Home 5 Itineraries 5 A romantic road to paradise

A romantic road to paradise

8 Days

4 Cities

6 Experiences


Couple | Epicurean | Honeymoon | Wildlife

Travel Itinerary

Day 1

Private transfer from airport to hotel

Fisher Island Club ★★★★★ (2 nights)

Rest of the day at leisure to enjoy the surroundings

Private Art Deco & Cocktail tour

Experience the history and glamour of South Beach on this relaxed indoor tour. Your guide will take you back in time to the transformation of South Beach from swampland to a playground for the wealthy. Get exclusive access to gorgeous lobbies and stunning panoramic rooftop views. Listen to captivating stories about history, unreliable heroes, the influence of the mob, and Hollywood, and gain insight into the rise of Art Deco, the elements, and design all while sipping on a signature cocktail.

Art deco glass containing a refined cocktail topped with an orange quarter.
Day 2

Little Havana Food & Cultural tour

Discover the vibrant culture and rich history of Miami’s Little Havana neighborhood. Immerse yourself in the unique Cuban atmosphere of this “national treasure,” recently recognized by the National Trust for Historic Preservation. Explore its historical, political, and artistic contributions to Miami’s culture, nestled in the downtown area just a short drive from South Beach, and uncover fascinating cultural landmarks along the way.

Boat tour to Siltsville

Join this 2-hour Biscayne Bay Adventure Tour to explore historic Stiltsville in Biscayne National Park. Discover seven colorful houses on stilts, once speakeasies during Prohibition. Learn about its intriguing history, from rumored connections to Al Capone to its designation as a top tourist destination. Dive into Stiltsville’s past, now incorporated into Biscayne National Park since 1968.

Day 3
Key West

Pick up car in Miami

Drive to Key West (about 4hrs)

Parrot Key Hotel & Villas ★★★★ (2 nights)

Sunset Sail tour in Key West

The perfect end to your island day with a sunset sail in Key West. Escape the crowds and capture the magic as the captain and mate raise the sails, shutting off the engine for a serene journey into the sunset. Enjoy the romance and charm of sailing through Key West harbor, past Mallory Square, and across the Gulf of Mexico to the Atlantic Ocean. Whether you take the wheel or simply take in the sights, let the sea stories of our crew transport you to distant horizons.

Day 4

Day at leisure to explore Key West on own

Explore Hemingway’s residence where he spent over a decade writing. Experience his lifestyle at two iconic Key West spots: Sloppy Joe’s Bar, frequented by Hemingway for rum tastings, and the La Concha hotel terrace, a favorite haunt of Tennessee Williams. Don’t miss the stunning sunset at Mallory Square.

Day 5

The Moorings Village ★★★★ (1 night)

Day 6

Airboat safari in Everglades Park

Join an exciting wildlife safari in the famous Everglades Park, a World Heritage Site. Climb aboard a small ultra-fast boat designed to navigate on this unparalleled landscape, and for close encounters with rare and endangered species like alligators, manatees, panthers, and flamingos. Explore the thrilling Gator Island and observe reptiles sunbathing lazily while expert guides provide insights into their behaviors and habitats.

A boat sailing through a swampy area of the Everglades Park.

Inn on Fifth ★★★★ (2 nights)

Day 7

10,000 Islands Ultimate Shelling Kayak adventure tour

Experience a rare kayak journey into the Ten Thousand Islands, exploring vast ocean floors and tranquil tide pools during optimal tides. Discover abundant seashells and rare marine life like colorful sponges, starfish, and sea urchins. Spend 1.5 hours dedicated to shelling and exploration on a remote island accessible only by kayak, while also spotting dolphins, manatees, sea turtles, and tropical birds for an unforgettable adventure.

Rest of the day at leisure to stroll on the beach of Naples and its pier

Day 8

Drop off car at Miami airport

Fly home