What I’m Packing + A Jack Rogers Giveaway!

Visor // Beach Tote (only $35!) // Glitter Jelly Sandals (I’m an 8.5 and wear an 8 in these; also available here) // Flip Flops // Swim Top // Swim Bottom // Bracelets

Today’s the day I’m headed off on a fun little vacation with some girlfriends for a few days!  Lanier had a few guy’s trips this past Fall, so it’s my turn this Spring and I cannot wait!  Sharing more of what I’ll be taking with me on today’s post.  That way if you follow me on Instagram and see me wearing something you like, you can easily shop it here.

For the Plane Flight // This is that top I was thinking about ordering over the weekend, and I’m obviously so glad I did.  Super comfortable and easy to toss on over just about anything. It’s also available here. // Sandals // Shorts // Necklace (new color for Spring)

Tanks // Sports Bras // Grey Shorts // Reflective Dot Shorts // Printed Leggings

While we’re there, I may try and work out.  Okay, so it’s probably not going to happen, but I’d rather just bring it, just in case.

Had to toss in my favorite pajamas.  The softest!

And since we’re talking favorites, you know how much I love the tassels on these cover-ups.  Absolutely loving this color combo!

Yay for bikini tops! // Tassel // Striped // Ruffle

So excited to get to finally wear all of these faves below – some I’ve had in my closet for well over a month, patiently waiting to go!

Embroidered Cover-Up // Tassel Earrings // Sandals

Floral Dress // Wedges

I finally get to wear my wedge sandals this weekend!  For fit, they’re true to size.  I’m an 8.5 and wear an 8.5 in them.  Sizes are selling out quickly, it’s also available here.

This one will definitely be worn on a night-out while we’re there. // Sandals

Such a comfy floral romper.  I don’t do rompers that often, but this one works so well.  Love the sleeves.

This cover-up was probably one of my first purchases for my trip.

Striped Kaftan // Scalloped Swim Top // Sandals

I feel like while everything I packed will be worn now, I’ll also be able to wear it on into this summer too.  It’s all pretty comfortable and conservative enough that I can wear it to our pool and the beach, and my kids won’t be wondering what exactly I’m wearing.

Alright, now on to the fun part!  A giveaway!  One lucky reader will win a pair of Jack Rogers in Bone, just like the ones I’m wearing above!  And also a Lilly Pulitzer Travel Journal!  All you have to do is tell me your favorite place you’ve ever been on Spring Break!  One entry per person, please.  Also, just wanted to give y’all a heads up that I always moderate my comments via email.  So if you enter and your comment doesn’t show up right away, don’t worry.  I’ll ‘okay’ it as quickly as I see your comments via email.

Giveaway ends on Monday at midnight!

Good luck!

In case you may have missed my most recent blog posts, check them out here…

Click to view post: Wednesday Whereabouts + What I Wore (be prepared for lots of pictures!)

Sweatshirt // Shorts // Watch // Ring

Click to view post: The Hanoi Cocktail + New Lilly Dress Love

Dress (also available here) // Sunnies

I hope y’all have a wonderful weekend!  As I mentioned yesterday, check out my Instagram for more updated photos of our trip throughout the weekend!


Hope y’all are enjoying your weekend so far!  By the way, loving everyone’s Spring Break stories!

346 thoughts on “What I’m Packing + A Jack Rogers Giveaway!

  1. My favorite place I’ve been on Spring Break was my senior year of college (MANY years ago) when we went to Key West. There were probably 10+ of my sorority sisters that traveled there as our last big blow out of college and it was AMAZING! We had no fancy hotel, no money just awesome friends and the thrill of Spring Break!

  2. I’ve never been on an extravagant spring break, but my favorite was Clearwater, FL with my lacrosse team in college!

  3. My mother and I took a girls-only trip to the most amazing resort in Mexico last year. I’m already planning to return in June with my husband!

  4. My husband and I got married over Spring Break (several years ago) and we went to Savannah, GA for our honeymoon. Loved it!

  5. Hi Ashley! Key West! Sloppy Joe’s and so many fun bars, warm weather, ritas and sunshine8-) Have fun on your girls trip this weekend!

  6. Last year my whole family (19 of us!) rented a big house in Sunriver, OR. Sun, snow, family – it was perfect!

  7. My favorite spring break trip was to St. Pete Beach, Florida, in college. The weather was terrible, but I had a great time with my sister and best friend.

  8. My favorite Spring Break was in college when a bunch of girls took a cruise to the Caribbean. Lucky there were lots of us because we ended up with a big group of old men travelling together! We still had tons of fun!

    Have fun on your trip!

  9. When it was my sister’s spring break she and I went on a cruise to the Mexican Riviera. What a great week. We got a great deal.

  10. We’ve done lots of Caribbean cruises, and St. John has been a fave…….but this year my husband and I snuck away (from CT) to Savannah and Charleston. I feel in love with both Savannah and Charleston. Such a great cities. It made we want to move south!

  11. We took our kids to Charleston, Mt. Pleasant, & IOP last year for their spring break and it was the best family trip! We got to blend relaxing family time with some incredible history, and phenomenal meals!!! The weather was perfect and our kids want to go again this year!

  12. Thanks to my work, I’ve only done one true spring break and it was in Daytona Beach. Our favorite getaway though is to Anna Maria Island! Enjoy your getaway.

  13. Last year, we did a lakehouse trip to Lake Oconee with 4 families. For grownups, it was a great spring break!

  14. Disneyworld when I was a Freshman in High School and my sister was a Senior. It was our last family trip before she went off to College.

  15. Cancun–my husband and I carried our son for Spring Break and it was the perfect family getaway!

  16. West Palm Beach, FL with a bunch of my girlfriends from college! A fun relaxing week catching up by the pool with cocktails in hand, cooking yummy dinners together and soaking up some sun away from snowy New England!

  17. Las Vegas my senior year of college with 14 of my pledge sisters. The most fun spring break trip I’ve ever been on!
    -Wendy H.

  18. My favorite spring break trip was to Disney World with my family when I was young! I still remember it like it was yesterday! xx

  19. We have always done Myrtle Beach growing up and that’s not my fave. But as an adult I’d have to say Costa Rica!

  20. My California coast road trip that ended at Disneyland was my favorite spring break trip 🙂 Thank you!

  21. My favorite place I’ve been on vacation was to Jamaica! It is the most beautiful place with the friendliest people!

  22. Actually mine was Charleston. My husband and I had never been so we went to check out the place and loved every minute there. Especially the Walking Ghost Tour.

  23. Sea Island, GA! It is the perfect mix of relaxation, beauty, great food and fun! They have such a rich history and every part of the Island is super family friendly!

  24. Love Key West. My family has a wonderful time share there. It’s a great family place!!! Love Lilly,Jack Rogers and your blog!!!

  25. Favorite spring break was a trip to Fripp Island, SC with my hubs as a “babymoon” So relaxing and fun!

  26. College Spring Break in 2002. We had all turned 21 so we drove to Key West from Tuscaloosa. It was so much fun!

  27. A girls’ trip to Chicago for St. Patrick’s Day! Definitely a fun, memorable trip! Enjoy St. John, definitely want to travel there someday! Cheers!

  28. SO much fun! I hope you’ll have an amazing time! My favorite place for spring break was Paris, while I was in college!

  29. Jamaica, my last year of college. My parents wouldn’t let me go to the Bahamas with my girlfriends because they thought it was too risky and the idea of boys going wasn’t even ok either ?. So they took me to Jamaica. Now that they’re gone, and it was a mess in the end, I’m so grateful for this time I had with them. At the time I was a little disappointed I couldn’t go with friends.

    1. I can tell you had amazing parents. They did the same thing with my two youngest sisters when they were in college…except it was Disney World! They made the excuse like, “well, when y’all were little and we went to Disney World, you both were the youngest and probably don’t remember Disney World, so let’s go back.” But in reality, it was the same as you, “let’s take them to Disney World, so they won’t go on their own Spring Breaks!” Haha.

  30. Hawaii! I went there for spring break when I was in college. I’m really looking forward to going to Charleston next week for the first time! I think the weather is supposed to be cooler than it has been? That’s okay though since I live in Florida.

  31. My favorite place for spring break was the Grand Cayman Islands! It was on a cruise, but that was my favorite place (-: have a great trip!

  32. Anywhere on Florida’s gulf coast – Seaside, Rosemary Beach, Destin. All beautiful year round!

  33. My sister and I take a trip together every spring to celebrate Mother’s Day (away from our kids haha) — any place with her is fun!

    Have a great trip!

  34. When I was in high school my mom and I went back to GA (where we’re from — Go Dawgs!) and spent the week there doing all the fun things we could think of. We went to Six Flags, walked through campus, went shopping at all the cool boutiques we could find. It was memorable for sure. Love spending time with my mama!

  35. My favorite place for spring break is down in Florida visiting my parents! Only see them a couple of times a year and as much as I would like to go somewhere with my friends, I can’t beat spending time with my family. My jacks are ALWAYS in my suitcase. Have a great weekend!
    xo elle // https://splashofpreppy.com

  36. Vegas – I have only been on one official spring break trip, so that doesn’t leave much competition for my favorite spot!

  37. Rosemary Beach, FL!! It reminds me of a little European town- such pretty architecture! And the sand is white and the water is the most beautiful shade of green. We ride bikes everywhere we go. If you haven’t been with your family, you must go sometime. My whole family loves it!!

  38. My favorite spring break was probably Myrtle Beach, SC shortly after returning from a deployment! I’ve been back since, but it has always been different.

    Now that I have a family (a little girl), I can’t wait to go on plenty of spring break and summer vacations with her!

  39. My Girl Scout troop in high school went on a cruise my senior year to Key West, Grand Cayman, and Jamaica! I had never been on a cruise before so it was such a fun experience!

  40. A few years ago, I went on a girls (family) trip, over spring bring to celebrate my aunt’s 40th birthday, to Puerto Rico. My mom, grandmother and I set up a few surprises for my aunt including canoeing in Mosquito Bay which is the brightest bioluminescent bay in the world. It was amazing! Every time we put a paddle in the water, that spot lit up. We went out after the sunset. Just beautiful. The next day, we split between shopping in Old Town Puerto Rico and in the ocean. The last day we toured the Bacardi Rum Factory and sampled a few rums I’ve never seen/heard of before. Altogether it was such a fun trip with some of the best women in my life.

  41. Key West with my girlfriends in college was so fun!! My husband and I did a 4 day trip to St. John’s this past year and loved it! I am loving all of your pictures and it’s making me want to plan a trip back there really soon!

  42. While in college, my dad to me to Costa Rica on a fishing trip. Just the two of us. I always look back on this time fondly.
    My sibling were a little jealous they didnt ask my dad to take them!

  43. So jealous of your trip! It’s harder to get away these days, but my favorite spring trip was to Sarasota, FL! Not the most exotic trip, but the beautiful beaches and cute little town can’t be beat!

  44. We usually don’t travel for spring break, but last year we went to San Diego with another family. This was our first trip to California and we had a fantastic time!

  45. My favorite place to go for spring break is ALWAYS Savannah for St. Patrick’s day! I’ve been for the past two years and it is always so much fun! It’s one big party for two whole days and everyone is so nice to each other and everyone wants to just have fun! Everyone’s outfits are great, the fountains are green! It’s beautiful! But the worst part is I’m one of the only ladies is who isn’t wearing Jacks!

  46. Best spring break trip was to New Zealand (side note it was college and I was studying abroad in Australia at the time). Can you please share where you are staying in St. John when you get back please? My husband and I are going at the end of April and I would love a recap of restaurants and things to do so we can get some good ideas.

  47. Anguilla for our honeymoon over spring break! Una Thurman stayed at the hotel next to us and we would see her and her children playing on the beach!

  48. We have a condo at Siesta Key, so that’s the only place I’ve ever gone. I love it though!!

  49. My favorite place was South Padre Island. It was the first time I had been to the Gulf. I was so amazed at how loud the ocean waves were! It was my first year of college. We also drove to Brownsville, while we were there and walked across the border to Mexico to go to the Markets. I remember buying 2 of the hand embroidered Mexican wedding dresses that I wore all summer! I’m kicking myself now fior getting rid of them. Such good memories!

  50. I grew up near a spring break town in Florida, so we also waited for spring breakers to come to us.

  51. Hi Ashley! Have a great time in St John!! We were there last year and I loved it, so I’m looking forward to seeing your pictures! My favorite spring break vacation was Hawaii – the islands of Maui and Kauai ? We can’t wait to return there some day. A nice pair of Jack Rogers would be a great item to pack 😉
    Have fun!!

  52. I never really did a big spring break trip, but my boyfriend (now hubby) took me to Scottsdale, AZ to visit family. the desert and mountains are gorgeous and we try to make a trip once a year.

  53. My favorite spring break was when me and my bestie got tattoos together!! It’s totally unlike me- but we have never regretted it! 🙂

  54. My favorite Spring Break was with a bunch of my sorority sisters my senior year in college. We all went to South Beach:)

  55. My favorite was a Spring Break trip back in college with girlfriends to Destin, Florida. So much fun!

  56. My boyfriend and I went to St John this past November for my 30th birthday. It was hands down the most amazing place I have ever been. We stayed in a privately owned condo, rented a jeep and went to any beach we wanted. Our favorite beach was Hawksnest Beach and our favorite bar was Joe’s Rum Hut. Go visit them from 4-6 for $3 anything you want! Right in Cruz Bay next to the beach bar. Have fun!!

  57. My favorite was a Disney Cruise with my hubby and kids. We stopped in the Grand Caymans and Cozumel.

  58. Ambergris Caye, Belize – we absolutely love it there!! It was Madonna’s inspiration for “La Isla Bonita” ?

  59. A Mediterranean cruise with stops in Italy, Spain, Greece and Turkey. Absolutely the best trip of my life with my husband and his family. Have a great trip!

  60. My best spring break was on St. John! When I graduated from college and had my first real pay check I took my mom on a vacation. As a child my parents chartered a boat with us for a week there and I loved it! I also got married on St. John on Cinnamon Bay beach! If you get a chance, head over to Caneel Bay for cocktails…beautiful resort. Have fun! Kara

  61. Eleuthera, Bahamas!! It was the best trip and my husband and I have memories for a life time. We plan to take our four there in the next year or so ?

    Enjoy your trip!!

  62. Hope you enjoyed your getaway, Ashley! Hands down, my favorite spring break trip was a cruise traveling to The Bahamas, St. Thomas, and St. Kitts, celebrating my grandparent’s 50th anniversary!! I not only I loved this trip because the sights were beautiful, but most importantly because every family member (all 26 of us, my grandparents, parents, siblings, cousins, aunts, uncles, etc..) were able to come along to celebrate the two people who made it all happen!! Coming from a big family, I’m sure you know how hard it can be to get everyone together!!

    -Sarah S.

  63. My husband I took our kids to Marco Island last year and it was great! Weather was between 70-80, the sand on the beach was like powdered sugar and it was incredibly calm and laid back. Definitely would recommend!

  64. WaterColor, Florida! The water is crystal clear and the town is the cutest! They have adorable food carts that are fun for kids and adults. I’m just dying to go back. Your instagram pictures have me itching to get away…

  65. My husband and I went to punts Cana last spring break without the kids!!!! Best trip EVER!

  66. Coming from up North my favorite Spring Break was a fun trip to Sunset/Ocean Isle Beach NC. Made me fall in love with the area and hope to one day move down!

  67. My favorite spring break will be this one 🙂 My best friend and I are headed to Cuba, Sans kiddos/husbands!
    I’m so excited for this Easter trip, and it’lol be my birthday ?

  68. Charleston! It wasn’t technically Spring Break, but it was in May after the end of tax season (CPA here) and our first vacation as a family of 3!

  69. Ecuador helping build houses- it was beautiful, the food was delicious and a little hard work never hurt anyone 🙂

  70. Long Island, NY was my home growing up, so my mom took us to many beaches to explore 🙂

  71. My favorite spring break trip was to Cabo. Just typing this has me really wishing we were there again!

  72. My favorite is always, Kiawah Island, South Carolina! <3 the beaches, the weather, the people….. the food & shopping in Charleston… amazing!

  73. My favorite spring break trip was a cruise to the Grand Cayman Islands! I happened to meet my (now) husband on that boat!

  74. My absolute favorite spring break was believe it or not, Panama City Beach. I met my now hubby there as sophomores in college, and we hit it off immediately!! I went there with the intention of having one “wild” spring break and fell completely head over heels in love on Day 1! ??

  75. Mine has to be the first time I went to Panama City Beach in high school – it was such a huge party all week long! I’m glad to have lived out those party days then , because it’s hard for this mama to stay up past 10 anymore ??

  76. Hawaii! But I would love to go to one of the islands like you and the girls did, it looks amazing!!

  77. My favorite spring break trip was when I was in college and my mom and I took a trip to Barbados. We rented a little scooter/motorcycle to drive around and had a minor accident and fell off and I can just see the little kids who had just got off the bus from school dying laughing at us and we were laughing really hard too! It was a funny memory and a beautiful place!

  78. When I was 17, my best friend and I went to Boston by ourselves (from Texas) for Spring Break. We had an amazing time riding the T, exploring college campuses and stuffing our faces with Dunkin Donuts (which we didn’t have in TX then!). Best trip ever!

  79. As a child, we spent every Spring Break, summer and weekend at Kiawah! So many great memories!

  80. It’s hard to beat the High School spring break days at The Summitt and Club La Vela in Panama City! Islamorada in the Keys with my best friends was my favo college spring break trip!! Now, Spring Break at the Masters with pimento cheese, egg salad, and pink lemonade is one of my favo traditions as an “adult!” ???
    Happy travels!! Soak up the rays!

  81. My favorite spring break trip is Bermuda!!! The color of the sand is gorgeous and there are so many cute secluded private beaches. Truly paradise!

  82. Caya Costa….this great little island on the Gulf in Florida. I’m a college professor, so we love getting a Spring Break in even though we’re in our late 30s!

  83. As I now have a son in college and a high school senior, our Spring Break trips to Beaver Creek, Park City, and Breckinridge are my FAVORITES. While I love the beach, our Spring Break trips skiing with our kids were some of our best vacations. Lots of great family time when you are all skiing together. Highly recommend taking your precious kids on ski trips…..such fun!!! Beaver Creek is by far my most FAV spot to ski!!!

  84. My favorite Spring Break trip has to be the one that I took with my daughter to your nexk of the woods…Charleston! We had the best time…I just can’t get enough of that city. :>)

  85. Love Five Islands Maine. Great bed & breakfast near by with access to kayaking all around the islands and a great lobster shack down the road. The key is to bring your own wine to the shack. It’s beyond amazing!

  86. Snowskiing at Schweitzer in Idaho! I absolutely loved Idaho & Washington. It was so nice to mix things up and do something different than go to the beach for spring break. Plus, you can’t really beat looking at a beautiful lake while skiing down a mountain.

  87. While I did the classic “college Cancun Mexico Spring Break” … my favorite will always be my spring break trip to Ireland! It was so fun to see where my family was from, where my grandma grew up and explore the cutest little city, Galway! An amazing experience I will always cherish.

  88. Zadar, Croatia with 15 friends who were living abroad. The city is beyond gorgeous and I can’t wait to go back one day!

  89. I know this sounds very cliché but I absolutely love where we live, Charleston, and traveled here for Spring Break many moons ago prior to making this incredible place home. But if I HAD to go somewhere out of town, it would be to Key West-to see my sister who lives there and spend time soaking up the Conch life.

  90. My favorite spring break was a trip to New Orleans with my mom and my sister! Amazing food, great sights, and so much history.

  91. My favorite spring break is now, going with my family to visit my parents on the gulf in Florida! 🙂

  92. I actually went to Virgin Gorda and Saint John last year for “spring break”! The nutella pudding at ZoZos was amazing! Headed to Key West Saturday and can’t wait.. although Charlotte has been pretty summer-like lately!

  93. One spring break stands out for me. One year in college about 12 of my friends and I road tripped from Savannah to Lake Michigan and stayed in a cabin on the lake all week. Fun memories before we headed our separate ways from college.

  94. NYC with my college roommate! It was my first time going, being from the midwest, and I just loved the experience!

  95. My favorite spring break trip was Port St Joe, FL. It was my senior year spring break in college with all my besties!!

  96. St. John!! We go every year! Pregnant now so we couldn’t go this year. Thanks Zika. Haha.

  97. Bermuda was my favorite! The beautiful beaches and wonderful views! Plus this is where my husband and I got engaged!

  98. My all time favorite place to go on Spring Break is our lake house (away from civilization) – I’m a teacher, so getting away from it all is ALWAYS welcomed 🙂

  99. Goodness I love St. John! My now husband and I had dinner at Zozo’s right after he proposed 🙂 Hope you are having a wonderful time! My favorite spring break trip was definitely Jamaica with my college girlfriends. Thanks for the giveaway!

  100. I feel like I’ve travelled all over the world, Dubai, lots of Europe, Central America, Egypt, china, India, but nothing beats the Southern California coast! Some good fish tacos and a sunset! San Diego is the best spring break spot!

  101. Destin, Florida! I went with some girlfriends from college. We laid on the beach with blankets on!! It was sooo cold! But of course lots of fun!

  102. Favorite spring break was probably Disney World – I went for my senior year in high school AND college spring breaks!

  103. My favorite trip has to be Belize! From the beauty of the water to the people to the experiences, it is a very humble country yet has so much to offer! I had to take 2 flights from the US, a pedal jumper, a taxi cab and a water taxi to get to the island and I did it all by myself! I’ve gone back a second time and feel brave and proud of myself for taking a risk and making it a challenge!

  104. My favorite spring break trip was when my husband and I went to Ocracoke for a few days. It is part of the Outer Banks in NC. It was a spur of the moment trip and we had a fabulous time. We rode bikes everywhere, ate fabulous food and just loved being on an adult vacation 🙂

  105. St. Thomas was my all time favorite vacation! I went several years ago with a few girlfriends and we had the best time. I left wanting to become a Rastafarian and just live the island life. Haha! I love the simplicity of life in the islands!!

  106. Huatulco Mexico. Last year. It’s not your typical Mexican destination but has some very nice resorts while still having a very local feel. We cook a wonderful cooking class, went snorkeling, shopping in the village and got lots of sun!

  107. My favorite spring break was my senior year of college. We took a cruise through the Caribbean and have so many fun memories!

  108. I took a girls trip to Seaside two years ago and it was wonderful and then went to Napa last year! The location may vary, but I look fun to this girls trip every year!

  109. There are a few memorable sb vacations that come to mind, but can I just saw that I cannot get the idea of a Georgia vaca out of my mind?! I would love a girl trip to Savannah and Charleston!

  110. I’ve actually never traveled on spring break, but my favorite vacation spot is the Outer Banks in NC!

  111. Hi Ashley,

    I had a strict mom who wouldn’t allow me to go away with friends, so she took me to Las Vegas herself! Best trip ever! We shopped, ate, and saw so many shows. So blessed to still call my mama my best friend!

    P.S. Thanks for posting all the pics and keeping me distracted as I am on bed rest for my pregnancy.

  112. My best spring break was a road trip from LA to Big Sue and Carmel on the Pacific Coast Highway. So many towns to stop and visit, great beaches, , good food, hiking and wonderful views of my favorite animal, the otter, in the ocean. A dream trip ❤

  113. Fave spring break spot was the FL Keys! I’ve stayed in both Key Largo and Islamorada during SB and it was great!

  114. The best place I went travelled to was Honolulu, Hawaii. I have never seen the ocean so blue. It was a postcard everywhere I looked. I can’t wait to go back!

  115. Even though I’m a major beach girl (hence my love of Jack Rogers), my fav spring break trip was to Ireland! My aunt and I flew to Dublin and then rented a car and drove along the southern coast! It was so beautiful and unlike anything else I’ve ever done. We drank Guiness, kissed the Blarney Stone, and stayed on a farm and bottle fed baby lambs! I highly recommend it, we had such a great time.

  116. My parents were just the sweetest to us when we were growing up. Every year they would pack us up and drive us all to Orlando for the best weeks we ever had at Disney World. I’m sure they would have rather gone to the beach or done something way less exhausting but they did it for us and they are the best memories we all have. This was so fun to remember on. What a great giveaway!

  117. My favorite place I’ve been on spring break was Sanibel Island! ?☀️? Hope you had a great trip!

  118. Bald Head Island. Not exotic but so fun to feel apart from the world of cars and more in tune with the laid back beach environment.

  119. Favorite spring break spot would be San Sebastian, Spain. Amazing food, wine, and wonderful beaches.

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