Key West Historic Seaport

Discover Key West’s Florida Marine Sanctuary on a boat tour. Explore the lush mangroves on a guided kayaking excursion, relax on a sandbar, and enjoy a tasty lunch with unlimited drinks. Hop onboard the boat and cruise through the crystalline waters of the Atlantic Ocean as you head toward the marine sanctuary. Keep a lookout for dolphins and sea turtles as you travel. Start with a guided kayak tour through the mangrove islands, keeping a lookout for local wildlife, with over 500 unique marine species in the area. Then, venture further into the wildlife sanctuary to a secluded sandbar. Enjoy a tasty lunch with options such as fresh local Cuban sandwiches, fried chicken tenders, veggie wraps, fruit and veggie trays, cheese and cracker platters, and pita and hummus platters. Help yourself to unlimited draft beer, wine, and soft drinks that will be available after lunch. At the sandbar, use the paddleboard or kayak to discover more of the area, go snorkeling, or just sit back and relax. Finally, relax on the return journey back to Key West.

Discover Key West on a day tour from Miami. Take 6 hours of free time to discover some of the highlights of the city including Duval Street, Mallory Square, the historic seaport, the Hemingway House, or the Fort Zachary Taylor State Park. Depart from Miami and travel along US-1. Admire beauty of the Everglades and the Florida Keys. Marvel at the iconic 7 Mile Bridge in Marathon, a testament to Henry Flagler's engineering prowess. Once in Key West, you'll have around 6 hours of free time to explore the area. Walk down Duval Street, the main street in Key West known for its vibrant nightlife, shopping, and dining options. Chill out in Mallory Square, a popular spot to watch the sunset and see street performers. Explore Key West Historic Seaport with its waterfront restaurants, shops, and boat tours. Visit the Hemingway House, the former home of author Ernest Hemingway, now a museum that offers tours of the property. Head to the Key West Cemetery, known for its quirky headstones and interesting history. Stroll through the Fort Zachary Taylor State Park with its beach, picnic areas, and a Civil War-era fort to explore. Visit the Key West Butterfly and Nature Conservatory, a beautiful indoor garden where visitors can see a variety of butterflies up close. Enjoy a photo stop at Southernmost Point Buoy, the southernmost point in the continental United States. Discover the Dry Tortugas National Park, a remote national park accessible by boat or seaplane, known for its pristine beaches and historic Fort Jefferson. Explore the Key West Aquarium, home to a touch tank and exhibits showcasing local marine life. After a day of exploration, relax on the return journey to Miami.

Celebrate Key West's diverse and abundant local fruits of the sea. This 3-hour guided small-group experience stops at 5 tasting locations, each carefully chosen to give you an eclectic view of Key West's best restaurants along the historic seaport. Enough for a hearty lunch, tastings are served from adored local eateries, tucked-away hidden gems, and a fisherman-owned seafood market. This tour will allow you to bypass the Duval Street tourist traps and go straight to the spots that the locals frequent to eat, drink, and discover the island. As you stroll the charming side streets and docks, you will experience the island’s seaport, as well as the rich industrial history which has transformed through the generations. Your friendly and knowledgable local guides will share stories of local industry, including the colorful past and historical landmarks. Following the tour, you can explore Old Town with confidence and take advantage of recommendations on restaurants, attractions, entertainment, and cultural offerings. You'll also receive a collection of exclusive recipes, ensuring that you can enjoy memories from this tour for many years to come.

Embark on a tour around the island of Key West. Your guide will be talking you through many points of interest around the island including Sunset Key, Mallory Square, and the A&B Marina. Make sure to keep an eye out for wildlife throughout the tour. About 20 minutes before the sunset, your captain will find a quiet and private spot to watch the sun drop into the water uninterrupted by other boats, people, or land! We have a cooler stocked with ice and bottled water and enough space for any food or drink you want to bring along.

Discover the life of Ernest Hemingway while he lived in Key West on this guided walking tour. Uncover where the author lived, worked, and played. Stop to try three different samples of Key West cuisine as you walk.  Meet your guide at the front gate of the elegant residence where the author lived during the 1930s, Hemingway House. Make your way to get some local treats to help energize you for your walking tour. Try some delectable food like grilled chicken caeser wrap, bean salad with mango poppy seed dressing, and Kermit's famous key lime pie. Find out where he watched and refereed boxing matches. See where he kept his boat the Pilar. Capture pictures of the bookstore where his books were sold. Stroll by his first apartment in Key West where he finished writing “A Farewell to Arms.” Make another stop visiting where the author used to catch the train. Observe where he used to fish and charter boats. Finally, head to Sloppy Joes which was a favorite watering hole for the writer. 

Key West’s Most Secluded Kayak & Sandbar Adventure – A Hidden Paradise Awaits! Step off the beaten path and into the untouched beauty of Key West’s backcountry on this one-of-a-kind kayak and sandbar adventure! Forget the crowded roadside rentals—this exclusive tour transports you by boat to the remote Mud Keys, a hidden gem deep within the Florida Marine Sanctuary. Paddle through winding mangrove tunnels, discover vibrant marine life, and experience the serenity of this protected paradise before unwinding at a stunning sandbar with unlimited drinks and lunch. What’s Included in This Epic Adventure? Scenic Boat Ride to a Remote Kayaking Spot – No roads, no noise—just miles of open ocean and backcountry beauty. Keep an eye out for dolphins, sea turtles, and exotic birds along the way! Guided Kayak Tour Through the Mangrove Tunnels – Navigate the intricate waterways of the Mud Keys, where stingrays, tropical fish, and other marine creatures thrive in this unspoiled ecosystem. Wildlife Encounters at Every Turn – From tropical fish gliding beneath your kayak to playful dolphins surfacing nearby, this tour offers once-in-a-lifetime sightings of Key West’s most incredible wildlife. Sandbar Escape – The Ultimate Island Getaway – After kayaking, we’ll cruise to a secluded sandbar, where you can relax in crystal-clear waters, snorkel, paddleboard, or float on a lily pad with a drink in hand. Unlimited Drinks & a Delicious Lunch – Sip on ice-cold beer, wine, mimosas, and soft drinks as you soak up the sun and indulge in a fresh island-style meal. Why This Tour Stands Out from the Rest No Other Company Goes Here – This is Key West’s ONLY guided kayak and sandbar tour to the Mud Keys. You won’t find this experience anywhere else! No Crowds, No Roads – Just Pure Backcountry Bliss – Escape the hustle of downtown Key West and step into a true hidden paradise. Perfect for All Skill Levels – Whether you’re a first-time paddler or an experienced kayaker, this easy, guided tour is perfect for everyone. An Authentic Key West Experience – This trip blends adventure, relaxation, and stunning scenery, making it a must-do for nature lovers and thrill-seekers alike. If you're looking for an off-the-grid Key West adventure where you can truly immerse yourself in nature, explore untouched waters, and enjoy a laid-back sandbar party, this is the tour for you!

The absolute best way to begin your day here in Key West is on the open water, with a warm tropical breeze filling the sails of a gorgeous traditional sailing schooner. Accommodations on the Appledore II are spacious. At 18' wide and no more than 49 passengers, there is plenty of seating and room to spread out. Commissioned as the second boat by the Smith family in a series of Appledores built for global exploration, she has all the amenities of a modern passenger windjammer. With Key West's Historic Seaport receding in the background, take a deep breath of fresh sea air and feel completely relaxed and invigorated at the same time. Take a turn at the wheel and see what it feels like to be a captain of a schooner. And if you always wanted to hoist sails on a tall ship, this is your chance. Sip cocktails and soak in your tropical surroundings. There is no better way to start your day in paradise! While enjoying your sail remember there is plenty to see on the water's surface or circling in the blue sky above you. Perhaps an osprey will plummet down to the water to catch its lunch or a pelican will make a splash landing near the schooner. A pod of dolphins may surface or you might spot a turtle floating by. New this season - Now we're also featuring cocktails in our all-inclusive price. Sails up with a Schooner Appledore signature Bloody Mary or Dark & Stormy. Request your own favorite cocktail from our treasure chest of top-shelf brands. Complimentary champagne and mimosas are served as well as poinsettia cocktails, premium beers, soft drinks and water to complete this upscale morning sail. So relax in your tranquil surroundings. Spread out and soak up the rays of our tropical sun.