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US & Spanish Virgin Islands Sailing Itinerary St Thomas to Puerto Rico

American Yacht Harbour Red Hook, St. Thomas
American Yacht Harbour Marina

Your Spanish Virgin Islands sailing itinerary begins in St Thomas, then you’ll sail to St Johns, Culebra, Culebrita “Little Culebra”, Vieques, and finish in Puerto Rico.

Day 1 — Red Hook, St. Thomas to Christmas Cove, Great St. James

You will begin your 8-day sailing excursion at Red Hook Harbor on St. Thomas. Enjoy a smooth 45-minute sail to the uninhabited island of Great St. James and jump into the turquoise waters at Christmas Cove for an afternoon swim and snorkel. The calm waters of this well-protected cove are a National Marine Sanctuary. Here you will see lots of fish, sea turtles, and friendly stingrays. Here you will overnight in this quiet and protective cove.

Day 2 — St. John

On day 2 of your journey, you sail to beautiful St. John Island. Though it is the smallest of the three U.S Virgin Islands, St. John has an unspoiled beauty that’s incomparable to anywhere in the Caribbean. With 60% of its land area comprising a pristine National Park, St. John’s is as far away as you can get from civilization. It is still just a short distance from upscale jewelry stores and boutiques.

Journey to Caneel Bay to visit the Caneel Bay Resort. It was built on the site of an 18th-century sugar plantation. For the “foodie” in you visit the Beach Terrace for buffet-style offerings as well as a la carte selections. You can also go for a more refined dining experience at The Sugar Mill Restaurant where you will be introduced to the herbs, spices, and native cuisine of St. John’s and the Virgin Islands.

Feel free to walk the grounds of this luxury beach resort, while enjoying the sparkling lights of St. Thomas on the distant horizon, before heading back to your private yacht.

For the more adventurous types, we head to Leinster Bay and Waterlemon Cay. These combined attractions are a snorkeler’s dream, and an interesting hike is also accessible. Calm and protected, Leinster Bay has extensive seagrass, with turtles, conch, and sea stars. Waterlemon Cay is home to a healthy and expansive coral reef and is considered one of the best (if not the best) snorkeling locations in all of St. John.

Together, they make a terrific destination for enthusiastic snorkelers. Landlubbers can hike 0.25 miles up the Johnny Horn Trail, which departs from Leinster Bay to Annaberg Plantation Ruins—a Dutch mill that was used for processing sugar cane.

Day 3 — Sail to Culebra, Fun Day at Sea

Early morning sail to Culebra. Enjoy a fun day at sea diving, kayaking, fishing, tubing, knee-boarding behind the dink, or relaxing in the sun on the trampoline or aft sun pad. Enjoy inspired cocktails and tasty cuisine onboard.

Day 4 — Explore Isla de Culebra

Locals call “Culebra an “island of nothing—no nightclubs, no casinos.” On this quiet and unspoiled island, the beach is your best bet for entertainment and Culebra beaches are amongst the finest in the world. Flamenco Beach is considered the second most beautiful beach in the world by Discover Channel and is by far the most popular beach in Culebra. This white sandy beach stretches along the entire bay, you will feel the Caribbean sun everywhere and wonder why you had waited this long!

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. You spend the night anchored at Dakity Reef.

Day 5 — Day sail to Isla Culebrita

The small uninhabited island of Culebrita is a nature reserve. It is part of the Culebra National Wildlife Refuge which protects large colonies of sea birds and nesting sea turtles. You’ll never get tired of watching the terns, red-billed tropicbirds, and boobies soar above the island and swoop down low to catch fish.

The island is home to one of the oldest lighthouses in the Caribbean. Visitors usually go hiking to the breathtaking top hill view. 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.

Stopover at a Beach on Vieques - Spanish Virgin Islands Sailing Itinerary
Beach on Vieques

Day 6 — Sail to Vieques

On Day 6 you sail to Isla de Vieques, which is like the Caribbean of the past: tranquil, lush, un-crowded, with natural beauty all around. The reason for this unspoiled beauty? Under US military control from 1941 until 2003, Vieques has remained relatively untouched by development and tourism. And, the island has the largest natural wildlife refuge in the Caribbean covering 3100 acres.

In Vieques, you cannot miss “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 in Vieques, especially at “Blue Beach”, and this island boasts miles and miles of spectacular and deserted beaches. Beach sands range from soft white to sparkling black. Each beach is unique with its own flavor and personality. Most likely you’ll have a beach all to yourself any time of the year due to the great number of small beach coves around the island.

For you history buffs, the Fortin Conde de Mirasol is certainly worth visiting. Built between 1845 and 1855, “El Fortin” (The fort) is the best place to learn about the island’s history and culture. The building was restored and it now houses a museum of Viequense art and the history of people dating back to the indigenous times. While visiting keep your eyes peeled over the land horizon. Vieques is famous for its feral horses that roam free over parts of the island, and you might just see some. They are descended from stock originally brought by European colonizers.

Another Vieques attraction is stargazing. The island is small and only has two small towns, light pollution is low which is the perfect condition for enjoying a sky full of bright stars. The dark black cloudless skies paint the perfect background for a fantastic show of stars. If you are quiet and listen, the stars twinkle and create a beautiful melody accompanied by the sweet serenading sounds of the Puerto Rican “coquis”.

Day 7 — Sail to Fajardo, Puerto Rico

As we near our final destination of Fajardo there are many small islands and cays to explore. Go for a diving and snorkeling experience at La Cordillera. It’s a marine reserve consisting of 12 miles of islets and keys to explore. Cayo Icacos provides endless diving, snorkeling, and shelling on the surrounding reefs and secluded beaches. Finally, Isla Palominos, a jewel of a tropical island, is the perfect place to anchor to watch your final Caribbean sunset over El Yunque’s rainforest.


After an active day at sea, Las Croabaos, visitors can hang out in typical restaurants and bars. Rosa’s Seafood restaurant” in Puerto Real is a highly recommended spot for traditional Puerto Rican cuisine. Grilled fish and lobster are their specialties.

Day 8 — Departure day

From the small city of Fajardo, you will transfer to Cabo San Juan Airport and fly home.

Flamenco Beach is a highlight of Spanish Virgin Islands Sailing Itinerary
Flamenco Beach

Whether it is deep-sea diving, snorkeling, or on-land sightseeing that interests you most, we will build a Spanish Virgin Islands sailing itinerary that best suits your interests and desires. This is just a sample of what your yacht charter adventure in the US & Spanish Virgin Islands may look like. Furthermore, weather or other outside factors may require your Captain to set an alternative course for the duration of your trip.

“As the wind blows, so shall the sail”.

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