Florida Keys: Marathon, Islamorada, and Key West

Florida Keys: Marathon, Islamorada, and Key West

Heart of Florida Keys

Fly in/out: Miami, Florida (MIA)

Recommended ages: Any

Ball Park Price: $1,000/person for up to five travellers (airfare not included)

Pace: Easy


Florida Keys Overseas Highway
Florida Keys Overseas Highway

DAY ONE: Fly into Miami International Airport , Florida (MIA) airport and drive the “Florida Keys Overseas Highway” or U.S. 1 to Marathon Key, Florida. (Approximately 1.5 hour drive). Check into house rental through VRBO, pick up keys at property management and check into home. Get provisions for house at Publix right on Overseas Highway in Marathon Key.

DAY TWO: Enjoy Marathon beaches and parks. Head over to Sombrero Beach for a rousing game of volleyball or Nukem, elimination style. Visit the Turtle Hospital on Marathon Key for a presentation and tour for extraordinary efforts to rescue and rehab turtles. Barbeque back at house.

DAY THREE: Take a Catamaran snorkeling tour on Spirit Snorkel to Sombrero Reef. When riptides are not too strong, the reef is quite beautiful. Head to Hungry Tarpon on Islamorada for incredible tarpon feeding experience where kids feed the crazy tarpons as they clamor and fight for their dinner. Then enjoy dinner at Hungry Tarpon’s outdoor deck.

Key West - Southernmost Point

DAY FOUR: Drive one hour south and spend a day on Key West and explore the Southernmost point in the United States. Shop on Duval street, stop for ice cream, visit the Hemingway Museum, Ripley’s Believe It or Not, and other highlights listed here. Towards sunset, enjoy dining and entertainment on Mallory Square watching fabulous street performers. Have dinner in the outdoor setting along the square at one of these restaurants.
(Make reservations especially for outdoor seating).

DAY FIVE: Spend ½ day fishing with Sea Squared Charters. Take advantage of the “Cook Your Catch” program offered through Sea Squared Charters and take your catch of the day to any recommended restaurants. Total hoot for kids and adults.

DAY SIX: Rent a boat through Captain Pip for exploring the bays and reefs off Marathon Key. Watch families of dolphins swim next to boat. Head to Islamorada for an outdoor dining experience on a white sand beach at Morada Bay Beach Cafe.

DAY SEVEN: Drive back to Miami International Airport and head home.

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Vacation Highlights

  • Called the boating and family destination of Florida, Marathon Key is a nice central location to enjoy all the Keys. Marathon is a 10 mile stretch of Island that has a homey feel with many locals living on the key. However, it has a lot to offer for a one week vacation. Marathon and the Keys are also easy to navigate and difficult to get lost as most landmarks are located directly on U.S. 1 or Overseas Highway. If you pass the point though, you may be stuck on a 7 mile bridge to turn around.
  • Sombrero Beach, in Marathon, is well maintained and is larger and considerably nicer than other beaches in the Keys. Sombrero Beach has a beachfront park, picnic facilities, a playground, and a protected cove for children.
  • There are many fishing and snorkeling charters available for Sombrero reef one of the best snorkeling areas for the Keys. The snorkeling was very good for kids once we had cooperative weather. Another highlight was renting our own boat to swim off the side and visit harbors and remote islands.
  • You can’t miss Key West, it’s literally at the end of the road. Walking down Duval Street, renting bikes, stopping at a rooftop restaurant and finishing the day watching the street performers at dusk was very entertaining.

Florida Keys Vacation Destination

Great Excursions

  • If your family is a turtle advocate, you’ll be impressed with the efforts of the Turtle Hospital in Marathon. The kids developed a great appreciation of the great cause in rescuing giant sea turtles and learning about the incredible work this hospital does.
  • We really enjoyed our full boating day on our own. It was so easy to rent a nice pontoon through Captain Pips and explore the Keys. We saw beautiful islands, reefs and playful dolphins throughout the boating adventure.

Explore Florida Keys

Places to stay

    Marathon Key Rental House

  • After searching extensively for a rental in Key West, we were really thrilled to stay on Marathon Key for it’s central location and slightly more economical choice. Our rental had all the amenities needed for a great spring break vacation with tons of space and sleeping options. The pool was a little small, but the kids didn’t seem to notice. We enjoyed the screened in porches and eating areas. The rental company was easy to work with.
  • Another option for a great rental that a friend stayed at with beautiful views but slightly smaller pool was found on VRBO.
  • A fabulous alternative to a house rental on Marathon Key is Hawks Kay. Not only is it a beautiful resort, they have special accommodation villas for families with special needs.


Hungry Tarpon

  • We enjoyed the “Cook Your Catch” program offered through Sea Squared. They will arrange reservations and send the fish forward.
  • The Hungry Tarpon restaurant was all about the experience of feeding the tarpons in the back of the restaurant.
  • We enjoyed the Morada Bay Beach Cafe right on the beach with a gorgeous sunset, great for family picture ops too. The restaurant also has a nice kids menu.


Key West Marina
Key West Marina
  • There are many house rental options in Marathon Key and there really isn’t much of a chance to get a “bad location”. Do negotiate your rental price even if you are renting in peak season. Ask for extra fees (like heating a pool) to be included.
  • Plan your Key West excursion during the weekday at Mallory Square if possible. The entertainers are still there but not quite as many crowds. Often the weekends have multiple cruise ships at the port which can make Key West very congested.
  • Jet ski rentals and kayaks are also available at different locations along the keys. To help select the right rental, try this directory of Marathon watersports.
  • Make reservations for your special dinner locations to avoid longer waits. During peak season, the outdoor seating restaurants can get quite crowded. Make your reservations on Opentable.com for your best selection.

Before You Go

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