A Weekend in Cabo

Happy Wednesday, friends! Wowza, we are having some gray, dreary days… definitely making me miss the Cabo sunshine! Mr. SP and I had our annual New Year’s getaway earlier this month, and this year we chose Esperanza in Los Cabos, Mexico (thanks to an unbeatable Black Friday Sale!)!

Most of our marriage, we’ve forgone gifts in favor of travel, and these January getaways have become our Christmas gift to each other. We look forward to this time all year, as a chance to unplug, reconnect, and reflect on the previous year. Basically like marriage boot camp… with guacamole!

Here’s a peek at our weekend, along with what I packed and wore. We only ventured away from the resort once, so it’s not much of a Cabo Travel Guide, but will hopefully give you some inspiration for any upcoming warm weather trips… or at least, add a little sunshine to your day.

White Swimsuit (XS) | Sarong | Straw Hat | Sunglasses | All-Weather Bangles

We normally choose the Cancun side for these trips, but the Black Friday Sale at Esperanza was too good, so we opted for Cabo this year. It’s only our second time in the area (we were in Cabo for Spring Break when Covid hit, and had to cut it short to get home before travel was halted!), and the first difference we found was the weather!

Cabo in January is dry and arid, with cool breezes and chilly evenings… basically perfect! We arrived a few days after the New Year, so Esperanza was still decorated for Christmas!

Sugarplum Travel Tip: We arranged private transfers to and from the airport via the hotel, and it was about a 40-minute drive.

Perched on the cliff, Esperanza is a boutique hotel with just 56 gorgeous rooms, each quite large with views of the ocean… especially ideal since it’s whale season, and we were able to see them from our balcony each morning! (The hotel provides high-powered binoculars for exceptional viewing.)

Sugarplum Travel Tip: While the hotel itself is small, it’s adjacent to over 100 Esperanza residences and time shares, some as large as 4-bedrooms. Perfect for families, but also means busy restaurants and pools. With it being high season, we oftentimes missed out on finding an empty pool chair or dinner reservation before 9pm.

(All New!!) GLxHSP Decked Out Day Dress (code SUGARPLUM10) | Leather Slide Sandals | Straw Hat | Sunglasses | All-Weather Bangles

Floral Halter Maxi Dress (Small, Tangerine) | Strappy Sandals | Straw Clutch (Nat1) | Teardrop Earrings

Esperanza is located on a quiet cove with a small walkable beach, but the water is quite rocky, so not really swimmable. There are adults-only and family pools, each with views of the sparkling sea, along with a handful of chairs on the beach, all with full-service food and drinks. They even bring you a small cooler of ice waters, and provide SPF and lotions!

Straw Hat | Woven Leather Tote Bag | Book

Scallop Swimsuit | Straw Hat | All-Weather Bangles

Pocket Tee | Swim Trunks

Swim Top (size 4) | High Waist Swim Bottoms (size 4) | Palm Leaf Cover-Up Shorts (Small) (Similar HERE) | Flip Flops | Straw Tote Bag | Straw Hat | Sunglasses | All-Weather Bangles | Teardrop Earrings | VExHSP Grace Necklace

We booked through my friend at Elevate Travel, which gave us free breakfast… and Esperanza does breakfast right! There’s an extensive menu, but we opted for the robust buffet each morning, and it kept us full until late afternoon!

There are three restaurants on property, each with incredible food and a beautiful setting (and quite pricey!). They’re all open-air and casual, so I was typically in flip-flops or with wet hair. Everything is charged to the room, so there’s no need to carry a wallet or worry with gratuities (they’re included in the rates).

Sugarplum Travel Tip: Cabo itself is more of a ‘scene,’ so while I was casual around the property, if you venture out of the resort to some of the popular spots, like Flora Farms, Acre, or Bagatelle, you’ll see a super-stylish crowd.

Organic Cotton Button Down | Gauzy Wide Leg Pants (XS) | Flip Flops | Straw Hat | Woven Leather Tote Bag | Sunglasses | VExHSP Grace Necklace | All-Weather Bangles

One-Shoulder Sweater Tank | Palazzo Pants | Leather Slide Sandals | Straw Clutch (Nat1) | Teardrop Earrings | All-Weather Bangles

Aside from the weather and the whales, another thing we loved about Esperanza were the sunrises and sunsets… both happen over the sea, so you can view them from your room or pool area!

Sleeveless Sweater (Small) | Tropical Pants (size 4) | Strappy Sandals | Woven Handled Tote Bag | Straw Hat | Sunglasses | Teardrop Earrings | All-Weather Bangles

I packed a handful of swimsuits and lightweight sundresses (along with a jean jacket for the chilly evenings)… including our best-selling GLxHSP Decked Out Day Dress, now available in two new prints! It’s truly a wear-anywhere style, perfect for home and vacation.

Fit Tip: I’m in a size XS, and code SUGARPLUM10 will save you 10%!

(All new!) GLxHSP Decked Out Day Dress (code SUGARPLUM10) | Strappy Sandals | Straw Clutch (Nat1) | Sunglasses | Teardrop Earrings | VExHSP Grace Necklace | All-Weather Bangles

While the property may have been busier than most of the resorts we visit, the rooms at Esperanza were exceptional! We had a beach view casita, with an oversized bathroom, double shower and vanity, soaking tub, and an enormous balcony with hot tub!

They include twice-daily service, and little treats and amenities were left for us each day.

Sugarplum Travel Tip: Request a room on the top floor for the best views! (They have elevators.)

This striped shirtdress was one of my most-worn pieces I packed… I wore it belted to lunch, loose to the spa, and even open over a swimsuit!

Fit Tip: I’m in a size XS, which was a touch big, but it shrunk to the perfect size in the dryer.

Striped Shirtdress (XS) | Flip Flops | Woven Belt | Woven Handled Tote Bag | Straw Hat | Sunglasses

This maxi dress continues to be a vacation-favorite…I have it in blue, as well, and have packed it for multiple trips over the years. (See it in Mexico HERE and Bora Bora HERE.)

Floral Halter Maxi Dress (Small, Tangerine)

Scallop Swimsuit | Crochet Shorts | Woven Leather Tote Bag | Straw Hat | Sunglasses | All-Weather Bangles

Esperanza has a beautiful spa on-property, with a range of services, along with a steam room, hot tub, and cold shower available free-of-charge for hotel and time-share guests.

I ordered coffee service to the room on our first morning, but the sticker shock had us visiting the on-site coffee bar each morning after. We loved grabbing an early cup, then walking down to the pool to watch the whales before the rest of the property woke up.

This chic dress is a recent new Amazon find, and so comfy! I love how easily it dresses up or down, and packs like a dream. (I also have it in the blue and white print, see that HERE.)

Halter Dress (Small) | Straw Hat | Sunglasses

Striped Shirtdress (XS) | Flip Flops | Straw Hat | Sunglasses

Sleeveless Sweater (Small) | Tropical Pants (size 4) | Strappy Sandals | Straw Hat | Woven Handled Tote Bag | Sunglasses | Teardrop Earrings | All-Weather Bangles

A jean jacket or light sweater is a must for evenings in Cabo (in January, anyway!).

One-Shoulder Sweater Tank | Palazzo Pants | Jean Jacket (code CASSIE15) | Leather Slide Sandals | Straw Clutch (Nat1) | Teardrop Earrings | All-Weather Bangles

Some friends from Dallas happened to be staying in Cabo at the same time, so we met them in town one night for dinner at La Lupita. The tacos were incredible, the live music so good, and the town is darling!

Sugarplum Travel Tip: Cabo is quite spread out, with two main towns, each upwards of an hour apart depending on where you’re staying. We took a taxi via the hotel, and it was 45-minutes and about $50 each way.

Strappy Floral Dress (XS) | Strappy Sandals | Woven Handled Tote Bag | Sunglasses | VExHSP Grace Necklace | All-Weather Bangles

White Swimsuit (XS) | Sarong | Straw Hat | Sunglasses | VExHSP Grace Necklace | All-Weather Bangles

We had a wonderful time and we’re always grateful to get away together, but for us, Cabo is better suited for a girls trip or family adventure (there’s so much to do!). When it comes to a couples trip, we prefer the quiet and magic of the Mayan culture on the Maroma side (Belmond Maroma and Hotel Esencia are our favorite romantic getaways there!).

And if you’re looking for something off the beaten path, we adored Casa las Tortuga on Isla Holbox and the newly-opened Casa Chablé in the Sian Ka’an Biosphere Reserve!

So tell me… what kind of vibe do you prefer for a couples getaway… a bustling scene, or a quiet escape? What places are your faves for a long, romantic weekend? We’re always looking for new spots!


Girls Getaway | Casa Maroma & Casa Chablé
Snapshots from Maroma
Great Stays | Hotel Esencia
Great Stays | Belmond Maroma
Great Stays | Casa de Sierra Nevada
Trip Report | Weekend in San Miguel de Allende
Great Stays | One & Only Mandarina
Trip Report | Isla Holbox, Mexico
A Day in Tulum, Mexico
Resort Ready!


Le Taha’a Resort | A Gem in French Polynesia
Great Stays | Four Seasons Bora Bora
Trip Report | Whidbey Island, Washington
Trip Report: Maui, Hawaii
Trip Report | Pine Cay, Turks & Caicos
A Day in Santa Cruz
Snapshots from Big Sur
Trip Report | Vieques, Puerto Rico
What to Pack for a National Parks Trip
Trip Report | Santorini, Greece
Anna Maria Island
Trip Report | Exuma, Bahamas
Swimming with Pigs in Exuma
All Cruise Posts HERE

Leave a Comment


  1. Kim Henrichs wrote:

    Ahhhhhhhhhhhh I love Cabo so much! I go to San Jose del Cabo twice a year (with luck) and it’s just won my heart.

    Beautiful photos!!

    Posted 1.24.24 Reply
    • Cassie wrote:

      Love that so much, Kim!!!

      Posted 1.24.24 Reply
  2. Kelsey wrote:

    I love the scallop swimsuit, I’ve already added it to my cart! Thanks for always sharing such incredible finds!

    Posted 1.24.24 Reply
    • Cassie wrote:

      Ah thank you so much Kelsey, your comment made my week! xo, C

      Posted 1.24.24 Reply
  3. Lisa wrote:

    What a fun getaway! I’ve been to Cabo a few times in the past year and it’s lovely, but I agree, more of a family getaway. My favorite romantic getaway is Paris in the fall – perfect weather, no crowds. Bora Bora is also on my bucket list.

    Posted 1.24.24 Reply
    • Cassie wrote:

      Paris in the Fall sounds absolutely creamy, Lisa!!! And I truly cannot recommend Bora Bora enough! xo, C

      Posted 1.24.24 Reply
  4. Heidi L Ferguson wrote:

    We LOVE Cabo- but, I think your experience really depends on where you stay. We’ve eaten dinner at Espranza and it’s gorgeous too – just a different look – dessert vibes. We’ve stayed at The One & Only Palmilla twice (just us two empty nesteres) and are headed there for a third time NEXT WEEK to celebrate my 50th!!! I’m beyond excited! The resort is unlike anything else in Cabo- they have one of the two only swimmable beaches there. The most magical adults only pool – they will reserve your chairs for the week you stay! We love Flora Farms (cooking class is SUCH a fun day!) Eating dinner there again this time. Have eaten at Acre and yes, it’s a scene. We sat down to eat there and my husband started to FREAK OUT – Sammy Hagar and his wife were celebrating their anniversary there (he lives in Cabo) at the table RIGHT next to us. You could reach out and touch them! They were so friendly and sweet and they invited us to an “unannounced” concert the next night at Cabo Wabo (agreed- the city is not for me). But, he told us to ask for __ and they had our names, escorted us to a table and we enjoyed the concert – my husband was FREAKING OUT (he’s 52). Anyway, since we will be there in Jan – we are going on a Zodiac Whale watching tour!!!! I’m beside myself! I did see where you’d made a quick post about how good La Lupita was so I made reservations there for our one night in the “city” Thanks for the recs and your pictures and you are gorgeous as always! Hope you brought your own slippers this time – LOL!

    Posted 1.26.24 Reply
    • Cassie wrote:

      All of that sounds AMAZING, Heidi!!! What a fun trip!!! Have fun next week!

      Posted 1.29.24 Reply