Islamorada Travel Guide

Things to Know

Located in the Upper Florida Keys, Islamorada is the perfect US destination for a quick tropical weekend getaway. On Islamorada you’ll get all the beauty and charm of the Florida Keys without having to travel all the way to Key West. 

What is the weather like in Islamorada?

As with much of the Sunshine State, weather on Islamorada is great for visitors most of the year. Even during the winter months, highs will reach the upper 70s. 

Hurricane season in Florida runs from August to November, but don’t let that deter you from visiting at this time. Rates on rooms will drop significantly, and if you book with a flexible cancellation policy, the savings are worth the risk. 

How to get to Islamorada?

Islamorada is a short 1.5 hour drive from Miami making it easy to fly into MIA and rent a car. The scenic highway into the Islamorada makes the drive worth it! 

Having a car is a necessity when visiting Islamorada. Even though the island is small, it is not walkable and public transportation/Uber is not very accessible.

Where to Stay in Islamorada?

Islamorada has a great variety of boutique hotels that offer the same charm and beauty as Key West but at a much lower cost! 

Amara Cay Resort 

Amara Cay is where we chose to stay during our visit to Islamorada, and we absolutely loved it! The resort has a huge private beach (which is hard to come by in the Keys), a beautiful zero-entry pool, an instagram worthy lobby, lawn games, and free ocean kayak and bike rentals. 

Great news if you’re an American Express Platinum or Gold Card holder because Amara Cay is part of Amex’s Hotel Collection. As a part of your stay, you’ll be eligible for a room upgrade at check-in and receive a $100 resort credit. 

Cheeca Lodge & Spa

Offering one of the only spas on the island on site, if you’re looking for luxury Cheeca Lodge is the place to be! Cheeca is perfect for those looking for a romantic weekend getaway – be sure to book a room with one of the private soaking tubs on the balcony! 

Islander Resort

Boasting an extensive beachfront, two saltwater pools and a hot tub, the Islander Resort is perfect if you are looking to unwind and relax! The resort also offers complimentary access to kayaks, paddle boards, snorkel gear, and bicycles. 

La Siesta Resort & Marina

Perfect for large groups, La Siesta has the cutest and most colorful cottages, houses, and villas. La Siesta also has its own private beach and zero entry pool!

Postcard Inn Resort & Marina

Featuring classic hotel rooms and oceanfront cottages, Postcard Inn is great for families or groups needing a little extra space. The resort features a small private beach

What to Do in Islamorada?

Fishing Charter

Islamorada is known as the sport fishing capital of the world, so going out on a fishing charter is a must during your visit! 

Lot’s of companies offer full and half day excursions! Check out some of the top rated companies below: 

Sea House Private Charters

Hound Dawg Charters

Captain Easy Private Charters

Drop Back Fishing Charters

Snorkeling

Islamorada is home to some of the best snorkel spots in the U.S.! Be sure to plan an excursion to one of the popular reefs on the island or rent a boat or jet ski for a day trip! 

The shipwreck at the Alligator Reef Lighthouse has over 500 species of marine life and is one of the best snorkeling destinations in all of the Florida Keys! If you have time to check out more than one spot, Cheeca Rocks and Hens & Chickens are other top reefs to visit offshore of Islamorada and Upper Matecumbe Key.

Sunset Cruise

Key West isn’t the only place to catch an amazing sunset in the Florida Keys! Booking a sunset catamaran cruise is the perfect addition to every itinerary – bonus points for excursions with an open bar! 

Watersports

The only thing better than sipping a margarita watching the sunset in the Florida Keys, is getting out on the crystal blue waters! Jet ski, boat, and kayak rentals are easily accessible and great options for those without a boat or those not wanting to commit to a full-day excursion. 

Many of the resorts featured above as a Where to Stay destination include free watersport rentals in their resort fees, so be sure to check out the options at your resort before paying for a rental! 

Explore Village Square

Village Square at the Tradingpost is the cutest collection of outdoor boutiques and restaurants. Grab a coffee from Cafe Moka or a burrito from Bad Boy Burrito and explore the boutique, gardens, plant shop, and art club!

Where to Eat in Islamorada?

Breakfast

• Midway Cafe & Coffee Bar
• Cafe Moka @ Village Square
• Green Turtle Inn 
• Mangrove Mike’s Cafe

Lunch/Dinner

• Morada Bay Beach Club
• Square Grouper 
• Ziggy Maddogs 
• Ciao Hound
• Mrs Mac’s Kitchen

Can’t decide where to travel next? Check out more Probably Out of Office destination guides here.