Victoria Futrell, a senior at the College of Charleston in South Carolina, is a Margaritaville College Ambassador. Follow all of her adventures on Instagram at ms.victoriaf. To apply for a future semester or to learn more about the ambassador program, visit the program’s website.

I recently took a magical trip to Key West and fell in love (even more) with living on island time. While there is a lot to do on Key West, it could easily be overwhelming. There is so much of nightlife, as well as water sports, great food and beach-going to keep track of. Therefore, I’ve created the perfect itinerary for your next trip to this sunny yet palm-shaded paradise! And keep in mind ~ I love living like a local, so I tried my best to take the road less traveled while exploring the island.

(Note: This itinerary does not include travel time or hotel check-in, simply island adventuring.)

Day One

9 a.m. – Breakfast at Bistro 245

Whether you’re staying at the new Margaritaville Key West Resort and Marina or not, this is the place to eat breakfast!

It’s delicious, Caribbean-style, open air and waterfront. I recommend it 100%.

11 a.m. – Beachin’ at Sunset Key

This beach will not disappoint ~ you actually have to take a boat to get to it! Although you’ll have to purchase beach passes to access this private beach, its worth it and definitely the best beach in the area! Most of the keys are made up of coral, so the beaches tend to be rocky and small.

I recommend staying a while at this white sand beach! It even has its own jumping dock, lounge chairs, towels, and you’ll be served lunch or drinks if you’d like! We took snorkeling gear but the wind made it impossible to snorkel that day, so we decided to fall asleep on our beach chairs instead!

7 p.m. – Dinner at Latitudes

While I do recommend Latitudes and the Sunset Key beach in the same day, it is a tricky thing to plan out (depending on where you’re staying on the island)! Both the beach and Latitudes are on Sunset Key, which you’ll need to access via a boat that departs from the Margaritaville Marina.

Luckily, we were staying at the Margaritaville Resort so when we were done at the beach, we rode the boat back to the resort, changed, and then headed back to Latitudes a couple hours later! I thought it was super fun because I love boat rides, but you may want to bring a change of clothes if you plan on going right from the beach to dinner.

Latitudes is an extremely nice restaurant and it is very high-end! It is truly such an amazing experience. We got to sit in large leather chairs that made us feel as if we were in a fancy living room. It’s right on the water and definitely worth the price. Just remember to make a reservation before you go ~ the boat to Sunset Key won’t let you board unless you have a beach pass or reservation.

Day Two

8:30 am – Breakfast at Banana Café

This place is wonderful and so charming ~ my love for yellow was truly captured here! It’s in the heart of the city, on Duval Street, and the food is to die for! I ordered the La Provencal crepe {this was before I was vegan}, and we got mimosas for the table…of course!

10:30 am – Conch Tour

While the Conch Tours can be a bit cheesy, I will say that they are essential to learning about Key West quickly and heat-free! You’ll get to see all of the Old Town neighborhood, learn about Key West’s history, and ride around on a cool little train! As someone who studies architecture and preservation though, I have to point out that they did make up a lot of the different styles of architecture around Key West. Nonetheless, it was still a great time and the tour guides truly love what they do!

12:30 p.m. – Lunch at Roof Top Café

This is a cute little ‘tree-house’ lunch spot! Seriously, our table on the upper deck was next to a tree trunk stemming through the floor. From the outside, Rood Top Café seems small, but boy is it magical inside! This is a must see!

2 p.m. – Bike riding around the island

Make sure to ride through all of Old Town! The historic charm captured my heart and made me want to live in every house we passed!

6 p.m. – Danger Charters Sunset Sail

I cannot speak more highly of this adventure! Read more about it in my last blog post here. Captain Bosco and his crew are pretty amazing though, and we even got to be part of their new drone video!

Day Three

10:30 a.m. – Fury Jet Ski tour

Through Fury Water Adventures we took a two hour jet ski tour (P.S., I now have a Florida boater’s license!) that went for 28 miles around the lower keys! The tour first starts in the Margaritaville Marina, passes around the cruise ships, and then goes out through the lower keys! Warning: As much fun as this adventure is, your legs will hurt for a couple of days after! I never knew how sore jet-skiing makes you!

1 .p.m – Lunch at Margaritaville

My favorite place of all and a Key West staple. There’s just something magical about visiting Margaritaville and feeling like you’re part of Jimmy Buffett’s history and career success.

6 p.m. – Dinner at Sunset Deck/Sunset Celebration at Mallory Square

Sunset Deck is located at the Margaritaville Resort, and overlooks Sunset Key and the most beautiful sunsets! The colorful tables and chairs add so much character to this rooftop bar/restaurant and the margaritas are to die for too!

8 p.m. – Drinks at Sloppy Joe’s

Sloppy Joe’s is a Key West must-see! There’s always a great band, happy people, and great vibes. I recommend for drinks once the sun has gone down!

Day Four

10 a.m. – Breakfast at Cuban Coffee Queen

I think I mostly loved Cuban Coffee Queen for the story behind the brand. That’s actually what brings most of Key West to life! You can read more here and when you visit, be sure to order the café con leche and some other treats! Take a photo with the famous post card wall too!

11 a.m. – Walk around the waterfront

Right near Cuban Coffee Queen is an amazing waterfront with shops, bars, and museums. If anything, take a walk down the docks and admire the boats or visit the Dry Tortugas Museum (for the love of preservation…this one’s close to my heart!).

1 p.m. – Garbo’s Food Truck

This eatery is completely unexpected and SO GOOD! It’s actually located behind Grunt’s Bar…that’s right…down the driveway and in the backyard sits the smallest food truck with the friendliest people! The menu is small but not anything short of amazing! I wish we had more time on our trip to go back honestly! Also, how perfect is their website?

2:30 pm – Duval Street shopping

Super touristy but so much fun! There are a ton of local shops here and it truly is magical! Just remember that it gets a little crazy with so many bars nearby. In my opinion, Duval Street is a major part of the Key West charm and character.

6 p.m. – Sunset Pier

I swear y’all, the sunsets here are to die for! Check out my time lapse here. The food and drinks are great too, but make sure to arrive early enough before the sunset to get a good seat!

Day Five

12 p.m. – Louie’s Backyard for lunch

This place is amazing and my new favorite spot in Key West! It’s on the east side of the island and a must visit!

Louie’s backyard is located in a old historic home that has views from every table! Part of the restaurant is even over the water too! Not only are the food and piña coladas amazing, but watching the dogs on the beach is super entertaining too!

1:30 p.m. – Beach at Louie’s Backyard

This beach is small but the water is crystal clear and beautiful! Take a dip and relax!

2:30 p.m. – Moped time

We ended up renting mopeds from a little place near Louie’s because parking is free by the restaurant. So we decided to explore the island in the open air! This was such a fun thing to do for four hours, and we stopped at the following places along the way:

4:30 p.m. – Dessert before dinner at Blue Heaven

AMAZING! There are chickens running around outside and the Key Lime Pie is to die for! Blue Heaven is its own piece of paradise located under the trees and jungle of Key West.

5:30 p.m. – Southernmost Point

A photo-op destination! Hopefully the line isn’t too long!

7 p.m. – Rum and Reggae Sunset Snorkel

So Fury Water Sports does it again with this one…they are such great hosts, and the huge catamaran we sailed on made everything more beautiful! This trip was three hours and took us on an hour-long boat ride out to the reef just before sunset. We got to snorkel for an hour and then drink some rum on the way back. Seriously, there is no better way to end a vacation!

8 p.m. – Waterfront Brewery for dinner

And to top it all off, find yourself at this waterfront brewery on the sunset side of the island. My favorite part about this delicious stop was that it sits above a marina. And trust me when I tell you that boat watching is probably my favorite activity of all time. You’ll also get any beer samples you’d like, and the seafood is to die for!

My trip to Key West was truly beautiful and inspiring too…I recommend y’all visit at some point in life!

xoxo,

Victoria