Admit it, there is nothing quite so awesome as getting to take that two-week vacation with your family. You work hard all year and you deserve to spend those two weeks relaxing and having some major fun.

Of course, you can only have this relaxation and fun AFTER you’ve spent hours – if not weeks – researching to come up with the PERFECT place to spend your vacation. You almost need a vacation from planning your vacation!

Well, to make your life easier, we want to help you plan this year’s vacation. We’re about to share with you one of the top travel destinations in the country and also give you some ideas for local activities and even hotel recommendations. So be sure to read this ENTIRE article.

But let’s start out with a little clue, you and your family will be heading to Islamorada, Florida to swim with dolphins!

Why Visit Islamorada?

The Florida Keys is one of the most gorgeous areas of the country. Islamorada is actually comprised of six of these keys located between the saltwater wilderness, barrier reefs and Everglades National Park. The area is regarded as one of the best areas in the state for sport fishing and many visitors charter boats for a guided fish tour, or just to swim and snorkel in the warm, turquoise waters.

But there are other things to enjoy in Islamorada other than fishing and splashing around in the water. Dining options are fantastic and if you like fresh seafood, you’ll never want to leave. (We’re going to share a couple of awesome restaurants for you to check out in just a little bit so keep reading).

There are also great shopping and entertainment options. And for those who like a bit of culture on vacation, be sure to take in fine art and music while strolling through the Morada Way Art and Cultural District.

But perhaps the very best attraction the area offers is Theater of the Sea, a facility that offers unforgettable swim with dolphins experiences.

Islamorada, Florida

Islamorada Florida Keys

Fun Times in the Florida Keys !

Dolphin Swim Programs in Islamorada

Are you one of those people that has always had a love for and fascination with dolphins? If so, you’re definitely not alone!

What is it about dolphins that makes us fall in love with them? Maybe it’s their impressive acrobatic displays. It’s as if gravity gives them a break. Maybe what we love is how friendly and smart they are. Or maybe it’s a combination of all of these wonderful traits that captures our hearts and minds.

If you’ve always wanted to get up close and personal with these majestic sea creatures, then we encourage you to head to Islamorada to swim with the dolphins.

Here are just some of the dolphin programs available at the facility:

Florida Keys Dolphin Swim

Swim with the Dolphin

This 30-minute program is perfect for those individuals who are strong swimmers. You’ll be able to interact with a dolphin and experience many of their trained behaviors such as dorsal towns, hugs and foot pushes. You’ll also get to spend some free time snorkeling and swimming alongside them in the beautiful lagoon.

Book Your Dolphin Swim

Wade (non-swim) with the Dolphin

This is a great program for groups with very young children or for someone who is not a strong swimmer. You’ll be able to stand in 3 to 4 feet of water and interact with the dolphins. You can request behaviors such cradles and kisses, and just splash around with your new dolphin friend. We’d also like to note that if you have a big party and some will be doing the swim program and some the wade program, the facility will do everything in its power to try and get all of you into the same pool. Simply make that request when you arrive that day and they will do their best to accommodate you.

Book Your Dolphin Encounter (non-swim)

Theater of the Sea – A Day Full of Fun and Wonder

Theater of the Sea is a spectacular looking facility. You will definitely enjoy the pretty lagoon and lush, tropical gardens. Opened in 1946, the family-owned and operated facility works tirelessly to ensure the animals in their care are healthy and thrive. They also work hard to make sure each visitor leaves with wonderful memories and a huge smile on their faces.

Now, while we definitely think swimming with dolphins should be your top priority, we wanted to let you know there are other numerous opportunities to have fun at the facility. Here are a handful of awesome things to do:

Swim with the Sea Lion

This is a very unique experience to interact with sea lions, also called puppies of the sea. You’ll be in another natural saltwater lagoon and will be able to have the sea lions do trained behaviors such as hoop jumps and hugs.

Paint with the Sea Lion

When you go on vacation, you tend to bring home a bunch of ho-hum souvenirs and T-shirts. Well, here’s your chance to bring home something truly unique and special. You can have a sea lion create a one-of-a-kind art piece with the specific colors you have chosen.

What’s really great about this program is that all proceeds go towards the facility’s animal enrichment program.

Swim with the Sharks

Want some heart-stopping thrills but still be safe? Then you’ve got to check out the swim with sharks program. You’ll be able to feed, pet and hold nurse sharks while seated on an in-water bench. Strong swimmers will also be able to snorkel with them and other tropical fish in the saltwater lagoon.

Meet the Sea Turtle

How would you like to feed and interact with an endangered sea turtle? Proceeds from this program also go toward the facility’s animal enrichment program.

Crocodilians

Did you know that Theater of the Sea is home to two awesome American alligators and one Cuban-American crocodile? Do you know the differences between alligators and crocodiles? If not, you can learn all about them in this cool program while you also get to observe a training session.

Birds of Prey

The facility also happens to be home to a Great Horned Owl that was deemed non-releasable due to human imprinting. These birds are absolutely amazing and you’ll learn all about them in this fascinating program.

Bottomless Boat Ride

As we mentioned, the main lagoon is a very pretty body of water. Why not hop in a bottomless boat and go for a tour. You’ll learn historical information about the park as well as get photo and viewing opportunities of native wildlife.

Getting to Theater of the Sea

Theater of the Sea is located halfway between Key West and Miami and is fairly easy to get to by car. So you have a couple of different options:

Rent a Car

If you are flying into Florida, consider renting a car at the airport. Driving to the facility will be relatively easy, depending on time of day and how much traffic you experience.

Uber/Lyft

If you don’t want to rent a car, you can always use an app like Uber or Lyft. Fares should be pretty reasonable, and if you have a large party and everyone chips in, it will be very affordable.

Map

Accommodations in Islamorada

When it comes to comfortable and affordable accommodations, Islamorada has no shortage of options. Here are a few we recommend.

Islamorada, Florida

Islamorada Hotels

Cheeca Lodge & Spa

When you imagine going on a relaxing vacation, what images come to mind? Turquoise water? Swaying palm trees? Sweet ocean breezes that kiss your skin? Well Cheeca Lodge & Spa is the tropical oasis that can give you all you are imagining and hoping for in a vacation resort.

The hotel is both tranquil and romantic, so it makes the perfect location for couples. The accommodations combine casual elegance with top notch amenities.

If you are looking for a laid-back vacation that offers comfort and everything you need to relax, this is the place for you! With over 200 spacious rooms and suites and three dining options, as well as 27 acres of lush gardens, this hotel will make you want to never leave.

81801 Overseas Hwy
Islamorada, FL 33036
(305) 664-4651

Pelican Cove Resort & Marina

The pelican Cove Resort & Marina was recently awarded the TripAdvisor Certificate of Excellence in 2019. That may be because the hotel embodies the relaxed lifestyle that is associated with the Florida Keys.

Not only are guests provided a choice of 63 luxurious suites right on the water, but they also have access to a pool, saltwater lagoon, a cabana bar, café, marina, water sports and fishing charters. You’ll simply never be bored while staying at this resort.

84457 Overseas Hwy
Islamorada, FL 33036
(305) 664-2321

Postcard Inn Beach Resort & Marina

This hotel is a real favorite among visitors and locals alike. Located just minutes from Key Largo, the iconic resort blends the retro, throwback atmosphere of a nostalgic American beach vacation with modern amenities like WiFi, iPod docks and flat-screen televisions.

Each beachfront room exudes a fresh island vibe, offering crisp white linens and nautical décor. Many rooms also have a balcony with splendid Marina and Atlantic Ocean views.

You also have the option of staying in one of the hotels relaxing and stylish beach cottages. These airy oceanfront cottages feature contemporary decor, nautical accents, and a color scheme that inspires FULL relaxation.

84001 Overseas Hwy
Islamorada, FL 33036
(305) 664-2321

Amara Cay Resort

Amara Cay is for the vacation seeker—for the ones that want to take-it-all-in and never-miss-a-moment crowd. It’s the resort for the social minded who want to find the relax crowd and always looking for new friends on vacation.

Amara Cay is a constant hum of laughter and conversation. It’s tiki bar casual and very island-style crowd. It’s never rowdy and never too loud. The guests are refined but not uppity & hip but not hipster. Always welcoming—inviting you to join in and satisfy your craving for more.

With Ocean Front Rooms, Suites and Stand rooms. A great get away resort.

80001 Overseas Hwy
Islamorada, FL 33036

(305) 664-0073

Things to Do in and Around Islamorada

While we definitely think you should put “Swimming with dolphins” on the top of your activities list, there are some other terrific activities in the area to enjoy.

Things to do Islamorada Keys

Grab a Bite at Islamorada Fish Company

If you go to Islamorada you HAVE to have at LEAST one meal at this iconic restaurant. This place began as a tiny marina snack bar known for its fresh-from-the-docks seafood but it’s now an acclaimed Bass Pro Shops dining destination.

The fish sandwiches are world-famous and when you go, you MUST go for a sunset meal. This is what the place is KNOWN for. But there are other great and tasty options on the menu such as signature cocktails, delicious (and exotic) appetizers, fresh-daily seafood, hickory-fired rotisserie chicken, wild game, grilled steaks, sandwiches, salads, and their amazing Key Lime Pie! You have GOT to try the key lime pie.

81532 Overseas Hwy
Islamorada, FL 33036
(305) 664-9271

Lorelei Restaurant and Cabana Bar

Another great dining option we wholeheartedly recommend you make time for is Lorelei Restaurant and Cabana Bar. Without question you are going to taste some of the best seafood you’ve ever had in your life!
The place has some pretty breathtaking views of the world-famous sunsets and they have sunset celebrations each night with live entertainment. The restaurant serves breakfast, lunch and dinner and also has a kid’s menu.

96 Madeira Rd
Islamorada, FL 33036
(305) 664-2692

Florida Keys Brewing Company

The Florida Keys only has one production brewery and this is it! Located in the heart of the Morada Way Arts and Cultural District, this small micro-brewery brews close to 30 styles of beer annually. So go on in to the tasting room and sip some of the best micro-brews around. They’re open every day between 1pm and 9pm.

81611 Old Hwy
Islamorada, FL 33036
(305) 664-9722

History of Diving Museum

If you are a diving enthusiast, you’ll definitely want to head to the History of Diving Museum. This place “is dedicated to collecting, preserving, displaying, and interpreting artifacts, antiques, books, documents, photographs, and oral history relative to the History of Diving.”

When you think about it, how is it that somewhere during man’s evolution, we got it into our mind’s that we would explore the depths of the ocean? How did it all happen? What we do know is that the state of Florida, particularly the Keys played, a big part in the story of diving.

82990 Overseas Hwy
Islamorada, FL 33036

(305) 664-9737

Rain Barrel Village

You know you’re going to take a LOT of selfies on your vacation, but if you really want to take one that will give your family laughs for years to come, then you’ve GOT to head to Rain Barrel Village to take a selfie with Betsy the GIANT lobster.

When you’re done with Betsy, spend some time strolling through the lush, tropical gardens, then head inside the studios there to look at some pretty handmade crafts, contemporary artwork, beachwear, home goods and Florida Keys-inspired souvenirs. We DARE you NOT to buy some of these items!

86700 Overseas Hwy
Islamorada, FL 33036
(305) 521-2043

Local Information

Great Weather in Islamorada, Florida

Islamorada Weather

Weather

Remember at the beginning of this article I mentioned just how much planning goes into a vacation. Well, a lot of that planning has to do with WHEN you should go. After all, you’ve waited all year for these two weeks, and you don’t want your two weeks ruined by bad weather! The last thing any parent wants is to be stuck inside a crowded hotel room with three children under the age of 12 with nothing to do because it’s raining.

The good news is, the weather in Florida is really nice a good portion of the year. After all, they don’t call it the “Sunshine State’ for nothing! Having said that, there are definitely those times of the year when it’s better to visit Florida than others.

Summers in Florida, as you might imagine, can get very hot and very sticky. This definitely isn’t the best time to visit.

You also certainly don’t want to go during hurricane season, which is between June and October, with the peak being August and September.

The absolute best times of the year to visit Florida are during winter and spring. During this time, the temperatures are mild, usually staying in the low to mid 70s during the day and slipping down into the 50s at night.

Just understand that, since this is the absolute best time to visit Florida, everyone and their mother will be going then. So it’s important to book your plane tickets and hotel rooms early, so you can avoid paying premium prices. Also, be sure to book your visit to Theater of the Sea.

Festivals & More!

There is always some kind of fun to be had in Islamorada, Florida. From sporting events to festivals, concerts and outdoor festivities, there is always something going on.

You can visit this link to view some of the activities that may be going on when you visit.

Helpful Travel Links

Key West Chamber of Commerce

Islamorada Travel Guide

If you and your family will be heading to Florida this year on vacation, we definitely recommend you spend most of your time in the Islamorada area. And, while there are a ton of fun activities to enjoy there, please make sure you make some time to swim with the dolphins. That will be an experience you never forget!

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