The Key to the Perfect Road Trip

An eerie calm falls overhead before the next roll of thunder. I’m in a double kayak, paddled by the arm power of my son, Mark, as we glide through giant mangroves. It’s a balmy 32 degrees in The Florida Keys and I’m completely out of my comfort zone and thrilled at the same time.


Bill Keogh leads our expedition around Big Pine Key and carries with him a wealth of wisdom about the local wildlife. A giant insect claws his way up the mangrove stalk looking remarkably like a tarantula spider with black furry legs but Bill insists the mangrove crabs are completely harmless. We see fish jumping out of the water and a barracuda slithers over the coral – the odd shipwreck makes navigation even more interesting. It’s possible to book a tour online with Bill who provides all the equipment needed.

Postcard Inn

We started our road trip at Islamorada with a stay at The Postcard Inn. This charming hotel is set on the waterfront with 151 beach-chic guestrooms, suites and cottages, three restaurants, including the historic Holiday Isle Tiki Bar, made famous for its creation of the original Rum Runner cocktail. The Ciao Hound sets us up for the day with a slap up breakfast and the hotel’s Raw Bar restaurant offers incredible views.  Postcard Inn

As we cruise down the 113 mile long Highway One, ending at Key West, we have lots to see along the way. With only one road in and out of the Keys there’s no need for GPS and this cuts out the usual family navigating arguments. Our first night we eat at chef Michaels, famous for amazing seafood. I asked for a collection of yellowtail snapper and barracuda. Portions are large as to be expected and we found hogfish and lionfish on the menu too – making the Florida Keys, a great foodie destination too.

Robbies of Islamorada

We wake the next morning in preparation for another boat trip, which involves first having lunch at Robbie’s of Islamorada. The Hungry Tarpon Restaurant is decorated with dollar bills outside the bar and for $5 we buy a tin can of small silver fish to feed the large tarpon fish that hang around the marina. The waters are crystal turquoise making it easy to see the coral and array of colourful fish below and we can’t wait to get on to the water.


Sundance Watersports have been operating from Robbie’s Marina since 1995 and offer some of the best snorkeling on the keys. We hop on board the catamaran, ‘Blue’, as Captain Luke first gives a safety talk and with his crew. We sail for an hour and a half out to Alligator Reef where the boat anchors next to coral and we see angelfish, butterfly fish, parrot fish and a barracuda.

While Mark joins those brave enough to dive down a little further to see the perfectly friendly nurse sharks I get an ecology lesson from Captain Luke. The coast line is covered in places with a species of seaweed called Sargassum that trawls the Caribbean. Captain Luke gathers a small bucket of the mustard coloured algae where tiny crustaceans harbour and explains how this food is nutritious for some in the eco-system. The trip makes a great day out with music and plenty of opportunities to sunbathe on deck with no alligators!


Fishing is one of the most popular activities on the Keys, a tour takes between four hours but ideally lasts a full day. It’s no surprise that Ernest Hemingway opted to stay here and enjoy the fishing for 8 years while passing through in 1933. His house in Key West is a big draw for book lovers and anyone interested in history. Scattered throughout this charming shutter clad residence the six toed cats laze in the sunshine. There’s no mistake this is their domain and all descendants of Snow White, a six-toed cat Hemingway gave to his son that he found at the local naval base. Joe DiMaggio is the current alpha cat of the fifty four that scour the estate and he takes pride of positioning sprawled across Hemingway’s double bed, covered in a cream damask quilt. For me as a writer the big thrill was seeing the novelist’s study and collection of hats and artefacts that he gathered from around the world. The museum is open every day and includes a twenty minute tour.


Hemingway set his novel, To Have and Have Not at Sloppy Joes Bar, and today its walls are covered in fishing photos and Hemingway memorabilia. It’s a hopping spot for young and old and after dinner we dance to rock classics performed by Dirk who has control of the stage and crowd. His bucket overflows with five and ten dollar bills in appreciation of the atmosphere he creates. Although this isn’t the original building where Hemingway caroused many nights away the Blue Heaven down on Front Street is still intact. The stage where Hemingway refereed boxing bouts now hosts bands and with a quirky craft shop and excellent restaurant serving the very best Key Lime Pie, makes it a must visit. Apparently Key West goes all out at Halloween making it a great time to visit and get into the spirit with full on spooky costumes.

Key West Boutique

Key West is a hive of activity day and night making parking difficult, so we stayed on Stock Island Marina close by at The Perry Hotel. The 100 room boutique hotel is decorated with smooth wood finishes with rustic metal details that recall the area’s iconic maritime heritage. Located beside a state-of-the-art 288-slip marina, the pool deck overlooks the working waterfront and is an oasis of calm with stylish bedrooms. Offering shuttle service throughout the day and evening to Key West it left us free to explore at leisure.


Key West celebrated 200 years in 2023. To get our bearings the conch train tour is good fun and passes by the most Southern point in The United States. It sets off beside Mallory Square where locals and tourists flock in the evenings to watch the sunset. Effigies of people who played an important role in the story of Key West are commemorated here. Tennessee Williams is among the famous busts along with the 33rd US president Harry S Truman who made the little White House down the road a regular point of retreat in the fifties. Since 1890, history has left its mark on the Truman Little White House. Initially it served as the naval station’s command headquarters during the Spanish-American War, WWI and WWII.

In 1946 the historic building first served as the winter White House for President Harry S. Truman and by later presidents during Cold War responses. Today, the House is a public museum, retreat and place of government business by United States leaders.

On the Water

One of the highlights of Key West is Sunset Sailing on Danger Charters. Not only do we get to watch the sun go down on a massive schooner, we are given a taste of wines from around the world accompanied by tasty tapas. The cumulonimbus cloud resting above the horizon in the distance put on a great show with fork lightening while we dance on deck to Bob Marley and Abba. Certainly one for the bucket list and no doubt I’ll be dragging it out from the memory chest in the future.

Great Food

Marathon is a great base to explore the Florida Keys located around mile marker 60. From there it’s not far to Duck Key where we enjoy our highlight meal of the trip at Angler and Ale overlooking Hawks Cay Marina. The menu focuses on the quality and freshness of its locally sourced ingredients with favorites including Whole Fried Snapper, Grouper Cheeks, Ceviche of the day, and Tuna Nachos.  Guests also have the option to ‘Hook N Cook’ where they can bring in their fresh catch of the day and have the chef prepare it that evening. All this is washed down with locally brewed ale and Mark and I agree it’s probably the best meal we’ve ever eaten in the USA.

Grassy Flats

We stay at Grassy Flats Resort and Beach Club on the last leg of our road trip. The oceanfront all-suite resort has private verandas and full kitchens, and offers two and three-bedroom suites. It’s an eco-friendly resort that promotes sustainability initiatives such as plant-based detergents, the exclusion of pesticides and herbicides from on-site gardens, and a seaweed composting program. The eco system is fragile but at Grassy Flats every effort is made to protect the unique asset that living so close to the water involves.

End of the Road

While Mark is bathing in the pool I sit next to the sargassum covered shore and look out at the cerulean blue sea. A tiny green lizard pokes up from behind a rock to keep me company while I scribble notes about our adventure. Maybe it’s Hemingway’s shadow hanging over me that inspires after our remarkable week. The Florida Keys are a wonderful destination for all ages and lovers of nature, wildlife and the water. I think we’ve found the key to the perfect road trip.


Michelle was a guest of tap air

For everything you need to know about The Florida Keys see

To travel on a similar package with Platinum Travel see

or call 01-8535000

7-night Florida Keys Road Trip with Platinum Travel

Travel September 2023
Inclusive Car hire for 7 days
2 at Postcard Inn, Islamorada
2 nights at Grassy Flats Resort 7 Beach club, Marathon
3 at the Perry Hotel in Key West
All airport taxes
24/7 emergency number throughout your stay

From €2075 per person

Flights included with TAP airlines via Lisbon.