“You Make the Memories, We’ll Make the Arrangements”

A 7-night USVI-SVI Sailing Itinerary is unique. You can enjoy the sights, activities, and cuisine of both the United States Virgin Islands and the Spanish Virgin Islands all in one fun-filled vacation. Note that this is only a sample. You and your captain will discuss your interests and preferences before setting sail.

Yacht Haven Grande Marina, St. Thomas, USVI
Yacht Haven Grande Marina, St Thomas

Day 1 St Thomas USVI

Begin your 7-night USVI-SVI Sailing Itinerary at Yacht Haven Grande Marina on St Thomas. After a brief safety meeting take a very short sail to Water Island. This small residential island (the smallest of the USVI at just 490 acres) is home to Honeymoon Beach, a pretty, white sand beach lined with palm trees.


  • Swim. The beach is typically surf-free and deepens gradually so it is perfect for small children.
  • Snorkel. The clear water makes it easy to spot marine life.
  • Have dinner on board your yacht or, if you prefer, dine ashore in Frenchtown, St. Thomas.

St. Thomas harbor, USVI-SVI Sailing Itinerary 7-Night
Start your vacation from St. Thomas.

Day 2 Sail to Isla de Culebra

Your captain will raise the sails for an early morning voyage to Isla de Culebra (20 miles downwind). Enjoy a fun day at sea.


  • Snorkel
  • Dive
  • Kayak
  • Fish
  • Tube or knee-board behind the dinghy
  • Relax in the sun on the trampoline or aft sun pad
  • Enjoy hand-crafted cocktails and tasty cuisine prepared by your yacht’s private chef

USVI-SVI Sailing Itinerary 7-Night alfresco dining
Breakfast alfresco.

Day 3 Explore Isla de Culebra

Locals say Culebra is an “island of nothing—no nightclubs, no casinos.” On this quiet and pristine island, the beach is your best bet for entertainment. Fortunately, Culebra beaches are amongst the finest in the world. Flamenco Beach is considered the second-most beautiful beach in the world by Discovery Channel and is by far the most popular beach in Culebra. If Flamenco’s mile-and-a-half stretch of cinematic white sand and turquoise water grows old, try hiking 24 minutes to Carlos Rosario Beach, a premier snorkeling spot. The snorkeling and scuba diving around Culebra are truly outstanding. Hard and soft corals abound in the shallows and magnificent reefs encircle the island.

USVI-SVI Sailing Itinerary 7-Nights  Isla de Culebra


  • Hike
  • Snorkel
  • Play beach games
  • Swim
  • Picnic

You’ll spend the night anchored at Dakity Reef.

Day 4 Sail to Isla Culebrita

The small uninhabited island of Culebrita is a nature reserve and part of the Culebra National Wildlife Refuge, which protects large colonies of sea birds and nesting sea turtles.

The island is home to one of the oldest lighthouses in the Caribbean. Hike to its breathtaking location at the top of a large hill. Better yet, visit the seaward pools known locally as “the Jacuzzis,” a series of shallow natural sea-fed pools filled with warm water. The “jacuzzi” action comes when the surf refreshes the water supply. You can also snorkel nearby reefs and ledges or dive the Cayos Ballena, Tiburon, and Geniqui a mile to the north.

USVI-SVI Sailing Itinerary 7-Night - Enjoy scuba diving
Yacht TRUE STORY offers onboard scuba diving.


  • Hike
  • Jump in a natural Jacuzzi
  • Snorkel
  • Dive

Day 5 Sail to Vieques

USVI-SVI Sailing Itinerary 7-Nights Vieques
Vieques. Photo by Ethan Jameson on Unsplash

In Vieques, you must see Mosquito Bay, considered the world’s largest and brightest bioluminescent bay. The luminescence is caused by micro-organisms (dinoflagellates) that dart away from boats, leaving eerie neon-blue trails of phosphorescence. Kayaking through these amazing waters is an experience not to be missed!

Snorkeling is excellent here, especially at Blue Beach. What’s more, you can walk for miles on nearly deserted beaches.


Anchor for the night and enjoy the sunset.

Day 6 Sail St Croix

On day six, you’re off to St Croix (35 miles). This unique Caribbean island offers a lot to see and do the largest of the US Virgin Islands. In the charming town of Christiansted, you’ll find quaint restaurants, breezy courtyards, and unique shopping opportunities. You can easily spend an entire day “getting lost” in this town.

Crucian Gold, on Kings Warf, sells Crucian hook bracelets exclusively designed and manufactured by a Crucian—a great memento of your trip to Christiansted.

Tucked in among the shops you will discover some wonderful restaurants. Dine outside in the balmy air in a courtyard flanked by stone columns, Danish arches, trees, and gardens. Enjoy the view from your table on a hilltop verandah or enjoy the homey atmosphere of a local deli, café, barbeque, or burger stop. Munch on conch fritters or crack open clawless Caribbean lobster.

USVI-SVI Sailing Itinerary 7-Night - Frederiksted, St Croix
Frederiksted, St Croix


  • Hike
  • Shop
  • Dine
  • Explore
  • Horseback Ride

Day 7 Explore St. Croix

After a relaxing morning, make plans for the day. There is still much to explore on St Croix. You may want to rent a Jeep to drive for the day. Since the roads are bumpy, a Jeep is the best bet for traveling.

History buffs may enjoy walking to historical sites. The old town of Christiansted boasts five of them within walking distance of the waterfront, including Fort Christiansted (built-in 1734). Be sure to visit the spooky underground dungeons.

Visit the Whim Greathouse and museum. This is the only sugar plantation museum in the Virgin Islands. See the old slave quarters, Great House, cookhouse, sugar mill, and factory complex.


  • Rent a Jeep
  • Walk
  • Historical sites.
  • Cruzan Rum Distillery
  • Frederiksted rainforest
  • Whim Greathouse

Day 8 Sail Back to St. Thomas

On your final day, sail 30 miles back to Water Island for one last day of fun soaking up the sun and enjoying the Caribbean waters.

Contact us at 1-321-777-1707 or complete this form to discuss your vacation plans.