything fancy or glamorous behind and I bring only the essentials.  No designer bags, barely any jewelry, minimal makeup, and cozy basics like a cashmere scarf, skinny jeans, comfy shoes (this is key!), an easy silk dress, a long sleeve blouse, a leather jacket, a trench, one pair of simple heels, a fedora, a V-neck sweater, a white T-shirt, a black cami, a bikini, a sarong, a workout outfit and a plaid button down or chambray.  These pieces are all interchangeable and can be worn so many different ways.  For luggage – I never go anywhere without my trusty Longchamp duffle bag, Meli Melo brown leather tote (which folds down), and TUMI carry on suitcase.

For this week’s Wellness Series giveaway – I am SO excited to be giving one lucky reader this gorgeous, sleek and durable TUMI suitcase and my all-time favorite classic brown handbag from Meli Melo (a $1500 value!)   To enter, simply sign up for my newsletter, comment below “Signed up,” follow me on Instagram and Meli Melo, then comment on my latest Instagram post with Charlie “Signed up!”  Congrats to Linsy Goodson for winning last week’s giveaway!  I’ll choose this week’s giveaway on Monday ;)









Tumi suitcase c/o (enter to win it below!)  |  Vintage scarf (similar)
Meli Melo bag (enter to win it below!)  |  Maison Michel hat
Gigi New York x With Love From Kat luggage tag
Longchamp duffle  |  Ikea bookshelves and rack

Jessica Alexander Photography

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