Exploring Key West's Most Captivating Tours

Key West Tours

Visitors to Key West are often very excited to arrive and to get out, stretch their legs and walk around. Our Conch Republic is certainly compact enough to explore on foot and you can also hop on a bike or a train, just as well. Our concierge is more than delighted to help plan your stay and we encourage you to discover all the pleasures of niche tours to help you live like a local during your stay in one of our Key West Vacation Rentals.

Conch Train Tour

Climb aboard and embark on a captivating journey through our rich history as our train tour takes you back in time from the era of settlement through the flourishing railroad days, the challenging times of the Depression, and the unwavering patriotism during World War II. This immersive experience comprises 12 convenient stops for the trolley, strategically designed to showcase an array of shopping, dining, attractions, and significant sites. With trolleys visiting each stop every 30 minutes, you can "see what you want when you want," perfectly catering to your style.

Your ticket to the Hop-On Hop-Off tour grants you unlimited access throughout the day, allowing you to delve into the history, lore, and legends of Key West at your own pace. The train tour itself spans approximately 90 minutes, encompassing a full loop through Old Town and making three designated stops. It offers a fantastic opportunity to marvel at the sights and a captivating narrative of Key West's lore and stories, ensuring an entertaining experience for all passengers. So, come aboard and join us for an unforgettable exploration of Key West's captivating past.

Snorkeling & Diving Tours

What better way to enjoy our Key West sunshine than to dive right in? Key West has a wide array of watersports — from snorkeling and parasailing to jetting around on WaveRunners. Add a full-day catamaran excursion and make a day of it with full breakfast and buffet options as dolphins frolic alongside. Fort Zachary Taylor is perfect for snorkeling close to shore. It’s widely considered to be the best beach in Key West. It's located at the southernmost tip at the end of Southard Street on the Truman Annex. The historic fort was built in 1866, and the snorkeling is just as amazing as the structure. A naturalist’s escape to the Dry Tortugas is highly recommended. Visitors never tire of the beautiful sandy beach surrounded by turquoise waters. The warm shallow waters make it easy to experience thriving coral while spotting sea stars, queen conchs, and other marine life. You’re very like encountering a sea turtle or bottlenose dolphins, too. Best of all, if you make the trip on the ferry, they provide complimentary masks, snorkels, and fins! Water activities guides also host several types of tours for groups. We recommend the double dip. It’s a tour that lasts about three hours, and their catamarans take you to two different reefs. Guests love boats with a stairway to the sea for ease of entry and exit, freshwater showers on board, and shaded lounge areas. They also provide complimentary snorkel gear, snacks, and beverages.

 Butterfly Cottage

Sunset Cruises

To upgrade your Key West visit, make it something really special. Experience the magic of our sunsets without the crowds. What better way to get your island groove than out on the sea chasing the sun? Opt for a popular cruise with live music and lots of tropical food and drink. There are also small group sailings with wine and cheese pairings, champagne tastings, and specialty cocktail menus. Romance the seas aboard a schooner, catamaran, a motor boat, or a luxury yacht. The captains and their crews will set the perfect course for some of Key West’s most scenic hideaways with breathtaking views. Picnic lunch on a private island, snorkel with some of the most beautiful sea creatures, and experience our beautiful coral reefs while waiting for the sunset.   

Key West Food Tours

Key West is the best place to enjoy Floribbean cuisine and enjoy a foodie adventure. Since, at various times, there have been European, Asian, and African influences along with those from the Caribbean and Latin America, there's something for everyone. Sample our food and culture by booking a small group tour. Start by joining a sip and stroll through Key West's craftiest bars and hidden spots while enjoying local cocktails and food. Savor the flavors of the ocean with a guided tour that also highlights our maritime history and influences. Neighborhood walking tours will sate your appetites for Victorian homes, shotgun, and conch-style homes. There are even special tours designed around the delights of Jimmy Buffet and the grand adventures of Ernest Hemingway.

Seaplane Tours

Flying in an amphibious seaplane allows guests to have the capability of landing on water, as well as on land. Private charters to and from Marathon and Islamorada are a common choice. Flying at a low-level above the water allows amazing opportunities to see wildlife in the water such as turtles, rays, dolphin, hammerheads, and tarpon. Additionally,  other sights above the water include Old Mallory Square, Fort Zachary Taylor, The Southernmost Point of The Continental U.S., Sunset Key, Christmas Tree Island and Sand Key Lighthouse at the reef. We highly recommend the ultimate experience to see the Dry Tortugas and Ft. Jefferson

Hemingway Home Tour

The Ernest Hemingway Home was the American residence of Hemingway during the 1930s, and it's the most popular tour in Key West. Start with a guided tour and then enjoy full access after with full access to the house, the gardens, and Hemingway's actual writing studio. Be inspired to write your masterpiece in the same space where he wrote so many. See a wall display of the Pilar and many photos of Hemingway’s fishing adventures. The museum is open every day of the year, and you can purchase tickets right at the gate.


Sunshine and Shenigans

Plan Your Key West Vacation


Booking your Key West Vacation Rental is just the beginning! Historic Key West Vacation Rentals is here to help you plan the rest of your vacation. Our little Key West island offers endless fun-filled activities such as water excursions, historical tours, fishing charters, and transportation options for your vacationing pleasure. Our experienced, friendly and super knowledgeable concierge specialists have a flair for elevating your Key West experiences. We'll provide just the right personal touch to your experiences and assist you with your individual needs. Our concierge services are complementary no matter which of our luxury vacation rentals you choose to stay in. Select Butterfly Cottage from our nightly collection, Serene Lily from our weekly selections, our brand new monthly rental Sunshine and Shenigans or The Truman Suites grouped in a private compound with shared amenities like its gorgeous pool and an outdoor deck for your team-building group or family and friends. They also provide the perfect accommodations for your destination wedding party.

The Truman Suites


Our Key West rentals are refined and luxurious, and our team is more than happy to recommend Key West's most exciting adventures and tours. How soon can you get here?