Naples Florida Weekend Trip

Sharing all the details on my Naples Florida weekend trip! I grew up visiting in grandparents in Naples (they would go each winter) and my husband and I went last year to visit. So, this is my second time visiting since moving to Florida and it’s once of my favorite spots!

My mom came down from Ohio for this girls trip and it was an amazing 5 days! I think the last trip we did together was my senior year of college to Chicago, so it was long overdue! We stayed at Inn on 5th, which is the cutest boutique hotel ever in the best location. It’s about 1 mile from the beach and next to all the shopping and restaurants. The Naples Pier is also walkable as well, and it’s a beautiful walk filled with huge ocean front homes and lush foliage. We spent hours walking each day because everything is so gorgeous!

I will break our Naples Florida weekend trip down day by day below, with what to do and all the best restaurants below. Keep scrolling for all the details!

Check out my last Naples Florida Weekend trip here.

Sizing reference: I am 5’4″ and typically XS in tops and 25 in bottoms.

Day 1: Travel to Naples

Naples is an easy 2.5 hour drive from Tampa (flights are usually much cheaper to Tampa than Naples). We started our Naples Florida weekend trip in Sarasota. We stopped at Shore in St Armonds Circle for some lunch. The rustic bread was SO good with 3 different spreads. The crab cake salad and kale caesar were amazing as well. It was super easy to get a reservation there and enjoy the outdoor patio.

After lunch we did a little shopping and walking around St Armonds Circle, and it was a really nice afternoon!

I wore this cute tank from Southern Roots during the day. Use code Styledjen for 10% off their entire website!

Outfit Details:

Tank (c/o), Shorts (c/o), Earrings (c/o), Sunglasses, Initial Necklace (c/o), Key Necklace (c/o), Belt, Louis Vuitton Bag

Dinner at The French

The French was amazing for our first night! It was easy to make reservations and the outdoor seating was beautiful. The crispy brussels sprouts were my favorite! We also got the fried squash blossoms, beet salad and shaved carrot salad.

I wore this adorable yellow dress to dinner! Wearing my normal XS.

Outfit Details:

Dress (c/o), Belt (c/o), Sandals, Earrings, Initial Necklace (c/o), Key Necklace (c/o), Louis Vuitton Bag

Day 2: Lunch at Osteria Tulia

If you follow my blog closely, you’ll know Osteria Tulia is my favorite spots to stop at driving through Naples! We went for lunch and got the crispy calamari, burrata and caesar salad. Their outdoor patio is gorgeous and it’s easy to make a reservation!

This kimono is another cute item from Southern Roots and was perfect for hot and sunny Naples. Use code Styledjen for 10% off your entire purchase!

Outfit Details:

Kimono (c/o), Tee (c/o), Shorts (c/o), Sandals, Earrings, Initial Necklace (c/o), Key Necklace (c/o), Sunglasses

Dinner at Caffe Milano

Caffe Milano was a super cute spot! My pasta had fresh black truffle shaved on top, and oh my word was it amazing! I swear you could smell it across the room! My mom got the spaghetti and clams and it was good, but I don’t think there was enough wine sauce.

Someone actually stopped me in the middle of the street to ask where I got this dress! It was such a steal, I am so happy I snagged it! Wearing my normal size 0.

Outfit Details:

Dress, Sandals, Earrings, Initial Necklace (c/o), Key Necklace (c/o), Louis Vuitton Bag

After dinner we sat by the gorgeous pool and enjoyed some wine. I wore this skort on our walks every single day. I am so glad I got it! It fits true to size.

Outfit Details:

Sweatshirt (c/o), Skirt, Earrings, Initial Necklace (c/o), Key Necklace (c/o)

Day 3: Lunch at Osteria Tulia

We had to stop at our favorite spot again for lunch! This time we ordered the beet salad with fresh peaches and the parsley risotto with calamari. Oh my goodness, were they amazing!

I wore this cute terry cloth dress during the day and it’s really the perfect vacation piece. It fits true to size.

Outfit Details:

Dress (c/o), Belt (c/o), Earrings (c/o), Initial Necklace (c/o), Key Necklace (c/o), Sunglasses, Louis Vuitton Bag

It was a nice day, so we spent some time at the pool. I normally wear a 6 in swimwear, and this one piece fits true to size. The back is full coverage too, which I like!

After the pool, we went over to the Waterside Shops where all the high end stores are and looked around. It was a great little spot! Chad and I have been there before because True Food Kitchen is over there. My mom and I had a great experience shopping at Van Cleef & Arpels there, and she got a gorgeous necklace. On our last girls trip to Chicago, I got a Van Cleef necklace, so I think we have a little tradition now lol.

Outfit Details:

Swimsuit (c/o), Coverup, Hat, Earrings (c/o), Initial Necklace (c/o), Sunglasses

Dinner at Truluck’s

Truluck’s is my second favorite spot in Naples after Osteria Tulia. The service is out of this world and it’s the perfect fancy dinner spot. We even got a call the next day making sure we enjoyed our meal. We ordered calamari, caesar salad and the wedge salad. Their wedge is one of the best I’ve tried!

I wore this beautiful maxi dress from Southern Roots to dinner and felt so fabulous! It runs true to size and I am wearing the XS. Use code Styledjen for 10% off your entire purchase.

Outfit Details:

Dress (c/o), Earrings, Initial Necklace (c/o), Key Necklace (c/o), Sandals, Louis Vuitton Bag

Day 4: Lunch at The Cafe

I didn’t get any photos, but The Cafe is a great brunch and lunch spot. I had the Mediterranean wrap and my mom had the veggie panini. Another spot we stopped at daily was Gelato & Co. It is a new spot and their gelato was incredible! My favorite was the peanut butter.

I wore this dress out walking and it is lined in terry cloth so it’s great for summer. We saw a momma and baby dolphin swimming together and it was such an amazing experience to see them! There are usually dolphins near the Pier, so it’s a good spot to watch. The mom started chasing this fish super fast and throwing it in the air. She sped right along the beach almost near the sand and everyone was cheering. It was so fun to see!

Outfit Details:

Dress (c/o), Necklace (c/o), Sunglasses, Louis Vuitton Bag

This suit is super flattering and fits true to size! I can’t get over how gorgeous the pool was at the hotel!

Outfit Details:

Swimsuit (c/o), Coverup, Necklace (c/o), Sunglasses

Dinner at Osteria Tulia

Our last night, we had dinner at Osteria Tulia since it is the best! I had the clam pasta and peanut butter and chocolate cake for dessert. Wow, were they both amazing.

We caught an epic sunset on the last night! The sky was unreal right after it stormed. It was a great way to spend the last evening!

I wore this cute boho maxi that would be great into fall also! It fits true to size. The next morning before heading out, we went on a nice walk and ate our last lunch at Osteria Tulia, and then got gelato (of course). It was such a wonderful and unforgettable trip!

Outfit Details:

Dress (c/o), Necklace (c/o), Earrings, Sandals, Louis Vuitton Bag