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Saint John: The Perfect Winter Destination

Warm up with a visit to the smallest of the three main U.S. Virgin Islands in the Caribbean

By Abigail Thorpe

Inland Northwest winters are long, cold and snowy. And while we all enjoy the beauty of the season and its accompanying outdoor adventures like skiing and snowshoeing, area locals know that once the holidays are over, the grey days can start to feel long and dreary. This time of year is the perfect opportunity to take off to the warm, balmy climate of the Caribbean for a few days—or weeks.

Situated just 4 miles from Saint Thomas, Saint John is the smallest of the three U.S. Virgin Islands, but it boasts a laid-back, quaint and non-commercialized atmosphere that makes it many travelers’ favorite U.S. Virgin Island.

Winter is the best season to visit Saint John. Temperatures are perfect for exploring the island and beaches—typically in the mid-70s or low 80s—and hurricane season doesn’t start until June. With that said, it’s also the Caribbean’s busiest season, and lots of tourists descend on the area from all over the world.

Saint John is just 9 miles long and 5 miles wide, with just over 4,000 permanent residents, making it a small, welcoming island where visitors can truly get to know the people and culture. Nicknamed “Love City,” there’s a reason visitors and locals alike fall under Saint John’s spell.

The Virgin Islands National Park covers over half of the island, and beautiful, pristine beaches dot the coastline throughout. There are multiple opportunities to hike, explore the island’s history, head into the waters for a boating or snorkeling adventure, or relax on the beach. And with minimal development, the island has retained its unspoiled beauty.

There is no airport on Saint John, so your journey to the island will begin in Saint Thomas. Once you fly into Saint Thomas, the easiest and most affordable way to the island is by passenger ferry. It is a short ferry ride across, and there are multiple departures throughout the day. You can also book a private water taxi, or charter a boat for a day or weekend trip to the island.

Where to Stay

Part of Saint John’s charm is that it has no all-inclusive resorts. There are two main settlements on the island: Cruz Bay located on the west side of the island is Saint John’s main economic and entertainment hub, and Coral Bay on the east, the center of plantation life on the island in the early 1700s, and now the quieter, more remote and picturesque side of the island. There are several restaurants and bars in Coral Bay, though accommodations are fewer.

The main resorts on the island are the Westin St. John Resort located in Cruz Bay, which features studios and one-, two- and three-bedroom villas; the Gallows Point Resort in Cruz Bay, which is situated on a 5-acre peninsula with breathtaking views; and the Grand Bay Resort, situated hillside overlooking Cruz Bay.

Other resorts, hotels and inns like the Sea Shore Allure and Lavender Hill Suites are scattered throughout Cruz Bay and provide exceptional access to the beach, as well as inviting accommodations.

For many visitors, however, the most ideal way to experience Saint John is by renting a local villa. Ranking in size from small island cottages to multi-bedroom estates, there are hundreds of villas available for rent throughout the island that provide the true Saint John experience.

What to See

People come to the Caribbean for the beaches, and Saint John certainly has its share of pristine coastline. You’ll want to spend the majority of your time exploring the various beaches on the island, and swimming and snorkeling the crystal-clear waters.

Trunk Bay is the most popular beach on Saint John, attracting crowds of visitors throughout the year, and for good reason. Its picture-perfect white sand beach and aqua waters provide the perfect place to relax on the beach and take in the views, and there is ample opportunity to snorkel, swim, sail and dive. The underwater trail near the shore is particularly fun for beginning snorkelers.

Caneel Bay is the location of the Caneel Bay Resort (which is undergoing restoration after destruction from hurricanes), and the hot spot for the rich and famous. Its 170 acres boast seven beautiful beaches, all open to the public.

Another must visit is Cinnamon Bay, which offers a beautiful white sand beachfront, hiking trails, windsurfing, ruins, and glimpses of wild donkeys! You can even camp at Cinnamon Bay (if you want a few nights of roughing it in the Caribbean).

For more remote and quiet beaches, head east toward Coral Bay. Salt Pond Bay is a remote, tranquil yet rocky beach that offers good snorkeling and mesmerizing tide pools. Lameshur Bay Beach, west of Salt Pond Bay along the south coast, is even more remote, and you have to brave a bumpy dirt road, but the beautiful sands and clear snorkeling waters are well worth the effort. There are also trails to explore in this area, but keep in mind facilities are few and far between, and make sure to lock up cars and possessions.

Besides beach lounging, hiking and snorkeling, a great way to explore the island is via kayak or stand-up paddle board (SUP). Many of the beaches or resorts offer rentals, and you don’t want to miss seeing the island and its beautiful bays and shorelines from kayak or SUP.

If you’re looking to head further out, book a charter for the afternoon and go island hopping to the many surrounding small islands. You can book a charter with others to save on cost, or you can select a charter for just your group. Either way, exploring the many islands, cays and islets that make up the U.S. and British Virgin Islands will be a memorable part of your trip.

You may be here for the beaches, but don’t forget the Virgin Islands National Park. Along with picturesque beaches, the interior of the park offers hikes to explore the historic plantations that once dominated this island, as well as ancient petroglyphs carved by the Taino Indians. Take a tour at Annaberg Sugar Plantation Ruins, situated in the National Park, and go back in time to 1780 and the days of sugar plantations. The island’s past of slavery is part of its history and story, and an important part of understanding the Saint John of today.

Transportation between Cruz Bay and Coral Bay is easy. You can hop on one of the local Vitran (Virgin Island Transit) busses for cheap, although the schedules are somewhat unreliable, or book a taxi. Taxis have set rates, which usually range from $5 to $14. If you want your own transportation, rent a car, bike or moped during your stay, but keep in mind the island is hilly, so you’ll be getting quite the workout on a bike.

Where to Eat

There are lots of restaurants throughout Saint John, many of them located in the hub of Cruz Bay, so you can dine somewhere different every meal, if you choose. From seafood to Caribbean specials, Italian and fusion, there is something for everyone, plus a lot of signature dishes that carry their own local flare.

A notable spot you won’t want to miss in Coral Bay is Aqua Bistro, which offers a more formal outdoor sit-down restaurant or the water-view outdoor round bar. The menu specializes in seafood, and there is live music most nights. It’s the perfect hangout after a day lounging at the beach. For a more divey, casual experience, head over to Skinny Legs, a beloved burger spot in Coral Bay.

High Tide is a local (and tourist) favorite in Cruz Bay. The grill and bar is located on the water, and you can even walk through the sand to get there. Sip from a Caribbean island favorite: the Painkiller, created in the 1970s at the Soggy Dollar Bar in the British Virgin Islands.

One of Saint John’s longest-running restaurants is The Lime Inn, a fun Caribbean-atmosphere hot spot where you can choose from a creative list of Caribbean classics.

No matter where you land in Saint John, you’re sure to enjoy a vacation like none other, with delicious food, epic scenery and the most incredible beaches you can ask for. Here, island time truly is a thing.

Note: As of time of print, the U.S. Virgin Islands are open although operating with enhanced screening protocols due to COVID-19. Keep in mind COVID test results may be required to enter the islands, as well as mandatory quarantine if necessary. Face masks and enhanced safety measures are required. Some restaurants or businesses may be temporarily closed. Make sure to check before your time of travel to see if protocols have changed.


  • At just over 19 square miles, Saint John is the smallest of the three main U.S. Virgin Islands.

  • The Virgin Islands National Park covers over two thirds of the island, and includes over 100 historic sites.

  • The U.S. purchased Saint John, Saint Thomas and Saint Croix from Denmark in 1917 for $25 million in gold coin.

  • Saint John is nicknamed “Love City”, and affectionate moniker harkening to its romantic and friendly atmosphere.

  • Trunk Bay is home to the Coral Reef Underwater Park Trail, a self-guided snorkeling trail in the Virgin Islands National Park.


  1. Rent a local villa for the ideal Saint John experience.

  2. Go snorkeling at Trunk Bay, one of the highest-rated beaches in the world.

  3. Check travel restrictions and requirements before you visit, as well as local closures or safety requirements while traveling in Saint John.

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