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The Yachtsman’s Caribbean: Exploring the U.S. & British Virgin Islands

Program Number: 21328RJ
Start and End Dates:
12/19/2013 - 12/27/2013;
Duration: 8 nights
Location: U.S. Virgin Islands/British Virgin Islands
Price starting at: $4,245.00 - Price may vary based on date, departure city
Program Type: Adventure Afloat Study Cruise; Small Ship Cruising
Meals: 22; 8 Breakfasts, 7 Lunches, 7 Dinners    
Meal Options: Low Salt    

Discover the stunning natural beauty and intriguing history of the Virgin Islands on this small ship voyage. On the intimate Yorktown, sail into secluded harbors that can’t be accessed by huge ocean liners but that have long been loved by seasoned yachtsmen. Study marine life with onboard naturalists, explore undisturbed tropical environments onshore and learn the stories of pirates who once hid in these beautiful coves.

Activity Particulars

Walking up to two miles per day on forest trails. Some stairs without railings. Other activities include swimming, snorkeling, and kayaking. Mobility is essential, as small boats and tenders are sometimes used for disembarkation and re-embarkation.

Itinerary At-a-Glance

Saint Thomas (U.S. Virgin Islands), 1 night; aboard Yorktown, 7 nights.

Days 1-2:
Arrival Saint Thomas (U.S. Virgin Islands) / embark Yorktown:

An expert-led walking excursion in Charlotte Amalie, the island’s historic capital, includes Blackbeard’s Castle. Journey to the St. Peter Great House and Botanical Garden to examine some of its 200 species of West Indian plants and trees. Lodging: Waterfront resort.

Day 3:
Jost Van Dyke (British Virgin Islands):

Navigate the Sir Francis Drake Channel en route to Jost Van Dyke. Anchor in beautiful White Bay to snorkel, swim or go ashore on this lovely island of white-sand beaches and colorful birdlife.

Day 4:
Tortola & Peter Island:

On Tortola, explore Mount Sage National Park, where lush ferns, guavas, elephant ears and mahogany trees grow on the slopes of a volcanic peak. Continue to privately, largely undeveloped Peter Island to hike or swim.

Day 5:
Virgin Gorda:

Enjoy a full day to discover Virgin Gorda, a beautiful island of quiet coves and secluded beaches. Experience the unique geology of “The Baths” and explore the Caribbean dry forest environment of Gorda Peak National Park.

Day 6:
Cooper Island & Norman Island:

Anchor at sheltered Manchioneel Bay for a morning of swimming, snorkeling or kayaking in crystal-clear waters. Continue to Norman Island, the uninhabited isle thought to be Robert Louis Stevenson’s inspiration for “Treasure Island.”

Day 7:
Saint John (U.S. Virgin Islands):

After a refreshing morning swim, set out on a shore excursion to Virgin Islands National Park, which encompasses 60% of the island. The park is home to 140 species of birds, 302 species of fish and 740 species of plants.

Days 8-9:
Saint Thomas / disembark / departure:

Return to Saint Thomas and savor a day to relax or discover more of the island’s historic landmarks independently.


Built and registered in America and staffed by American officers and crew, the Yorktown is the perfect vessel for exploring America’s great coastal waterways. With a draft of only nine feet, it can sail where larger vessels cannot go, and its American registry allows it to operate domestic itineraries unavailable to foreign-flag ships. Passengers enjoy an informal onboard atmosphere and tend to spend much of their time underway enjoying lectures and concerts in the lounge or reading and relaxing on the sun deck.

Meals and Lodgings
   Windward Passage Hotel
  Charlotte Amalie, St. Thomas, Virgin Islands 1 night
  At Sea, Virgin Islands 7 nights
 Windward Passage Hotel
Type: Resort
  Description: Caribbean resort overlooking Charlotte Amalie Harbor and within walking distance of shops, restaurants, and entertainment options. The Windward Passage has 150 airy rooms with private balconies, tiled floors, modern amenities, and Caribbean-inspired decor.
  Contact info: Veterans Drive - Charlotte Amelie Waterfront
Charlotte Amelie,   Virgin Islands
phone: +8778197959
  Room amenities: Rooms have private bathrooms, AC, private balcony, free WiFi, mini refrigerator, coffee maker, in-room safe, flat screen cable TV, iron/ironing board, hair dryer, telephone, and tiled floors.
  Facility amenities: Freshwater pool, spa, fitness center, beauty salon, restaurant, gaming center, lounge, and bar. The property offers a complimentary van service to nearby attractions.
  Smoking allowed: Yes
  Elevators available: Yes
  Additional nights prior: Subject to availability. Room types and prices are subject to availability. Please contact your program coordinator, Holbrook Travel, at 1-800-866-7111 or for assistance in booking additional nights.
  Check in time: 4:00 PM

Type: Cruise Ship
  Ship Information: At 257 feet long, 43 feet wide, with a draft of eight feet, the Yorktown is able to maneuver in secluded waterways and visit small ports that are inaccessible to larger vessels.
  Contact info: 132 East 70th Street
New York, NY 10021 USA
phone: 866-459-8853 x 0-0000000
  Room amenities: All cabins have air-conditioning and small, private bathrooms with continental-style showers.
  Facility amenities: Returning from excursions, guests enjoy complimentary refreshments, afternoon tea and all-day coffee in The Lounge, a gracious space for relaxation, surrounded by panoramic windows. Before or after dinner, cocktails are served to live music performed by the ship’s pianist. Other Yorktown features include: •Internet access (additional cost)* •Window-lined lounge with panoramic views •Dining room surrounded by windows •Swimming platform *Note: Before purchasing onboard internet service, please note that the andwidth is relatively narrow and speed is correspondingly slow. Participants will be able to send and receive email messages and check your email accounts without difficulty. However, it is not suitable for ‘surfing’ the web, downloading files of any significant size, or attempting to stream audio or video.
  Smoking allowed: No

Travel Details
  Start of Program:
Arrivals into Cyril E. King Airport in St. Thomas, US Virgin Islands. Hotel check-in starts at 4 p.m. You will be staying at Windward Passage Hotel that night.
  End of Program:
Morning disembarkation at Crown Bay Marina. Departures from Cyril E. King Airport in St. Thomas. You will be staying at Yorktown the night before.
  Required documents:
The Participant Information Form is required.
  Parking availability:
Not applicable.
Transportation (For Independent Travelers)
To Start of Program
  Location:  Charlotte Amalie, St. Thomas
  Transportation to site: Licensed taxi services are available at the Cyril E. King Airport. A taxi ride from the airport to Charlotte Amelie costs approximately $15.
  From End of Program
  Location:  At Sea
  Transportation from site: Taxi service is available at the Crown Bay Marina in St. Thomas.
Equipment Requirements: No,snorkeling equipment is provided on the boat .
The prices listed for commercial services and facilities that are not included in the program cost, such as airport shuttles or extra nights lodging, are subject to change without notice. Since Road Scholar cannot guarantee the accuracy of these prices, we strongly suggest contacting the companies directly for the most up-to-date information.

Daily Schedule

Day 1: Flights from the U.S./Arrivals in St. Thomas, U.S. Virgin Islands.
(Thursday, December 19)
 Arrive To: Arrivals at St. Thomas' Cyril E. King Airport. After collecting your luggage, please look for the local Road Scholar representative waiting with a Road Scholar sign in the arrivals hall.

Transfer to the hotel.

Please note that this is a travel day and does not include any meals. Hotel check-in starts at 4 p.m.
Accommodations: Windward Passage Hotel

Day 2: St. Thomas -
Embarkation on Yorktown.

(Friday, December 20)
 Breakfast: Breakfast at the hotel restaurant.
 Morning: Orientation to the program.

Lecture: The Virgin Islands

Enjoy a walking orientation to Charlotte Amalie’s charming historic sites, starting with an introduction to St. Thomas and its history during a visit to Blackbeard’s Castle (circa 1679). From the castle, walk downhill via Villa Notman (circa 1860), the Crown House (circa 1740), and the Haagensen House (circa 1822). Visit Hotel 1829, then head to Emancipation Garden, a local park dedicated to the end of slavery, before finishing at Fort Christian—a National Historical Landmark constructed in the late 17th century.
 Lunch: Lunch at local restaurant.
 Afternoon: Have your cameras at the ready as we travel to Drake's Seat, a scenic spot on St. Thomas' West End, to enjoy beautiful views of Magen's Bay. According to local lore, Sir Francis Drake visited this spot in order to look out for enemy ships traveling through the Drake's Passage.

Continue to St. Peter Greathouse and Botanical Gardens to enjoy the estate's 200 varieties of West Indian plants and trees, as well as tropical specimens from around the world. The self-guided nature paths invite visitors to learn about the plants that make up the lush and colorful gardens.

Finish your explorations with a stop at Mountain Top. This popular lookout is located on the highest point on St. Thomas and affords incredible panoramic views of Magen's Bay and nearby islands.

Transfer to Crown Bay Marina and embark on the Yorktown.

Attend a welcome briefing and safety drill.
 Dinner: Welcome dinner on board.
Accommodations: Yorktown
Meals Included: Breakfast, Lunch, Dinner

Day 3: Jost Van Dyke -
Exploring Jost Van Dyke Island/Swimming and Snorkeling.

(Saturday, December 21)
 Breakfast: Breakfast on board.
 Morning: Enjoy a leisurely morning as we navigate the Sir Francis Drake Channel en route to Jost Van Dyke.
 Lunch: Lunch on board.
 Afternoon: Anchor at White Bay. The beautiful bay on Jost Van Dyke is sheltered by a barrier reef and lined by a white-sand beach.

In addition to being a great swimming and snorkeling destination, this island also offers good hiking and birding opportunities.

Diamond Cay National Park is located off the east shore of the island. Despite its diminutive size, the park is an important nesting site for boobies, pelicans, and terns.
 Dinner: Dinner on board.
 Evening: Enjoy ship's evening entertainment.
Accommodations: Yorktown
Meals Included: Breakfast, Lunch, Dinner

Day 4: Tortola and Peter Islands -
Road Town and Sage Mountain National Park/Hiking, Swimming, and Snorkeling at Peter Island.

(Sunday, December 22)
 Breakfast: Breakfast on board.
 Morning: Depart from Soper's Hole on Tortola and navigate to Road Town--the island's capital.

Explore the Sage National Park for a hike through the rainforest. Mount Sage is the highest point in the British Virgin Islands standing more than 17,000 feet above sea level. Kapok and mahogany trees thrive in the protected rainforest and park pathways are lined with ferns, mountain guava, and elephant ears. The breathtaking views of surrounding islands are one more bonus afforded to those who choose to visit this site.

Time to explore Road Town on your own, or enjoy swimming and snorkeling at a local beach.
 Lunch: Lunch on board.
 Afternoon: Navigate to a small privately owned island for afternoon activities.

A short crossing to Peter Island provides opportunities for hiking on paths and swimming and snorkeling from local beaches.
 Dinner: Dinner on board.
 Evening: Enjoy ship's evening entertainment.
Accommodations: Yorktown
Meals Included: Breakfast, Lunch, Dinner

Day 5: Virgin Gorda -
Exploring Virgin Gorda's Treasures.

(Monday, December 23)
 Breakfast: Breakfast on board.
 Morning: Disembark at Leverick Bay Marina on Virgin Gorda for a full day of explorations.

The beautiful island in the British archipelago has many interesting and exotic sites, including The Baths, Gorda Peak National Park, and a number of attractive, secluded beaches.
 Lunch: Lunch on board.
 Afternoon: Continue exploring Virgin Gorda.
Return to the ship.
 Dinner: Dinner on board.
 Evening: Enjoy ship's evening entertainment.
Accommodations: Yorktown
Meals Included: Breakfast, Lunch, Dinner

Day 6: Cooper and Norman Islands -
Swimming, Snorkeling, and Kayaking at Manchioneel Bay/Experiencing the Marine Life of The Caves.

(Tuesday, December 24)
 Breakfast: Breakfast on board.
 Morning: This morning we will anchor at sheltered Manchioneel Bay, Cooper Island for a morning of swimming, snorkeling, and kayaking activities. Cistern Point and its surrounding coral reefs is an especially good site for snorkeling.
 Lunch: Lunch on board.
 Afternoon: After lunch, disembark at Norman Island, reputed to be Robert Louis Stevenson's inspiration for "Treasure Island." Anchor at The Caves. Crystal-clear water, brightly colored coral, and abundant marine life make this an outstading spot for swimming and snorkeling.
 Dinner: Dinner on board.
 Evening: Enjoy ship's evening entertainment.
Accommodations: Yorktown
Meals Included: Breakfast, Lunch, Dinner

Day 7: St. John -
Water Activities at East End/Hiking at Virgin Islands National Park/Cruz Bay Town.

(Wednesday, December 25)
 Breakfast: Breakfast on board.
 Morning: Anchor at East End, St. John for a refreshing morning swim before moving on to Cruz Bay.

Enjoy a full day of island explorations including an opportunity to visit the Virgin Islands National Park. The national park encompases more than half of the island, protecting not only a variety of flora and fauna, but also important historic sites.
 Lunch: Lunch on board.
 Afternoon: Continue with explorations of St. John.

Since the ship will be anchored at Cruz Bay overnight, participants will be able to enjoy the town leisurely.
 Dinner: Dinner on board.
 Evening: Enjoy ship's evening entertainment.
Accommodations: Yorktown
Meals Included: Breakfast, Lunch, Dinner

Day 8: St. Thomas -
Dock at Crown Bay/Free Time at Charlotte Amalie.

(Thursday, December 26)
 Breakfast: Breakfast on board.
 Morning: Morning docking at Crown Bay Marina.

Spend the day relaxing and exploring Charlotte Amalie on your own or join an excursion to some of St. Thomas' historic landmarks.
 Lunch: Lunch on board.
 Afternoon: Continue with free time opportunities on St. Thomas.
Return to the ship.
 Dinner: Farewell dinner on board.
Accommodations: Yorktown
Meals Included: Breakfast, Lunch, Dinner

Day 9: Departures -
Disembark at Crown Bay/Flights to the U.S.

(Friday, December 27)
 Breakfast: Breakfast on board.
 Morning: Transfer to the airport to board flights back to mainland U.S.
Meals Included: Breakfast
Important information about your itinerary: Every effort has been made to ensure the accuracy and completeness of the information featured on this website. Itineraries are based on our best information at this time. Circumstances beyond our control may require us to adjust itineraries or other details. We regret any inconvenience this may cause and appreciate your understanding. Information will be sent to you from your Program Provider approximately three weeks prior to the program start date. The prices listed for commercial services and facilities that are not included in the program cost, such as airport shuttles or extra nights lodging, are subject to change without notice. Since Road Scholar cannot guarantee the accuracy of these prices, we strongly suggest contacting the companies directly for the most up-to-date information.

Suggested Reading List

Virgin Islands Map - US & British

Author: Borsch Maps

Description: Laminated map of both the U.S. and British Virgin Islands.

Fodor's U.S. and British Virgin Islands

Author: Fodor's Guidebooks

A History of the Virgin Islands of the United States

Author: Isaac Dookhan

Description: This book takes a look at the Virgin Islands’ social and economic impact on European and American societies. Interesting facts help to paint a clearer picture of the type of people who settled the islands and their daily struggles.

Lonely Planet U.S. and British Virgin Islands

Author: Karla Zimmerman

Puerto Rico & Virgin Islands Wildlife Viewing Guide

Author: David W Nellis and Defenders of Wildlife

Seabirds: An Identification Guide

Author: Peter Harrison

Description: This is the definitive book on the seabirds of the world. It covers most of the known species, each illustrated in color, with different plumages, postures and views to provide visual information not previously available in any book. Features: 312 species, 88 color plates showing over 1500 birds, 324 color range maps, and clear text treating each species in depth.

Snorkeling Guide to Marine Life

Author: Paul Humann

Description: Humann's photographs of the fishes, corals, invertebrates and plants of the Caribbean are perfect to take along in the boat or to the beach.

The Colonial History of the Caribbean from the Antilles to the Virgin Islands

Author: S. B. Jeffrey

The Night of the Silent Drums: A Narrative of Slave Rebellion in the Virgin Islands

Author: John L. Anderson

Description: An interesting account of the historic slave rebellion that took place in the Danish West Indies between 1733 and 1734 on what is now St. John.

Tropical Trees of Florida and the Virgin Islands: A Guide to the Identification, Characteristics and Uses.

Author: T. Kent Kirk

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