Take A One Day Road Trip to Islamorada, Florida Keys

Heading south for a break from winter becomes the popular play for many travelers as winter approaches in the north. For east coasters in the US it often means trips to Florida, the sunshine state.  Such trips do not need to stick to beaches around the selected airport or the magic found in Orlando, but can go beyond the mainland with a road trip to the Florida Keys.

US1 to the Florida Keys

Driving Jew Fish Creek Bridge into Key Largo, FloridaKeys

Driving into the FloridaKeys

Decide to take one of America’s most beautiful drives and road trip to the Florida Keys. To start rent a car in Florida in advance, pick it up at Miami or Fort Lauderdale Airport after arrival and head further south.  Don’t just visit the local Fort Lauderdale Beaches or explore  things to do in Miami but keep driving further south and take US 1 down to the Florida Keys and visit Islamorada for the day.  Such a trip might call for the upgrade to the convertible for the open views of the water on the drive and definitely make sure one purchases the sunpass option. Cash is no longer accepted on the Florida Turnpike the fastest way to the islands.

On a Florida Keys road trip most people head straight all the way through to Key West and look for a Maragritaville moments, but that is over a 150 miles from Miami. So, perhaps just take one day and do less distance and explore more of upper Florida Keys to get a different, closer experience driving just a few miles for each stop.

Welcome to islamorada, Florida Keys

Welcome to Islamorada

Directions in the Florida Keys are given with either Ocean (Atlantic Ocean) or Bay (Florida Bay) side and also with a mile marker (mm). The end of the road is mm 0 and that is located in Key West. On this road trip adventure we are staying in Islamorada and traveling from mm88 and mm77. It’s just an eleven mile stretch, but make sure you give yourself time as traffic, single lane driving and slower speeds (45mph) make a few miles take a little longer than probably expected. Remember this is island time.

No worries though, the ride is often scenic especially if you rent that convertible as the views of the water over the bridges will be worth any delays.  And when you decide to do it, here is just one great way to spend the day.

Visit The Rain Barrel

betsy the Lovster outside the Rain Barrel, Artisan shps in Islamorada, Florida

Time: 9am-10am. Place: Rain Barrel at MM87 (Bayside)

Walk through to visit local artist creations and also browse the many “keyzie” trinket collections that serve as reminders for living a “life on the rocks” here in the islands. Stop by the local coffee spot and order a Cuban style coffee too to perk up for the adventures ahead and of course, don’t miss the chance to capture a picture of Betsy, the local iconic Florida Keys Lobster. She is a tourist favorite.

Eat Your Way through the Florida Keys with a Food Tour

Florida keys Food Tour in Islamorada, Florida Keys

Time: 10:30am-2:30pm; Place: Meets behind Islamorada Library at mm 81 (Bayside)

A great way to experience any destination, especially for first timer visitors, is through its local food tour. In Islamorada the Florida Keys food tour provides tastes of local cuisine, shares the unique history of the Florida Keys and even discusses the many Bloodline scenes shot on location for fans of the Netflix drama. A two mile hike or rather stroll never tasted so good with multiple stops in popular restaurants for plenty of locally famous food including dishes appearing on Guy Fieri’s Diners, Drive-?Ins and Dives and its local award winning craft brewery.

Feed the Tarpon at Robbie’s

Robbies in Islamorada, Florida Keys

Time: 3:30-5pm; Place: Robbies Marina located at mm77 (Bayside)

After the food tour head a little bit further down the road to Robbie’s to take in local Keys artisan shops. Here is a second chance to find souvenirs for family, friends or even a few personal items to serve as a reminder about living the good (island) life.  After the shops, head to the marina to purchase a bucket of fish to feed the gigantic tarpon. Get down close to the water and reach out over the dock. Then let the fish jump from the water and take the bait. Although the fish are monster sizes, their lack of teeth makes it safe if someone can actually not flinch and leave there hand out over the water. Also when the pelicans are in town, definitely don’t leave the buckets unguarded.

A Kayak shack at Robbie’s provides the option to rent paddle boards or kayaks. It’s a unique paddle back into the mangroves. Guided tours are also available including a sunset kayak.

Catch the Sunset at Marker 88

sunset at marker 88 in inslamorada, Florida Keys

Time: arrive 30 minutes prior to Sunset; Place: Located at mm 88 (Bayside)

Prefer cocktails, dinner and the local island music vibe over for sunset then give oneself a little time to get to a local bayside restaurant. As to where to go, well no one in the Florida keys is without opinions but one place high on many lists in Islamorada  because of its setting (adjacent to a small beach) is Marker 88.

Plan an early (prior to the sunset) arrival and take the first cocktail on the beach. Enjoy any wait time. Here visitors can put their toes in the sand or dip them into the crystal clear water and can watch the sunset from Marker 88 even before sitting for dinner. As to what to order, local fish of course.

That’s a great way to spend a day road tripping to the Islamorada in the Florida Keys, but there is plenty more to do and see as one day is never enough to take it all in. Next time rent the car for a few days to spend the night or longer.  But be careful when some people stay longer, they may end up moving here. Trust me it happens, I know.

Stay Road Tripping, Craig

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