Starlight Sailing Charters – Gay US Virgin Islands Sailing Tours

Author: , January 26th, 2018

Starlight Sailing Charters

Starlight Sailing Charters provides friendly and fun private sailing vacations aboard the large, modern, and luxurious sailing yacht, Starlight. Starlight sails November through May in the wonderful Virgin Islands and Eastern Caribbean.

During Summer Months, Starlight sails from Sag Harbor, New York on exquisite Hamptons day charters and sailing vacations. A Starlight vacation is wonderful for a special occasion, or a fantastic way to relax and escape in paradise. Starlight accommodates up to six guests, but is also appropriate for smaller groups and solo travelers.

Captain Toby Stull is your host for charters exploring paradise in the Virgin Islands, St Maarten and St Barths, Antigua and Lower Caribbean. With a lifetime of sailing experience and a decade chartering in the Caribbean, Capt. Toby knows exactly where to bring guests and how to tailor your experience depending on your desired activities aboard.

Our vacations can be booked as “captain-only,” on which guests eat half their lunches and dinners at local Caribbean restaurants, or “all inclusive” where a chef joins to prepare all meals. Either way, Delicious onboard meals can be suited to all types of dietary restrictions. Also, the Captain’s adorable yet unobtrusive boat dog, “Bamboo,” joins on all charters.

See the Starlight Sailing Charters Expanded Listing on Purple Roofs Here

AREA Gay Friendly Bed and Breakfasts, Hotels, and Vacation Rentals

Pink Condos on Sunset Beach – Lesbian Owned Accommodations in St. Croix, USVI

Author: , July 3rd, 2017

Pink Condos on Sunset Beach

Periodically we’ll feature one of our properties here to let our readers know about some great gay friendly places to stay:

Truly paradise, The Pink Condos have it all, beach, sunsets, snorkeling, relaxation and privacy!!!

Featuring four 1BR, 1 Bath condos and a 2 BR, 2 bath unit on one of the most beautiful beaches in the Caribbean.

Wake up every morning to the beautiful blue water and watch the post card sunsets in the evenings from your private spacious balcony.

See the Pink Condos on Sunset Beach Expanded Listing on Purple Roofs Here

Gay Friendly Bed and Breakfasts, Hotels, and Vacation Rentals in the US Virgin Islands

Bolongo Bay Beach Resort – St. Thomas, US Virgin Island

Author: , May 28th, 2017

Bolongo Bay Beach Resort

Periodically we’ll feature one of our properties here to let our readers know about some great gay friendly places to stay:

Bolongo Bay is an intimate Caribbean resort offering All-Inclusive and Room Only rates. We also offer some fantastic honeymoon, wedding, girls escape, and tour and attraction packages. We’re all about getting away from home and having fun in the sun.

Our Caribbean resort features a variety of complimentary water-sports, gift shop, and a freshwater swimming pool with its own swim-up bar – enjoy a tropical drink under the Caribbean sun while you relax away your cares. Bolongo Bay is home to St. Thomas Diving Club, a five star PADI facility.

We also have a small gym on-site with treadmills, stair-masters, an elliptical cross trainer, and a recumbent life cycle.

Bolongo Bay Beach Resort is casual, fun, and private – a Caribbean beach resort with an emphasis on great customer service. We’re on a long, palm tree-lined beach overlooking the lovely waters of the Caribbean on St. Thomas.

We have sixty five ocean-front guest rooms just steps from the sands of the beach, and all of our rooms come with terraces with fantastic water views.

We also offer ocean-front studios and 2 bedroom condos just up the beach from the main property, perfect for families or groups of friends who want larger accommodations on Bolongo Bay.

We have two restaurants on-site, both open air: the Lobster Grille beside the pool lit with romantic candle light and Tiki torches, and Iggies Beach Bar & Grill.

Bolongo Bay Beach Resort doesn’t have elevators, marble tiles or chandeliers – we’re not an upscale property, but we offer large, bright, clean rooms with stunning views of the Caribbean – a real Caribbean vacation

Bolongo Bay is a family-owned resort – we’ve run the resort for over thirty years. Do you want to have a true Caribbean resort experience? Come to Bolongo Bay, and experience the Virgin Islands firsthand!

See the Bolongo Bay Beach Resort Expanded Listing on Purple Roofs Here

Gay Friendly Bed and Breakfasts, Hotels, and Vacation Rentals in the US Virgin Islands

Rainbow Room At Sloop Jones – St. John, US Virgin Islands

Author: , March 18th, 2017

Rainbow Room At Sloop Jones

Periodically we’ll feature one of our properties here to let our readers know about some great gay friendly places to stay:

Commune with nature and art in The Rainbow Room by Sloop Jones, a quiet retreat on St. John in the US Virgin Islands.

The Rainbow Room is a spacious one-bedroom with high ceilings and tons of natural light, a large bathroom with shower, a kitchenette, and a large porch with screened in area and blissful water view. Walk less than five minutes and you’re on the neighborhood’s private, secluded beach.

It’s located on the same peaceful property as the famed Sloop Jones art studio and gallery, but in a separate, stand-alone guesthouse.

Lush tropical grounds surround the cottage, displaying nature’s bold and sensual palette. You will enjoy vivid and fragrant tropical flora that attracts butterflies and hummingbirds.

Visit while the jasmine or ylang ylang is in bloom, and your nose will have an ambrosial experience of a lifetime. Become friends with the silent predawn hour after the insects have stopped buzzing and before the birds begin to chirp.

The Rainbow Room is located on an enchanting piece of property, yes. But even better, the island is magical in and of itself. People who love St. John will tell you it’s a treasure of an island. A jewel.

About two thirds is reserved as National Park, saving the island from overdevelopment. As such, St. John’s beaches are unspoiled and high-rise free.

A nature lover’s paradise with tons of trails and ample snorkeling, St. John is also a great place to relax, imbibe, and shop. So if exercising on vacay isn’t your thing… no problem.

The Rainbow Room is on the remote East End of St. John, perfect for people who REALLY like to get away from it all.

Quiet and sparsely populated, the East End offers scenic vistas of St. John and the British Virgin Islands. Plus, a starscape that will honestly-not-just-saying-this take your breath away. And probably bring tears to your eyes.

Also. There are wild donkeys and goats.

For the soulful traveler who yearns for a balance of solitude and connection, serenity and stimulation, The Rainbow Room will arouse your senses and rejuvenate your spirit.

And it may very well become your happy place.


  • WIFI
  • Coffee maker
  • Toaster oven
  • Microwave
  • Small fridge
  • Screened in porch with water view
  • 5 minute walk to secluded, private beach
  • Private, off-street parking
  • Large shower
  • Queen bed
  • 15 minutes to Coral Bay – the nearest stores and restaurants
  • 30 minutes to the North Shore beaches
  • 45 minutes to Cruz Bay

See the PROPERTY Expanded Listing on Purple Roofs Here

Gay Friendly Bed and Breakfasts, Hotels, and Vacation Rentals in AREA


Sopra Mare – Gay Friendly US Virgin Islands Vacation Rental

Author: , December 4th, 2016

Sopra Mare

Periodically we’ll feature one of our properties here to let our readers know about some great gay friendly places to stay:

Sopra Mare (Above The Sea) is a stunning 1,600 sq. ft. Cliffside villa, built in 2010 on solid native rock set atop Maria Bluff in the most exclusive location in Chocolate Hole with crashing surf below.

This villa offers gated privacy with a one mile level walking circuit on paved roads while you sip your morning coffee and watch iguana’s cross your path. The villa is continually cooled by a slight gentle breeze which generally assures no biting insects. Nana type doors offer expansive full ocean views from the large master and accompanying ensuite bath. Ceiling fans in all rooms and full individual frosty air conditioning in each bedroom.

Laze away in the pool on colorful rafts and turn on the pool lite show when the sun goes down – If it’s the right time use the villa binoculars and watch the Rolex Sailing Cup from the balconies with a cool beverage or dolphins, turtles and the occasional whale. Sopra Mare has everything you would expect from an island home; convenience, elegance and comfort.

.Other features include full laundry, digital cable, two connections for your iPod or MP3 player, wireless high-speed Internet. Bose speaker system for Bluetooth with your laptop or phone and a new 42″ flat screen TV.

When you put your head down for the night you’ll experience the luxury of Ritz Carlton Pacific Coast king size pillows and heavenly bedding. Sweet dreams!

We want you to enjoy the full villa experience – therefore; if just two of you, unlike other villas the second bedroom is NEVER locked off from your access.

We continually upgrade all aspects of the villa to maintain the highest caliber demand and expected by our guests.

My Villa Manager – will greet you dockside. Then escort you to your vehicle and your new “second home” where you’ll find a complete meal and wine awaiting. No need to shop the first night!

Less than five minutes to town of Cruz Bay which offers excellent jazz at several locations on Saturday and Sunday including the famous Beach Bar – partial setting for my first book about St. John ‘Keep Left.’ Shopping and night life abound in Cruz Bay.

NOTE: If you’re considering Sopra Mare make reservations six to twelve months prior to your vacation dates. WE RENT VERY FAST.

See the Sopra Mare Expanded Listing on Purple Roofs Here

Gay Friendly Bed and Breakfasts, Hotels, and Vacation Rentals in the US Virgin Islands

Windwardside Main House – Gay US Virgin Islands Vacation Rental

Author: , July 17th, 2016

Windwardside Main House - US Virgin Islands

Periodically we’ll feature one of our properties here to let our readers know about some great gay friendly places to stay:

Welcome to the Windwardside Main House, an elegant retreat with lovely furnishings, a beautiful view and lush tropical gardens. It is the most intimate and traditional of all of our homes in Coral Bay.

The design is reminiscent of a bygone era in the caribbean but the amenities are modern and designed for comfort.

My husband (a retired builder on the island) and I designed this home. We have years of experience of offering visitors to the island an unusual experience that brings them outside of their day to day life but is a comfortable and welcoming home away from home. Recent renovations to the house have added much to its beauty and charm.

Sunday to Sunday rental. Internet throughout villa.

See the Windwardside Main House Expanded Listing on Purple Roofs Here

Gay Friendly Bed and Breakfasts, Hotels, and Vacation Rentals in the US Virgin Islands

Sago Cottage – Gay Friendly US Virgin Islands Vacation Rental

Author: , July 13th, 2016

Sago Cottage

Periodically we’ll feature one of our properties here to let our readers know about some great gay friendly places to stay:

Our charming home Sago Cottage is nestled into the hillside over Coral Bay on St. John. It is a traditional West Indian cottage- brightly painted with lots of shutters, very open and airy. A true tropical retreat with great views and no nearby neighbors. Our covered decks overlook the Caribbean sea and have beautiful sunrises and moonrises. It is the perfect spot for a romantic holiday for two- with cooling breezes and a captivating view you may never want to leave this idyllic hideaway.

This Cottage is perfect honeymoon destination. Many of our guests have gotten married on island. We can offer suggestions for an LGBT friendly officiant if you decide to tie the knot on St. John.

The covered porches were designed and furnished with comfort in mind. They hold a small dining table, reading chairs and a porch swing to while away the rare rainy afternoon.

The view to the south and east is of the eastern end of St. John, the neighboring British Islands and the Caribbean Sea. The cozy interior of Sago Cottage has a distinctly quaint feel without sacrificing modern conveniences. There is a fully equipped kitchen, a full size dining room and a small but comfortable living room. The bedroom features a queen sized four poster mahogany bed, hand made on St. John and is a perfect place to wake up to a day in the islands. The colorful louvered shutters serve to filter the light as well as frame the ocean views throughout the cottage.

Location: Coral Bay, St. John, U.S. Virgin Islands. Windwardside Guest Cottage is located in quiet seclusion with mesmerizing views of Coral Bay, nearby islands and the Caribbean Sea. The house is situated two thirds of a mile up a little used road in Coral Bay. Surrounded by tropical plantings and marvelous vistas, you are still just a short drive to a cool splash in Salt Pond Bay or other equally inviting white sand beaches.

Restaurants, shops and watersports are all available within two miles in Coral Bay. The main town on the island, Cruz Bay, is located 8 miles away. The airport is in St. Thomas which is reached via a twenty minute ferry ride. (Ferries leave every hour on the hour and cost $7 each way).

See the Sago Cottage Expanded Listing on Purple Roofs Here

Gay Friendly Bed and Breakfasts, Hotels, and Vacation Rentals in the US Virgin Islands

Featured Gay Friendly Accommodations: Great Expectations, St. John, US Virgin Islands

Author: , February 10th, 2016

Great Expectations

Periodically we’ll feature one of our properties here to let our readers know about some great gay friendly places to stay.

Great Expectations is recommended in USA Today Travel’s “Where to rent a villa on St. John” and rated: the #1 vacation villa on St. John by travelers on Trip Advisor (awarded their coveted Certificate of Excellence), 5 stars (the highest rating possible) on VRBO and Home Away. It comfortably accommodates up to 15 adults plus children in 6 air-conditioned bedrooms. Great Expectations is located in the southwest part of St. John about a 5 minute drive from Cruz Bay with stores where you can purchase any food or beverages you need as well as excellent restaurants. The Villa is uniquely sited about 100 feet above the Caribbean Sea and offers both sunrise and sunset views.

See the Great Expectations Expanded Listing on Purple Roofs Here

Gay Friendly Bed and Breakfasts, Hotels, and Vacation Rentals in the US Virgin Islands

Featured Gay Accommodations: Sand Castle On The Beach, St. Croix, US Virgin Islands

Author: , April 8th, 2015

Sand Castle On The Beach

Periodically we’ll feature one of our properties here to let our readers know about some great gay friendly places to stay.

Sand Castle On The Beach Resort welcomes you and your loved ones to vacation in a beautiful, tropical environment. Beachfront on the Caribbean Sea, enjoy the newly added amenities on this special property. There are two pools on site – one beachfront, the other clothing optional. Titillate your senses and nourish your soul! Relax and unwind from your everyday pressures in the comfortable, laid-back surroundings. Make new friends from around the world at the Sand Castle On The Beach Hotel in Frederiksted, on St. Croix in the United States Virgin Islands.

See the Sand Castle On The Beach Expanded Listing on Purple Roofs Here

Gay Friendly Bed and Breakfasts, Hotels, and Vacation Rentals in the US Virgin Islands

The Spanish Virgin Islands

Author: , September 2nd, 2014

Spanish Virgin Islands - Apple Maps

The Spanish Virgin Islands are the westernmost, most undeveloped, and least known slice of the much larger Virgin Islands pie.

Twenty-one mile-long Vieques, the largest Spanish Virgin is located 12 miles west of Saint Thomas in the adjoining US Virgin Islands.
The smaller main Spanish Virgin, seven-mile-long Culebra, lies nine miles north of Vieques.

Twenty-three smaller islands ring Culebra, all together composing the enchanting archipelago of the Spanish Virgin Islands.

Puerto Mosquito, known as Bio Bay in English, in Vieques is considered the brightest bioluminescent body of water in the world!

Bioluminescence is light produced by a chemical reaction, which originates in a living organism.

Tiny organisms, halfway between plant and animal, in the water cause the bay to glow a dazzling bright blue at night.

The spectacular light show is strong enough to read a book by at midnight even on a moonless evening.

The superstitious Spanish conquistadors considered the curious lights to be the work of the devil, and struggled to extinguish the natural phenomenon, dropping enormous boulders to crush the satanic forces they believed were lurking beneath the surface, fortunately without success.

In fact, the boulders only served to corral the resilient organisms more closely, intensifying their brilliance!

Long, and narrow cigar-shaped Vieques is ringed by dozens of pristine beaches all excellent for swimming, some best suited for surfing, others ideal for diving, most of them featuring fine white powder sand, except for appropriately named “Playa Negra,” which has jet black magnetic volcanic sand.

Of course, kids will have a ball building black sand castles, and dragging magnets along the coast collecting metallic particles.
Sort of a natural, super-sized “etch a sketch.”

Watch countless, up to six-foot long, scaly green pre-historic looking iguanas sunning themselves on smooth white boulders at the shoreline.

Crescent-shaped Flamenco Beach on neighboring Culebra features fine white coral sand, and is considered the most beautiful beach in the Caribbean. Flamenco beach is situated on a narrow strip of land sandwiched between two bodies of water, the Caribbean Sea to the north, and Laguna Flamenco to the south.

Leatherback, Green and Hawksbill sea turtles nest on Culebra, and its many outlying islets.

Impregnable Fort Vieques, built in 1845 to defend the archipelago against pirates, which now houses the Vieques Museum of Art and History, is the most impressive icon remaining from the four centuries long Spanish colonial era.

A massive three hundred year-old Ceiba tree is another major attraction, and popular photo op onVieques.

Fresh caught seafood is superb throughout the islands. Conch, pronounced “conk,” a type of sea molusk ceviche, ensalada de carrucho en espanol, empanadillas which are lobster, crab, conch, or beef filled baked pastry turnovers, all served with black beans and fried plantain are popular across the island chain.

Inexpensive, lobster-on-a-stick, sort of like an upscale corn dog is popular at street stands in the Spanish Virgin Islands.

Iguana flesh, the other white meat, sometimes called mountain chicken, is abundant in the Spanish Virgin Islands. The tasty reptile is not endangered here as it is in some other places in the West Indies.

There’s regular passenger ferry service for under $5 round-trip between Fajardo on the northeastern coast of Puerto Rico, Vieques and Culebra. Water taxis are great for short trips.

A moderately more expensive transport option is by scheduled seaplane. The low aerial views seaplanes afford are not to be missed. Of course, if money is not an object you can charter a luxurious sailing ship to explore the islands. But you don’t have to spend mucho bucks to enjoy these tranquil isles.

Spanish is the predominant and official language in the Spanish Virgin Islands, but just about everyone also speaks English. You will never have a problem if you speak English only. The US dollar is the sole currency, and you are protected by the familiar US legal system.

American citizens don’t need passports, nor visas to enter, or to stay as long as they like in the Spanish Virgin Islands.

Ernie Alderete is an Angeleno-based adventure travel writer ready to get his feet wet, and challenge his comfort level. He’s always the first to sample the most exotic cuisine, whether it be fresh-caught piranha in Manaus at the center of the largest rain forest on earth, or charcoal roasted guinea pig in Cuzco, colorful capital of the ancient Inca Realm. Dinner could be slow cooked in a pit dug in the desert sands of Wadi Rum within sight of the Red Sea where Lawrence of Arabia once fought, or simple boiled beans in a cave in the remote highlands of Chihuahua shared with a native Tarahumara Indian. The author may be reached at:

US Virgin Islands Gay Travel Resources

Image via Apple Maps