Last Updated On: July 27, 2017

Since I’m from Chicago, I love to get out of the city for long weekends to warmer places during the colder months. One of my favorite places to go when it’s cold is South Beach. I have been going to South Beach pretty much every year since 2009 so I feel like I know the area really well. You can use my guide to help you plan where to stay, where to eat and have drinks, and where to shop to have a really fun, relaxing girl’s weekend in South Beach. You can also download and save my checklist below to help you plan!

Before you go

South Beach can be pretty pricey, especially at some of the nicer, luxury hotels. However, the whole reason I want to go to South Beach when it’s freezing in Chicago is to lay and relax by an amazing pool and enjoy a cocktail or two. So, I really do my research when booking a hotel. Here are some tips to booking a luxury hotel in South Beach.

  • Research your dates to make sure there is nothing major going on in South Beach. Spring break, a huge conference, a big event all will really increase hotels prices by a lot.
  • Even though I usually go when it’s cold, plan a weekend during the summer while prices are lower.
  • Use a website like Expedia to book your flight and hotel to save you a good amount of money.
  • If you are going with girlfriends you can split the room to save you all money.
  • My biggest tip if you really want to stay in a luxury hotel is to use the app Hotel’s Tonight. You can book seven days in advance and the closer you are to your arrival date the rates really drop. Here’s what we have done in the past. We book our hotel when we have landed! It is a risk but just trust me, you will always find something. It’s a big enough city and you will really get the best deal by waiting and using Hotel’s Tonight. We have stayed at some of the best and most luxury hotels in South Beach for like 1/2 the price. Also, if you get there early you can use the pool all day while you wait for your room. Well worth it.
  • If you are worried about waiting you could book a cheaper hotel for one night and then look for a nicer hotel for the next night or look for hotels with free cancellation policies if you find something better.
  • You also might want to book some reservations at restaurants before you go. I always use open table and I will give you some recommendations to some of my favorite places below.

My favorite hotels in South Beach

Here are some of my favorite hotels that I’ve stayed at over the years in South Beach and they are all well worth it!

  • 1 Hotel South Beach – The rooftop pool absolutely amazing. They have a fun DJ on the weekends, great cocktails, and the view in incredible. The hotel is a little far from Lincoln Road but it’s worth the walk.
  • The Palms Hotel – This was the first luxury hotel we stayed at in Miami and probably still one of my favorites. It’s a little far from everything so you can easily Uber to wherever you want to go. But, if you just want to mainly be by the pool all weekend, this is the hotel to go to.
  • Royal Palm South Beach – I used to LOVE staying this hotel. I just loved the rooms and how fun and chill the pool was. This hotel is also in a great location to walk to everything in South Beach. Each guest is treated really well and made to feel really special. The only downfall about this hotel is it’s become a little more family-friendly than others. When I’m hanging out in South Beach, that’s not what I’m looking for.
  • The Nautilus – If you are looking for another trendy hotel like 1 Hotel, then this hotel is very similar. The rooms were smaller but really cool and I really loved the pool.
  • The Raleigh – We stayed here a few months ago and I loved it! The backyard pool is perfect and the whole hotel has a great southern feel which I really loved.
  • SLS South Beach – I haven’t stayed here yet, but it’s next on my list. But I’ve been here for dinner and drinks a few times and the pool looks incredible. Very chic and posh!
  • Z Ocean Hotel – (full disclaimer) I actually got engaged at this hotel, so it will always be special to me. The suites are amazing with their own private rooftop and hot-tub. They do have a pool as well. Maybe a little too romantic for a girl’s trip but I just had to add it.

Day #1 – Pool day and some shopping and exploring

To get the most out of your weekend in Miami book your flight early. Arriving by late morning is perfect. You can head straight to your hotel and if your room is not ready, the front desk can hold your bags, you can freshen up and change in the bathroom, and head right to the pool for a few hours.

After spending a few hours at the pool. Head to your room to get ready to do some shopping and exploring. First, walk to Lincoln Road. Lincoln has tons of well-known stores and some fun restaurants. No cars are allowed on this street so you can walk freely wherever you want. After exploring Lincoln, head over to Collins Ave. You will want to stop to shop/browse at a famous Miami boutique called The Webster. You can’t miss it because The Webster is known for their old, brightly painted cars that are always parked out front. This is also a great spot to take some photos! Continue strolling around Collins and Washington Street (a street over) for more shopping at some cute boutiques.

For dinner in South Beach, you really have so many options! If you want a really nice, trendy dinner then make a reservation at Prime 112. It’s like the Mastros of South Beach. The food is amazing and you might spot a celebrity or two. South Beach also has some other trendy, famous restaurants like STK, The Bazaar (amazing tapas), Joe’s Stone Crab Miami (gotta go for the key lime martini) and Katsuya. I also suggest the first or 2nd night to have dinner on Espanola Way at Havana 1957. It’s the most adorable little street and definitely worth walking through it at night. You can also dine at Dolce at The Gale South Beach and be sure to have a cocktail before or after inside The Gale at The Regent Cocktail Club which was just nominated one of the best bars in the world. I also really like Naked Taco for a fun more chill dinner or late lunch with great margaritas. The restaurant at the back of The Raleigh Hotel is really pretty and also has really good food. It’s a great spot for lunch or dinner.

Espanola Way

*My biggest tip about dining on South Beach is to stay away from the restaurants and patios right along Ocean Drive. These places are so expensive for just ok food. They make their money of cocktails and they don’t list their prices. Also, remember that tip is included at almost all places in South Beach.

You might also like A Girl’s Guide to a Long Weekend in LA

After Dinner

After dinner, I love to do some hotel cocktail hopping. Start on Ocean Drive at The Ritz and sit on the back deck along the boardwalk. Then head to the Delano (very pricey but you have to take a walk through the back garden), SLS, The Raleigh, and the Shore Club to just name a few. I like to walk in and out of all the hotels along the strip and decide as I go where to grab a cocktail. On certain evenings, you can go up to the rooftop bar Watr at 1 Hotel to get a cocktail. There’s a smaller section for the public and going up to see the view before dark is a must.

Day #2 Versailles, and Coconut Grove

Start the morning by having coffee and a light breakfast at either Paul or Nespresso Cafe on Lincoln Road. The Raleigh also has a cute little coffee bar for to-go coffees as well. Of course, you want plenty of time to relax at the pool. But, if you feel like doing a little exploring outside of South Beach. Rent a car and head about 30 minutes to Versailles Restaurant for some famous Cuban food and coffee. I literally dream about the Cuban coffee! There’s really nothing else like it. After you explore Versailles then head over a short distance to Coconut Grove. This is a cute little artsy area with some cute boutiques and restaurants. After, head back to South Beach to get ready for another great dinner. If you have time before dinner walk the boardwalk to your restaurant. You can get a glimpse at the back of each hotel to see all the amazing backyards.

boardwalk on South Beach

Day #3 More pool time, Lincoln Road Antique Flea Market

Request a late check out if you can and relax at the pool before your flight or stop by a few places you haven’t tried yet from my guide.The hotels will let you use their amenities all day until your flight if you don’t get a later checkout. If you are in South Beach on a Sunday, I also highly checking out the Lincoln Road Antique Flea Market on Lincoln Road. It takes place every other Sunday and I’ve found some amazing vintage pieces at this market.

Download my Girl’s Guide to a Weekend in South Beach

Feel like you are ready for South Beach? Download and save my guide to help you plan a fun and relaxing girl’s weekend!

Free Download: Save a copy of this checklist I made:
A Girl’s Guide to a Weekend in South Beach


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