Typical Itinerary

Every charter is customizable to your desires. Here is a typical vacation with us in the Virgin Islands.



Day one - arrival

Upon reaching the islands by flying to Charlotte Amalie, Saint Thomas (USVI) or Road Town, Tortola (BVI), guests will take a cab to the planned port of Red Hook (USVI) or Nanny Cay (BVI).

Captain T will greet you and direct you and your party aboard your new floating sanctuary.

Once inside, you will be greeted with our refreshing, signature welcome treat. After settling in, Captain T will work alongside you to help plan each stop amongst the week’s sailing route. Depending on the direction of the wind, the route may be best executed with a “sails in our favor” approach, but rest assured, Captain T will always customize your trip to meet your wishes and exceed your expectations. From there, guests will enjoy a gourmet lunch of grilled chicken with goat cheese spring mixed salad, complemented by pistachios, dried cranberries, sprouts, apple slices, prosciutto, and a freshly prepared lemon Dijon dressing perfected by professionally trained, Chef Rebecca.

S/Y Anastasia will then begin her sailing expedition through the pristine turquoise waters of Nanny Cay, where a refreshing swim and vivid snorkel will begin to awaken your ambitious adventures. The British Virgin Islands provide one of the world’s best surroundings for sea life and unscathed beaches. After your initial plunge, Captain T and First Mate Rebecca will introduce you to their exceptionally artistic capabilities with craft cocktails and nonalcoholic offerings, which are especially enjoyed under the warm Caribbean sun. Following a warm shower and a plentiful wine accompanied dinner, enjoy star gazing on the plush front loungers and netted trampolines at the front of your private yacht.



day two- norman island

You decide when to begin your next voyage upon fueling your day with the familiarity of succulent bacon, an abundance of breakfast pastries, custom egg dishes and fresh tropical fruit- all while dining al fresco alongside the picturesque Virgin Beaches. The fully automatic espresso machine is custom programmed to deliver a consistently satisfying trophy of coffee at the push of a single button.

Land or maritime conquests will begin once T and Becca have made sure you are fully satisfied from your meal. A fulfilling sail will land you at your subsequent destination of Norman Island, also known as Treasure Island. Here, you can take in the glistening sun on your own personal flotation raft or chill out atop the floating island with your family and friends while you catch a glimpse of the vibrant, living coral beneath you. Explore the caves of Treasure Island and see where Blackbeard hid his treasure. Lastly, end your afternoon with a shot ski at Willy T’s! You and your crew can jump off the front of the bar ship’s upper deck as you splash into what we hope is your first of many stays on Anastasia. Rebecca will have hors d’oeuvres waiting your arrival back from Willy T’s. After another unforgettable dinner, stargaze, boat dance, and let the calm waters rock you to sleep in your king bed suite.



day three - peter island & salt island

Wake up and fall in love all over again on Honeymoon Beach at Peter Island. If you would prefer a picnic lunch, on this secluded, hidden beach Rebecca can make your culinary dreams come true. Let Captain T take the kids water skiing or knee boarding while you and your partner enjoy some R&R on shore. We will happily book you a Sea Stone Massage or a Recharge Treatment at the Peter Island Resort and Spa while the others stay among the bay and play.

For the more adventurous and scuba certified, Master Diver, Captain T will initiate your earliest dive to see the RMS Rhone at Salt Island. A swift tender ride aboard your private dinghy boat will have you feeling like true voyagers before submersing to one of the world’s most legendary wreck sites. Pristine waters allow for maximum visibility among the many dive sites in the BVI.

Come back aboard for an afternoon of wine tasting and cheese pairing while the sun sets over Tortola. A perfect way to take advantage of the padded flybridge. This 360-degree view offers the perfect stage for the infamous Christmas card settings your friends and family jealously admire.



day four - cooper island & virgin gorda

Cooper Island Beach Club is hands down the best place to check out one of the finest stocked rum bars in the Caribbean. A true look at the life of the local mooring ball business of those who live ashore will help put into perspective just how remote your location truly is here on Cooper Island. Grab the Eno and head ashore for some private hammock lounging around the Beach Club. Once your cravings set in, Rebecca and T will escort you back to your isolated yacht for a satisfying lunch and a gracious sail to the epic Virgin Gorda.

Take the vessel’s waterproof backpack and underwater GoPro camera with you on your next adventure here at the Baths of Virgin Gorda. T will guide you to the towering rock formations and tranquil baths at a calculated hour to avoid the crowds of the cruise liners. This way of seeing the baths will offer you the most exclusive visit to this site you and your group will ever experience. Catch another glorious sunset and enjoy the unlimited playlist of island tunes on the onboard surround sound and Fusion Radio. Dinner, star gazing, sleep, repeat.



day five - virgin gorda

Wake up again in Virgin Gorda and let the swaying palm trees convince you to never leave. After another gourmet breakfast, sail to the northern area of Virgin Gorda to the newest dive site, The Kracken, The Wreck of the Kodiak Queen. This impressive architectural site was recently added to the area, and with its massive octopus structure atop the military ship, this site has quickly become the most talked about among those in the islands and beyond. We are certain it will satisfy that underwater selfie you’ve been seeking while also adding to the bucket list of dive sites you have now begun!


day six - Mosquito Island, Necker Island, Prickly Pear Island & Saba Rock

Stay docked in Virgin Gorda and take advantage of your high powered tender boat. A quick ride to Little Necker Island with Captain T will help put into perspective the multipart estate Sir Richard Branson has built in the British Virgin Islands. Then, take your guided tour of Richard Branson’s private estate on Mosquito Island with Gumption Tours. A portion of your admission fee will help support positive youth within Gumption’s I.S.P.Y. Organization.

This tour is exclusive to Gumption and one you will not soon forget!

For bragging rights, add to your koozie collection at the Bitter End Yacht Club located at one of the furthest points of the cluster of British Virgin Islands. You’ve gotta be able to say you’ve been to the “Bitter (sweet) End” of the BVI. Check out the lush landscape and take in the sight of impressive sailing yachts around you. If you’re interested in becoming a true sailor the Bitter End Yacht Club has been teaching week long instruction courses since 1985. You will end your stay with Anastasia and begin your next adventure here. For more information contact the BEYC- http://www.beyc.com/index.php/contact-us

If you’d rather let Captain T continue guiding you on his journey, then hop back on Anastasia and pick up anchor for another smooth sail to Prickly Pear Island and Saba Rock. Saba Rock is the cutest island in the BVI. At only an acre and a half its charm is immediately apparent as you approach this gem. After a little snack and shop on Saba Rock, have the crew whisk you back to your floating oasis for another flavorful dinner close to the peerless shores of Prickly Pear Island.


day seven - Anegada

Set sail to the furthest most island of Anegada and check out true remote exoticness. This far off escape grants its guests shallow, calm waters, great for stand up paddle boarding. The barrier around the island helps protect the natural reefs below and an ATV tour through the undeveloped land mass will have your appetite rising for another decadent creation perfected by Chef Rebecca. After the day’s activities, try your own hand at bartending aboard Anastasia. Captain T will instruct you on how to create your own tropical drinks for you and your squad, or just sit back, relax and enjoy the afternoon sun while your hard-working crew makes your most exotic imaginations become reality. After sunset, enjoy an ice-cold Carib lager with your local lobster dinner at the picnic tables on the beach of one of the most incredible islands in the Caribbean. Other yachting guests gather here to help support the local community’s main source of income, lobster fishing. Settle in and let the bright stars shine down on you in paradise.



day eight - jost van dyke

Along your sail to the last island of your dream vacation, Captain T will assist you in setting out the trolling rods for the day’s big catch. There is plenty of big game from Anegada to Jost Van Dyke that will more than feed your group for lunch. What better way to enjoy your five-star meal than to add some freshly caught fish. You may have heard of the infamous Soggy Dollar Bar where the pain killer claims was first created. Many people check out their online webcam while at work and day dream of joining the many crowds here before heading over to Foxy’s for the evening. If you would rather enjoy your last day in the quiet area, close to Little Jost Van Dyke, seclusion can best be achieved here. Bust out all the amazing toys Anastasia has to offer and go out with a bang. Rebecca can work the boat’s GoPro video camera for your group to help capture the fun you’ve been having with us all week!


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day nine - saint john & saint thomas, usvi

Throughout the week and up until the last minute, Captain T will have all documents and custom and border checkpoints properly arranged for you and your crew to make your experience effortless. On your last full day you will soon again be among the islanders at Saint John and off to explore the 7,000 plus acres of this island’s National Park. There are over two dozen hiking trails for all levels of hikers. Savor lunch onboard before taking a helicopter tour from Saint John around the other islands for an aerial view of all the places you have conquered this week. Then, enjoy duty free shopping after a quick sail to Saint Thomas. Have Rebecca arrange a meal on shore at the Old Stone Farmhouse (http://www.osfhvi.com/venue), a 200-year old plantation farmhouse offering classic American cuisine (operation is seasonal).



day ten - departure

After your last evening in utopia wake up in Saint Thomas or head over to Tortola, depending on your airport of departure. Before breakfast, Captain T will make sure all accommodations have been verified with the taxi company to get you to the airport after your closing brunch accompanied with your favorite flavored espresso drink, quintessential Bloody Mary bar, and tea and biscuits. Take a look at the calendar for the upcoming year and plan your next adventure in paradise onboard Anastasia with T and Rebecca. You will surely need something to look forward to and to help ease the pain of having to jump ship and fly back to reality.