Virgin Islands Itinerary: Ultimate Guide from USVI to BVI

This Virgin Islands itinerary has been created from my personal vacations to the Virgin Islands, so let me start by saying there isn't any better way to visit the Virgin Islands than island hoping. That's the only way you will experience the best of the region, discovering the highlights of both US Virgin Islands (USVI) and British Virgin Islands (BVI)? Don't settle for less!

How Many Days Do You Need to Visit the Virgin Islands?

This is a 8-day itinerary, but I have done trips from four to 12 days to the Virgin Islands with family and friends, and all of those vacations were incredible. If you are short in time, of course, you will need to focus on the key locations, but I can guarantee the Virgin Islands won't disappoint, and your group will still have the vacation of a lifetime.

What Makes the Virgin Islands Unique?

The Virgin Islands are a sailing dream destination. With steady trade winds, short passages between islands, turquoise waters, and beautiful beaches, there’s no better place to set sail. Add to all this Virgin Islands's proximity with major U.S. cities, consistent weather - even in the winter -, lively snorkeling spots, and the vast offer of services around sailing catamarans, that make sailing such a smooth experience.

Rich History and Culture

The islands have a fascinating history that includes influences from African, European, and Caribbean cultures. This is reflected in their architecture, cuisine, and vibrant festivals.

Understanding the Virgin Islands

What Are the US Virgin Islands (USVI)?

The US Virgin Islands comprise three main islands: St. Thomas, St. John, and St. Croix. Known for their rich history and Virgin Islands National Park. The USVI is a must-visit for adventure seekers, with highlights like Maho Bay, Cruz Bay, Christmas Cove, and Water Island.

What Are the British Virgin Islands (BVI)?

The BVI includes over 50 islands, with highlights like Virgin Gorda, Anegada, and Jost Van Dyke. Famous for its luxury yacht culture, the BVI offers secluded beaches and calm waters, vibrant snorkeling, and award-winning beach bars .

The best Virgin Islands itinerary includes both US Virgin Islands and British Virgin Islands

A big mistake my family and I made the first time we visited the Virgin Islands was to fly directly to the British Virgin Islands and make it a British Virgin Islands vacation, skipping the US Virgin Islands all together. Once my family and I decided to start our trip from the US Virgin Islands, it was a game changer.

Fly to US Virgin Islands to spend more time vacationing

There’s a direct flight to St. Thomas Airport from major U.S. cities, and just a 15-minute transfer from the airport to Yacht Haven. If you have flew from the US to British Virgin Islands with connections and took a 30 - 40 minutes cab ride to your boat, you know how much time and stress this saves you.

If spending more of your vacation time on the sea versus dealing with airport shenanigans isn't enough to make up your mind, add to that the beautiful beaches of St. John, in USVI, like Maho Bay, variety of sea creatures, lively beach bars, Cruz Bay's nightlife, and so much more.

Pro tip: You still need a passport to enter the British Virgin Islands, but when you travel with Sea Dog, our crew takes care of the immigration coming in the BVI while your group enjoys the water on a nearby bay. We also send a private driver to pick you up at the airport and drive you back there when it's time to go home.

Summary of the Ultimate Virgin Islands Itinerary

This 8-day Virgin Islands itinerary offers the perfect blend of relaxation, adventure, and unforgettable moments, showcasing the best of the US Virgin Islands (USVI) and British Virgin Islands (BVI):

Day 1: Discover Christmas Cove and Maho Bay, renowned for its calm waters, sea turtles, and stunning Caribbean sunset.

Day 2: Explore the best snorkeling in the region at The Indians, visit The Caves, and go to Willy T’s Floating Bar to partake in its iconic tradition of jumping into the crystal-clear waters. Grab a drink at the Pirate's Bight Restaurant to watch the sunset.

Day 3: Discover the awe-inspiring Baths on Virgin Gorda, where massive granite boulders form tidal pools and caves. Later, sail to North Sound to visit Saba Rock and the Bitter End Yacht Club, two iconic destinations perfect for mingling, dining, and enjoying the serene ambiance.

Day 4: Spend the day at Cooper Island, home to the eco-friendly Cooper Island Beach Club and the Caribbean’s largest Rum Bar. Don’t miss snorkeling at Cistern Point, a vibrant marine hotspot.

Day 5: Sail to Anegada, a flat coral island with pristine white sand beaches and some of the best snorkeling at Loblolly Bay. Wrap up the day with a fresh lobster feast at Potter’s by the Sea or The Wonky Dog.

Day 6: Relax at Sandy Spit, a tiny sand island with just a few palm trees in the center, surrounded by crystal-clear waters. Continue to Jost Van Dyke, where you can head to White Bay to visit the legendary Soggy Dollar Bar, birthplace of the Painkiller cocktail, and enjoy Foxy’s in the evening.

Day 7: Check back into the US Virgin Islands at Caneel Bay, then explore Cruz Bay, a vibrant town known for its shopping, restaurants, and nightlife. Head to The Windmill Bar for breathtaking vistas, and end the night with music and cocktails on the beach.

Day 8: Conclude your journey on Water Island, a hidden gem of the USVI. Relax on Honeymoon Beach, take a short walk to Fort Seagarra, and toast your adventure with a sunset drink at The Windmill Bar, taking in panoramic views of the Caribbean.

Day 9: Return to the award-winning Yacht Haven Grande marina, where you can enjoy its world-class amenities before bidding farewell to this unforgettable adventure.

Your Ultimate Virgin Islands Itinerary in detail

Day 1: Set sail to Christmas Cove and then Maho Bay, famous for sea turtles spotting

Morning Arrival in St. Thomas

Arrive at St. Thomas Airport in the US Virgin Islands and take a short transfer to your luxurious catamaran. Your crew will welcome you and get ready to set sail to Christmas Cove, known for its vibrant snorkeling. Pizza Pi, a floating pizzeria serving delicious wood-fired pizzas, is a very cool experience, that you don't want to miss.

Afternoon: Explore Maho Bay

Continue to Maho Bay, one of the St. John most famous north shore beaches, in the US Virgin Islands. Calm waters and abundant sea turtles await you on Maho Bay Beach. Snorkel or paddleboard while enjoying the serene surroundings.

Evening: Enjoy the stunning Caribbean sunset at Maho Bay

Relax on deck at Maho Bay with a sunset cocktail, taking in the breathtaking view of the Caribbean Sea.

Day 2: Norman Island and The Indians

Morning: Snorkeling at The Indians

Stop at The Indians, in the British Virgin Islands, a group of rocky islets off the coast of Norman Island. This world-class snorkeling spot is home to vibrant coral reefs and abundant underwater life. Snorkel among schools of tropical fish and take in the incredible underwater scenery.

The Indians is also one of the most popular scuba diving locations in the region.

Midday: Explore The Caves

After snorkeling, visit The Caves, a series of grottoes along Norman Island’s coastline. These caves are steeped in pirate lore and offer unique snorkeling opportunities where you can spot shimmering fish and admire the play of light inside the caverns.

Afternoon: Sail to Norman Island

Set sail for Norman Island, a legendary destination rumored to have inspired Treasure Island by Robert Louis Stevenson. Known for its pirate history, hidden caves, and clear waters, Norman Island is a must-visit.

If you’re in the mood for something livelier, head to Willy T’s Floating Bar, a well-known hotspot for fun and drinks. One of the most famous traditions at Willy T’s is jumping off the boat into the crystal-clear waters below. Guests of all ages participate, cheering each other on and creating unforgettable memories. After your jump, climb back aboard to enjoy a refreshing cocktail, mingle with fellow sailors, and soak in the lively atmosphere that makes Willy T’s a legendary stop in the British Virgin Islands.

Evening: Moor at The Bight

End your day at The Bight, a sheltered anchorage in the British Virgin Islands with calm waters.

Day 3: The Iconic Baths and Virgin Gorda

Morning: Discover The Baths on Virgin Gorda

Visit The Baths, an iconic British Virgin Islands attraction on Virgin Gorda featuring granite boulders, tidal pools, and caves. Your captain will get you close enough for you to swim ashore or to a nearby dinghy dock so you can take a cab to reach the beautiful beach. Wander along the trail to Devil’s Bay for breathtaking views.

Pro Tips:

• The trail at The Baths is now one-way. Start at Devil’s Bay and take your time to enjoy the views.
• Poor Man's Bar at the Baths was named by US Today one of the best beach bars in the Caribbean.

Afternoon:  Explore Saba Rock and Bitter End Yatch on Virgin Gorda

After a day of exploring The Baths and Devil’s Bay, sail to North Sound, a serene and protected anchorage surrounded by lush hills and calm waters.

Enjoy visiting Saba Rock, known for its laid-back vibe and upscale food, and make sure to head to Bitter End Yacht Club, an iconic destination right next door to Saba Rock. Both offer stunning sunsets and luxurious amenities.

You can take a short walk on the sand, enjoy drinks at the beach bars, and mingle with other groups.  Both locations have a dinghy dock, making it easier for all guests to reach the shore.

Evening: Enjoy a quiet evening on the Caribbean sea or head to back to Saba Rock or Bitter End for dinner

If you are up to dining up, make that decision early in the day and have your crew placing reservations for your party. You can expect delicious fresh seafood in both places. If you feel like relaxing on the catamaran, enjoy fresh seafood prepared by your chef in the peace of one of the most protected harbors in the Caribbean sea.  

Day 4: Cooper Island Beach Club and Rum Bar

Morning: Set Sail to Cooper Island

After breakfast, sail to Cooper Island, home to one of the most popular stops in the BVI.

Midday: Relax at Cooper Island Beach Club

Once settled, head ashore for a cold drink at the eco-friendly beach bar. Rum Bar has the largest selection of rum in the region and was appointed for the best rum in the Caribbean by US Today in 2024. You can also grab a drink or a bite at the Cooper Island Beach Club. The entire area of the beach club facing the see has lovely outdoor lounge areas for your party.

Afternoon: Snorkel at Cistern Point

Don’t miss the snorkeling at nearby Cistern Point for a close encounter with colorful marine life. We saw a few sea turtles last time we were there. You will love the vibrant coral and have the chance to observe teeming sea life.

Insider Tips: Cooper Island Beach Club has a beautiful beach and calm waters. Perfect for kids to play

Day 5: Off the Beaten Path in Anegada

Morning: Sail to Anegada

Unlike other islands in the BVI, Anegada is a flat coral atoll with white sand beaches and tranquil vibes.

Midday: Snorkeling at Loblolly Bay

Discover Loblolly Bay, one of the most beautiful snorkeling spots in the Virgin Islands. The colorful reefs and abundant marine life make it a must-see.

Evening: Lobster Feast at Potter’s by the Sea

Indulge in freshly grilled lobster at Potter’s by the Sea, a local favorite.

Set your course for Anegada, a flat coral island known for its beautiful beaches and the best lobster in the Caribbean. Unlike the towering islands around it, Anegada feels like a world of its own. Visit Loblolly Bay, a very special snorkeling location, or explore Horseshoe Reef, one of the largest barrier reefs in the world.

For dinner, indulge in freshly grilled lobster at Potter’s by the Sea or The Wonky Dog.

Adventure Tip: Rent a moke (a small, open-air car) to explore Anegada’s stunning coastline at your own pace. While at it, visit the famous Cow Wreck Beach Bar.

Day 6: Sandy Spit and Jost Van Dyke

Morning: Sandy Spit

Start your day at Sandy Spit, a tiny uninhabited sand island, with palm trees, surrounded by crystal-clear waters and perfect for swimming or relaxing.

Afternoon: White Bay on Jost Van Dyke

Head to White Bay, home to the legendary Soggy Dollar Bar, where the famous Painkiller cocktail originated, and appointed the number one beach bar in the Caribbean by US Today in 2024. The bay’s pristine white sand beach and turquoise waters provide the perfect backdrop for relaxation or adventure. Spend time beach-hopping or simply floating in the calm, clear waters with a Painkiller cocktail in hand.

Evening: Great Harbour

Anchor at Great Harbour and enjoy live music at Foxy’s, with a laid-back island atmosphere.

Day 7: Vibrant Nights in St. John and Cruz Bay

Morning: Head back to US Virgin Islands and visit Cruz Bay

After breakfast head to Caneel Bay to check back in to the US Virgin Islands. Directly adjacent to one of the most colorful and authentic small towns in the USVI, Cruz Bay. Caneel offers stunning examples of St. John beaches, shining Caribbean waters, daytime snorkeling, and water sports opportunities from your yacht.

Afternoon: Shopping at Cruz Bay

A dinghy ride to Cruz Bay offers fantastic shopping, beach bars, and a short ride to one of the most memorable look-off vistas on the islands, The Windmill Bar.  

Evening: Nightlife on Cruz Bay

Avail yourself of the fabulous nightlife of Cruz Bay completely with your choice of live music with your feet in the sand, fabulous restaurants, or high-end cocktail bars.

Day 8: Water Island, US Virgin Islands Hidden Paradise

Morning: Honeymoon Beach

Conclude your journey on Water Island, one of the hidden gems of the USVI. Relax on Honeymoon Beach, a tranquil spot with calm waters and soft, white sand.Along with the many activities provided, a local beach bar will surely melt your troubles away with the first sip of the Water Island specialty, paddle-whackers.

Afternoon: Explore Water Island

Take a short walk to Fort Seagarra or enjoy kayaking and paddleboarding in the bay.

Evening: The Windmill Bar

Celebrate the end of your adventure with a dinner at the yacht, enjoying a peaceful view of the sea.

Day 9: Farewell from Yacht Haven Grande

After Breakfast move from Water Island back to the award–winning, world-class marina of Yacht Haven Grande and say your goodbyes. If you have time before your flight out of the USVI, enjoy the many amenities of the marina grounds, including restaurants, shopping, pool and volleyball.

Final Thoughts

This 8-day itinerary showcases the best of the Virgin Islands, combining breathtaking landscapes, vibrant local culture, and exhilarating sailing. Whether you’re enjoying a sundowner on the flybridge of your Yacht or diving into the crystal-clear waters, every moment is unforgettable.

So, ready to hoist the sails and chart your own course through paradise? The Virgin Islands await!

Frequently Asked Questions (FAQs)  

1. What makes the US Virgin Islands a must-visit destination?  

The US Virgin Islands offer a mix of stunning beaches, rich history, and vibrant culture. A well-planned US Virgin Islands itinerary can include highlights such as Maho Bay, Trunk Bay, Cinnamon Bay Beach, and the trails of the Virgin Islands National Park. These locations feature lush greenery, palm trees, and turquoise waters perfect for snorkeling or relaxing.

2. How does a Virgin Islands itinerary differ from a BVI sailing itinerary?  

A Virgin Islands itinerary typically covers both the US Virgin Islands (USVI) and British Virgin Islands (BVI). The BVI sailing itinerary is more focused on exclusive experiences, such as visiting Virgin Gorda, Leverick Bay Resort, Monkey Point, and secluded destinations like Mosquito Island and Marina Cay. Combining both regions in your itinerary allows you to experience the best of each.

3. What are some additional places to visit if I have extra time?  

If you have additional days, consider adding these spots to your itinerary:  

- Coral Bay (St. John): A quieter alternative to Cruz Bay with laid-back vibes.  

- Guana Island: A private island perfect for hiking and snorkeling.  

- Marina Cay: A charming destination known for its tranquil waters.  

- Monkey Point: A hidden gem for snorkeling with vibrant reefs and teeming sea life.  

- Leverick Bay Resort: A lively spot in Virgin Gorda with restaurants, bars, and water sports.  

- Cane Garden Bay (Tortola): A picturesque beach with plenty of dining and live music options.

4. Where are the best beaches to visit in the Virgin Islands?  

The Virgin Islands are home to world-class beaches. Some of the must-visit spots include:  

- Trunk Bay (St. John): Famous for its underwater snorkeling trail.  

- Cinnamon Bay Beach (St. John): Known for its expansive shoreline and nearby Reef Bay Trail.  

- Honeymoon Beach (Water Island): A tranquil gem with calm waters.  

- White Bay (Jost Van Dyke): Home to the legendary Soggy Dollar Bar.

5. Are there good hiking opportunities in the Virgin Islands?  

Absolutely! The Virgin Islands National Park offers incredible hiking trails such as:  

- Reef Bay Trail: Leads to ancient petroglyphs and a historic sugar mill.  

- Johnny Horn Trail: Connects Coral Bay to scenic overlooks.  

- Ram Head Trail: Provides panoramic views of St. John’s rugged coastline.

6. What should I know about visiting Virgin Gorda?  

Virgin Gorda is a highlight of any BVI sailing itinerary, famous for The Baths, its granite boulders, and pristine beaches. Don’t miss Leverick Bay Resort for dining, shopping, and water sports, or the nearby serene spots like Mosquito Island and North Sound.

7. Are there lesser-known snorkeling spots I should explore if I have additional time?  

While popular spots like The Indians and The Baths are amazing, here are some lesser-known gems:  

- Monkey Point: Located on Guana Island, it offers vibrant reefs and a peaceful atmosphere.  

- Nearby Pelican Island’s South Shore: A hidden gem with colorful marine life.  

- Cistern Point: Located near Cooper Island, this spot is perfect for snorkeling in calm waters.

8. What is the best way to enjoy both the USVI and BVI?  

Plan a balanced itinerary combining the highlights of both regions. Start with a US Virgin Islands itinerary featuring St. John’s natural wonders like Cinnamon Bay Beach and Virgin Islands, and then transition to a BVI sailing itinerary, exploring Virgin Gorda, Marina Cay, and Anegada.

9. What are some must-visit attractions in the Virgin Islands National Park?  

The Virgin Islands National Park on St. John covers over 60% of the island and includes:  

- Trunk Bay: Perfect for snorkeling and swimming.  

- Cinnamon Bay and Beach: Ideal for kayaking and relaxing under the shade of palm trees.  

- Reef Bay Trail: Known for its petroglyphs and historical ruins.  

10. Should I visit Cane Garden Bay ?  

There is so much to see in the Virgin Islands, it's hard to hit all the spots in a short trip. Located on Tortola, Cane Garden Bay is a picturesque beach surrounded by vibrant local culture. It’s perfect for relaxing on the sand,  and sipping a drink at beachfront restaurants under swaying palm trees.