Ultimate Guide to a Florida Keys Family Vacation

Ultimate Guide to a Florida Keys Family Vacation

This guide is meant to help New Orleans families planning their next tropical island vacation to the Florida Keys. We are all about sharing family traveling tips whether your next adventure from New Orleans is to the mountains, Disney, or the beach! As always, please do your own research and talk with other families. If you love the idea of a beach vacation but are looking for a one-day trip, consider the Mississippi Gulf Coast, such as Gulfport. There is also a list of drivable destinations from New Orleans for every budget here. And if you end up staying right here in New Orleans, we have dozens of ideas for kid-friendly outings in New Orleans, too. But, if you are looking for a Caribbean Island vacation but don’t want to leave the continental United States … look no further! This guide will help you plan your next family vacation to the Florida Keys. 

How to Get There

I have been visiting the Florida Keys for nearly 20 years. My first trip was with my then-college-boyfriend (now, husband) and his family in 2003. I fell in love and have been back at least nine times since. Our family now returns every other summer and we typically travel via automobile. It is a long drive to be sure, but we love the convenience of being able to pack all we need, towing a boat, and having a vehicle for our stay. Of course, there is the option to fly. The options are to fly into South Florida (Miami {MIA} or Ft. Lauderdale {FLL}), the middle Keys (Marathon International Airport {MTH}), or the Southernmost Key (Key West International Airport {EYW}).

Where to Stay

We have stayed in resorts, townhouses, and single-family houses. I can personally vouch for the following resorts we have stayed in and loved: Hawks Cay Resort in Duck Key, Tranquility Bay Beachfront Resort in Marathon, and Angler’s Reef Resort Villas in Islamorada. Other than those, our preference is to rent a house through VRBO or Airbnb that includes a boat slip, private pool, and enough room for our family. We typically stay in the middle Keys (Islamorada or Marathon) but have on occasion stayed farther south in Long Key, Big Pine Key and Cudjoe Key. We genuinely love them all. Many people immediately think of Key West when the Florida Keys are mentioned, but there is so much more fun to be had than Key West offers. I have only been to Key West on three of my Keys vacations and only for a day trip. It is fun and worth a visit but not necessary and more adult-centered with shopping, bars, restaurants, and nightlife as its drawing point.

What to Do

The Florida Keys is a vacation for everyone in the family. I truly believe that. That said, there are some caveats worth mentioning. If you are looking for a beach vacation, you’re better off in Pensacola or a similar Gulf Coast destination. But if you are looking for that escape to a tropical island but aren’t quite willing to deal with international travels, then the Florida Keys is the trip for you. I say all that because the Keys are made up of limestone, and the beaches there are not the white sand we are used to on the Gulf Coast. Our family prefers to explore the beauty of the Keys largely via boat. You can 100% do it without bringing your own or renting one, but you will want to be on a boat for much of your trip as the water, and what’s in it, is breathtaking.

If you are traveling with little ones, make sure you consider their personality and temperament. If you do the Keys with little ones and do not have family that is hands on, I strongly recommend either bringing a sitter or changing expectations. We did the former. I have done the Keys with a one-year-old and no extra helping hands … it was not enjoyable for me. We learned quickly and brought our family babysitter along for several trips until my youngest was old enough to hang with the big kids for longer boating excursions. That said, there is plenty of fun for all ages. Our family likes to boat, fish, lobster, and snorkel … activities that aren’t as easy to accomplish with a toddler in tow. But there is much more to be done than our typical activities.

Excursions ::

Helicopter Scenic Tours

Sunset Sail Key West

Robbies of Islamorada :: Feed the tarpon, shop the open-air market, dine, and plan your excursions including jet-skis, kayak and paddle board rentals, snorkeling, sunset cruises, parasailing, eco-tours and boat rentals.

Bud N’ Mary’s Marina :: Fishing, diving, scuba and lodging.

Charter Fishing :: There are so many options. Call the nearest marina to schedule your charter fishing trip.

Snorkel & Scuba :: The opportunities are endless and one reef is more beautiful than the next. If you do not have a boat, google will be your friend.

Take the boat to a sand bar

Lobstering & Stone Crabbing :: depending on when you visit the Keys, you will need to check what is in season to harvest.

Key Largo Princess Glass Bottom Boat Tour

Fun Outings ::

Theater of the Sea

Aquarium Encounters

Robbie’s of Islamorada

World Wide Sportsman

Lobster Shack/Rain Barrel

Visit a brewery – Islamorada Brewery & Distillery in Islamorada (include No Wake Zone & Frozen Key Lime Pie in your flight selection) and Florida Keys Brewing Company

Boat Rental ::

If we don’t have a boat to bring with us, we rent one in the Keys. Do your own research to find a reputable supplier and the adage “you get what you pay for,” rings true. If you are not an experienced boater, navigating the waters can be challenging due to wavy conditions in the Atlantic, heavy boating traffic, and sand bars and shoals.

Shopping ::

There is not a whole of “shopping” to be done in the Florida Keys. There is too much other fun to be had. But I would recommend stopping in the stores located near where you are staying, even if they don’t look like much on the outside. Islamorada Mercantile and Ocean Gardens are two stores I always check out when in the Keys. Key West has the most options in terms of shopping.

Day Trips ::

Key West – Rent bikes and traverse the island while stopping to grab a drink, do some shopping and taste some of the delicious eats. Take a tour of the Ernest Hemingway House and grab a slice of key lime pie from Kermit’s Key West Key Lime Shoppe.

Dry Tortugas National Park

Bahia Honda State Park

Where to Eat

Casual Dining:

The Beach Cafe at Morada Bay in Islamorada

Lazy Days in Marathon & Lazy Days South in Marathon

Burdine’s for burgers in Marathon

7 Mile Grill in Marathon

Upper Crust Pizza in Marathon

Angler & Ale at Hawks Cay

Island Fish Company in Marathon

Island Grill in Islamorada

The Square Grouper in Islamorada

Fine Dining ::

Butterfly Cafe at Tranquility Bay in Marathon

Chef Michael’s in Islamorada

Pierre’s Restaurant at Morada Bay in Islamorada

What to Pack

The essentials are bathing suits, SPF Shirts, sunscreen and flip flops. That is the attire 90% of the time you are in the Keys. If you are driving, you can obviously pack more, and we certainly do. We bring all of our snorkel, fishing, lobster (if we visit during mini season) and boating gear. If you are going to book excursions to do any of those activities, they will have the gear you need at those places. Pack lightly and enjoy!

Have you taken a family vacation to the Florida Keys? Did we miss anything? Let us know in the comments.


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