June 10, 2020

Best Fall Vacation Deals in the Virgin Islands (2022)

Millions of visitors flock to the Virgin Islands every year, and their white sand beaches and turquoise waters make it an attractive getaway for romantics, sun worshipers, business people and more. You may not know it, but during the autumn months, unbelievable package vacation deals abound, making it an excellent choice for an inexpensive Caribbean getaway.

Virgin Island Deals and Discounts

Three rustic islands make up the U.S. Virgin Islands: St. John, St. Thomas, and St. Croix. All three of them have the white sand beaches and gorgeous tropical foliage that everyone knows and loves. From all exclusive hotel packages to luxe villas for groups, we’ve put together the following guide for each island to help you decide on which one to book your excursion.

First up, is St. John, and if you book one of the fall vacation deals, you can see yourself relaxing in luxury for budget prices.

Trunk Bay St John VI

The incredible Trunk Bay at St John, on the Virgin Islands

St. John Virgin Islands (U.S.)

The traditional nickname of St. John is “Love City.” However, it is also known as the “Beverly Hills of the Caribbean” because of its luxury and signature experiences. St. John is the most secluded of the three islands because two-thirds of the island is comprised of national parklands.

Travel Tip: Be sure to visit the National Park because you’ll likely spot ancient Taíno petroglyphs on the rocks and plenty of wildlife during your hike on one of the many hiking trails St. John has to offer. The rest are made up of a dozen or so gorgeous beaches, several of which are popular with vacationers, Trunk Bay being a notable one.

About Cruz Bay, St. John

Cruz Bay is home to perfectly manicured beaches lined with beautiful and lofty palm trees. Travel is often by ferry and taxi, and with a number of exquisite restaurants, bars, and shops, you won’t run out of things to do in Cruz Bay. Several of the numerous hiking trails on St. John are located right in Cruz Bay and lead to beaches. Vendors at the beach offer paddle boarding, snorkeling, kayaking and more…

The Hills, one of the vacation resorts located in Cruz Bay, offers discounted rates for fall vacationers so that you and your party can enjoy the the peace and quiet of “off-season” in luxe, Italian-style villas.

The Hills of Cruz Bay, St John

The true beach experience is there for the taking in Cruz Bay, St. John, and the waters there are crystal clear and inviting. The Hills offers a 22-villa condominium community that is visible from Cruz Bay. If you stay in a villa in The Hills, St John during a fall getaway vacation, you’ll be happy to know you can get a steep discount when you reserve your stay. The villas are a combination of two, three and four bedrooms, and every one of them is designed to have a prime view of the water. There are fun activities outside of The Hills, and driving just a short distance takes you to a collection of eclectic shops, restaurants and bars.

Papaya Villa

The spacious and palatial Papaya Villa at the Hills has an ocean view through oversized windows, allowing you and your guests to enjoy beautiful St. John and its surrounding waters.

The villa’s patio and pool are perfect for catching fiery sunsets while kicking back and enjoying the island’s signature tropical drink, the Painkiller. Guests staying at Papaya Villa will enjoy amenities such as the full kitchen and dining area (perfect for cooking and serving up hulking crustaceans), private pool, Clubhouse restaurant and a Caribbean cocktail bar with billiard table.

The Clubhouse is also business meeting-friendly, and it has WiFi, a monitor for presentations and comfortable seating. Those in St John for business will appreciate the business mecca that the Papaya Villa offers. Leisure activities nearby include boating, shopping, wildlife viewing and water sports. Information on the discounted stay at the Papaya Villa is below. The $580 per night is discounted from the regular charge of $725 per night.

Papaya Villa at The Hills, St John

The stunning Papaya Villa at The Hills, St John

Papaya Villa, St John
Nightly rate (2 guests) $745
Tax 12.5%
Bedrooms 3
Bathrooms 3.5
Total cost (3-night stay) $1957.50
Dates requested 9/24-9/27
RT airfare from NYC (per person) About $300
Total Cost (room + air fare) $2,457.50
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One question you’ll want to be answered is, does the place advertised look like the brochure? Expedia verified travelers reviewed the villas and rated them as superior. One reviewer had this to say about Papaya Villa, “My stays at the property were terrific. The quaint island allows for a variety of activities. You can hang out at the beautiful beaches, hike on nature trails, swim with sea turtles, go boating, or even visit the BVIs for the day.”

The Pineapple Villa at the Hills St John is also available at a discount. The villa has a small dipping pool, and you can stay at this property for a $300 nightly rate plus the hotel tax.  The total for two guests for three nights at the Pineapple Villa is a little over $1000 without airfare. Vacation rentals at the Hills are often listed with 25% off and sometimes more on specific villas during certain weeks.

St. Croix, Virgin Islands (U.S.)

There is a piece of tropical paradise with your name on it, and it is the balmy island of St. Croix. The island is nicknamed the Twin City for its two towns, Frederiksted on the western end and Christiansted on the northeast part. St. Croix is less populated than St. John and St. Thomas, and that makes it a perfect destination to get total relaxation or some one-on-one time with your special someone. Couples and other vacationers who shun touristy spots will appreciate the Twin City’s natural wonders and the friendly, optimistic spirit of the locals living there who are called Crucians.

Must-see vacation spots in the Twin City include the pristine, untouched and unforgettable Buck Island. This “Caribbean Gem” is renowned for its magnificent scuba and snorkeling opportunities, massive coral reef, and a unique ocean ecosystem that hosts 250 species of fish.

You can have the St. Croix experience by staying in Frederiksted since certain hotels there are offering deep discounts during the autumn months. One of them is the Sand Castle on the Beach.

About Frederiksted, St Croix

Stepping into Frederiksted is like going back to colonial times, and it is known as “Freedom City” because of its role in the emancipation of slaves in 1848.  Here, you find a bustling port surrounded by noteworthy colonial attractions such as 18th-century Fort Frederick and restored sugar plantation, Estate Whim Sugar Mill. While the town is history and culture-rich, it’s also a hot spot for boutique shopping, beach activities and ecotourism. You’ll find the Sand Castle on the Beach here, and it is located 0.6 miles from the town’s center and about a five-minute drive from the Sandy Point National Wildlife Refuge.

Sand Castle on the Beach

Many hotels in St. Croix had to do extensive remodeling after the punch felt by Hurricane Maria in 2017. One of them is the adults-only Sand Castle on the Beach hotel, and they have handled repairs quite nicely. Sand Castle is situated on one of St. Croix’s most beautiful swimming beaches, and rooms come with terraces that overlook the Caribbean sea. The Beach Side Café at the hotel serves daily fresh-catch seafood, international dishes and tapas.

There is also a bar and lounge on-site that serves craft-made cocktails and mocktails made from fresh juices. Don’t overdo it, though, and miss spending time at nearby Rhythms at Rainbow Beach. Trip Advisor lists a visit to top-rated Rainbow Beach as the #1 Top Attraction in Frederiksted, followed by Rhythms at Rainbow Beach at # 2. Rhythms is also the original home of the “Lime in the Coconut,” and island musicians often give live performances there.

Sand Castle on the Beach, St. Croix
Nightly rate (2 guests) $207
Tax 12.5%
Rooms 1 Studio, 1 King Bed, Patio
Bathrooms 1
Total cost (3-night stay) $828
Taxes and fees $103.52
Subtotal $931.52
Dates requested 9/24-9/27
RT airfare from NYC (per person) About $300
Total Cost (room + air fare) $1,531.52


Google reviews for the Sand Castle were largely positive, with one traveler saying that the hotel is a “true relaxing, friendly, stress free place.” The owners were often praised for their friendly nature and hospitality by Google reviewers, also. Kayaks and snorkeling equipment are available to rent at the Sand Castle’s reception and Frederiksted has an ideal setting for sailing and jet skiing. One snorkeling enthusiast and Google reviewer commented that the hotel was a “great West End place with views of sunsets and calm water for snorkeling.”

St. Thomas, Virgin Islands (U.S.)

If you are planning a Virgin Islands vacation, then St. Thomas’s warm waters and history of swashbuckling adventure can let you be your own pirate of the Caribbean. The Virgin Islands are chock full of pirate lore, including one yarn about French pirate Jean Hamlin. Although Hamlin wasn’t as famous as Captain Kidd and Blackbeard, he eluded capture with the assistance of St. Thomas governor, Adolph Esmit. Tours from St. Thomas city, Charlotte Amalie, can take you to the highest peak on to see the pirate castles of Bluebeard and Blackbeard.

The isle of St. Thomas is nicknamed Rock City because it is essentially one huge mountain. Also, its picturesque beaches are so lovely that they even strike beach snobs with awe. St Thomas is also known for being a Caribbean shopping mecca where you can find pirate bounty in the way of inexpensive jewelry and as a port of call for cruise ships. In the spirit of pirates, ships and the rum of St. Thomas, this last autumn escape has you taking to the high seas in a discounted cruise.

7 Night Eastern Caribbean Cruise

Budget-savvy travelers often visit Caribbean paradise through cruise lines. Departing from Miami, Florida in from October 24 through October 31, a cruise on Carnival’s 7 Night Eastern Caribbean Cruise costs $46 a night for seven nights. For a total of $319, you get to visit four Caribbean ports of call, including Charlotte Amalie, the largest city in St. Thomas. You can also call to get the absolute lowest rate possible, so the cruise can potentially be even cheaper. Stops at POC can last anywhere from six to ten hours, and vacationers can get off the cruise ship and spend time hitting the local shops, relaxing on the beach, swimming or snorkeling.

Day to Day Itinerary

Day Ports of Call Arrival Departure
day1 Miami —Not Applicable 3:30 PM
day2 At Sea —Not Applicable —Not Applicable
day3 Grand Turk Island, Turks & Caicos 8:00 AM 4:00 PM
day4 San Juan, Puerto Rico 1:00 PM 9:00 PM
day5 Charlotte Amalie, St. Thomas, U.S.V.I. 7:00 AM 3:00 PM
day6 Amber Cove (Puerto Plata), Dominican Republic 10:30 AM 6:00 PM
day7 At Sea —Not Applicable —Not Applicable
day8 Miami 8:00 AM

If you are a landlubber and want to stay in traditional lodgings vs. a boat, there are inexpensive hotels galore in St. Thomas. Cheap 3-star hotels average about $263, and the cheapest roundtrip airfare from NYC is around $287. Seven nights plus flight index will run you about $2,822 on average.

The siren song of a Caribbean vacation beckons to you, so be sure to book some of the best fall vacation deals in the Virgin Islands before they are snatched up.

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