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Puerto Rico gay sailing cruise

Puerto Rico Gay Sailing Cruise

Puerto Del Rey, Isla Palominos, Culebra, Bahia del Almodovar, Flamenco, Playa Tamarindo, Esperanza, Mosquito Bay, Ensenada Honda, Green Beach, and more!

8 Days From/To Puerto Del Rey (San Jose), Puerto Rico

February 23 – March 2, 2019


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Puerto Rico Islands gay sailing cruiseOur new gay sailing cruise destination for 2019: Puerto Rico! This week is a GaySail Exclusive (clothes optional) Cruise on a luxury catamaran for 10 persons. Puerto Rico, Spanish for “Rich Port” is a tropical island in the Caribbean. Amazing experiences await everyone on this beautiful island. The capital San Juan is very gay friendly and is the perfect place to stay if you enjoy a rich cultured city and a hot nightlife. San Juan is the most populated area within Puerto Rico and has plenty of gay friendly hotels and gay bars to make every gay traveler feel comfortable. Condado Beach is the perfect spot to soak up the Caribbean sun and mingle with the local LGBT community and gay tourists.

With short travel distances and some of the Caribbean's most pristine beaches, a gay sailing cruise in Puerto Rico is idyllic. Enjoy line-of-sight navigation and year-round warm weather, and the solitude of uncrowded anchorages. The relatively compact cruising grounds, calm seas, and mild winds make this an ideal destination for relaxed gay sailing cruises. Relish in secluded tranquility and embrace freedom on the water with a vacation in this easily accessible sailing paradise offering sheltered anchorages and sufficient moorings throughout.

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Caribbean islands gay sailing cruise


Puerto Rico’s “Passage Islands”, or Spanish Virgin Islands, are a best-kept secret within the Caribbean and an idyllic destination for a GaySail Exclusive vacation. Purity meets paradise as you cruise calmly from the Puerto Rican coast to the SVI’s – Isla Palominos, Culebra, and Vieques, with a number of secluded inlets and cays in between. Not far from the more well-known U.S. and British Virgin Islands, the Spanish Virgin Islands are blessed with protected anchorages, well-preserved reefs, flourishing marine life populations, and uncrowded white sand beaches.

The first week (this week) is a GaySail Exclusive (Clothes optionial) Cruise, the second week we offer a GayNudeSail Cruise. We sail with a luxury catamaran with room for 10 guys. 4 cabins with double bed and 2 smaller crew cabins in the front with acces from the deck. As a single you can book the crew cabins or share a cabin with double bed, and we will accomodate you with someone in the same age range.


Puerto Rico Islands gay sailingcruise map


Puerto Rico Gay Sailing Cruise Itinerary

Day 1 - Welcome to Puerto Del Rey Marina
Puerto del Rey Marina is the largest marina in the Caribbean. Boarding start at 5.30 pm. We will recieve you with a welcome drink, show you your cabin, make an introduction round with all the guests, do the first briefing and go for dinner.


Day 2 - Isla Palominos
To begin our 7-day journey in the Spanish Virgin Islands, we will enjoy an easy northern eastward sail from Puerto Rico to Isla Palominos. This short cruise won’t take long so you’ll have plenty of time to get settled in and enjoy a peaceful first night aboard your yacht.
Isla Palominos is a small island just off the east coast of Puerto Rico. What this island lacks in size, it makes up for in lush preserved scenery. Between the crystalline jewel-tone waters and the blanket of soft sugar-like sand, Isla Palominos truly delivers a piece of unspoiled paradise.


Day 3 - Culebra
After waking up in SVI paradise and enjoying a fresh cup of coffee from the deck of your yacht, we will head east towards the island of Culebra. Before arriving at Culebra’s Ensenada Honda, we stop by the little island of Caya Luis Pena along the way for a relaxing lunch and an afternoon swim. There are plenty of moorings to accommodate us and the snorkeling here is excellent. We also have the option of making a pit stop in Caya Luis Pena, an idyllic place to break for lunch.
After departing Ensenada Honda, we will spend the day visiting Culebritas, an uninhabited wildlife refuge. There, you can hike to the old lighthouse at the top of the cliff and enjoy one of the Caribbean’s best beaches – Tortuga Beach. Then we head back to the southeastern coast of Culebra for anchorage in Bahia de Almodovar.


Day 4 - Flamenco & Playa Tamarindo
Today we bid farewell to the southern side of Culebra then spend the day at one of the top-ranked beaches in the world – Flamenco Beach. From there, we continue cruising around the northwest coast of Culebra until we arrive at our next overnight location in Playa Tamarindo.


Day 5 - Esperanza & Mosquito Bay
Wake up early today because we’ll be venturing southwest to the largest of the Spanish Virgin Islands – Vieques. Before long, we’ll be arriving at Esperanza for a lovely overnight stay. This easily accessible town is located on the south side of the island and is home to the famous Mosquito Bay, which is a must-see attraction in the SVI.


Day 6 - Ensenada Honda, Vieques
After witnessing nature’s magic at Mosquito Bay, a quick and calm eastern cruise will bring us to Vieques’s Ensenada Honda. This majestic cove will allow you the freedom to explore secluded mangroves while soaking up the serene salty air that runs wild throughout this unspoiled paradise. Before mooring in Ensenada Honda, we may wish to stop at Curacas or Le Chiva beach, two of the many impressive places you’ll discover along the way.


Day 7 - Green Beach
We will spend our last day doubling back across the south side of Vieques, stopping at any standout beaches or coves we may have missed and then head to Green Beach, located on the western tip of the island. You won’t want to miss the sunset so be sure to get settled in early enough to enjoy your last evening in Caribbean paradise.


Day 8 - Puerto Del Rey Marina
For our final cruise, we plan to arrive at the base by 10am and then it is time to say good bye to your new friends.


This itinerary is subject to change. Local circumstances such as weather may influence the itinerary.


Gay Clothing Optional Sailing cruise


Gay Puerto Rico sailing cruise


Travel Infotmation

Getting there
San Juan Luis Muñoz Marin International Airport (SJU). Most major airlines service San Juan as well as a few Caribbean airlines.

Taxis are readily available outside the airport's arrivals terminals. Most are metered, though some have flat rates to popular destinations. A taxi transfer to the Puerto Del Rey Marina is about 45-50 minutes and costs approximately $85 USD plus tip, which is customarily 15%.

Entry Requirements
U.S. citizens coming from mainland destinations do not need passports to enter Puerto Rico. US citizens only need to have some form of official government issued picture identification to enter Puerto Rico such as a current driver's license or a photo-identification card issued to non-drivers by a state's motor vehicles department.

Visitors from other countries, including Canada, need a valid passport to land in Puerto Rico. For those from countries requiring a visa to enter the U.S., the same visa is necessary to enter Puerto Rico. All travellers entering the USA under the Visa Waiver Program require an e-Passport with an embedded electronic chip. Travellers not in possession of e-passports require a valid USA entry visa.


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Puerto Rico Gay Sailing Cruise Prices

Tour Date Description
Special Offer
Per person
€ (EUR)
Regular Price
Per person
€ (EUR)

Cruise Only, Per Person, Double Occupancy. This cruise is including the service of a gay skipper and gay cook, accommodation on board of a spacious, luxury, new sailing catamaran, welcome drink, breakfast, lunch, soft drinks, harbor fees, tourist taxes, gasoline and cleaning. Not included dinner (on the shore in local restaurants) and alcoholic drinks.

€ 1525

€ 1695

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Price does not include payment card charges.


Special Airfares


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