Straight Trippin': 2021 Annual Family Summer Vacation

Updated: Nov 21, 2021

I LOVE our vacations, but there’s something particularly special about our annual family summer vacation.


We always enjoy the summers together and the annual summer trip is our way to close out summer fun with a bang.

With COVID, last year’s annual summer vacation looked a lot different. But now with more safety precautions in place, we felt comfortable with the kids flying. I started to think of places to visit. I’ve shared this a lot, but Florida is one of my favorite places to visit. I’m a beach girl and there’s just so many beautiful beaches in the state. I also love that the flights aren’t too long. From the DC area, it takes us a little under 2.5 hours.


We decided to try Hollywood, Florida. There were a few parts of Florida I want to visit, but after research and talking with a few women in a moms' travel Facebook group, I decided this was the right choice!


We used a travel agent for this trip. We plan most of our trips ourselves, except international trips. Using a travel agent really comes in handy and we value their professional expertise. We narrowed our search down to two resorts. The travel agent raved that we should for sure go with one of our top choices - Margaritaville Hollywood Beach! And the funniest thing happened. When I went on my birthday trip this year, we spent time in Miami and Hollywood, Florida. We stumbled across the resort. It wasn’t intentional and we were really wowed!


Ok, now let’s get into the trip!


For our travel agent, we used Julie of Suite Dreamz Travel! Overall, we had a great experience! We’ve used travel agents before, but I really enjoyed my experience with Julie. One thing I liked was how detailed she was when discussing the resort options. Julie wrote paragraphs about her thoughts. She didn’t just send a quote or rush through a conversation to get us booked quickly. I highly recommend her!


For flights, we flew Southwest Airlines. I know this might be crazy, but I don’t really like Southwest LOL. I’ve flown with quite a few airlines and this one always seems to have drama LOL. We paid for upgraded seating to sit together (over $100 more). I don't like the idea of potentially having to depend on asking someone if we can sit together. A lot of moms in the travel groups mentioned they don’t mind their kids not sitting by them. For me, that’s completely not an option and I’ll pay any fee to ensure we sit together.


I also feel like some of the employees aren’t very helpful. The employee had an attitude with multiple people trying to understand which group they should go in. As a customer, it's not always clear. We paid extra, but still weren't in the first group, which was a bit confusing. It also always feels like the hunger games when going to get seats.


Overall the flight was great though. We sat near great people and everyone was friendly. This was Rori’s first flight, so I was a bit nervous about how she would act LOL. We brought tons of snacks and toys. She did pretty well, but I’m glad it was a short flight. There were times when she was busy and trying to get down LOL.


We did a red eye flight, so we could get there earlier which was a great decision. I don’t like flying and getting to a place so late that you miss most of the first day. We arrived early and were able to drop off our items. The only challenge was that the travel day threw off Rori's nap and she had cranky moments throughout the day.


We arrived at Margaritaville! We were amazed at the door. On my birthday trip, we saw the outside of the resort, but that does it no justice. It was truly amazing.


The room was even more beautiful. I loved the chic beach themed room and our view was amazing.


We then settled in and headed right out the door.


One thing that I love about Margaritaville Hollywood is that it’s beachfront. I didn’t realize it when we booked. You literally step outside of your hotel and there’s the beach. This was really great and I felt a sense of peace that my kids could run over to the beach without having to worry about traffic.


The pools were amazing and included a waterfall. The only downside is that their pools close a bit earlier (7pm) because there are turtles near the water and having the light at night would draw them into the hotel and they could potentially harm themselves. There’s also an adult pool on the upper deck that stays open later. Although you can easily find hotels that are less expensive, Margaritaville is totally worth the splurge.


The beach water is nice and warm and the sand is great. It does have a bit more shells than some, but overall really walkable.


Right outside the hotel and beach is the broadwalk (not boardwalk). It has eateries and local shops. They also had lots of live music and overall everyone was really friendly. I’ll be honest, compared to some broadwalks, it doesn’t have as many food and shopping options, but it's definitely is enough for your trip.


Margaritaville is also has a lot of restaurant and bar options. We ate at the resort often. The cocktails are also really great and I had a frozen drink everyday (I’m dreaming of one now!)


We also scheduled a family photoshoot. I love taking pictures in different states. It’s a great way to capture memories and the place we visited. We had a shoot with Yanelis Torres Photography. She was really great and patient (which is so important for family photoshoots LOL).


We decided in advance that we would do relaxed looks, since we already knew we would be swimming the day of our shoot and didn’t want to worry about having the “perfect” tailored look after swimming.


I ordered our family shirts in advance and we bought jeans before our trip. The shoot was perfect and really captured who we are.


On our trip, my family did the FlowRider ride which was funny. I wasn’t brave enough! As a family we rode the surrey bikes which were so fun!


We also had dinner on the beach. I've always wanted to do this. It was a major hit and I highly recommend!


We also went to Flamingo Gardens which was so much fun! We spent the entire day there feeding animals, learning about plants, and much more. This is also a must-do activity!



This was an amazing trip and I encourage families or adults looking for a laid back vibe to stay here!


Want to know more about my trips? Follow me on Instagram!




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