“You Make the Memories, We’ll Make the Arrangements”

Experience the United States Virgin Islands (USVI) on a USVI Sailing 7-nights Itinerary for a unique and memorable vacation. Delight in the local sights, natural beauty, incredible activities, and amazing cuisine. Of course, this itinerary is just a sample. If you have sailed before, you are aware that weather conditions might affect where you sail.

St Thomas Yacht Haven Grande
St Thomas Yacht Haven Grande Marina

St Thomas, St Croix, and St John are the three main islands. Together with about 50 other minor islands and cays, they compromise this US territory. You will fall in love with this region where you will find everything from peaceful serenity and secluded bays to vibrant entertainment and culinary delights, not to mention the most delightful white-sand beaches and crystal-clear turquoise waters.

Day 1 St Thomas – Great St James Island

Meet your crew at Yacht Haven Grande Marina in St Thomas and motor sail to Christmas Cove, Great St James Island. This tranquil cove has immaculately clear waters, sea turtles, abundant marine life, and a wonderful undeveloped shoreline.


  • Diving – at Cow and Calf
  • Snorkeling – Fantastic right off the boat or along a rock ledge that’s covered with a multitude of fan and brain coral teeming with colorful tropical fish. Other desirable snorkeling spots include The Stragglers and Cabrita Point.
  • Walking the beach – Look for shells and sand dollars
  • Watersports – Tubing, wakeboarding or foiling
  • Relaxing – Relax on the deck of your yacht and savor the sunset. Have pizza from Pizza Pi, a famous floating restaurant/sailboat serving some of the best pizza in the Caribbean

Day 2 Christmas Cove – Caneel Bay/St John

Today, sail from Christmas Cove toward the cut between Mingo and Lovango Cay.

If the waves look particularly fabulous for surfing, try it right here towards the left. Should the action be too calm, sail around to the backside of Lovango Cay. Here, enjoy a fabulous lunch on board your yacht, between Lovongo and Congo Cay. The current here is very strong, so be especially mindful if you are in the water.

After lunch, head over to Caneel Bay, St John. From your boat, you will be taken by dinghy to the gorgeous sands of Honeymoon Beach. The wave action at this beach is very calm unless the ferry from St Thomas creates some. The white sand is soft, and some coconut palms provide shade from the hot tropical sun. Moreover, the shallow water allows easy access to the beach.


  • Kayaking
  • Stand-up Paddle Boarding
  • Snorkeling
  • Dining. Have a smoothie, frozen cocktail and delectable local food at Bikinis on the Beach Bar & Grill. Open from 9 am to 5 pm. Sandy runs the bar and is well-liked for her pleasant smile and great service. There’s live music on Tuesdays, Thursdays and weekends.

You’ll overnight in Caneel Bay after the dinghy brings you back to your yacht.

Adventure awaits you on the Catamaran Sea Boss. On your USVI Sailing 7-nights Itinerary
Adventure awaits you on Catamaran Sea Boss

Day 3 Caneel Bay – Maho Bay

While still in Caneel Bay for the morning, you might want to coordinate a dive with one of the local Cruz Bay dive boats, if your yacht does not offer this service. If you prefer, head to Maho Bay for some wonderful snorkeling and awesome beaches.


  • Diving – Caneel Bay. If your yacht doesn’t have onboard diving, your crew can arrange rendezvous dives.
  • Snorkeling – Maho Bay. From the boat you can see beautiful sea turtles and colorful marine life, including octopus. Swim to shore and walk on magnificent beaches.
  • Beaches – while on Maho Beach, check out Maho Crossroads, a pop-up village, consisting of a Tiki Bar on a movable trailer, a converted VW Bus food-truck and the Love Maho Beach Boutique.
  • More Snorkeling – Within dinghy distance from Maho, you can access more amazing marine life close to Whistling Cay. Ask the crew for the best spot.

Spend the night in Maho Bay.

Day 4 Maho Bay – Waterlemon Cay

Wake up in the relaxing Maho Bay/Francis Bay area. Look for sleepy turtles feeding on seagrass. Sail on down to Cinnamon Bay to do the snorkel trail. If this is too much water activity for you, go ashore and explore the Cinnamon Bay Plantation ruins. It’s an easy walk that you can do in your flip-flops.


  • Spotting Sea Turtles – Maho Bay is famous for its green sea turtles. They can be seen more easily early in the morning or late afternoon.
  • Snorkeling Cinnamon Bay – This bay, with its small coral colonies, offers shelter for lots of fish, crabs and lobsters.
  • Exploring and walking – Definitely explore the Cinnamon Plantation ruins. Starting in 1680, this shore was occupied for decades by settlers of various nationalities. The Danish established large sugar cane plantations.

From Maho Bay, sit back and savor the ride to Waterlemon Cay.


  • Snorkel Waterlemon Cay – This is the # 1 snorkeling destination on St John. Waterlemon Cay has a shallow reef where coral heads create a habitat for a multitude of fish and other marine life. A little further out there’s a steep drop-off where sea turtles swim between an amazing display of sea fans.
  • Hike to the Annaberg Plantation – Explore the ruins of the plantation and take an Instagram-worthy shot with the windmill. In 1780, the Annaberg Plantation was one of 25 active sugar producing factories. Other products were molasses and, of course, rum. The trail also offers wonderful views of the surrounding area.
  • Stand-Up Paddleboard around the harbor.
  • Lounge on the floating docks.
Waterlemon Cay St John USVI
Waterlemon Cay St John USVI

Day 5 – Waterlemon Cay – Hansen Bay

Depart Waterlemon Cay and motor sail around the east-end of St John. Although this is usually a calm transit, a south swell can make the journey a little bit bumpy for the last 20-minute stretch. Once around the corner, you will anchor for the day in Hurricane Hole. This private little harbor is a storm-protected bay with mangrove trees and a multitude of fish.


  • Kayak – along the shore between the mangrove trees. Mangroves are important nursery habitats for juvenile reef fish. Keep an eye out for star fish.
  • Swim – close to shore to see beautiful fish nurseries.
  • Snorkel – How about a Mangrove Snorkel? You will see anemones, spaghetti worms and upside-down jellyfish.
  • Have the captain take you in the dinghy to Lime Out – You will love this floating bar and taco boat. In fact, you can swim right up to it, no fins required. Sit on one of the circular green floats or at the bar. Munch on tasty tacos, drink local juice, hibiscus tea or a hand-crafted cocktail — all in the comfort of the Caribbean sea.

Before the sun gets too low, dinghy back to the boat for the ride to Hansen Bay, where you will spend the night.

While at Hansen Bay, snorkel around the corner to see the rocks and coral that form Pelican Rock. You might even see some sea turtles up close, or even large rays, jacks, and pompano fish.

Day 6 Hansen Bay – Salt Pond/Lameshure Bay

Hoist the anchor and head around the point to Salt Pond. Pick up one of five park moorings. If they have been taken, your captain will sail to Lameshur Bay. Salt Pond is accessible by dinghy from there, weather permitting. Once on Salt Pond, you will need to lace up your sneakers to explore.


  • Hike the Rams Head Trail – Grab your water bottle and hit this trail with a gorgeous view at the end. Depart Salt Pond and head west to Lameshur or Little Lameshur. Explore this piece of the past and walk perhaps to Reef Bay ruins and see some fantastic petroglyphs. Little Lameshure Bay has a short hike to some sugar mill ruins, which make a perfect location for a family portrait or group photo.
  • Read about the NASA Tektite Project prior to hiking there – In 1969, the Tektite project was just beginning, right here on St John. Four marine scientists descended to a depth of about 50 feet, where they would live and work for the next 60 days. Until then, a human had never lived and worked under the sea for that long.
  • Snorkel – Little Lameshur Bay has some of the best snorkeling on St John. Search the crystal-clear water for marine life and sea turtles in between the seagrass.
  • Swim – Shallow water makes this a great spot for safe swimming. The location is well protected.

After a full day of activity, it’s time to relax. Enjoy a delicious meal created by your chef, then sit back and enjoy the magnificent Caribbean sunset on the deck of your yacht.

snorkeling in crystal-clear waters on you USVI Sailing 7-night Itinerary
Snorkeling in the crystal-clear waters Photo credit: Maja Novak on Unsplash

Day 7 Lamshure Bay – Cruz Bay and Lovango

Depart Lameshure Bay for Cruz Bay.

Spend the afternoon shopping at the jewelry stores or take part in some of the local festivals.


  • Shopping at Cruz Bay – Wharfside Village. A variety of interesting stores, conveniently located in the center of Cruz Bay, next to the ferry landing wharf. It is a pleasant place for the entire family to buy souvenirs, browse and wander.  

Once back on the boat, head over to Lovango Resort for your overnight stay.

Lovango Resort – is a one-of-a-kind private island, only a short boat ride from St John or St Thomas. Enjoy a cocktail at the infinity pool or have an exquisite meal at the Waterfront Restaurant. Chef Belie’s culinary approach is making sure that the Caribbean-inspired menu offers only the freshest regional ingredients.

Day 8 Lovango – Buck Island and return to St Thomas/Charlotte Amalie

Today, on your USVI Sailing 7-nights itinerary, you will sail toward Charlotte Amalie. The first stop will be Buck Island, located about 2 miles south of St Thomas. This National Wildlife Refuge is the perfect place to spend your last day making memories.


  • See the historic lighthouse – only one of three lighthouses in the US Virgin Islands built by the Danish.
  • Bird watch – frigate birds, laughing gulls, terns and red-billed tropic birds
  • Snorkel – Crystal clear waters reveal gorgeous coral reefs, brilliantly colored marine life, and endangered resident sea turtles.
  • Scuba Dive – the Cartanza site. Since this site is at a depth of 85 feet, it is too deep for snorkeling. However, it is perfect for the recreational diver.

From Buck Island, it’s an easy sail into Charlotte Amalie harbor. This area of St Thomas offers wonderful shopping and historic sites.


  • Shop – at a multitude of quaint stores and boutiques. You will find a present for everybody on your list.
  • Walk – along cobble stone alleyways and climb steep streets. Here you’ll find a wealth of buildings that provide insight into the colonial life of the past. Charlotte Amalie is listed in the Registry of Historic Places.
  • Visit Blackbeard’s Castle – built around 1674-1680 as a watch tower for guarding Charlotte Amalie.

Find your way back to the boat and gather your belongings. Say goodbye to the crew who will arrange transportation for the 15-minute taxi ride to the airport. Vow to be back as soon as possible.

You can follow this itinerary and you might just be on the best yacht charter vacation, ever!

Contact us at 1-321-777-1707 or complete this form to discuss your vacation plans.