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O'Shaugnessey Family SCUBA Diving Off 65ft S-Y LOLALITA with Capt. Gio. Photo by Capt. Gio in the Caribbean

Deep Dive with Marine Life on Sail Catamaran LOLALITA

“At the beginning of the week you said this would be the best week of our lives and you delivered! Thank you for all the drift snorkeling, SCUBA and shark adventures! The food was great and the table settings were always a nice surprise! Thank you guys, we hope to see you again!”

~ J. O’Neill, recent LOLALITA guest in the Bahamas

Best Play Date Ever

Diving may be frowned upon in football (soccer), but more and more it is enthusiastically encouraged under the sea. As adventure travel trends up and technology shows us what we could be experiencing in our planet’s waters, snorkeling, SCUBA diving and free diving are booming in popularity worldwide.

So, when the experienced crew of the 65ft sail catamaran S/Y LOLALITA takes their guests on deep dives into the ocean, they mean “we have a play date with marine life”. Are these the best play dates ever? You better believe it. Lives are changed forever – and for better.


“There’s so much below the water’s surface to see, it gives you a totally different perspective on the world … and that’s just something you never forget.”

~ C. Hewitt, recent LOLALITA guest in the British Virgin Islands

Relax. Revive. Dive.

The S/Y LOLALITA is a beautiful 65-foot bespoke Privilege Yard catamaran. Her luxurious accommodations for up to 8 guests include a midship king master suite and 3 queen guest suites. 

LOLALITA’s much-loved crew of three brings vast culinary skills and attention to detail, luxury and fun to discerning charter guests. She boasts a host of water sports activities and is dive-equipped.

She went through a year-long refit in 2018/2019 and features a wide open deck space for lounging, relaxing and dancing! This means that whether LOLALITA takes you to the British Virgin Islands, Turks and Caicos, Panama or their other special destinations where other boats don’t go, the party is where you are – on LOLALITA!

“Lolalita is a beautiful vessel and you all make it extra special. I really enjoyed spending time together and getting to know the crew. You all were amazing and made our experience so memorable. I appreciate your dedication and genuine care for making everything happen smoothly.” 

S. Rosetta, recent LOLALITA guest

In the Shallow

It was a thrill to learn that Captain Giovanni Damiani, a.k.a. Capt. Gio, and crew will be sailing LOLALITA in Turks and Caicos in February 2020. Generally, there are no other luxury charter boats in the Turks and Caicos because of its shallowness.

Luxury and Adventure

Sailing on the LOLALITA with Capt. Gio is a gift to charterers. 

“This trip is the culmination of luxury of adventure that the British Virgin Islands have to offer and that you in particular offer on this ship [the LOLALITA] that’s just remarkable. That juxtaposition, you don’t find that often.”

~ The Vallins Family, recent guests in the British Virgin Islands

A Few of My Favorite Things

Snorkeling and SCUBA diving from the boat’s wide diving platform with expert crew makes for epic vacations. LOLALITA’s Captain Gio and crew like to ask guests what their favorite thing is about the charter they’re on. 

Some people love exploring underwater shipwrecks. Others love exploring caves on land. Surfing, wakeboarding and swimming with wild dolphins so close that you could touch them consistently rank high as well.

Bond. Family Bond.

Families who charter LOLALITA find that their shared adventure tightens family bonds. Friends report it, too, of course.

Parents sometime worry that children on charters will be bored or glued to screens. All reports say otherwise and to that point, a recent LOLALITA guest said of his multi-generational family’s time on the charter:

“My favorite experience was seeing everyone in the water, either diving or snorkeling or just having a good time.”

~ The Vallins Family, recent guests in the British Virgin Islands

National Gio-Graphic

LOLALITA’s Captain Gio grew up in London and, at an early age, wanted to be like naturalist and documentary-maker Sir David Attenborough. At 16, he decided to become a marine biologist and started saving for a yacht to sail the world, studying the oceans and making documentaries, like his hero. 

Captain Gio’s first documentary about spearfishermen in Jamaica caught the attention of Island Records owner and Bob Marley producer Chris Blackwell, who sponsored Gio’s second documentary which was published by National Geographic.

Captain Gio’s story is so rich that our next blog post will be devoted solely to his personal and professional journey. We’ll also let you know when his next documentary is available for viewing.

Super Crew

Sailing catamaran LOLALITA is crewed by an energetic and accomplished team. Happy charterers site Raven’s attention to detail and expert diving. They also note Martina Markel’s spectacular food for every palate and diet.

“Our week aboard Lolalita was nothing less than magical! A week of amazing food, excellent service and unlimited adventure with a gorgeous backdrop to top it all off. Lolalita is a wonderful boat but the crew makes her superb! This wont be our last adventure, we will see you again soon!”

~ J. Good, recent LOLALITA guest

Diving in Panama

LOLALITA and crew are westward-bound for more diving later this year. You can check out some beautiful footage from this stunning diving destination: Panama!


Epic Center

To get a taste of the epic adventures guests are having on LOLALITA, visit the boat’s YouTube Channel here.

“We could write an epic book about our week. Every day was perfect! Your genuine passion for your craft and creating memories for your guests exceeded all of our expectations. We look forward to more adventures with you in the future.”

~ O’Shaughnessy Family, recent LOLALITA guests in the British Virgin Islands


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