
Newport's newest sailing charter supporting The Breast Cancer Research Foundation and The Three Angels Fund
Exclusively for private groups of up to twelve guests, Ladybird is ideal for families, bachelorette parties, small corporate occasions and other close-knit gatherings. With flexible pricing based on group size, you’ll enjoy a fully private experience with only your guests onboard, guided by a professional, friendly crew dedicated to making every moment memorable!
Private sailing cruises for up to 12 guests in beautiful Newport RI.
For each sail, we proudly contribute $5 each to The Three Angels Fund and The Breast Cancer Research Foundation, with the hope that in future years, a larger share of profits can be dedicated to these great organizations that support breast cancer research and family support.
The last five years have moved swiftly for the Antique Yacht Collection family. We welcomed a baby, expanded our business with the addition of Baywatch and some phenomenal crew, and celebrated Alana—the Boss—fighting and initially beating breast cancer. Later, we scaled down by selling Temma, our first charter boat, explored new professional and lifestyle avenues, and even relocated briefly to Connecticut. But in the summer of 2023, we discovered that Alana’s cancer had returned, metastasized as two brain tumors. In February 2024, Alana devastatingly passed away, leaving behind her family and the business we built together.
As the new boss, I needed a way to honor my wife's memory. In the spring of 2024, I made the spontaneous decision to purchase a little Friendship Sloop sailboat that had fallen on hard times after the loss of its previous owner, also due to cancer. Alana and I always built businesses together—this one was created to give back and celebrate her legacy as a devoted wife, daughter, mother, and leader.
For each sail, we proudly contribute $5 each to The Three Angels Fund and The Breast Cancer Research Foundation, with the hope that in future years, a larger share of profits can be dedicated to these great organizations that support breast cancer research and family support. The last five years have moved swiftly for the Antique Yacht Collection family. We welcomed a baby, expanded our business with the addition of Baywatch and some phenomenal crew, and celebrated Alana—the Boss—fighting and initially beating breast cancer. Later, we scaled down by selling Temma, our first charter boat, explored new professional and lifestyle avenues, and even relocated briefly to Connecticut. But in the summer of 2023, we discovered that Alana’s cancer had returned, metastasized as two brain tumors. In February 2024, Alana devastatingly passed away, leaving behind her family and the business we built together. As the new boss, I needed a way to honor my wife's memory. In the spring of 2024, I made the spontaneous decision to purchase a little Friendship Sloop sailboat that had fallen on hard times after the loss of its previous owner, also due to cancer. Alana and I always built businesses together—this one was created to give back and celebrate her legacy as a devoted wife, daughter, mother, and leader.
Our Story:

There's nothing more American than the classic Friendship Sloop sailboat. Originally built in small fishing and lobstering towns in Maine, these versatile working vessels eventually spread to other locations along the East Coast. Alongside catboats and schooners, they form some of the most iconic American maritime silhouettes.
Ladybird, formerly known as Tupelo Honey, was once a cornerstone of the downtown Boston charter boat scene, operating for years! When the Antique Yacht Collection acquired her, we knew we had our work cut out for us and have been diligently preparing her for summer 2024.
Our first major project was painting the boat pink! This bold choice initially elicited mixed reactions from the traditional boating community—some loved it, while others were less complimentary. However, once people learned more about our story and what this new chapter for Ladybird represented, they were quick to say, “I LOVE IT!”
Friendship Sloops are renowned for their seaworthiness, maneuverability, and remarkable sailing attributes. Sailing on a Friendship Sloop is like taking a step back in time, with its big gaff-rigged mainsail and long bowsprit. As the boat heels, you get close to the water, and at times it can be quite thrilling. But don’t worry—we won’t tip over, thanks to the tremendous amount of ballast in the keel at the bottom of the boat.
There's nothing more American than the classic Friendship Sloop sailboat. Originally built in small fishing and lobstering towns in Maine, these versatile working vessels eventually spread to other locations along the East Coast. Alongside catboats and schooners, they form some of the most iconic American maritime silhouettes. Ladybird, formerly known as Tupelo Honey, was once a cornerstone of the downtown Boston charter boat scene, where she operated for many years. When the Antique Yacht Collection acquired her, we knew we had our work cut out for us and have been diligently preparing her for next summer. Our first major project was painting the boat pink! This bold choice initially elicited mixed reactions from the traditional boating community—some loved it, while others were less complimentary. However, once people learned more about our story and what this new chapter for Ladybird represented, they were quick to say, “I LOVE IT!” Friendship Sloops are renowned for their seaworthiness, maneuverability, and remarkable sailing attributes. Sailing on a Friendship Sloop is like taking a step back in time, with its big gaff-rigged mainsail and long bowsprit. As the boat heels, you get close to the water, and at times it can be quite thrilling. But don’t worry—we won’t tip over, thanks to the tremendous amount of ballast in the keel at the bottom of the boat.
The Boat:

From intimate gatherings with your close friends or family members, to larger celebrations, we have customizable pricing structures that reflect your specific needs!
This adaptability allows you to choose a charter that aligns perfectly with your itinerary and budget, whether it's a few peaceful hours on the water or an a half day adventure.
We believe in making the magic of Ladybird accessible to various groups, giving you the freedom to create an experience that feels as special as your friends & family!
From intimate gatherings with your close friends or family members, to larger celebrations, we have customizable pricing structures that reflect your specific needs! This adaptability allows you to choose a charter that aligns perfectly with your itinerary and budget, whether it's a few peaceful hours on the water or a half day adventure. We believe in making the magic of Ladybird accessible to various groups, giving you the freedom to create an experience that feels as special as your friends & family!
Flexible Group Sizes:

All our charters aboard Ladybird are private. This means it’s just you, your guests, and our professional crew. You have the entire boat to yourselves to enjoy a truly exclusive and personalized experience. We do not offer public sails, ensuring that every moment on board is tailored to you and your group.
Whether you’re taking in the stunning views of Newport Harbor with its historic lighthouses, grand mansions, and iconic sailing culture or exploring the hidden coves and tranquil waters, Ladybird offers a unique experience steeped in maritime tradition. Our flexible group sizes and customizable pricing options allow us to accommodate a range of party sizes and charter durations, from intimate gatherings to larger groups seeking a memorable day on the water.
With Ladybird’s classic lines and striking pink exterior, your private sail around Newport Harbor becomes more than just a boat ride—it’s an experience that combines history, elegance, and exclusivity. We aim to make every charter unique, whether you're celebrating a special occasion, sharing a relaxing day with friends and family, or simply embracing the thrill of being on a timeless Friendship Sloop.
All our charters aboard Ladybird are private. This means it’s just you, your guests, and our professional crew. You have the entire boat to yourselves to enjoy a truly exclusive and personalized experience. We do not offer public sails, ensuring that every moment on board is tailored to you and your group. Whether you’re taking in the stunning views of Newport Harbor with its historic lighthouses, grand mansions, and iconic sailing culture or exploring the hidden coves and tranquil waters, Ladybird offers a unique experience steeped in maritime tradition. Our flexible group sizes and customizable pricing options allow us to accommodate a range of party sizes and charter durations, from intimate gatherings to larger groups seeking a memorable day on the water. With Ladybird’s classic lines and striking pink exterior, your private sail around Newport Harbor becomes more than just a boat ride—it’s an experience that combines history, elegance, and exclusivity. We aim to make every charter unique, whether you're celebrating a special occasion, sharing a relaxing day with friends and family, or simply embracing the thrill of being on a timeless Friendship Sloop.
Private:

Our 2 hour sail is perfect for those who want to enjoy pure sailing and take in the iconic sights of Newport Harbor.
Our 3.5 hour sail offers an expanded experience, providing more time not just to sail, but relax in the sunshine, explore some coves, and anchor at your leisure. This longer option allows for a more easygoing pace, where you can fully immerse yourself in the beauty of the harbor, bring a picnic on board, and make memories with your group!
2 hour or 3.5 hour adventures daily!
Our 2 hour sail is perfect for those who want to enjoy pure sailing and take in the iconic sights of Newport Harbor.
Our 3.5 hour sail offers an expanded experience, providing more time not just to sail, but relax in the sunshine, explore some coves, and anchor at your leisure. This longer option allows for a more easygoing pace, where you can fully immerse yourself in the beauty of the harbor, bring a picnic on board, and make memories with your group!
Time:


There are so many establishments conveniently located near our pickup and drop-off dock, making it super simple to grab a take-away picnic before boarding!
Within a leisurely stroll, you'll find Mother Pizzeria, celebrated for its artisan-style pizzas crafted with naturally fermented dough and baked in a Neapolitan-style oven.
For a fusion of flavors, Yagi Noodles. offers bold American interpretations of Chinese and Japanese comfort foods, featuring handmade noodles from freshly milled local wheat.
The Quencher provides a diverse menu of American favorites.
These establishments make it effortless to grab a bite for your voyage!
Should you prefer, you're welcome to bring your own food and beverages aboard. We supply all necessary plates, silverware, cups, and cutlery to ensure a seamless dining experience. Ladybird is also equipped with a cooler stocked with ice, ensuring your provisions remain fresh and your drinks perfectly chilled throughout your sail!
There are so many establishments conveniently located near our pickup and drop-off dock, making it super simple to grab a take-away picnic before boarding! Within a leisurely stroll, you'll find Mother Pizzeria, celebrated for its artisan-style pizzas crafted with naturally fermented dough and baked in a Neapolitan-style oven. For a fusion of flavors, Yagi Noodles. offers bold American interpretations of Chinese and Japanese comfort foods, featuring handmade noodles from freshly milled local wheat. The Quencher provides a diverse menu of American favorites. These establishments make it effortless to grab a bite for your voyage! Should you prefer, you're welcome to bring your own food and beverages aboard. We supply all necessary plates, silverware, cups, and cutlery to ensure a seamless dining experience. Ladybird is also equipped with a cooler stocked with ice, ensuring your provisions remain fresh and your drinks perfectly chilled throughout your sail!
Food & Beverage:

Sailing aboard Ladybird, our traditional Friendship Sloop, offers more than just a journey through Newport Harbor's historic waters. We can navigate to secluded anchorages nestled among the mansion-dotted coves, where you can anchor, and stop for a picnic! This experience combines the timeless charm of classic sailing with the relaxation of a private retreat, creating lasting memories on the water, a little something for everyone.
Sailing aboard Ladybird, our traditional Friendship Sloop, offers more than just a journey through Newport Harbor's historic waters. We can navigate to secluded anchorages nestled among the mansion-dotted coves, where you can anchor & have a picnic.
This experience combines the timeless charm of classic sailing with the relaxation of a private retreat, creating lasting memories on the water, a little something for everyone.
Not into Sailing? No Problem!

Our captains and crew are passionate about sailing, hospitality, safety and Newport's vibrant history & waterfront. They are seasoned professionals, each holding the necessary qualifications and certifications to ensure your safety and enjoyment aboard Ladybird.
The vessel is fully compliant with U.S. Coast Guard regulations and possesses a Certificate of Inspection (COI), affirming that both the boat and crew meet the highest professional standards.
Our captains and crew are passionate about sailing, hospitality, safety and Newport's vibrant history & waterfront. They are seasoned professionals, each holding the necessary qualifications and certifications to ensure your safety and enjoyment aboard Ladybird.
The vessel is fully compliant with U.S. Coast Guard regulations and possesses a Certificate of Inspection (COI), affirming that both the boat and crew meet the highest professional standards
Our Captains & Crew:


Sound System & More:
There’s something timeless about the combination of sailing and music—the way a playlist can elevate the feeling of gliding across the water, turning a simple trip into an unforgettable experience.
On Ladybird, our Bluetooth sound system provides the perfect sound backdrop for your journey.
Other features include:
A small bathroom on board, a cooler stocked with ice, water, & sparkling water, comfortable seating & a fun crew!
There’s something timeless about the combination of sailing and music—the way a playlist can elevate the feeling of gliding across the water, turning a simple trip into an unforgettable experience. On Ladybird, our Bluetooth sound system provides the perfect sound backdrop for your journey.
Other features include:
A small bathroom on board, a cooler stocked with ice, water, & sparkling water, comfortable seating, and fun crew!
Location:
Our embarkation and disembarkation point is the charter dock at Perrotti Park, conveniently situated next to the Newport fire boat. This central location offers easy access to the heart of Newport, with ample parking options nearby, including the Gateway Center Parking Lot
Perrotti Park features comfortable seating areas overlooking the dock, providing a pleasant waiting environment for our guests. Given Newport's bustling summer season, we recommend arriving early to account for potential traffic and parking delays. Our vessel adheres to a precise schedule; if you arrive ahead of time and the boat isn't at the dock, please rest assured it will arrive shortly. We kindly ask guests to remain in the park's seating area until invited to board, ensuring a smooth and timely departure.
Our embarkation and disembarkation point is the charter dock at Perrotti Park, conveniently situated next to the Newport fire boat. This central location offers easy access to the heart of Newport, with ample parking options nearby, including the Gateway Center Parking Lot. Perrotti Park features comfortable seating areas overlooking the dock, providing a pleasant waiting environment for our guests. Given Newport's bustling summer season, we recommend arriving early to account for potential traffic and parking delays. Our vessel adheres to a precise schedule; if you arrive ahead of time and the boat isn't at the dock, please rest assured it will arrive shortly. We kindly ask guests to remain in the park's seating area until invited to board, ensuring a smooth and timely departure.