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Mom-Daughter Weekend Getaway in Miami

Mom-Daughter Weekend Getaway in Miami

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Posted on February 26, 2026

February in Chicago is hard. We were craving UV, and chose Miami due to its vibrant culture and beautiful beaches.

Trip Recap

  • Day 1: Exploring Miami was a dream—delicious food, charming hotel, and rooftop pool bliss!
  • Day 2: Sunkissed day: beach chairs, fine dining, and vibrant Miami vibes.
  • Day 3: Another perfect beach day filled with great food and stunning hotel lobbies!
  • Day 4: Miami's vibrant culture and warm hospitality left us wanting to return.

Highlights

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    The Betsy was fabulous. From the location, to the throwback vintage art vibes of the beautiful hotel itself, and the staff!!

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    Gustavo manages the rooftop pool and creates the perfect vibe for relaxation, service and comfort!

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    Pizza in "The Alley" of The Betsy...and nightly ice cream just next door.

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    Love the "Betsy" roll which is their signature sushi roll. Their burger is unreal.
    From our meal at JL (Michelan Star) to the pooside menu, all food is delicious.

Day 1

We took the first flight from O’Hare to Miami. We arrived at our eclectic, beautiful hotel right on Ocean Drive. The Betsy is located right on the northern tip of South Beach, so it's perfect if you want to explore Midbeach Miami down to South Beach. We were kindly greeted, and the super sweet bellman could tell we had a goal to get to our rooms asap. We changed quickly and headed straight to the rooftop pool on the sunny, warm 78-degree day. There were no chairs available, so we enjoyed above par cocktails and mocktails by Gustavo, the most charming, cool, and attentive bartender. By the time lunch arrived, two chairs opened up, and we enjoyed our delicious lunch, melting into our rooftop heaven.

Dinner was at a Cuban restaurant in Espanola Way, a touristy yet beautiful block of restaurants upon restaurants. We loved our little tower of goodies. We then found ourselves in the nearby Lincoln Road shopping district, shopping and finding some cool things, including from the Israeli pop-up, Tfu Tfu. Loved our new crochet beach dresses from Sol + Sorbet, locally made. Many shops in the mall offer mass-produced, obscenely overpriced beachwear, shope after shop. This place was legit!

Our nightly tradition of ice cream at our hotel began that evening, built into the alley of The Betsy. Pistachio with toasted coconut on repeat. For Jeannie, it was, of course, the cafelito, with chocolate dusting. Amazing and yum.

The Betsy South Beach
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Espanola Way
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Lincoln Road
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SOL + SORBET, Lincoln Road, Miami Beach, FL, USA
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Day 2

Beach goals today. The Betsy, just across the street from the beach, offered complimentary chairs and umbrellas. We sprung for the “bed,” with an adjustable canopy, chairs, and an umbrella still. We had our own little area, which is what we like. These are the things I like to splurge on. The cost was $130, and to me it’s worth it. Front row comfort to gorgeous Miami Beach. The water was similar in temperature to Lake Michigan in June, so we braved it, and it was glorious.

Betsy sources an exceptional crew of people for their beach service, so we felt safe leaving our sunscreens and basics while we explored down the tropical path toward mid-beach. We had lunch at “Ocean Club,” at the upscale “Setai” hotel. We could sense this place was quite the scene, but perhaps too much, from the staff as well.

Dinner was fabulous that night at the Michelin Star "LT Steakhouse" at The Betsy. The front patio ambiance is a great spot to people-watch, not to mention the throwback feeling you get here…always a pianist playing in the stunning lobby, and in the evening, a jazz singer accompanying. Art-filled, classic vintage photography and beautiful art of every kind abound. Vibes are next-level, sort of "tropical-deco" 1930's/1940's era.

The Betsy South Beach
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LT Steak & Seafood
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Day 3

Another beach day. The attendant arrives at 9:30 am, so we arrived at 9:15 to throw our things on our favorite beach bed again. Yep, we are those people! It was Valentine’s weekend, so the beaches ended up packed.

I fetched lunch for us back at the Betsy…the food is phenomenal. We loved the burger and the Betsy sushi.

Dinner at the pizza place adjacent to the ice cream place, in the Betsy “Alley.” Also in the alley you will see the iconic “egg,” which separated two sections of the Betsy, as it seems they acquired the the adjacent hotel to expland, which also wonderfully allowed them a rooftop pool (in addition to a smaller and lovely courtyard pool).

We finally enjoyed the exceptional pizza in the alley and loved Will, our waiter who gave us tips on cool hotel lobbies to check out.

We did some shopping post-dinner, loving the boutique at the W Hotel. Afterward, we continued toward Midtown to explore the rooftops and lobbies of the beautiful Hotel 1 and Faena. We exited toward the path behind Faena, then followed it along the beach back toward South Beach. Faena's pool grounds are incredible, and we the gorgeous elephant sculpture is an incredible site!

The Poolclub Monaco, between 22nd &, 23rd Street, Miami Beach, FL, USA
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The Alley, Collins Avenue, Miami Beach, FL, USA
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1 Hotel South Beach
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Faena Hotel Miami Beach
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Day 4

We awoke early our last day which was a Sunday, to be sure to grab some rooftop chairs, our thought to make it easier to leave at 2 pm for the airport.

I’m glad we let ourselves be pampered by Gustavo with fabulous refreshmnents and lunch, and refreshign swims. He’s one of those people that makes a place. He’s that kind of person that makes you want to return to a place. Our association with Gustavo makes us think of Betsy, and we will return. Also, we loved our housekeeper. Her beaufiful smiling face, and of course we take care of our housekeepers because girls are messy in hotel rooms! She made our room perfect, and I could see from the kind eyes she cared, and so did we.

The Betsy Poetry Rail is an homage to poets who shaped Miami literature by including their diverse, historic, and contemporary voices. It expands through the alley way and begins atop the ice cream place.

The front desk and bellman took such great care of us, and Kelsey warmly addressed a question i had on the bill.

We will be back for the art, the food, the location and best vibes. Jeannie loved the color and culture of Miami. I’m so glad she was able to experience it. Next time we will venture deeper to eperience Cuban music and culture. This time…it was all about ease, shopping, and of course the UV.

The Betsy South Beach
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Anything you would add or do differently?

  • I would have looked ahead and reserved dinner at Mila, a Miami dinner hotspot!