Sailing with 'Sophisticated Lady'


The Caribbean

We offer Caribbean Sailing Vacations in many popular destinations that include, but are not limited to, The British Virgin Islands, St. Thomas, St. Johns, The Spanish Virgin Islands, Saint Maarten, St Barts, and more! If you have a particular destination in mind, just ask!  Charters are available in the Virgin Island areas from November through end of May.  During the summer months we have exotic locations further South in Grenada and the Grenadines, St Vincent, etc... so if you have an exotic port you'd like to visit, just ask!!

Remember, 'Sophisticated Lady' is your private sailing yacht for the duration of your sailing vacation... she goes where you want to go! Sailing Vacations in this truly spectacular place on Earth book up fast as you can well imagine, so make your reservation early to guarantee your holiday dates!!


Sample Itinerary ~ The Virgin Islands

Day 1: Board your yacht in St. Thomas and after lunch, enjoy a leisurely sail (or motor sail) to Frances Bay on St. John. Have an afternoon swim, then walk the beach and enjoy a Caribbean sunset. Savor a delicious dinner either in the cockpit under the stars or below in the coziness of the main salon.

Day 2: Perhaps make plans for a "wedding in paradise". After breakfast depart for Leinster Bay, also on St John, for snorkeling, exploring and a hike to a sugar mill. Return for lunch and then proceed to Jost Van Dyke to clear customs into the British Virgin Islands.

Explore Jost, visit Foxy's and other well known beach bars. This is also a good spot for a West Indian meal ashore at moderate prices - an island pig roast perhaps?

And, a great place for some evening revelry in the form of a "jump up" (party).

Day 3: Depart Jost van Dyke for a quick sail to Sandy Spit for a morning of beachcombing and snorkeling.

Sail on to Cane Garden Bay, Tortola - (listen carefully to Jimmy Buffet's song MaƱana, and he sings about sailing in to Cane Garden Bay!)

Stay in Cane Garden Bay for the evening or sail on to West End, Tortola for lunch and a trip ashore to Pusser's Landing for a "Painkiller" and shopping.

Day 4: Sail on to the Bight at Norman Island and visit the "Wille T" (a floating bar and restaurant) or Billy Bones ashore for local roti (spicy curry wrapped meat and vegetables) and sunset cocktails or after dinner wildness (Billy Bones announces Happy Hour with a blast from a pirate cannon!).

Snorkel the water level Caves at Norman Island. This island is nicknamed 'Treasure Island', as it is rumored to be the basis for Robert Louis Stevenson's Treasure Island.

Sail on to Cooper Island for lunch. Enjoy an afternoon sail to Trellis Bay on Beef Island. After dinner, go to the Last Resort for Tony Snelling's musical review or have a relaxing drink at Pusser's Marina Cay.

Day 5: Sail to Virgin Gorda, and visit the famous Baths, which are world famous house-sized boulders that form fascinating pools and grottoes to explore.

After lunch, sail on to North Sound, and visit the Bitter End Yacht Club for snorkeling, boardsailing, water-skiing or hiking.

Almost any activity can be found in the islands, year round!

Day 6: Depart North Sound after morning activities and lunch for a sail to Peter Island, where there is a great beach on Deadman's Bay and excellent snorkeling in Great Harbor.

Visit Peter Island Yacht Club - a very upscale place for a dinner ashore ( jackets required in season ) if that's your preference.

Day 7: More water sports in the morning (possibly a SCUBA dive on the coral-encrusted 1867 wreck of the British mail steamer R.M.S. Rhone).

Following lunch, sail to Cruz Bay on St John to clear U.S. Customs. Check out the cute local boutiques here or sail on to Christmas Cove on Great St James island for one more chance at snorkeling or other watersports.

Enjoy your last evening aboard with another glorious Caribbean sunset, and a special dinner prepared by your chef.

Day 8: After breakfast (with a farewell Bloody Mary or Mimosa, perhaps?) and a final swim, return to Red Hook Bay on the east end of St. Thomas, or to the main harbor on the south side, Charlotte Amalie. Downtown St Thomas offers some very fine last minute duty free shopping before you catch your flight home.

General Charts of the Area: