2019 Travel Plans and our Wishlist

Jess Ann Kirby explores Hawaii with an afternoon paddle boarding on Mauna Kea

I always like to think about places we want to go at the beginning of the year because it gets me excited for all the possibilities of the year ahead (and helps me survive winter). We don’t always get to every place on our wish list of course but it’s still fun to write down our dream destinations. In 2018 we traveled to Saint Petersburg, Beaver Creek, Hawaii, San Francisco, Woodstock, and Portugal (travel post coming soon). I also visited Aspen and Santa Barbara, and Philadelphia and Finland with Anthropologie. It’s crazy because I was honestly thinking at the end of the year that we didn’t do that much travel and when I wrote it down I realized it was quite a lot. And honestly, we are a little burnt out. Don’t get me wrong we feel super lucky to get to travel to amazing places, but it’s exhausting, it is work. There is little down time (I think we loved Saint Petersburg so much because it was the one trip we didn’t really work). It’s also really hard leaving the animals behind, we hate it, and Craig has a bad back so flying is tough. Anyhoo, nobody cares, haha, but I say all of that to say our plans are a little different this year. And who knows, we’ll see where this year takes us.

Jess Ann Kirby enjoys apres ski in the Sweaty Betty thermal top and North Face red snow pants
Jess Ann Kirby soaks in the sun in a Solid and Striped Anne Marie One Piece bathing suit in Hawaii | My Favorite Mineral Sunscreen

In February we are headed back to St. Pete. Yes, we really loved it. It just had such a great vibe, good food, beautiful beaches, and obviously amazing weather (fingers crossed for that again). It’s also pretty affordable for us to get there and stay there. We were initially planning on staying for a month, but our big picture plans changed and we decided not to do that. If you have any great recommendations for stuff to do there let me know!

Vermont. As I shared in my goals last week, we are hoping to buy another fixer upper this year and our dream is to get one in Vermont. We are hopefully headed there this month to check out a few different areas we like and see some houses (I will film for YouTube and take you along!). Obviously there’s a lot that needs to happen before we buy, but we are both really excited about this and since it’s one of our biggest priorities we’ll probably be up there a lot this year.

In March, my youngest brother turns 30 so we are all going to Barcelona to celebrate. I’m excited as I’ve never been (none of us have) and I’ve heard great things. We found super cheap flights which is awesome and will probably stay in an Airbnb. If you have any recs please share! Definitely would love to know good neighborhoods to stay.

In the spring we are headed to Portland, Oregon. I’ve been wanting to visit Portland forever and I’m super excited about this. We are planning to drive south from Portland to San Francisco and probably stopping a few days in Bend where my brothers will meet us so they can climb and Craig can mountain bike.

This summer I am headed to Atlanta for the first time to speak at a conference in August. I’m nervous about the speaking part but excited to check out Atlanta.

I’m hoping to do a trip to NYC this year. I have this weird relationship with the city. I have so much nostalgia about when we lived there and remember it fondly but when I actually go, I get severe anxiety and pretty much want to leave immediately. It’s happened the last few times I’ve gone and I haven’t been back. There are so many people I want to go visit and hang with so I really want to make that happen this year. I think making the trip less about work and more about just a regular trip to the city might help, we’ll see.

We have some other places we’d love to go, Costa Rica, Moab, British Columbia, but we are focused on saving money so those will have to wait. I’d love to hear about any trips you have planned and what’s on your travel wish list this year!

Jess Ann Kirby visits Finland during the winter and enjoys seasonal adventures for the holidays | Click. Read. Love. 1.8.22
Jess Ann Kirby visits snow puppies while on a trip to Finland
Jess Ann Kirby hikes to the top of Mount Tom in Woodstock, Vermont.

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  1. Kristin wrote:

    Crete, Greece is on our bucket list this year for our one big trip. Anywhere with a beach please! We are also heading to Rhode Island and Vermont for weddings later this summer. I’ve never been to Vermont so I’m excited to check it out!


    1.9.19 | Reply
  2. Katie Carlin wrote:

    I dm’d you the best Barcelona airbnb. Moab is one of my favorite places I’ve ever been- I have some great recs there and a perfect airbnb as well if you end up booking the trip!!

    1.9.19 | Reply
  3. Emily wrote:

    I’m set to get married in August but have been planning my 30th birthday trip in London in July for 3 years so it might be crazy but I’m still doing it! Lake Tahoe for a girl’s weekend and probably a weekend in Newport as a mini-moon while we plan our big honeymoon trip for Spring 2020. I always try to make it up to Boston for a weekend to see friends!

    1.9.19 | Reply
  4. Brittany wrote:

    I hear you on the travel is tough part! I used to LOVE traveling and while I still do, my anxiety has gotten so much worse with age & I can hardly think about flying anymore without feeling anxious. I’ve been all about the road trips lately 😉 Sounds like a great list you’ve got there, though! And love the idea of a vacation house! Our dream is Avalon, NJ, someday!

    1.9.19 | Reply
  5. Jherell wrote:

    You’ve encouraged me to tentatively plan out my trips for the year! Some places on my list include: Philly (my fav), Cleveland (first time; it’s close to my hometown in Western NY) and New Orleans (first time!).

    1.9.19 | Reply
  6. Carson wrote:

    What conference will you be speaking at in Atlanta? I will be at the apparel show 2nd week of August.

    1.9.19 | Reply
  7. Erica wrote:

    We went to Bend on a family trip two years ago (after taking a 4 week road trip from Arizona up the coast of California into Oregon…with a 10 month old and 2 year old) and wanted to move there immediately. Ultimately we decided not to for several reasons (small job market, relatively expensive, hard to fly in/out), but it helped us figure out where we wanted to live next. We landed in Denver last August and love it. All this to say, Bend is the best!

    With two kids, a new job for my partner and not living close to family, most of our trips now involve visits to the grandparents. Not as exciting as the other travel spots on your wish list and others!

    1.9.19 | Reply
  8. Christia wrote:

    We are taking the kids on a cruise in February. I have an overnight trip to ATL in February as well as a work trip to NYC in February. Wild times that short month. We will probably go somewhere for Christmas…I’m thinking Miami for the food???

    1.9.19 | Reply
  9. Lauren Lockwood wrote:

    I loved Barcelona!! I stayed in a great Airbnb right outside the Parc de la Citudella. Highly recommend! Here’s the link: https://www.airbnb.com/rooms/283231?eluid=3&euid=a7b03c84-c0fd-866d-c140-42bd4f5d758c&guests=1&adults=1. It is a little small for more than 2 people though!

    1.9.19 | Reply
  10. So many great places on the list!
    I love Vermont, we used to go camping in Jamaica every Summer when I was younger and then we took like 5 or 6 years off before I started going again with a few friends. Now I think it will be going back to a family tradition for a few years at least.
    Hopefully going on a belated honeymoon to Italy/Greece in the Spring. I’ve been to both but my husband hasn’t been out of North America before and he loves ancient things so I figured it was a good place for him to start!

    1.9.19 | Reply
  11. Katelyn wrote:

    For staying in Barcelona, maybe reach out to the lovely folks at Gimme Some Oven (https://www.gimmesomeoven.com/) for recommendations! Maybe you can even collaborate on something in the future 🙂

    1.9.19 | Reply
  12. Haylee wrote:

    This year we are hoping to make it back to Argentina! We want to see Patagonia/Bariloche. We lived in the city there for a year and a half but it was mission-related so we didn’t do a lot of sightseeing. We want to go visit old friends and travel around a bit more 🙂

    As far as Barcelona goes, I LOVE Barcelona. I would live there in a heartbeat. I would recommend staying relatively close to the city because it’s very walkable and you won’t lose time taking the train to and from every morning when it isn’t really needed (you can find places with decent rates closer in). I would just recommend being careful about staying in Gothic Quarter because people party pretty late into the night and you’ll hear it in your room.

    As far as experiences go, the two stand-outs were a sailing trip and a horseback riding experience through “Barcelona’s Tuscany.” If you decide to sail, definitely take an anti-nausea beforehand though because half of us on the boat spent the last hour staring at the sky trying to keep it together haha. The water is pretty choppy there in the summer.

    The horseback riding was my absolute favorite and I LOVED the place we went to and our host. It was an experience through airbnb: https://www.airbnb.ie/experiences/23568?source=homes_pdp. It’s a bit of a day trip from the city but it’s so worth it. The countryside is beautiful, and David was so great to talk to and learn more about the Catalan landscape and culture from.

    Gosh, wrote half a novel. Cheers!

    1.9.19 | Reply
  13. Lisa wrote:

    Atlanta is great if you get out of the downtown/midtown/buckhead area. See the new Center for Civil & Human Rights. Check out some of the fun neighborhoods and great restaurants. If it’s blazingly hot, head north and take a hike along the Chattahoochee (or tube it!).

    1.9.19 | Reply
  14. Meghan wrote:

    Let’s hang if you come to NYC!! Also, in case it is helpful: https://www.witwhimsy.com/2018/08/14/how-to-spend-48-hours-in-portland/ (I dream of those doughnuts!!)

    1.9.19 | Reply
  15. Marisa wrote:

    We went to Barcelona in 2017 and stayed in the northern part of the city. An area called Gracia and LOVED it! We went to Madrid too but Barcelona had so much personality and the area we were in was more quaint even though it was a big city! I liked the narrow streets but then how they’d open up onto little squares with restaurants and people hanging out. Hope this helps!

    1.9.19 | Reply
  16. Audrey wrote:

    I honestly relate to the anxiety that the city brings. I’m from the Midwest, but my fiancé and I have been exploring medical residency training in NYC to be closer to his family. When I’m there with him for vacation I can relax and enjoy all that the city has to offer, but when I am there by myself for work/interviews I feel like a fish out of water. I’m such a small town girl at heart! Glad to know I’m not the only one who feels this way! Thanks for sharing!

    1.9.19 | Reply
  17. Mackenzie wrote:

    My mom lives near St Pete! I absolutely love it. You should go to the Don Cesar, it’s the best hotel ever. Also, there is a restaurant called the Columbia, it’s amazing… and The Bate Shop is a quaint, but super fresh food and we usually see dolphins!

    1.9.19 | Reply
  18. Ally wrote:

    Hi Jess – I live in Boston but travel to Atlanta a lot for work. There are a ton of great restaurants to check out (I’ve basically never had a bad meal) and my favorites are The Optimist, South City Kitchen, Cooks & Soldiers, and JCT (in that order).

    1.9.19 | Reply
  19. Courtney wrote:

    Best advice about having a better NYC visit. Stay in a cute Airbnb in a chill and calm area of Brooklyn (Ft. Greene, Carroll Gardens, etc). It will massively take the edge off of the whole experience. I couldn’t live here if I had to live/work/play in a Manhattan 24/7 either.

    1.10.19 | Reply
    • Jessica wrote:

      Yeah we lived in Brooklyn for the majority of the time we lived in NYC which is why I think I could do it for as long as I did. Haha!

      1.10.19 | Reply
  20. Alex wrote:

    My husband and I went to Barcelona this past summer and stayed at Eco Boutique Hostal Grau: https://www.hostalgrau.com/en/. It was near the Gothic Quarter but it was surprisingly quiet and a nice sanctuary away from the chaos. 🙂 We loved Barcelona, enjoy!

    1.10.19 | Reply
  21. Tara wrote:

    We were in Barcelona last Sept and loved it!! Things to do:
    – La Rambla – main tourist shopping area.
    – Rent bike, explore the cite and ride down to beach. We did this the first day to get a lay of the land. It’s a great way to cover a lot of ground. The rental bikes are all over the city
    – Ciutadella Park w/ Arc de Triomf – can stop by on the way to the beach if you bike
    – Casa Batllo – Gaudi apartment, buy tickets online ahead of time. They have an audio/visual tour that shows the house as it was originally built with 3D. It’s phenomenal.
    – Sagrada Familia – buy tickets online. Amazing!!!!
    – Park Guell – close to Sagrada Familia (this was a little underwhelming for us)
    – Catedral (in Gotic neighborhood) – wear pants or longer skirt/dress (past knees). This was the most beautiful cathedral we saw in Spain and is a must see!
    – Magic Fountains – we missed this but it was recommended to us by a few people. I think they are only Thurs-Sun and specific times at night
    – FC Barcelona soccer game / tour of the stadium
    – The beach!!

    – Bar Canete – off La Rambla, make reservations **this was our favorite. Sit at the bar, waiters are hilarious
    – Tapeo – in El Born, make reservation **another favorite
    – Santaugustina – in El Born
    – Alsur Cafe – a few locations around the city, cute little cafe for breakfast or a snack

    W Hotel on the beach is supposed to have amazing rooftop views (we didnt make it there)

    We spent most of our time in the El Born neighborhood. It seems sketchy at night but we walked around there every night and never felt unsafe.

    1.13.19 | Reply
  22. Megan wrote:

    I have family in St. Pete so I’ve been a bunch. Definitely recommend downtown Dunedin, it’s a little further up the peninsula but recently restored, right on the water, and there’s so much life! Everytime we go I demand we go to The Living Room on Main for tapas, SO good!! There’s also a ton of breweries and other cute restaurants in that area that are worth a look. Enjoy!

    1.13.19 | Reply
  23. Sarah wrote:

    I am a NYC transplant to St. Pete. If you are staying downtown St. Pete I would suggest staying at Vinoy which is a historic Floridian pink hotel second to the Don Cesar which is the only hotel you should stay at near the beach. As for places to eat! Paul’s Landing, Lolita’s, Left Market, the Gateway and Ane! Things to do…kayak, live music at the Hideaway, bike the Pinellas trail and St.Pete Shuffle on a Friday night is a must! Tampa is 30 minutes away and has a lot to offer too! Hope this helps!

    1.13.19 | Reply
  24. Jennifer wrote:

    My hubs and I will make our first trip of the year to Breckinridge with a small group of friends to snowboard and then in February just the two of us to Cabo! Never been so excited about that. Las Vegas for a wedding in March and hopefully somewhere beachy for our family vacation with our two littles.

    1.13.19 | Reply
  25. Susan wrote:

    Barcelona restaurant recommendation….the best Italian meal of my life (and I have been to Italy) was at a restaurant in Barcelona called Da Greco. The risotto is so good that it will bring tears to your eyes.

    1.13.19 | Reply
  26. Sarah Cz wrote:

    Barcelona is amazing.
    Cera 23 is fabulous for dinner…small back alley type of place but with amazing blackberry mojitos. Then you need to visit just about anything Gaudi’ designed but for sure the Segrada Familia…dont go on sunday though….and worth doing the audio tour.

    1.14.19 | Reply
  27. I live in ATL! I can’t wait for you to come see… We have such a great food scene and fun outdoor activities. Let me know if you need any recommendations, I would be happy to act as tour guide or send some options your way! What conference is it in August? I would love to go to hear you speak.

    Sounds like some great plans for 2019!

    1.14.19 | Reply
  28. Lauren St Clair wrote:

    Just came back from Costa Rica, highly recommend!

    1.14.19 | Reply
  29. Campbell S wrote:

    I just confirmed a bachelorette weekend in St. Petersburg for the end of March! My best friend (and I) is a big fan of the warm laid back beach vibes and we decided end of March worked best. While we’ve enjoyed our trips to Newport, end of March wouldn’t work (yikes). So while I was researching Florida, I remembered you went last year and it looks like it’ll be perfect. We’re far more of a beach bar group than a night club group.

    Can’t wait to see more recommendations for the area!

    1.15.19 | Reply
  30. Wow!!! great list of places. but this year, I would like to go hunter valley wine tours in Australia with my friends.

    3.1.19 | Reply
  31. messi wrote:

    I live in ATL! I can’t wait for you to come see… We have such a great food scene and fun North India Tour Packages outdoor activities. Let me know if you need any recommendations, I would be happy to act as tour guide or send some options your way! What conference is it in August? I would love to go to hear you speak.

    3.14.24 | Reply

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