2018 Travel Plans and Wishlist

Jess Ann Kirby relaxes under the palm trees on Smathers Beach in Key West, Florida
Image above via
Given one of my goals for 2018 is to take at least one trip a month I thought it would help to start writing down where we want to go. Of course I have some dream destinations that we might not get to this year, which is ok, but I also have some places nearby that I want to explore more. In 2017 we traveled to Key West, Ireland, Bermuda, Panama, Tulum, Vermont, San Francisco and Charleston. Funny when I wrote that all out I realized we actually did a lot of traveling last year! We already have a few trips planned, and we’re excited for more exploring and adventuring in 2018. Travel is truly one of the best ways to get inspired, and you honestly don’t have to go far or spend a lot of money, sometimes a 30-45 minute drive is all you need.
Jess Ann Kirby goes Cliff Jumping at Admiralty Park in Bermuda
Jess Ann Kirby wears a one shoulder swimsuit, Levi's cut off shorts and a straw panama hat in Tulum, Mexico

Image left // Image right

To start the year off we are headed to New Hampshire for a week this month. We always regret not heading up north during the winter. It’s just so beautiful and peaceful and the perfect place to enjoy winter to the fullest. We love to snowboard so we’re planning on heading to the mountain for a day or two and then doing some cross country skiing and maybe even renting snow mobiles.

In February we are headed to St. Petersburg in Florida for a friend’s wedding. I’m actually really excited about this (for obvious reasons-give me a beach and a marg and I’m set) but we’ve never been to this part of Florida. You guys sent so many great recommendations on Instagram the other day, thank you!

We were supposed to head to Costa Rica this month (the first place Craig and I traveled to together over 10 years ago-we were babies!). That didn’t come together in time so I think we are headed there in March.

As most of you know half of my family lives in California, my Mom and brothers, so we are planning to head to San Francisco for Easter (probably one of our favorite places to visit of all time). Hoping we can hit up Napa and Big Sur while we’re there.

We loved Ireland so much we’re going back! We are planning a trip for July to explore the Ring of Kerry.

I am embarrassed to admit this but I’ve never been to Martha’s Vineyard. In my defense I think a lot of us that grow up in New England, particularly Rhode Island (more specifically Aquidneck Island), get stuck here because in the summer, why would you want to leave? That said, Martha’s Vineyard is a place I really hope we get to explore this year.

A place where the beer flows like wine where beautiful women instinctively flock like the salmon of Capistrano. A little place called Aspen (sorry pretty much fave movie of all time). Excited to head back to Aspen in August for my cousin’s bachelorette party.

We LOVE Block Island and yet, year after year, we don’t make it out there. It’s such an easy trip, seriously a 25 minute ferry ride. Block Island feels like another world, it’s truly magical so that’s high on the list of places to visit this year.

Continuing the close to home theme, Providence is such a great city (seriously only 30 minutes from our driveway) and we NEVER go. We are hoping to spend a proper weekend there to really explore and share our favorites with all of you.

I don’t know if it is going to happen this year but we both REALLY want to visit Portugal. My Dad went a few years ago and hasn’t stopped talking about it.

Image left // Image right

Jess Ann Kirby grabs a photo of the beautiful flowers on building fronts in Casco Viejo, Panama City
Jess Kirby wearing a French Connection White Embroidered Maxi Dress in Panama City

Leave a comment

This site uses Akismet to reduce spam. Learn how your comment data is processed.


  1. Brittany wrote:

    Great travel list! We are off to Costa Rica in February – I am so excited – have never been and will be a nice break from CT snow. I totally agree about local travel too, we’ve never been to Boston and live in CT so that’s on my list!

    1.10.18 | Reply
  2. Sam wrote:

    I LOVE the scalloped back of your black bathing suit in the first picture. I’m headed to Siesta Key in early May, any chance you’ll be doing a bathing suit and summer wear post? I really need to update my bathing suits and summer clothing but get so overwhelmed with all the choices when looking.

    1.10.18 | Reply
  3. Tina wrote:

    My boyfriend and I are headed to Ireland in June – we are so excited, neither of us have ever been before! Obviously loved your blog post and video (i’ve watched this atleast 5 times…) about your trip to Ireland this past summer. Definitely took notes on a few places we MUST see while we are there!

    1.10.18 | Reply
  4. Lexi wrote:

    Love your travel posts. MV is a favorite yearly destination of ours! Looking forward to how you see the island! cheers!

    1.10.18 | Reply
  5. Rach wrote:

    These are great travel plans! We plan on going to Portugal this year and I am so excited about it! SF is one of my favorite cities too!


    1.10.18 | Reply
  6. Mary-Katherine wrote:

    This is such a fun list and I love that you included so many that are close to home! Those are often the ones people forget about but so often there are places nearby that feel completely different!!

    When you head out to CA, you should really try to get to Sonoma! I grew up in Sonoma but went to high school in Napa so I’m very familiar with the area and I gotta say: Sonoma is better! Napa is fantastic don’t get me wrong and if that’s all you have time for it will be a great trip but Sonoma is smaller and more quaint, still has tons of amazing restaurants, and has the cutest downtown square. It’s kind of like Stars Hollow, just absolutely picture-perfect. Plus, I think you would love Scribe Winery!!

    xo Mary-Katherine

    1.10.18 | Reply
  7. Emily wrote:

    I love a travel bucket list! Portugal does sound like a dream. We just got back from Big Sur and I cannot recommend it enough! Absolutely stunning!

    1.10.18 | Reply
  8. Baigin wrote:

    The Ring of Kerry in Ireland is absolutely incredible. You will LOVE it. Loving the wellness challenge and always love to see your travel content.

    1.10.18 | Reply
  9. Sara V wrote:

    My husband and I travel several times per year and we were diverted to Martha’s Vineyard thanks to the Houston hurricane (long story). It is a place that I would go back to again and again. I had moderate expectations for what it would be and it blew me away with it’s low key, relaxing atmosphere. I loved it.

    1.10.18 | Reply
  10. Emma wrote:

    Jess you’re so right — I grew up in Newport and have never been to Martha’s Vineyard or Nantucket and only to Block Island a few times!

    1.10.18 | Reply
  11. Shloka wrote:

    Lots of amazing travels coming up and I can’t wait to see all the imagery from your trips!


    1.10.18 | Reply
  12. Taylor wrote:

    Sounds like you have soooo many great plans! I’ve never been to ANY of these places (lol) so I am wanderlusting haaaard. I have a trip for June lined up for Toronto, never been there in warmer months so I’ve been getting excited. Loving the close to home theme – sometimes those are the best trips and just as much of a mental reset.

    1.10.18 | Reply
  13. Jen wrote:

    We loved visiting Block Island, especially with our bikes, and I miss being able to bike or even walk downtown/city in Providence. One of my girlfriends and I plan to meet in Lisbon this year! x

    Jen | affecionada

    1.11.18 | Reply
  14. Vanessa wrote:

    I’ve been to San Francisco once before and it was awesome there! So much to see and do, I’d love to eventually go back. This year, I’m hoping to at least take ONE trip. Last year, I had booked a trip to London in May but then had to cancel it because my grandmother ended up passing away that month. So, this year I’m hoping to re-book that trip.

    1.11.18 | Reply
  15. Emily wrote:

    I LOVED Lisbon. Would like to go back to Portugal and explore the Algarve.

    1.12.18 | Reply
  16. Cam wrote:

    I hope that you’ll visit all the places that you want to see, especially Portugal.

    1.30.18 | Reply
  17. K&E wrote:

    So many awesome places. Excited to see your posts about them <3 Xoxo, K&E

    2.12.18 | Reply
  18. Beth wrote:

    Whoop for 2018 travel! We’ve just come back from Holland and going back to Catalonia, Spain ?? with the family late summer – I’m married to a guy from Dublin ? so looking forward to more Ireland posts!! (If you have time pop over to the UK we have super beautiful countryside like the Cotswolds which will melt your heart or the Norfolk coast which will prop remind you of beaches from home!) Happy 2018 travels ?Xb

    2.14.18 | Reply
  19. Ann wrote:

    Portugal is amazing. May I suggest you add the Azores to your list. With direct flights out of Logan and PVD, it’s a short 4.5 hr flight. It’s called the Hawaii of the Atlantic for a reason. Amazing hiking, food, vistas (on the top 5 in the world for most vistas per aware km. Its truly my favorite amd i cannot wait to retire there some day. We were just in Bermuda last week and I kept commenting that it did not have the vistas that Sao Miguel has.

    3.19.18 | Reply
  20. Lauren wrote:

    I saw you’re going back to Ireland and specifically doing the Ring of Kerry. We just got back and the entire trip was incredible. There’s a point on the top of the ring (called Kerry Cliffs on Google maps) that looks cheesy from the road where signs say ‘Best View in Ireland’ we wouldn’t have trusted it but Rick Steves swore by it and holy mother of God it really beat everything we had seen on the trip (including Cliffs of Moher)

    Also, not sure if you did Dingle on your last trip but it was definitely our favorite spot and we did 2 nights there. The Slea Head loop easily rivals the Ring of Kerry (definitely more spots to stop) and the bars and restaurants were quaint but also awesome. (Global Village Restaurant, Foxy John’s Bar, Dick Mack’s bar, just to name a few) Hike the Eask Tower through a sheep farm and definitely hike Dunmorehead (close second to Kerry Cliffs).


    6.13.18 | Reply

Most Popular

The Latest: