LGBT Owned and Fun for Everyone

Please look below at just a few of our many testimonials.  Our charters are by no means exclusive to any demographic.  We are an LGBT-owned and operated company.  Our guests range from couples, families of all types and groups of friends.  Appropriate ages range from eight months to eighty-eight (or anyone who is young at heart).  We invite you to sail with us whoever you are.  We just want everyone to be comfortable.   We also want you to know that while some of the stereotypes don’t hold true, some do.  Notably, our service is fantastic, fabulous and meticulous.  Trust me, you’ll love us.

“Sailing the USVI and BVI has been the dream vacation that we saved for my 40th birthday. We were beyond nervous about picking the right captain and the right boat as we could not imagine a week aboard with the wrong choice. The captain, Toby, and crew, Will, were HIGHLY knowledgeable and professional but at the same time so naturally flexible, easygoing and fun to be around. Their immense knowledge of the islands and other boats in the area was absolutely impressive and in hind sight, imperative. They knew the ins and out of of every island, the timing to visit each island , every restaurant to go to for dinner and every MUST DO experience that we didn’t even know that we wanted to do. The boat, Starlight, is stunning, clean , spacious and well appointed. The main cabin provided the deepest sleep that I desperately needed (mom of two). The breakfasts/ lunches and cocktails aboard were plentiful and delicious. They covered more than you can imagine in a week, had the gear that we needed and came on adventures to keep us safe while at the same time ensuring your privacy and romantic alone time. Daily operations of the boat were done seamlessly and safely and every anticipated need, including a serious food allergy was handled almost magically. This double Birthday/ Valentines Day trip was an adventurous, relaxing and romantic week-long cruise for two, executed with class, professionalism and easygoing fun. We will be returning without a doubt as we are forever ruined and can no longer imagine just sitting at a resort for a week. Thank you so much Toby, Will and Bamboo for a life changing first days of 40!!”

Lori and Jay, Montauk

Captain Toby was very accommodating and the boat was very comfortable. Everything we needed on the boat was well planned and thought out. Toby was very familiar with all the places to go in the USVI and the BVI and he really tailored the trip to our specific needs. I would highly recommend Toby and his


Lori and Jay, Montauk

This year my wife and I decided to try something different for the New Year Holiday period. Sitting at a resort pool or beach just didn’t seem to intrigue us this year. I could have never guessed when we booked with Toby and Will, that we would have this much of a wonderful experience. This is my only experience with chartering a sailboat, but with that said I can assure you that you’ll never receive the personalized service on any other chartered sailboats as we did with Toby and Will (it’s just not possible) Toby and Will own this wonderful sailboat that is very well appointed. We slept in the master cabin that was positioned in the aft portion of the boat. It came with it’s own well appointed bath/shower and there was plenty of room in the cabin to move about comfortably. The parlor was a wonderful open space if you choose to spend time below deck…but that’s not where you want to be while on vacation. We spent all our time on deck enjoying the scenery and sun. Each day Toby and Will helped us decide where we wanted to sail and what kind of activities we wanted to enjoy. They couldn’t have been more accommodating. Toby has so many great ideas that it’s sometimes hard to choose. We visited several islands, most we had never heard of before and a few of them completely uninhabited. Remember, You are in complete control of your time and whether you want to spend day hiking, snorkeling, paddle boarding or just sunning yourself…or a combination of them all. If you want to stay longer in a particular destination or head out earlier, just say the word and that’s what will happen. To top off this wonderful experience was the incredible food that Will prepares while you’re onboard. It was simply amazing….and Amazing may be an understatement. There is no way that you could get this kind of dining experience on any other sailboat…and not at this price. Toby and Will not only act as your Capt and first mate, but they also act as your tour guide, chef, teacher of paddle boarding, historian, sailing instructor and dingy captain. I could go on and on and on, but in a nutshell, you couldn’t do better anywhere else in the Caribbean. Oh. And I almost forgot their very sweet dog Bamboo. She is a wonderful dog and very well behaved that you almost forget that there’s even dog onboard.

Lawrence G. – Houston, TX

“My wife and I just spent 2 weeks sailing on Starlight in the Virgin Islands with Toby; it was outstanding in every way. The boat was comfortable, sailed well, was a joy to live aboard, a true classic yacht. Captain Toby knows his boat and the American and British Virgin Islands very well, is professional, personable, and completely dependable, a rare combination especially on a boat.”

Jan and Kitty – Santa Fe, NM

“We stay on board starlight sailboat for 8 days. Had the chance to liaise with the captain beforehand to set up our goals/style of holidays and make sure we were on the same line. He was a force of proposition. The trip cas really relaxing (exactly what we were looking for), the ship is beautiful and the captain a great host. Always in a good mood and always attentive to our needs. Sailing was fantastic. Every problems that occurred (there are always some when sailing) were raised with absolute calm and addressed diligently. Safety was unquestionable which was important since we were traveling with two kids. Once again Toby was a perfect host, and a great force of proposition which made our holidays unforgettable!”

Fred  – Paris, FR

“So, my friend and I planned a rather last-minute trip to the Virgin Islands for peak winter season, figuring it would be no problem to get hotels. Well, we quickly realized just how stupid we were, until I unearthed Captain Toby and the beautiful Starlight, after which we could not have counted ourselves any more fortunate. We booked a 4-day sail through the BVI, and it was by far the highlight of the trip. The ship was gorgeous, comfortable and well-maintained. Captain Toby could not have been a better companion – experienced, easy-going, flexible, and fun. I had looked into chartering in this area, and this was by far the best deal I found. Not only did prices include breakfast, lunch, gas, and insurance, but we paid for 3 nights on board and Toby gave us basically four full days, even dropping us off on another island so we wouldn’t have to take any ferries, despite that fact that he really did not have to do that. We both LOVED our time aboard Starlight, and I honestly cannot wait to book and come aboard again. Thanks so much, Toby. Say hey to Bamboo!”

Katie – Brooklyn, NY

We had a great weekend learning about the best spots in the area and learning how to sail and live on a sailboat.

Norm and Wendy – Miami, FL 

Captain Toby and Captain Will made our Christmas holiday perfect in the BVI’s. The boat was meticulously cared for with lots of room to play and cherry and teak finishes throughout. Captain Will is a 5 star chef and we never expected such a fine culinary experience on a boat. Toby and Will both have impressive professional pedigrees and a lifetime of experience on the ocean providing extra piece of mind. Bamboo added an extra special touch to our stay. We can’t wait to book our next trip.

Frank and Donna, Denver, CO