The luxury Upper Florida Keys Trip you Deserve & Can Afford!
Although I was born & raised in Islamorada, I also spent half my life in North Carolina. Post covid my friends from up north have been asking for recommendations on planning the perfect trip to the Upper Florida Keys. So here it is, your local guide to planning the ultimate Florida Keys Trip!
Affordable Stays in the Upper Florida Keys
These Condos are in the prime location of Tavernier. Which is your ideal spot, located between Key Largo & Islamorada providing you with many options for dining/bars & adventure. Probably most affordable stay down here starting at around $200 something a night. However, these only have two bedrooms. You also have access to tennis courts, marina, bar, beach, hot tub, etc.
This hotel is located directly in the heart of Islamorada & is just a free ride to anywhere you’d like to go in the city of Islamorada, by using the freebie app. Freebie is a free uber that the Village of Islamorada pays for to limit drunk driving!
The postcard is around $300 something a night which is affordable for the Keys & one of the nicest resorts down here. This hotel overlooks the sand bar & is connected to a marina, so you’ll be able to see fishermen coming in with their catch, etc.
This hotel is ideal for boaters! With the availability to park your boat right outside your hotel room. The location is prime. You’re right next door to the Casa Mar Village which offers paddleboard tours, scuba diving, snorkeling, boat rentals & a waterfront bar/dining which offers fresh seafood straight off the boat.
Luxury Stays in the Upper Florida Keys
The top place to stay. Offering golf, spa, lush landscaping, hot tubs, waterfront restaurants, jet ski tours, beach access, multiple pools & more. This will be one of the most relaxing stays of your life & it is truly in the heart of everything Islamorada has to offer. You can walk to the best breweries, restaurants, etc.
Known best for its debut on the Netflix show, bloodline. This is probably the most luxurious stay in Islamorada. With our own waterfront hut, The moorings are located right next to cheeca & you are allowed all their amenities.
This is the only all-inclusive stay in the Florida Keys. Although the pricing can look a little scary it’s worth every penny. They offer everything from bikes, boating tours, food, drinks, yoga, spa & so much more. This is the vacation of your dreams, you’ll feel as if you’re on your own private island in the Caribbean!
Best Stays for Big Groups
Great location & amenities. Very clean & coastal stay.
Bring your boat here, located right next to the Islamorada sandbar. Equipped with hot tub & pool. You’re also within walking distance to three of my favorite spots. Island Grill, Hog Heaven & Ocean View Pub.
These Stays offer everything from private chefs to private charters. Definitely the luxury vacation of your dreams.
The Best Local Bars
Mar Bar is THE best kept local secret. Hidden on the canal you’ll watch fishermen come in with their catch, including stone crab claws. These are the most affordable & fresh claws on the island at just $4 a claw. They also have a great selection of local beers & crisp wines.
Known best for their Wednesday night flip nights, where you flip a coin & have a 50/50 chance of getting your drink for free. Great pub food & yummy drinks. Located on the water so you can come by boat too!
Where everyone goes when they want to keep the night going. Hog Heaven has something for everyone. Located on the water they usually have live music on a floating dock in the back & a DJ inside with more of a club vibe. Open till 3 am usually!
This is the perfect place to keep the party going. Pool tables, darts, etc. This is your typical dark pub with loud music & a full bar!
Florida Keys Brewery is a staple in the community. If you like drinking games & live music this is the place for you. On the third Thursday of every month, you’ll find the ‘Art Walk’ where little vendors come with art, wine, food trucks, live music, etc.
Best Resturants in Islamorada
Sunsets here are heavenly. This property is gorgeous, a very sandy beach with a very luxurious vibe. They have great cocktails & their cheese board is heavenly!
Hands down best sushi on the island. Go for their happy hour 5-6 pm Mon-Thurs! You can’t go wrong with ordering anything from the happy hour menu. My favorite is the stuffed avocado & hogfish roll!
BEST view out here on a sunny Sunday this place is a MUST. Order anything you can’t go wrong & the drinks are always perfect.
Square Grouper offers it all. Ambiance, creative cocktails & mouthwatering dishes! They do not take reservations & usually have a wait so the earlier you get there the better. If there is a wait ask the host about the new bar upstairs, Sunset Lounge. This Lounge offers fun cocktails & yummy apps, however, it’s known best for a steller view & sunsets to die for.
Best Waterfront Restaurants in Key Largo:
Live music, stunning sunsets, order the tuna nachos/bloody for brunch or the key lime colada! Must check out the tiki taxi where you’ll float & drink around the bayside.
Locals spot, marina views, fun bar games, order blackberry mojito & smoked fish dip!
Great brunch, oceanfront dining, order the bang bang shrimp/tuna nachos/ spicy marg!
**Check out my other blog ‘Florida Keys Adventures to book your adventure today!
*** If you’re flying out of NC I suggest booking with Allegiant airlines & getting a rental car in Fort Lauderdale, then driving down. P.s Fort Lauderdale is also another great spot to plan a fun day.