• Skip to primary navigation
  • Skip to main content
  • Skip to primary sidebar
  • Home
  • About/Hire Me
    • About Me
    • Hire Me
    • Contact
    • Family
    • Faith
    • FAQ
    • My Running Story
    • Recipes
  • Disney
  • Fitness
    • runDisney Information Page
    • Fitness
    • Races
  • Parenting
  • Travel

Through Heather's Looking Glass

  • Disney
  • Fitness
  • Travel
  • family
  • About Me

Just Let Go at TradeWinds Island Grand

March 24, 2021 | Travel

Disclosure: This post is sponsored by TradeWinds, however, all opinions are my own.

A couple of summers ago, we attended a blogger day event at TradeWinds Island Grand, and had SO much fun. We had never spent the night and definitely didn’t have time to see everything on that day, so we were super excited to be invited back to stay two nights.

Tradewinds Island Grand

This resort is on St. Pete Beach, and is very walkable to shops and restaurants. There are actually two resorts within walking distance to each other (RumFish is the other one.) The grounds are peaceful and relaxing, There are multiple pools and restaurants, and Starbucks in the lobby!

We were given a tropical view one bedroom suite, and it was super spacious! When you walk in, there were two queen beds, a closet and a dresser with a TV.

Tradewinds Island Grand

There was a door to shut on the far end, and a hallway that led to the bathroom.

Further down the hall opened up into a spacious living room with pull out couch, full kitchen, and balcony. The refrigerator was huge, you could easily go grocery shopping (Publix right down the street) and cook some of your meals if you are on a budget. (But be sure to try some of the yummy restaurants, too!)

Tradewinds Island Grand

Our view was expansive! We could see the beach, a pool, and the whole city. It was awesome!

Tradewinds Island Grand

We of course immediately headed down to the beach, Emma Kate did some “surfing” and went down the waterslide. We also did some exploring and couldn’t wait for a full day the next day! We learned there is an adults only pool, as well as miniature golf!

Tradewinds Island Grand

We were also treated to a gorgeous sunset from our balcony before heading to dinner. It was perfect, pictures just don’t do it justice.

Tradewinds Island Grand

We had dinner at the other TradeWinds resort, RumFish. They have a super cool restaurant with a giant fish tank!

Don’t worry if you don’t get to sit close to the tank, there is a viewing area anyone can walk up to and see the fish.

Our meal was delicious! This place books up fast, so be sure to make a reservation on their website!

The next day we were pumped for a full day in the sun. One of the great things about Tradewinds Island Grand is that they don’t nickel and dime you. You pay a resort fee but it covers SO much like Wi-Fi, parking, beach cabanas, waterslide, two fitness centers, cornhole, tennis, paddleboats, and more!

It was also super easy to go back and forth from the beach and pool, or to go to the pool bar to grab a drink or food. It’s all close by! (Emma Kate is laughing in the below picture, not crying haha!)

Tradewinds Island Grand

When we got hungry we simply walked up to Salty’s and grabbed a table with umbrella overlooking the ocean and were served there. It was so nice and relaxing!

Then it was back to the beach and waterslide!

We eventually ended up back up at the pool for a bit before heading in for the afternoon. We had a sunset sailboat cruise to get to! Did you know that you can book tons of excursions and activities through TradeWinds Island Grand? We just had to go about a mile down the road to get to Dolphin Landings.

I was so excited for EK, it was her first time on a sailboat! They provided water and sodas, and we set sail at about 5:15. (sailing time depends on when the sunset is!)

We enjoyed a nice relaxing sail before getting out to open water to see the sunset!

It was so awesome seeing it from the water. We even got to see some dolphins playing!

It was a really fun experience! Pro tip: bring a jacket, it gets chilly fast out on the water when the sun goes down! We were brought back to the dock and we picked up takeout to have back at the room. It was a great way to end the evening!

We had the best time at TradeWinds Island Grand and would come back in a heartbeat. Amazing resort feel, so much to do, and so relaxing. We truly felt like we were on a secluded island somewhere tucked away from the world. I can’t wait for our next visit!

Related post: Sandals Ochi Beach

Like this:

Like Loading...

Sign up for my newsletter

Primary Sidebar

I am Heather Montgomery, a southern girl living in Knoxville, Tennessee with my husband Bobby, 11-year-old daughter Emma Kate, and our goldendoodles Dolly and Luna. I’m just a regular girl who likes to workout, travel, hang with my family, text, and eat chips and queso. Be sure to check out my “about me” page for more info!
Thank you for visiting, and feel free to contact me with questions, (or for PR inquiries or press trip invites) at Support@HeathersLookingGlass.com.

Please, no guest post requests. 🙂

More about me

Privacy Policy

You can also find me here:

  • Facebook
  • Instagram
  • Pinterest
  • RSS
  • Twitter
  • YouTube

Recent Posts

  • Free Travel Planning with Best Day Ever Vacations (Yes, It’s Completely FREE!)
  • Mom Must-Haves for a Basketball Tournament: The Ultimate Survival Guide
  • Why Spring Is the Sweet Spot for Family Vacation on Alabama’s Beaches
  • You’ll Get It When You Get Here: A Spring Break on Alabama’s Beaches That Actually Feels Like a Break
  • A Word for 2026

 

Search

How to Start a Blog

How to start a blog
We are a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for us to earn fees by linking to Amazon.com and affiliated sites.
  • Disney
  • Fitness
  • Travel
  • Family
#ZbarPartner I know these days won’t last forever, #ZbarPartner I know these days won’t last forever, so I’m soaking up every driveway game, every laugh, every little break in the grass. 🤍 

Lately our go-to has been Zbar Protein Snack Bars, especially the new Strawberries ‘N Creme flavor that is made with organic whole grain oats, real fruit, and protein to help support growing kids. It’s a snack she loves and I feel good about too. 

It’s a great little reset so she can get right back to doing what she does best, playing her heart out 💕

 #ZbarProteinStrawberriesnCreme @zbarofficial #Zbar
Getting older, I started noticing my hair wasn’t q Getting older, I started noticing my hair wasn’t quite the same. A little more thinning, my scalp hasn’t felt the same, and I’ve spent more time just throwing it up into a ponytail, and honestly not giving it much thought beyond that. 🤷🏻‍♀️

So I started becoming more intentional about actually taking care of my hair and scalp, and it’s such a small shift, but it really does make me feel better.

I’ve been using Mochi Health’s personalized hair support options, which makes it easier to stay consistent instead of guessing what to use. It fits into my routine and finally feels like I’m doing something proactive for myself instead of just hiding it in a bun. Check out the link in my bio for $40 off your first month.

#JoinMochi #MochiHealth #MochiPartner @joinmochi
✨ S U M M E R B L E S S I N G ✨ I’ve teamed up ✨ S U M M E R  B L E S S I N G ✨ 

I’ve teamed up with @bestdayeverblessings and some amazing accounts to make this blessing possible for someone. 

I N C L U D E S: 
✨ Luggage set
✨ Simple Modern XL beach bag 
✨ Simple Modern 40 oz tumbler 
✨ Turkish towel
✨ Roe Wellness mineral sunscreen
✨ Summer Fridays lip gloss
✨ Thread crossbody bag
✨ Threat minimalist wallet
✨200 💰 

👇T O  E N T E R👇

1️⃣ F O L L O W @bestdayeverblessings and everyone they  f o l l o w 
2️⃣ L I K E + save this reel 
3️⃣ T A G a friend

⭐️ B O N U S ⭐️ 
1️⃣ C O M M E N T  your favorite item
2️⃣ S H A R E  to your stories and tag @bestdayeverblessings 

Ends on 5/1 at 9:59 pm EST.  The randomly chosen recipient will be announced by @bestdayeverblessings on 5/3 
•
This is not affiliated with Instagram or any of the brands pictured. Must be 18+ to enter. Open USA/Canada.
✨ S U M M E R B L E S S I N G ✨ I’ve teamed up ✨ S U M M E R  B L E S S I N G ✨ 

I’ve teamed up with @bestdayeverblessings and some amazing accounts to make this blessing possible for someone. 

I N C L U D E S: 
✨ Luggage set
✨ Simple Modern XL beach bag 
✨ Simple Modern 40 oz tumbler 
✨ Turkish towel
✨ Roe Wellness mineral sunscreen
✨ Summer Fridays lip gloss
✨ Thread crossbody bag
✨ Threat minimalist wallet
✨200 💰 

👇T O  E N T E R👇

1️⃣ F O L L O W @bestdayeverblessings and everyone they  f o l l o w 
2️⃣ L I K E + save this reel 
3️⃣ T A G a friend

⭐️ B O N U S ⭐️ 
1️⃣ C O M M E N T  your favorite item
2️⃣ S H A R E  to your stories and tag @bestdayeverblessings 

Ends on 5/1 at 9:59 pm EST.  The randomly chosen recipient will be announced by @bestdayeverblessings on 5/3 
•
This is not affiliated with Instagram or any of the brands pictured. Must be 18+ to enter. Open USA/Canada.
POV: you said “it’s just a vacation” and now you’r POV: you said “it’s just a vacation” and now you’re weirdly attached to a boat already. 🥹

Embarkation day on the Disney Wonder out of San Diego is pure organized chaos in the best way. Bags everywhere, everyone buzzing, and that moment you step onboard and suddenly forget how to function like a normal human.

We’re talking: Where are we even going first? Do we eat or explore or both immediately? Why does this already feel like the best decision ever?

And then the sail a wave party happens and… yeah. You’re gone. Mentally, emotionally, everything. 😭

If you know, you know…embarkation day hits different 🚢✨

Thanks @bestdayevervacay and Disney for hosting us on this magical adventure! Use the 🔗 in my bio to let then plan a cruise just like mine, down to the last detail! 

#disneylandandsea #bdevambassador #bestdayevervacations #disneywonder #disneycruisine
Kind outside. Commentary inside.👀 #relatableconte Kind outside.
Commentary inside.👀

#relatablecontent #funnyreels #momhumor #reelsinstagram #viralreels
Today she’s the magic… but someday I hope she’s th Today she’s the magic… but someday I hope she’s the reason someone else feels it, and that I will have a front row seat to see it. 🥹✨

Disney cruises are the perfect multigenerational vacation because there is truly something for everyone. From kids clubs to adults only dining and entertainment, everyone can do their own thing and then meet back up together for a fun day ashore, in the dining room, or poolside. The options are limitless, and the memories are, too. ❤️

My friends at @bestdayevervacay understand how hard you work for your money and that you want the most magical, memorable, and stress free vacation possible. They are standing by ready and able to answer all of your questions and get your cruise booked. 🚢 

🚨 Even better? @disneycruiseline just announced a NEW discount! Kids sail 50% off in select sailings! But hurry only so many rooms are allotted for this offer. Fill out the form at the link in my bio, or comment the word “cruise” and I will DM you the form! Remember it’s FREE to have them book your vacation for you! No extra cost!

#disneylandandsea #disneycruise #disneycruiseline #bdevambassador #bestdayevervacations

Copyright © 2026 · Through Heather's Looking Glass · Theme by Bella Creative Studio

 

Loading Comments...
 

You must be logged in to post a comment.

    %d