A vacation to the Florida Keys should be on everyone’s bucket list. There is so much to do at a surprisingly affordable price. The Upper Keys, the closest keys to Miami, have so much to offer for vacationers who want to experience the Florida Keys without driving all the way to Key West. We recently checked out some of the affordable family travel attractions along The Upper Keys and put together this itinerary of 48 hours of affordable family fun in The Upper Keys to help you plan your next family beach vacation.

48 hours of affordable fun in key largo and islamorada

48 Hours of Affordable Family Fun in The Upper Keys

Affordable family travel is near and dear to my heart. I firmly believe that travel is something that everyone should experience, no matter how much money you have. You don’t have to spend a lot of money or travel far to enjoy the riches of travel. Want to learn how to travel with kids on a budget? Check out this post for more information.

My family and I recently visited The Upper Keys for a family wedding. My brother in law got married and we had the perfect excuse to visit Islamorada and Key Largo for a few days. The wedding was in Islamorada at Amara Cay resort. While we would have loved to stay at the beautiful resort, the rooms started at $400 a night for that weekend. Obviously an affordable family travel and personal finance blogger is not down for spending that much money on a hotel room. Ever.

We did what any cheap person would do: searched Airbnb and VRBO. After a fiasco with VRBO where our initial stay in Islamorada was canceled due to a double booking incident, we finally found an affordable place to stay in Key Largo.

Our Key Largo home away from home was approximately 30 minutes away from the resort in Islamorada. That gave us a great excuse to explore the upper keys during our stay. Each morning we would embark on the journey to Islamorada from Key Largo and take our time exploring all of the affordable tourist spots along the way.

Jackson with a shell in Islamorada. What to do in Islamorada with kids

What keys make up The Upper Keys?

Key Largo and Islamorada are two of the most well known keys in the Upper Keys because they are actually cities, not just keys. The city of Key Largo includes three keys: Key Largo, North Key Largo, and Tavernier. The city of Islamorada includes Islamorada, Plantation Key, Lower Matecombe Key, Upper Matecombe Key, Indian Key and Lightnumvitae Key.

As you drive from key to key you can spot signs that welcome you to each key as well as signs that welcome you to the different cities and fishing villages. It can actually be a little confusing to figure out where one city ends and another one begins in The Keys!

What is there to do in The Upper Keys with kids

What can you do in the Upper Keys?

So much! You can go snorkeling, fishing, diving, hiking and more. Some activities are pricey and others are affordable. That’s why I’ve put together this travel itinerary for you to figure out what can be done on a budget.

Affordable Family Travel Itinerary for The Upper Keys

There are so many affordable things to do in Islamorada and Key Largo that it was hard to narrow down the best things to do for an Upper Keys vacation. After lots of exploring, trial and error, my family picked this itinerary as the best one for exploring the upper keys with kids.

48 hours of affordable fun in the upper keys

Day 1 of 48 hours of Affordable Family Fun in The Upper Keys

Brunch at Mrs. Mac’s

Arrive in Key Largo just in time for brunch. Visit Mrs. Mac’s Kitchen for a chance to eat stone crab for breakfast during stone crab season (Oct through May). Specials come with a free mimosas. Sure, stone crab for breakfast sounds fancy and not affordable at all. However, this place has diner vibes and prices that make parents and kids happy.

After brunch take a drive to Founders Park Beach in Islamorada and explore the upper keys along the way. This will give you some bearings as you begin your 48 hours of affordable family fun in the Upper Keys.

Enjoying the beach in Islamorada

Explore the Beach at Founder’s Park

Spend the late morning and early afternoon exploring Founder’s Park Beach. The park can entertain you for hours. This is one of the only sand beaches in The Keys, not just Islamorada. While The Keys are surrounded by sand and water, it’s not common to find public beaches. In addition to the sand beach, Founders Park has a pool, marina, walking trails (including one along the jetty), and a playground. Admission is $8.00 per person to the park ($15 on holiday weekends) and an additional $3.00 to the pool.

Beach at Founder Park in Islamorada

Check into Accommodations & Head to the Grocery Store

Check into your VRBO or Air B&B in Key Largo. Head to the end of this post to read our tips for picking the best places to stay in the Upper Keys.

Run to the grocery store to stock up on snacks and a dinner option. Cooking at home on night one will save you some money. Take a walk around the neighborhood after dinner to get a better idea of where you are staying.

Day 2 of 48 hours of Affordable Family Fun in The Upper Keys

Breakfast at Pinecrest Bakery

Head to Pinecrest Bakery at mile marker 99 in Key Largo for Cuban coffee, baked goods, and breakfast. While the name denotes baked goods, Pinecrest is so much more than just a bakery. You’ll want to try one of the hot pressed sandwiches or savory pastries. And of course, the Cuban coffee alone is worth a visit.

Feed the Tarpon at Robbies of Islamorada

Pick up an extra cup of Cuban coffee at Pinecrest for the 30 minute drive to Robbies of Islamorada to spend the morning exploring the open air market, kayaking, paddle boarding, and feeding the tarpon. Tarpon feeding is a somewhat iconic activity in The Keys. One must feed the tarpon at least once during a visit to The Keys.

Feed the fish at Robbies in Islamorada. What to do in The Upper Keys

Admission to the dock is $2.25 a person and a bucket of fish is $4. Even if you don’t plan to feed the tarpon, paying to walk the dock is worth it just to get a close up view of the huge fish.

Feeding the Tarpon in Islamorada at Robbies

Lunch at Robbies

Stick around after feeding the tarpon and enjoy lunch overlooking the dock at the Hungry Tarpon Restaurant. Prices are pretty fair and not overly priced as tourist restaurants tend to be. The food is fresh and delicious, even if the wait is long. Enjoy a locally brewed beer from Islamorada Beer Company or Florida Keys Brewing Company.

Islamorada Beer Company at Robbies Hungry Tarpon

Explore a Park

The Village of Islamorada has lots of beautiful parks to visit.  Anne’s Beach at mile marker 73.5 is the most famous because it’s a beautiful sand beach with very little wave action, making it perfect for young kids. It’s currently closed due to damage during Hurricane Irma, but it’s worth driving by just to see if it’s open during your visit. Check out this list of all the parks.

Kayaking in Islamorada. What to do in The Upper Keys

Take a Walk through Windley Key Fossil Reef Geological State Park

Head to mile marker 84.9 to explore the Fossil Reef Geological State Park. Admission to the 1.5 mile trail is only $2.50 a person. The hammock trail is not paved so this is an adventure for kids who can walk and don’t need a stroller.

fossilized coral in Islamorada

Dinner at Reel Burger

Just because you aren’t staying at a fancy resort, doesn’t mean you can’t eat dinner at one! Reel Burger is the hotel restaurant located in Amara Cay Resort. You can choose to eat inside near the lobby or order your meal at the poolside tiki bar that overlooks the ocean. The restaurant is open to the public and staff welcomes you just like you were a guest. The only difference is that you can’t partake in the amenities such as kayaking, paddle boarding, or swimming. Still, you’ll feel like you are living a life of luxury while eating fish tacos oceanside!

drinks at Amara Cay in Islamorada

Day 3 of 48 hours of Affordable Family Fun in The Upper Keys

Breakfast at Key Largo Conch House

A friend of mine suggested we try Key Largo Conch House and I’m so glad we did. This place was by far my favorite place to eat during our entire trip. The coffee was good, the kids loved their pancakes, and I loved the shrimp and grits. It’s the perfect way to end your trip to The Upper Keys.

Shrimp and Grits from Key Largo Conch House in Key Largo. Affordable Family Fun in the Upper Keys


Your 48 hours of affordable fun in The Upper Keys are officially over! Pack up and head home. One suggestion is to drive through Homestead instead of Miami. There are dozens of nurseries along the way that specialize in wholesale orchids. I can guarantee that you’ll never find a cheaper orchid!

cheap orchid in Homestead FL

What else is there to do in Islamorada and Key Largo?

The activities listed in this itinerary are just a starting point. There are so many other fun things to do in the area at many different price points.

Islamorada is known as the sport fishing capital of the world for good reason. If you like to fish, you’ve got to take a fishing trip on your visit. While this isn’t exactly an affordable thing to do, it’s definitely worth it if fishing is your thing.

Other activities include snorkeling, diving, swimming with the dolphins at Theater of the Sea, and sunset cruises. All of these are a little more expensive, but worth it if you have the money.

What you need to know about VRBO and Airbnb in The Keys

Many of the rentals in The Keys are house boats. While this may be fun for older kids, it’s something to think twice about with young children. If you have kids, pay attention when booking and make sure you are booking a place that is safe for small children. We had a hard time finding a place that wasn’t directly on water. While many people might want that for the view, it can be scary when you have multiple small children! We stayed at this this 2 bedroom condo in Key Largo for $165 a night.

Have you been to The Upper Keys? What affordable fun do you suggest?

Affordable fun in Islamorada and the upper keys. #affordablefamilytravel

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