Overview
Come sail the Spanish Virgin Islands and explore the beautiful waters and islands of Puerto Rico with a group of fellow sailors. You can join by the cabin or charter your own boat through us and bring your partner, family, or friends. Either way, you’ll follow the same route and be part of the flotilla. We will visit Culebra and Vieques, known for their clear turquoise waters, beautiful beaches, excellent snorkeling, quiet anchorages and laid-back island atmosphere. Along the way, there will be opportunities to explore ashore, enjoy local food, and experience the famous bioluminescent waters of Vieques. There is also something reassuring about sailing with a group. Each day starts with a skippers meeting to review the weather and plan the day, and our experienced flotilla leaders are there to help when needed. Sharing dinners, stories and laughs with people who love being on the water is part of what makes a flotilla special, and often leads to friendships and connections that last well beyond the week. Come sail with us and discover the Spanish Virgin Islands together!
Itinerary
We recommend arriving in San Juan a couple of days before the flotilla so you have time to settle in and enjoy a little of Puerto Rico before we set sail. On Friday, April 23, we’ll organize a guided tour of historic San Juan, giving you the opportunity to discover the colorful streets, history and culture of Puerto Rico before heading to the marina. On Saturday morning, April 24, we’ll meet at Marina Puerto del Rey in Fajardo, our starting point for the sailing adventure. Once everyone is settled aboard and the boats are ready, we’ll sail to Isla Palomino for our first afternoon on the water, with time for swimming and snorkeling. From there, we’ll make our way to Culebra, exploring its beautiful beaches, clear waters, snorkeling spots and quiet anchorages. We’ll have time to go ashore, enjoy dinner and experience some of the island’s laid-back atmosphere before continuing on to Vieques. Vieques offers a different side of the Spanish Virgin Islands, with beautiful beaches, excellent snorkeling, local restaurants and the opportunity to experience its famous bioluminescent bay. We’ll spend several days exploring the island and its surrounding waters before beginning our return toward Fajardo. Our final night will be spent either around Punta Arenas or, conditions permitting, Cayo Icacos, giving us one last evening to enjoy the water before returning to Marina Puerto del Rey on Saturday, May 1.
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SATURDAY
We do our provisioning and arrive at Marina del Rey around 09:30AM to get settled on our boats.
We will go over the technical yacht features and get our chart briefing after which we will sail about 4NM to Isla Palomino. We will take a buoy and snorkel over nearby Pyramid Reef.
Dinner on board or at a local restaurant on the beach.
SUNDAY
Our destination for the day is Culebra and Cayo Luis Peña, about 13 NM away. Cayo Luis Peña is home to a turtle sanctuary and offers excellent snorkeling in clear Caribbean waters.
Later, we’ll continue to Playa Melones, where we’ll pick up a mooring. From there, we can take the dinghies ashore to Dewey, the main town of Culebra, for dinner and a chance to enjoy some of the island’s local atmosphere and entertainment.
MONDAY
After breakfast, we’ll explore the north side of Culebra, with the possibility of snorkeling at Carlos Rosario Marine Reserve and Bahía Tortuga, depending on weather, sea conditions and any local restrictions.
There will also be time to hike to the historic lighthouse or simply relax and enjoy one of the island’s natural tide pools.
We’ll finish the day in Ensenada Honda, Culebra’s main harbor, where we’ll anchor behind Cayo Pirata and take the dinghies ashore for dinner.
TUESDAY
If needed, we can replenish our provisions in the morning. Or, if you prefer, take the opportunity to rent a scooter or Jeep and explore more of Culebra on your own.
Later, we’ll sail to Dakity, a beautiful harbor with plenty of moorings and opportunities for snorkeling, depending on conditions. Nearby, Club Seaborne and Bahia Bay Resort offer options for drinks and dinner, making for a relaxed evening ashore.
WEDNESDAY
Heading south, our next destination is Vieques. With the prevailing winds, it should be an enjoyable sail to the more secluded Bahía Chiva, where we’ll spend the night at anchor.
Once there, we can enjoy the long sandy beach and, conditions permitting, explore some of the local snorkeling spots around Blue Tang and Isla Chiva. A relaxed evening aboard rounds out the day.
THURSDAY
We’ll sail along the south coast of Vieques to Sun Bay, where we’ll pick up a mooring and enjoy some time in the water, with snorkeling on the east side of the bay or a walk along the beautiful beach, depending on conditions.
Later, we’ll head ashore to Esperanza, with its lively waterfront promenade, small shops and local restaurants. In the evening, there is an opportunity to experience one of Vieques’ highlights—the famous bioluminescent waters. A guided kayak tour offers a chance to see the glowing waters up close and experience this unique natural phenomenon.
FRIDAY
Our last full day on the water takes us to the western end of Vieques and Punta Arenas, where we can drop anchor for a swim and enjoy one more beautiful afternoon on the water.
From there, we’ll make our way toward Cayo Icacos, where, conditions permitting, we’ll spend our final night aboard under the stars.
SATURDAY
Return to base by 10:00 am. Refuel and disembark.
Hosts
Capt. Jean and "Admiral" Mila
Jean and Mila, both U.S. Coast Guard captains, have been leading sailing flotillas since 2009, bringing a wealth of expertise and a love of adventure to every voyage. Jean, an ASA-certified instructor, and Mila ensure each trip is safe, enriching, and filled with memorable cultural experiences.
Lagoon 42 Private Cabin with Private Head
Guaranteed departure - on this trip - with 5 couples. We’ll confirm by January 15, 2027. Full refund if the trip doesn’t go.
FROM$2,950.00/pp
Lagoon 42 Owners Cabin
Guaranteed departure with 5 couples. We’ll confirm by January 15, 2027. Full refund if the trip doesn’t go.
FROM$3,450.00/pp
Skippered Lagoon 46 - Private Cabin w/private head
Guaranteed departure with 5 couples. We’ll confirm by January 15, 2027. Full refund if the trip doesn’t go.
FROM$3,950.00/pp
Gallery
Dates
April 2027
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