Recommendations

Welcome to Old Town Manor, where your Key West experience is our top priority. Our dedicated concierge team is here to ensure that your visit is filled with unforgettable moments tailored just for you. Let us take the reins and guide you through the vibrant tapestry of Key West, curating unique experiences that resonate with your interests and desires. Whether it’s exploring the island’s hidden gems, embarking on a culinary journey through local flavors, or discovering the best-kept secrets of the vibrant nightlife, our knowledgeable and passionate team is committed to crafting a personalized itinerary that reflects the essence of Key West and your individual preferences. Allow us to turn your vacation dreams into reality, and immerse yourself in the magic of Key West with the help of our expert concierge service.

Key West Bike Rentals - WeCycle

WeCycle – Bike Rentals

For our guests, renting a bike for your stay in Key West aligns with who our guests are for several reasons. The island’s compact size and flat terrain make it incredibly bike-friendly, allowing visitors to easily explore the area’s numerous attractions, beautiful beaches, and vibrant streets at a leisurely pace. By opting for a bike, our guests can bypass the hassle of parking and traffic, immersing themselves in the island’s laid-back atmosphere while enjoying the fresh ocean breeze. Additionally, biking provides a more intimate and authentic way to experience the local culture, affording the opportunity to stumble upon hidden gems, quaint neighborhoods, and stunning viewpoints that might be missed. Moreover, with free bike delivery and bike racks on the property, a bike rental is convenient and affordable, offering our guests the freedom and flexibility to tailor their exploration to their preferences and schedules. There are bikes on the property that can be rented by the hour using the following app, or for all-day or several-day rentals we can have your bikes delivered here on the property before you arrive.

Key West Art and Historical Society’s Cultural Pass

KWAHS – Cultural Pass

The Key West Art and Historical Society’s Cultural Pass offers our guests a comprehensive way to explore the rich cultural heritage of the Florida Keys. This pass provides access and value to four unique museums, including the Custom House Museum, Fort East Martello Museum, Key West Lighthouse and Keeper’s Quarters, and Tennessee Williams Exhibit. By offering a single ticket for multiple attractions, the Cultural Pass encourages individuals to immerse themselves in the diverse history, art, and literature of Key West, fostering a deeper appreciation for the local culture. Whether delving into the island’s maritime past, discovering the works of renowned artists, or exploring the legacy of influential literary figures, the Cultural Pass provides a convenient and enriching experience for all who wish to engage with the vibrant tapestry of Key West’s cultural identity.

Enjoy even greater value with a 20% discount by using our special code for our guests OTMVIP23

Sunset Sail Key West – Private Sunset Sail – 6 passenger

A private sailing charter offers our guests an unparalleled opportunity to experience the breathtaking beauty of Key West’s waters and indulge in a truly personalized and intimate sailing experience. Whether it’s a romantic sunset cruise for two or, a lively celebration with friends, the professional and friendly crew ensures that every detail is tailored to perfection. From the moment guests step aboard, they are treated to unparalleled views of Key West’s famous sunsets, crystal-clear waters teeming with marine life, and the gentle sway of the open sea, making your private sailing charters an unforgettable and magical adventure.

Key West Live Music Sunset Sail - Fury Commotion on the Ocean

Fury Water Adventures – Commotion on the Ocean

1: Set sail on a state-of-the-art catamaran and embark on a high-energy, two-hour sunset cruise featuring live music, unlimited cocktails, beer, wine, and a selection of appetizers. As the sun dips below the horizon, the vibrant atmosphere comes alive with dancing, socializing, and breathtaking views of the Key West coastline. Whether you’re looking for a lively evening with friends or a fun memorable date night, the Live Music Sail promises an unforgettable memory and great photos.

2: Partaking in a live music sunset sail in Key West presents a harmonious blend of captivating melodies and breathtaking natural beauty, offering an unforgettable sensory experience. As the vessel gracefully glides through the tranquil waters, the soothing sounds of live music create an enchanting atmosphere, enhancing the already picturesque sunset views. Whether it’s the soulful strumming of a guitar or the rhythmic beats of tropical tunes, the live music adds a layer of magic to the journey, making it an ideal setting for relaxation, celebration, and connection. This unique fusion of music and nature provides an exceptional opportunity for guests to unwind, socialize, and immerse themselves in the moment, all while being surrounded by the radiant hues of the setting sun and the gentle embrace of the sea. A live music sunset sail in Key West promises to be a truly mesmerizing and soul-stirring experience, leaving a lasting impression on all who come aboard.

Key West Snorkeling - Fury Water Adventures Double Dip

Fury Water Adventures – Double Dip/Snorkel Trip

If your priority is snorkeling, snorkeling, or snorkeling, then this trip is right for you. This custom-built, powered catamaran gets you to the reef faster than all others and will allow you to visit locations along the reef on the same trip. See angel fish, parrot fish, blue tangs, and other aquatic life on the reef. Professional instruction, Snorkel equipment, reef same sunblock, Sodas, beer, and wine are included.

Danger – Half+Full Day Sail, Snorkel, Kayak; Wind and Wine Sunset Sails

Morning Sail, Snorkel & Kayak Excursion

Embark on a tranquil voyage aboard a historic schooner with our Morning Half Day Excursion in Key West, tailored for an exclusive group of 20 or fewer. Kickstart your day with a 4.5-hour adventure on our shallow draft schooners, immersing yourself in the pristine waters. Delight in the morning serenity as you partake in snorkeling, kayaking, and sailing, carefully curated for a memorable experience, regardless of your expertise. Luxuriate in the laid-back ambiance while savoring complimentary alcoholic and non-alcoholic beverages, complemented by a delectable spread of fresh fruit, chips, salsa, and hummus. This morning excursion sets the ideal tone for your day, blending the allure of historic sailing with the excitement of aquatic exploration.

Afternoon Sail, Snorkel, Kayak & Sunset Excursion

Embark on a leisurely adventure aboard a historic schooner with our Afternoon Half Day Excursion in Key West, limited to an intimate group of 20 or fewer. Glide through the pristine waters, indulging in kayaking and snorkeling, regardless of your experience level. Revel in the breathtaking Key West sunset as the perfect conclusion to this unforgettable journey. Choose this afternoon option for a slightly later start, offering the same delightful activities as the morning tour, including sailing, while relishing complimentary alcoholic and non-alcoholic beverages, along with fresh fruit, chips, salsa, and hummus. Immerse yourself in the ultimate relaxation and enjoyment, making it one of the best ways to cap off your day.

Premium Day Sail, Snorkel &, Kayak with Lunch

The Full Day Excursion is the perfect trip for you all that love being out on the water. It’s got everything the half day does and then some. We will spend plenty of time snorkeling as well as kayaking around one of the mangrove islands. Weather permitting we will stop at an island with a beach or a sandbar while taking in all the beauty of our Florida Keys Ecosystem. Between activities, we will provide a full lunch while you relax and take in some sailing. Beer, wine, water, sodas, and snacks are also provided.

Key West Wind & Wine Sunset Sail AND Stock Island Wind & Wine Sunset Sail

Experience the epitome of elegance with Danger’s Wind and Wine sunset sail, an opulent journey featuring an exquisite selection of fine wines and upscale beers from across the globe. Indulge your palate with bountiful hors-d’oeuvres, all while gracefully sailing beneath billowing canvas sails aboard our Historic Key West Schooners. Recognized by Coastal Living Magazine as one of the top two Sunset Sails in North America, Danger Charters’ Wind and Wine Cruise offers an unparalleled blend of sophistication and relaxation for those seeking an intimate sunset sail. Nightly, we present a curated selection of eight fine wines, including four reds, three whites, and a Champagnoise, making it a haven for wine enthusiasts seeking an authentic experience. In addition to the exceptional wine, a variety of quality beers and hors-d’oeuvres are served, ensuring that the evening becomes an unforgettable prelude to a memorable night in Key West.

Watersport trips Key West - Fury Watersports Ultimate Adventure

Fury Water Adventures – Ultimate Adventure

Embark on a thrilling aquatic adventure with the All Inclusive Water Adventure trip in Key West This action-packed excursion offers a unique opportunity to explore the stunning underwater world of the Florida Keys as well as an exciting array of water toys. The journey begins with a picturesque cruise aboard a spacious catamaran to the vibrant and ecologically diverse coral reef. Here, you can snorkel alongside an array of colorful marine life, including tropical fish, vibrant coral formations, and even the chance to encounter majestic sea turtles and rays. Following the reef snorkel, the catamaran sets sail to a shallow-water playground as you enjoy lunch and beverages. There you can enjoy adrenaline-pumping activities such as parasailing, Jet Skiing, kayaking, water trampoline, water slide, and many other toys. If you’re a thrill-seeker this promises a full day of adventure and discovery in the breathtaking waters of Key West and is guaranteed to wear you out.

Glass bottom boat Key West - Fury Water Adventures

Fury Water Adventures – Glass Bottom Boat

Climb aboard the enchanting Glass Bottom Boat in Key West for a mesmerizing journey through the crystal-clear waters of the Florida Keys. Led by knowledgeable guides, this immersive experience offers an up-close encounter with the diverse ecosystem, providing a captivating glimpse into the underwater world without getting wet. From spotting tropical fish darting through the coral to observing graceful sea turtles and other mesmerizing sea creatures, the Glass Bottom Boat trip in Key West promises a unique and educational adventure, making it the perfect experience for families, nature enthusiasts, and anyone seeking to explore the beauty of the ocean depths.

Lazy Dog – Kayak and Paddle Board Tours

Lazy Dog – Backcountry Charter

Key West Fishing Charter - Booya Charters

Booya Charters – Offshore and Inshore Fishing

Engaging in offshore and inshore fishing from a center console boat with a charter captain in Key West promises an exceptional angling experience, tailored to the preferences and skill levels of fishing enthusiasts. The versatility of the center console boat allows for seamless navigation through various fishing environments, from the rich offshore waters to the intricate inshore habitats, ensuring a diverse and rewarding angling expedition. With the expertise of a seasoned charter captain at the helm, guests can benefit from invaluable local knowledge and guidance, maximizing their chances of landing prized catches such as marlin, tuna, snapper, or tarpon. Whether targeting deep-sea giants or navigating the shallow flats, the combination of a well-equipped center console boat and a skilled captain creates an optimal platform for a memorable and successful fishing excursion in the bountiful waters surrounding Key West. After a memorable day fishing, the captain will filet your fish, and our Guest Service Team will help reserve a restaurant that will prepare and cook up your fish.

Hydro Thunder – Golf Carts and Scooters

Renting a golf cart in Key West is a fantastic idea for several reasons. The island’s compact size and relatively flat terrain make it perfect for exploring via golf cart, allowing visitors to easily navigate the narrow streets and access areas that may be difficult to reach by car. Additionally, with limited parking and congested streets in the downtown area, a golf cart provides a convenient and efficient mode of transportation, especially for short trips to attractions, restaurants, and shops. Moreover, the leisurely pace of a golf cart ride allows for a more intimate and relaxed experience, enabling travelers to soak in the island’s charming atmosphere and vibrant culture while enjoying the cool ocean breeze. Ultimately, renting a golf cart in Key West offers a unique and enjoyable way to explore the island at your own pace, providing a memorable and immersive experience for visitors of all ages.

Renting a moped/scooter in Key West offers a convenient and thrilling way to explore the island’s unique charm. With its compact size and limited parking spaces, a moped provides the flexibility to easily navigate through the narrow streets and discover hidden gems that might be missed by car. The slow pace of the island perfectly complements the leisurely nature of moped travel, allowing riders to soak in the stunning coastal views and vibrant atmosphere at their own pace. Additionally, renting a moped can be a cost-effective option for solo travelers or couples, offering an affordable and eco-friendly mode of transportation while embracing the carefree spirit of this tropical paradise.

Key West Scooter Rentals - Pirate Rentals

Pirate Rentals – Golf Carts and Scooters

Renting a golf cart in Key West is a fantastic idea for several reasons. The island’s compact size and relatively flat terrain make it perfect for exploring via golf cart, allowing visitors to easily navigate the narrow streets and access areas that may be difficult to reach by car. Additionally, with limited parking and congested streets in the downtown area, a golf cart provides a convenient and efficient mode of transportation, especially for short trips to attractions, restaurants, and shops. Moreover, the leisurely pace of a golf cart ride allows for a more intimate and relaxed experience, enabling travelers to soak in the island’s charming atmosphere and vibrant culture while enjoying the cool ocean breeze. Ultimately, renting a golf cart in Key West offers a unique and enjoyable way to explore the island at your own pace, providing a memorable and immersive experience for visitors of all ages.

Renting a moped/scooter in Key West offers a convenient and thrilling way to explore the island’s unique charm. With its compact size and limited parking spaces, a moped provides the flexibility to easily navigate through the narrow streets and discover hidden gems that might be missed by car. The slow pace of the island perfectly complements the leisurely nature of moped travel, allowing riders to soak in the stunning coastal views and vibrant atmosphere at their own pace. Additionally, renting a moped can be a cost-effective option for solo travelers or couples, offering an affordable and eco-friendly mode of transportation while embracing the carefree spirit of this tropical paradise.

Key West Sandbar Snorkeling - Honest Eco

Honest Eco – Sandbar and Snorkel

Key West Jetski Tour - Fury Water Adventures

Fury Water Adventures – Island Jetski Tour

Embark on an exhilarating adventure with the Key West Jetski Tour, where the turquoise waters of the Florida Keys become your playground. Guided by experienced instructors, participants rev up their personal watercraft and cruise through the picturesque channels, exploring hidden gems and iconic landmarks. Feel the thrill of the open sea as you navigate through the warm waves, passing by lush mangroves and white sandy beaches. Whether you’re a seasoned rider or a first-timer, this jetski tour offers an unforgettable experience, combining the excitement of watersports with the breathtaking beauty of Key West’s coastal scenery.

Key West Food Tours

Key West Food Tours – Food Tours

The Key West Food Tour offers a delightful culinary exploration of this vibrant Florida island for our guests. Guided by knowledgeable locals, participants embark on a journey through the charming streets, discovering a diverse tapestry of flavors that reflect the rich cultural influences shaping Key West’s cuisine. From fresh seafood and Caribbean-inspired dishes to iconic Key Lime treats, the tour provides a mouthwatering experience, allowing visitors to savor the unique tastes that make Key West a true food lover’s paradise.

Key West Ghost Hunt – Ghost Tour

Hunt with the locals! Join Key West’s original haunted attraction and experience the spirits on the streets of Old Town. Hear true stories of murders, disease, and hurricanes, see the places where these things happened, and use authentic ghost-hunting equipment! We’re the only tour in town that starts and ends in two different haunted locations, including exclusive nighttime access into The Studios of Key West just a few doors down from the Old Town Manor.

Dolphin Watch Snorkel - Honest Eco

Honest Eco – Dolphin Watch and Snorkel

Key West Boat Rental - Sunset Watersports

Sunset Watersports – Boat Rentals

Renting your own boat in Key West provides experienced boaters with the ultimate freedom to chart their own course through the pristine waters surrounding the island. With a myriad of secluded coves, coral reefs, and picturesque islands to explore, having a private boat allows for unparalleled access to the region’s natural beauty and marine life. Experienced boaters can take advantage of the opportunity to create their personalized itinerary, tailoring the journey to their specific interests and preferences. From snorkeling in crystal-clear waters to fishing in prime locations, the ability to set one’s own pace and agenda ensures an unforgettable and customized aquatic adventure. However, renters should possess a strong understanding of local maritime regulations and navigational skills, as the open sea can present challenges that require a seasoned hand at the helm.

Sunset Watersports Key West Safari Ecotour

Sunset Watersports – Safari Eco Tours

Embarking on a Safari eco-tour in pistol boats in Key West offers a unique and exhilarating way to connect with the island’s diverse ecosystem. These specialized boats, designed to navigate the shallow waters and mangrove tunnels, provide an intimate means of exploring the Key West Back Country. Led by knowledgeable guides, the tours offer a rare opportunity to observe native wildlife up close, including birds, marine life, and other fascinating creatures in their natural habitats, all while driving your own boat. The small size of the boats ensures a personalized and immersive experience, allowing participants to access remote areas inaccessible to larger vessels.

Key West Dinner Cruise - Sunset Watersports

Sunset Watersports – Dinner Cruise

Embarking on a catamaran dinner cruise with live music in Key West offers everything from a delightful and romantic experience to a party with friends on the water. This leisurely excursion allows guests to unwind and savor cocktails with a delectable meal and music while being surrounded by the island’s breathtaking coastal scenery. The spacious and stable design of the catamaran ensures a comfortable and smooth cruising experience on the water. As the sun dips below the horizon, the tranquil ambiance and warm sea breeze create an idyllic setting for couples or groups to enjoy a sumptuous dinner. A catamaran dinner cruise with live music in Key West offers an unforgettable and enchanting way to savor the island’s beauty on the water.

Sunset Watersports Sip n Sail

Sunset Watersports – Sip N Sail

1: Set sail on a state-of-the-art catamaran and embark on a high-energy, two-hour sunset cruise featuring live music, unlimited cocktails, beer, wine, and a selection of appetizers. As the sun dips below the horizon, the vibrant atmosphere comes alive with dancing, socializing, and breathtaking views of the Key West coastline. Whether you’re looking for a lively evening with friends or a fun memorable date night, the Live Music Sail promises an unforgettable memory and great photos.

2: Partaking in a live music sunset sail in Key West presents a harmonious blend of captivating melodies and breathtaking natural beauty, offering an unforgettable sensory experience. As the vessel gracefully glides through the tranquil waters, the soothing sounds of live music create an enchanting atmosphere, enhancing the already picturesque sunset views. Whether it’s the soulful strumming of a guitar or the rhythmic beats of tropical tunes, the live music adds a layer of magic to the journey, making it an ideal setting for relaxation, celebration, and connection. This unique fusion of music and nature provides an exceptional opportunity for guests to unwind, socialize, and immerse themselves in the moment, all while being surrounded by the radiant hues of the setting sun and the gentle embrace of the sea. A live music sunset sail in Key West promises to be a truly mesmerizing and soul-stirring experience, leaving a lasting impression on all who come aboard.

Key West Snorkeling - Sunset Watersports

Sunset Watersports – Reef Snorkel

Snorkeling at the coral reef off Key West from a sailing catamaran offers an unparalleled aquatic adventure, combining the thrill of sailing with the mesmerizing beauty of the underwater world. Aboard the spacious and stable catamaran, guests can relax and bask in the warm sunshine as they journey to the vibrant coral reef. Once there, the clear, azure waters beckon snorkelers to immerse themselves in a kaleidoscope of marine life, including colorful fish, graceful sea turtles, and intricate coral formations. The catamaran’s convenient access to prime snorkeling sites ensures a seamless and comfortable experience for enthusiasts of all skill levels, while the gentle rocking of the boat provides a serene backdrop for post-snorkeling relaxation. This seamless blend of sailing and snorkeling creates a truly unforgettable and immersive connection with Key West’s marine wonders, making it an ideal choice for nature lovers and adventurers seeking an extraordinary and revitalizing experience.

Captain Conch – Split Charters

Captain Conch – Offshore Deep Sea Fishing

Captain Conch – Party Boat Fishing

Key West Eco Tours – Half Day Sail, Snorkel, Kayak

Key West Eco Tours – Kayak Paddleboard Tours

Key West Lighthouse Sunset Experience

KWAHS – Lighthouse Sunset Experience

The Key West Lighthouse Sunset Experience is very limited and exclusive and is popular with our guests. Witness Key West’s renowned sunset in elegance from the observation deck of the city’s historic and iconic Lighthouse, offering a 360-degree panorama of the historic district, Hemingway Home, the Southernmost Point, and the glistening ocean, creating the most sought-after sunset viewing in the Florida Keys. Previously a local secret, this exclusive experience is now accessible to all seeking something distinctive. Catering not only to newlyweds and honeymooners, the Lighthouse Sunset Experience has become a cherished addition to the bucket list of every small group or couple. This 90-minute experience provides private entry to the Lighthouse, Keeper’s Quarters, and surrounding grounds for groups of up to eight, and includes a complimentary bottle of wine or Prosecco, as well as artisanal meats, cheeses, or sweets, with vegan and vegetarian options also available.
There is simply nothing like the 360 view of the island and the sunset over the water and town, offered in the Key West Lighthouse Sunset Experience.

Fish Key West

Fish Key West – Offshore Deep Sea Fishing

Engaging in offshore and inshore fishing from a center console boat with a charter captain in Key West promises an exceptional angling experience, tailored to the preferences and skill levels of fishing enthusiasts. The versatility of the center console boat allows for seamless navigation through various fishing environments, from the rich offshore waters to the intricate inshore habitats, ensuring a diverse and rewarding angling expedition. With the expertise of a seasoned charter captain at the helm, guests can benefit from invaluable local knowledge and guidance, maximizing their chances of landing prized catches such as marlin, tuna, snapper, or tarpon. Whether targeting deep-sea giants or navigating the shallow flats, the combination of a well-equipped center console boat and a skilled captain creates an optimal platform for a memorable and successful fishing excursion in the bountiful waters surrounding Key West. After a memorable day fishing, the captain will filet your fish, and our Guest Service Team will help reserve a restaurant that will prepare and cook up your fish.

Fish Key West Reef Fishing

Fish Key West – Light Tackle Fishing

Engaging in offshore and inshore fishing from a center console boat with a charter captain in Key West promises an exceptional angling experience, tailored to the preferences and skill levels of fishing enthusiasts. The versatility of the center console boat allows for seamless navigation through various fishing environments, from the rich offshore waters to the intricate inshore habitats, ensuring a diverse and rewarding angling expedition. With the expertise of a seasoned charter captain at the helm, guests can benefit from invaluable local knowledge and guidance, maximizing their chances of landing prized catches such as marlin, tuna, snapper, or tarpon. Whether targeting deep-sea giants or navigating the shallow flats, the combination of a well-equipped center console boat and a skilled captain creates an optimal platform for a memorable and successful fishing excursion in the bountiful waters surrounding Key West. After a memorable day fishing, the captain will filet your fish, and our Guest Service Team will help reserve a restaurant that will prepare and cook up your fish.

Cowboy Charters

Cowboy Charters – Offshore Deep Sea Fishing

At Sea Key West – Offshore Deep Sea Fishing