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Fly into Puerto Rico’s booming capital, San Juan, to begin your charter across the brilliant Caribbean Sea. The region is home to many close, secluded islets and the Spanish Virgin Islands (SVI)— Culebra and Vieques. This combination of peaceful, intimate beaches and thriving villages appeals to both the quiet castaway and lively spirit, and is a huge reason travelers of all sorts flock to Puerto Rico and the Passage Islands.
Warm weather promises seven days of tropical ecstasy, year round, and short distance cruising makes it easy to plot your course. From irresistible Spanish cuisine to historic forts, this region’s unique culture awaits. Leave your passport at home and book your yacht charter with Virgin Island Sailing®.
There’s a full itinerary worth of activities and events to keep the whole family busy on your Caribbean yacht charter! With a number of gorgeous beaches and protected coves, relaxing anchorages are only a short distance away. While yachters love being on the blue waters, you can’t help but stretch your sea legs and explore Puerto Rico and its neighboring islands’ land-based treasures. Inland you’ll find rich military history, lush forests and upbeat villages, featuring Spanish cuisine, local shops and iconic landmarks. Don’t forget to check the events calendar below, and pencil in a music festival or island celebration during your getaway.
There are exciting activities happening year round on Puerto Rico and across the Spanish Virgin Islands, welcoming charter guests to join in on the tropical fun. Many of these events celebrate rich African and Spanish heritage, with merry music and local delicacies. Whether it’s twirling with masqueraders in painted horned masks at Carnival Ponceño or listening energetically to the cuatro-playing contest at San Juan’s Festival of Puerto Rican Music, get ready to mingle with locals and learn of its most cherished history. Check to see what riveting Caribbean festivities are planned during your getaway.
Three Kings Day
San Sebastián Street Festival
Fiesta de Reyes Isabelinos
San Blas de Illescas Half Marathon
Fiestas Patronales de San Benito Abad
Five Days With Our Land Fair
Sugar Harvest Festival
Puerto Rican Danza Week
LeLoLai Cultural Festival
San Juan Bautista Day
SoFo Culinary Festival
Aibonito Flower Festival
Luis Muñoz Rivera’s Birthday
El Gigante Marathon
Torneo de Pesca Interclub del Caribe
International Billfish Tournament
Fiestas Patronales de Nuestra Señora de las Mercedes
Fiestas Patronales de Santa Cruz
Maraton Segundo Ruiz Belvis
La Raza Day (Columbus Day)
National Plantain Festival
Fiestas Patronales de San Carlos Borremeo
Festival of Puerto Rican Music
Jayuya Indian Festiva
Puerto Rico Discovery Day
Old San Juan’s White Christmas Festival
Puerto Rico Heritage Artisans Fair
Hatillo Masks Festival
Puerto Rico is graced with that beautiful, warm Caribbean weather that travelers just can’t get enough of. Matched with its fairly short cruising distances, stunning line-of-sight views and relatively calm seas, it’s a charterer’s dream destination.
Like other parts of the Caribbean, the Spanish Virgin Islands experience high season during the winter months and low season during the summer months. Often times, the best time to cruise the sea is between December and April, when the winds remain between 15-25 knots, rains stay at bay and temperatures are warm and mild. Though, people hit the water all year long in this exotic region!
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Start your sailing vacation off at the largest marina of its kind in the Caribbean. There are many services that you can utilize before embarking on your yacht charter adventure. Also, you can explore the surrounding area of the rainforest, amazing beaches, and explore Old San Juan!
1 hours | 4 miles
Your true, sailing charter has begun after just a short sail across the Vieques Sound, this is a jewel of a tropical island. During the day, the reef on the northern shore is an excellent place to snorkel. At night, Isla Palominos is the perfect place to watch the sunset over El Yunque’s rainforest and dine on the fresh tuna or bonito you caught trolling out in the sound.
2.5 hours | 13 miles
The next place to explore is Cayo Luis Pena, just off the island of Culebra. This two mile long uninhabited, wildlife refuge has numerous hiking paths and spectacular secluded beaches.
0.5 hours | 2 miles
A great place to launch snorkeling or diving expeditions to the reefs off of Culebra, including Las Hermanas and Cayo Yerba. This anchorage also provides a majestic sunset view of the El Yunque rainforest. Imagine sitting in the cockpit of your sailing
charter at dusk dining on your own fresh catch with this incredible view! Culebra has a large turtle population and at the right time of the year you can witness turtle eggs hatching and the baby turtles making their way to the ocean.
2 hours | 7 miles
A great place to moor overnight is at Bahia Almodovar where visitors can go paddle boarding, snorkeling, kayaking or alternatively, relax next to the luscious surrounding mangroves.
1 hours | 4 miles
The anchorages on Culebrita are fairly deserted during the week, but the weekends are a different story. Everyone from Puerto Rico, with a fast power boat, seems to make Culebrita the weekend party destination of choice. It’s a fun destination to people watch. Dance on deck while listening to salsa music, share a drink or two with your group and then watch a sunset.
1.5 hours | 6 miles
Another location in the Vieques Islands is Ensenada Honda, which is a beautiful cove, covered in mangroves. Two picturesque beaches are Curacas and Le Chiva Beach, which offer overnight protected anchorages to spend the night relaxing. The area has an old military tower, reefs for snorkeling, kayaks, paddle boarding, and hiking.
0.5 hours | 1 miles
Anchor your sailing charter in Dakity Harbor for a day of snorkeling. Relax and take a moment to sit on one of the beautiful beaches that Ensenada Dakity offers. Pack a lunch and take in the rays and get ready to sail to Bahia de la Chiva, Vieques.
4 hours | 22 miles
On day five you’ll set sail southbound towards the island of Vieques. After rounding the eastern tip, you’ll sail along downwind to Bahia de la Chiva. This remote anchorage spot is unique in its exclusivity as it’s relatively inaccessible without a boat. You’ll enjoy the beauty and tranquility of Bahia Chiva, which features a large horseshoe shaped harbor with an island, Isla Chiva, in the middle of the bay. There’s a long white sand beach to explore and two great snorkeling spots: “Blue Tang” reef and Isla Chiva.
1 hours | 5 miles
One of the highlights to visiting Vieques is a night time trip to Mosquito Bay, said to contain the highest degree of bioluminescence in the world. The huge concentrations of micro-organisms gives off a glow when disturbed by movement in the water. One of the many private tour operators from Esperanza can take you on a night dive, kayak or electric boat trip to experience this remarkable phenomenon.
0.5 hours | 2 miles
Cast the mooring line loose and sail leisurely down the undeveloped south coast of Vieques to Sun Bay. Cruise in and pick up a mooring on the eastern side of the bay and enjoy some nice snorkeling or a long walk on the beach. Sun Bay is just around the bend from Puerto Real, where you can enjoy the lively town of Esperanza.
0.5 hours | 2 miles
Day 5 of our Puerto Rico Sailing Itinerary brings you to the Vieques Islands and the town of Esperanza, on the south of the island. Esperanza has a small port with a ‘waterfront walk’ or promenade (which is great to jump off), peaceful restaurants, horse riding, shops and is filled with culture, history and tradition.
0.5 hours | 2 miles
A beguiling expanse of magnetic black sand against a dramatic
cliff makes for a dreamy cove. Bring your camera, the landscape
is so inspiring. You’ll find beautifully shaped driftwood, rock
cliffs, desert-like bushes covering the cliff wall behind you, all
contrasting against deep black, golden sand, turquoise waters
and foamy white waves… simply magnificent.
3 hours | 18 miles
On the last of your charter sail to Isla Pinero. Here you’ll find lots of coastline where you can drop anchor. Isla Pineros is a great place to watch the sun set over the Caribbean horizon and sit back and have a cocktail or two and reminisce on all you saw and did on your Puerto Rico Yacht Charter.
1 hours | 4 miles
Sipping the last of your rum drinks on deck as the sun disappears below the horizon on this pristine piece of paradise. If you are looking for undisturbed anchorages, isolated pristine white beaches, spectacular snorkeling/diving, and onshore immersion into the Spanish Caribbean culture unaffected by tourism or development, then the Spanish Virgin Islands are for you!
Because U.S. citizens don’t need a passport to visit Puerto Rico, it’s no surprise the destination is so popular. A number of airlines— including American, Delta, United and JetBlue— offer direct flights to San Juan, the capital of Puerto Rico.
After landing at the San Juan Luis Muñoz Marin International Airport (SJU), it’s about a 50-60 minute taxi ride to Fajardo, where you’ll be able to start your Puerto Rico yacht charter.
Our friendly VI Sailing Concierge Team is ready to help you to find lodging, should you need to book a hotel prior to or after your charter, as well as to provide options for trip insurance. Some guests decide to travel to the neighboring British Virgin Islands after their SVI adventures, extending their vacations for few more days of paradise. Whatever you’re planning, don’t hesitate to reach out with questions!