Itinerary for Your Next Family Getaway to Clearwater, Florida

We love traveling with little Sebastian. He makes everything so much more fun! This last flight was already his 5th so he is getting adjusted quickly to flying. For this trip, we really wanted to find an area that was known for being kid-friendly. We also needed the place to be here in the US, warm weather, by the beach, direct flight, and lots to do. We landed on Florida! and couldn’t have been more excited to be back and partnering with the great folks at Visit Florida & Visit St. Petersburg Clearwater. It is the perfect family getaway for the weekend. Our trip started in Clearwater, where they are known for having the beast beaches in the country! So much fun!! We had 2 days before heading to our next spot in the Sunshine State.

For the New Yorkers, we took a direct flight from La Guardia, New York to Tampa, Florida.

Upon Arrival

  • Rental Car/Drive: Grabbed our luggage, walked about 50 yards, picked up our rental car and headed west to Clearwater Beach. It was a quick 30-40min ride. You drive over the causeway bridge and see all the lights coming from Clearwater Beach. It’s really cool!
  • Hotel: Since we took a late flight out of New York, we arrived at the hotel really late. Our hotel, Wyndham Grand, was gorgeous and right on the beach. We were tired from the day, so we unpacked Sebastian’s things and headed to bed.


  • Breakfast: Our morning started early having coffee on the patio looking at the ocean. We then headed downstairs for a delicious breakfast buffet. We sat outside on the deck overlooking the beach.
  • Spa: After breakfast, Matt and I took turns and each got a massage at the Pallavi Spa inside the Wyndham. It was so relaxing!
  • Lunch: Saltwater Fish Camp. The food, especially the oysters, were spectacular.
  • Beach: We walked off lunch strolling down the beachside promenade. The weather was amazing and the sand was as white as the driven snow.
  • Fun on the Water: Late afternoon we went out to see some dolphins with Tropics Boat Cruises. The bottlenose dolphin were so cool and looked the same as you see in the movies. They ride the wakes from boats and skim along the surface right next to us! We know Sebastian won’t remember anything but we will and it was so much fun to experience that with him!!
  • Dinner: Later that night we walked to a local favorite, Frenchy’s Rockaway Grill, for dinner. It was as good as advertised. A really cool, laid back, local hangout with amazing food. The fried grouper sandwich and key lime were off the charts delicious. We got extra key lime pie to go!!
  • PIER 60: As we walked home from dinner, we stop at Pier 60 to catch some local entertainment and pick up a few things from local vendors. This is a great spot for families with small children. They also have a large playground area for your kiddos, an easy way to tired them out before head to bed!


  • Breakfast: M0re delicious breakfast buffet at the Wyndham.
  • Beach Walk: Hung out at Clearwater beach, enjoying the water, and snapping pictures.
  • Pool Time: After spending some time at the beach, we headed to the Wyndham pool to relax and dip Sebastian’s toes in the water.
  • Aquarium: We got to see dolphins, sea turtles, fish, and otters at the Clearwater Marine Aquarium. It is a really cool rescue and rehabilitation aquarium just over the bridge from the hotel.

After finishing up at the aquarium, we packed up our things and headed out on the road. We had such a great time in Clearwater and it was the perfect start to our trip. Definitely a great spot to spend a long weekend with the family! Now to our next destination… Sarasota! Stay tuned for details!!

xo, Olivia

Thank you Visit Florida for sponsoring our trip and today’s post!


  1. Dana wrote:

    Okay, well now I’m even more obsessed with your little fam, Olivia! This trip looked so fun and I love that you’re exposing Sebastian to travel right from the start!

    Pink Champagne Problems

    Posted 5.15.17 · Reply
  2. Kim wrote:

    The beach looks amazing in Clearwater, Florida! And I’m obsessed with your family pics! Adorable!

    Simply Lovebirds

    Posted 6.5.17 · Reply

Leave a Comment

Are you in the know?

Subscribe to the newsletter for weekly behind the scenes content, special sale alerts, and more.