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Winter Aboard Lady Grace in Florida

Florida offers amazing opportunities on the water aboard private yacht, Lady Grace, which is available for vacation rentals in Key West and for seven-night, all-inclusive cruises. Lady Grace provides a relaxing retreat, the thrill of traveling on your own private yacht and itineraries that include some of the most unique and beautiful spots along the coast of southern Florida.

Key West Vacation Rentals – Including Day Cruises

Lady Grace loves to travel, but we recognize that some guests may prefer to stay in Key West for and have the entire boat to themselves, including the captain and crew quarters. If this is you, then enjoy a Vacation Rental in Key West aboard Lady Grace. When you rent Lady Grace, our crew will be nearby, but not staying aboard. You’ll have all 5 staterooms and 6 bathrooms to yourselves, which can accommodate up to 10 guests.

Each vacation rental includes one local day or sunset cruises in the Key West area and all the amenities described in our Key West description below.

All Inclusive Cruise Package

For guests who want to enjoy a vacation on the move, our seven-night, all-inclusive cruise aboard Lady Grace is for you. Key West is the center of our winter cruise program, and we offer three exciting cruise itineraries that expand on your visit to Key West. Enjoy 3-4 days aboard Lady Grace dockside while exploring Key West. In addition to your time in Key West choose one of three itineraries for an additional 3-4 days of cruising either to The Dry Tortugas; or through the Keys to Miami; or to The Ten Thousand Islands and Naples.

When you board Lady Grace for an all-inclusive cruise you can leave your worries behind and leave everything to us. Food and beverages, fuel, marina dockage, National Park fees, and a full crew, including a chef are included in your vacation cruise package. Each guest is catered to for the ultimate experience of a private yachting vacation. Enjoy luxury bedding and towels, laundry service, private bathrooms, bath supplies, beach towels, beach chairs, inflatable floating dock, floating toys, snorkel gear, paddleboards, bicycles and a captained beach landing craft to get you safely ashore. It’s all included on Lady Grace.

Food and drinks are also part of your vacation package. Our Chef will provision the boat and prepare the finest meals based on your preferences, which we get from each guest in the weeks before your vacation. Select beer, wine, and cocktails as well as water and non-alcoholic beverages are provided during your stay as part of the all-inclusive offering. For guests who enjoy cooking, our spacious country dine-in kitchen is equipped with a full-size refrigerator/freezer, a range, conventional and convection ovens, a microwave, wine fridge, and dishwasher. Our Chef can assist in provisioning and provide any needed support. If special celebrations are occurring during your stay, our crew will help with arrangements for a special dinner or celebration to ensure lasting memories.

Whatever option you choose, come aboard Lady Grace for a one-of-a kind, vacation in paradise.

~ Guest Reviews ~

“Rating 5 Stars! The yacht is beautiful, spacious, and well appointed; but Jamie and Kelly, the couple who captain and run the boat, can be the best part. Professional and thoughtful, they just ensure that you are comfortable, well fed with great food, and get to enjoy any activity that might be part of the trip. We won’t forget this experience and look forward to another opportunity to go back!” ~M.L. Stayed March 2024 (Google review)

“What An Adventure! Rating 5/5 – My family and I just spent an amazing week cruising around the Gulf Of Mexico visiting Key West and the Dry Tortugas onboard The Lady Grace. The accommodations were incredible with spacious staterooms to rival any luxury hotel…The whole experience was facilitated by an amazing, attentive, and wonderful crew who treated us like royalty! I am looking forward to my next adventure on The Lady Grace!!” ~B.R. Stayed February 2024 (VRLBI review)

 

Book Winter Rental

 

Southern style home painted white with dark green shutters, wrap around porch, and surrounded by green trees and bushes

Key West - Included in all Itineraries

Key West: Close to Perfect – Far from Normal – Our dockage in Key West is at the beautiful Stock Island Marina Village and includes full use of amenities such as three dockside restaurants and bars, waterfront swimming pool, two dog parks, fitness center, Private Captains Lounge, scooter rentals, direct access to the ocean and a shuttle to downtown. You’ll be at the best accommodations in the marina aboard Lady Grace while enjoying all the amenities of the village.

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Key West is closer to Cuba than to Miami and is Florida’s irreverent southernmost subtropical paradise. Key West hosts a unique blend of history, climate, natural beauty, cultural diversity, architecture and an unabashed romantic appeal. Palm-lined streets with gingerbread mansions and tin-roofed conch houses are prevalent in Key West, and were home to Ernest Hemingway, Tennessee Williams, Elizabeth Bishop, Robert Frost and Jimmy Buffett, just a few of the famous people who discovered solace and inspiration in the island city.

“Old” Key West provides plenty of opportunity for entertainment and fun! Shop among any of the niche boutiques along famous Duval Street, stop at Mile Marker 0, or the Southern Most Buoy for a photo, or try some authentic Key Lime Pie! With museums, historical sites, Mallory Square, Historic Key West Harbor, golf course, restaurants and bars, Key West never lacks for something to do. Concerts and events are plentiful in Key West and can be a wonderful contribution to your experience while exploring this vibrant city. “New” Key West hosts a variety of entertainment and restaurants to provide a complete a wide range of amenities that is sure to please all who adventure here. This energetic town has an upbeat vibe that our guests can indulge in while relaxing in this beautiful tropical paradise.

Key West International Airport is the closet airport to Lady Grace. Many cities have direct flights to Key West including Dallas, New York, Philadelphia, Washington DC, Chicago, Charlotte, Atlanta, Cincinnati and Nashville.

Antique black canon with old fort built into bunker near the ocean

Dry Tortugas National Park Itinerary

3 days cruising – Approximately a 6-hour cruise from Key West, Dry Tortugas National Park is one of the most unique destinations in our national park system. During this trip, Bocca Grande Key – a secluded beach accessible only by boat or seaplane – is a wonderful place to stop for some beach time. It is uncrowded and picturesque, with trails crisscrossing the Key. The perfect place to explore your own private paradise.

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Dry Tortugas National Park is a large, protected area of the Gulf of Mexico, surrounded by a group of keys only accessible by boat or seaplane, providing our guests with a unique setting for swimming/snorkeling/diving, exploring history, stargazing with zero light pollution, and walking among scenic seascapes and landscapes.

Our destination within the Dry Tortugas National Park is Fort Jefferson, which because of its distance from land, is the least visited National Fort in the United States. It is also the largest brick building in the United States with over 16 million bricks and was one of the most important third-system coastal fortifications. Lady Grace will anchor along the protected shoreline of Fort Jefferson for 2 nights, allowing you to enjoy a leisurely pace in these pristine island waters and an unhurried exploration of this 19th-century fort. Fort Jefferson is surrounded by an elevated trail which offers a new seascape at every turn.

You’ll also visit the military prison, where the Dr. who treated John Wilkes Booth after he assassinated President Lincoln, was held for years. Choose to explore Fort Jefferson on your own, or take the park guided tour that is offered daily. Fort Jefferson allows pets on the beach, providing a fun and exciting adventure for your furry companion to enjoy as well, and our captained tender is ready to take you and your dog to the beach whenever it’s needed.

Loggerhead island just off Fort Jefferson is the largest island within the park, and home to Loggerhead Lighthouse. Only accessible by private boat, this Lighthouse is an often-missed treasure for lighthouse enthusiasts. Loggerhead island spans 49 acres providing plenty of areas to be explored. From the comfort of Lady Grace, you can also snorkel or dive in these protected waters which marks the end of the third largest barrier coral reef in the world.

If you are a bird lover, Dry Tortugas is the perfect place to keep an eye out for a wide range of species that are rarely seen elsewhere such as the giant frigatebird or the sooty tern. Spring migration is a special time to see the frigatebird since Dry Tortugas is the only location in the United States where the frigatebird comes to nest. Nearly 300 hundred species of birds have been seen throughout the park. Binoculars are aboard Lady Grace to help guests watch all these beautiful birds.

For those who wish to explore a unique and unspoiled area, Dry Tortugas is the adventure for you, and doing it from the privacy and comfort of Lady Grace, with an attentive crew at hand, will give you memories to treasure.

Metal lighthouse surrounded by bright blue water

Florida Keys / Miami Itinerary

Key West (Lower Keys) 3 nights | Marathon & Islamorada (Middle Keys) 2 nights | Key Largo, Key Biscayne (Upper Keys) & Miami 2 nights. Spanning 150 miles of beautiful waterways and scenic islands, the passage between Key West and Miami, encompasses all the Keys – Lower, Middle, Upper – and includes some of the most unique cruising grounds on the east coast. At each stop, opportunities abound for sightseeing, swimming/snorkeling/diving, or just relaxing in beautiful surroundings.

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Lower Keys – Your time aboard Lady Grace will start or end in Key West, the heart of the Lower Keys, and one of the oldest and most interesting communities in America. Please see the separate section above for Key West details.

Middle Florida Keys Lady Grace will stay in Marathon Florida during our time in Middle Florid Keys. Marathon is home to the Turtle Hospital, the Dolphin Research Center and Aquarium Encounters, for viewing and learning about animal research and rehabilitation in the Keys. Marathon is also home of the famous 7-mile bridge which can be walked, biked, or trolleyed to Pidgeon Key, which has a museum and tour about the history of this area. Sombrero Beach or Bahia Honda State Park are among the best beaches in the Keys, and for snorkeling, Sombrero Lighthouse is one of the best spots in the Middle Keys. Not far from Marathon is the beautiful city of Islamorada. Explore Islamorada with a trip to the History of Diving Museum, or Robbie’s, an open-air market with shops, food, and for the adventurous, tarpon feeding right at the dock. For animal enthusiasts, the Theatre of the Sea is a fun stop for adults and kids alike.

Upper Florida Keys On the journey to Miami, you’ll cruise through the beautiful waters, coral reefs and mangrove forests of Key Largo and Key Biscayne and see some of the most beautiful stretches of tropical scenery in all of south Florida.

Miami is known for its vibrant nightlife, Cuban influence and stunning beaches, and is a nonstop opportunity to explore. You’ll cruise aboard Lady Grace through the skyscrapers of Miami on one of the most traveled waterways in Florida. Explore “Little Havana” full of restaurants, bakeries, cigar shops, galleries, and music. The Cubaocha Museum & Performing Arts Center is the perfect place to enjoy live music and dancing, see one of the rarest Cuban art collections, and indulge in a wide selection of rums. For an opportunity to buy local artist work, Futurama 1637 is the marketplace to purchase diverse authentic artwork and watch local artisans at work. Enjoy the nightlife of Miami along Brickell Avenue, home to upscale rooftop bars, trendy clubs, and elegant lounges providing nonstop entertainment. And at the end of an exciting day, return to the rest and relaxation of Lady Grace, your home away from home in the Florida Keys.

**Starting and Ending Point for this itinerary are different** and could start and end at either location. Recommended airports are Key West International, Miami International or Fort Lauderdale International airports. Please contact us for information. 

Two people sitting in chairs on the beach with setting sun in the background

Ten Thousand Islands / Naples Itinerary

3-4 days Key West | 3-4 days cruising Ten Thousand Islands and Naples – In addition to your itinerary in Key West, Lady Grace will take you on an exploration of the Ten Thousand Islands National Refuge which includes over 35,000 acres of islands in the Gulf of Mexico alongside the Everglades National Park.

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During our cruise keep watch for dolphins, shorebirds and other wildlife that are prevalent in the waters of the Everglades. Excursion options in this region include traveling deeper into the islands in our captained tender and visiting Everglades City, including its boardwalk through the Mangrove Forest, the famous Rod & Gun Club, which has hosted U.S. Presidents and other dignitaries, or an airboat ride through alligator territory. Or enjoy shelling in some of the most famous shelling beaches in Florida. Whatever your interests, get ready for natural beauty unique even in Florida.

This cruise includes the city of Naples, located on the Gulf of Mexico in Southwest Florida. Naples is known for its classy shopping, exquisite arts and culture, fine dining, family fun, and natural outdoors. These are just a few reasons why Naples has been ranked as the best place to live in the U.S. according to a survey by U.S. News & World Report. You’ll enjoy the finest accommodations aboard Lady Grace, while being in the middle of everything this lovely town has to offer. Whether it’s shopping or dining in the historic downtown area along Fifth Ave South and Third Street South, or gallery hopping, or sightseeing on the Naples Trolley or on a Segway, or visiting the Naples Zoo, or the world-renowned Naples Botanical Garden, or dozens of other attractions, your time in Naples will show you why this is the city where sophistication meets sunshine and serenity.

**Starting and Ending Point for this itinerary are different** and could start and end at either location. Recommended airports are Key West International, and Regional SW Airport in Ft Myers. We can also schedule you on the Key West Express boat between the two cities. Please contact us for information. 

Soft waves rolling onto a beach with setting sun in the background

Pricing Information

Key West Vacation Rentals – Including a Day and Sunset Cruise

  • March – $1,350 per night with a 3 night minimum. $9,000 for a full week (Receive a $450 discount for stays 7 nights or longer).
  • April – $1,100 per night with a 3 night minimum. $7,500 for a full week, (Receive a $200 discount for stays 7 nights or longer).
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Vacation Rental Details:

  • Minimum 3-night rental
  • Includes one local day or sunset cruise on Lady Grace in Key West
  • Includes 5 guest staterooms for 10 people, including the Captain and Crew quarters
  • Includes dockage and amenities at the Stock Island Marina Village – three dockside restaurants and bars, waterfront swimming pool, two dog parks, fitness center, private captains lounge, scooter rentals, and a shuttle to downtown Key West
  • Includes the full use of Lady Grace and all amenities on board – Bicycles, Paddleboards, Snorkel gear, Beach chairs & towels
  • Concierge services available for additional fee (local reservations, shopping, provisioning of the vessel)

All-Inclusive Cruise Package (For 6-8 People)

  • Key West / Dry Tortugas $29,995
  • Key West / Florida Keys & Miami $31,995
  • Key West / Thousand Island & Naples $33,995

All-Inclusive Details:

  • Includes our full seven-night cruise package in Key West and to one of the three destinations in the Lady Grace cruise program.
  • Includes 3 Guest Staterooms with private bathrooms for 6 guests (or 8 with smaller children on portable mattresses)
  • Includes dockage for 3-4 days in Key West and amenities at the Stock Island Marina Village – three dockside restaurants and bars, waterfront swimming pool, two dog parks, fitness center, private captains lounge, scooter rentals, and a shuttle to downtown Key West
  • Includes Chef and all food and beverages on board Lady Grace. Our chef will provision Lady Grace and prepare meals based on your preferences. (We send Guest Preference Forms to each guest in advance of cruise.)
  • Includes Captain and crew (Generally 4 people, including Chef/Steward)
  • Includes housekeeping services, sheets and towels, bath supplies, and daily turndown service. (On-board washer and dryer is available for personal items.)
  • Includes cruising for 3-4 days, usually for up to 4 hours per day, and all fuel and dockage costs at other ports of call.
  • Includes the full use of Lady Grace and all amenities on board – Bicycles, Paddleboards, Snorkel gear, Beach chairs & towels, Captained tender.

Guests are responsible for the cost of airfare or other transportation to and from Lady Grace, the cost of any outside excursions or activities other than National Park fees, and food and beverage while not on Lady Grace.

Tips for Captain and crew are not included and are encouraged.

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