Matt and Britney Weidert

Matt Weidert

USVI Sailing Itinerary: An Epic Week in the US Virgin Islands

I recently spent some time in the US Virgin Islands on my November USVI yacht charter and I was blown away!

Spectacular beaches, pristine scenery (thanks to the National Park), and fun eating/drinking/shopping in quirky towns such as Cruz Bay await you on a USVI sailing itinerary. These are also ways that make the USVIs unique from other nearby charter destinations.

Did I mention logistics are super easy? You can be on your catamaran within 30 minutes of landing. Seriously.

If you are a British Virgin Islands yacht charter regular, you are missing out if you haven’t yet visited the next door neighbor.

Consider adding the US Virgin Islands to your list of charter destinations. Check out my week-long USVI sailing itinerary as a starting point to inspire your next trip.
Try my figure 8 plan for a week-long yacht charter sailing the US Virgin Islands

Planning for prevailing USVI cruising conditions

For my plan, we’ll start in the Charlotte Amalie area for your USVI yacht charter and head to the north shore of St. John. From there we’ll continue clockwise and then make a figure 8 around St. Thomas.

As far as resources, all you need is the Cruising Guide to the Virgin Islands, which many of you might already have since it also covers the British Virgin Islands.

Why does this USVI sailing itinerary plan work?
  • With prevailing easterly trade winds, we get our upwind leg out of the way on the first day by motoring (or sailing) around the south side of St. Thomas, and then NE to St. John. You’ll have some protection in the lee of St. John to avoid a bumpy ride
  • Further upwind passages on the north shore of St. John are short and protected as you hop between the fantastic beaches and bays of the Virgin Islands National Park
  • It gives you a chance, mid-trip, to make a pitstop in Cruz Bay for re-provisioning, if needed
  • Cruising around the north shore of St. Thomas should be a beautiful, downwind sail under normal conditions
  • It leaves you for your last night at Water Island, a short motor back to the charter bases on St. Thomas
Your first night in the USVIs: Hawksnest Bay

A week sailing the US Virgin Islands

Day 1: Set sail for beautiful St. John and the Virgin Islands National Park

Even if you don’t sleepaboard and have a noon start for your charter, you should still have time to motor to the north shore of St. John where you’ll find the jewel of the USVIs: the Virgin Islands National Park.

The trip should take you about an hour and a half if you take the cut between Great St. James. Confirm this is not off limits, but we were permitted as long as we passed to the south of Current Rock.

You can pick from any of the many bays where overnight moorings are provided by the National Park Service. These bays are close enough together than you easily backtrack if needed.

Mooring fees in the National Park are $26. If you use them only during the day, they are free. Pay for them ashore or at one of the self-service floating fee stations.

My choice? I’d go for Hawknest Beach on the first night. A Hawknest sea turtle sighting is almost guaranteed. Stroll the beach, snorkel the many reefs, or go in search of the Mermaid’s Chair.
Pour yourself a sundowner and get ready for an epic Virgin Islands sunset. You’ve arrived in paradise!!
The mooring field at Maho Bay where you'll spend your second night

Day 2: Beaches, snorkeling, repeat

Beaches, snorkeling, repeat. That’s the plan for the next couple days as you make your way east. I like Maho Bay as a 2nd night overnight, but don’t get there until the afternoon.

Take your time. You have plenty of special bays to explore along the way. You may even consider doing this by dinghy in settled conditions.

Next door is Trunk Bay, one of the most photographed beaches, anywhere. The main attraction here is the Underwater Trail around Trunk Cay, just 30 yards off the beach. Follow along and read the submerged plaques to learn about the area marine life.
The often photographed Trunk Bay | Try the underwater snorkeling trail around the cay just offshore
At Cinnamon Bay, we enjoyed gazing at some of the most luxurious villas in the Caribbean that seem to hang from the cliffs. It’s quite a scene! Aside from this, the beach is great and there is a protected swimming area.

Onwards to Maho Bay. Spend the afternoon lounging on the beach. We loved it so much we spent two days here on our trip. The dinghy channel is on the left as you approach - go slow and watch our for snorkelers!

Check out Maho Crossroads, a fun local establishment that offers cocktails and some classic beach bar fare. Better yet? Bring along a cooler of your own cold Caribs.

Back on your yacht, get ready for an unobstructed sunset over the cays to the west.
Great sunsets from the mooring field at Maho Bay
Salt Pond Bay and a view of Ram Head in the distance

Day 3: Enjoying solitude at Salt Pond Bay

In the morning, you have plenty of time for more snorkeling and exploring of the area, if you wish.

The beach at Francis Bay is right next door, or you could dinghy over to the point at Whistling Cay.

Around the corner is Leinster Bay and Waterlemon Cay. Many people claim this is where you can find the best snorkeling in all of St. John. You can also check out the Annaberg ruins ashore.

Get ready to raise those sails as you come around to the south side of St. John. For a day-stop head into Coral Bay. Many charter crews enjoy the floating taco bar, Lime Out, or you can head ashore elsewhere for some shopping, lunch, or drinks.

If you want to explore Coral Bay a bit more, check out the Coral Bay Yacht Club’s Cruising Guide - it has lots of great info about area attractions.

Make your way to Salt Pond Bay and pick up an overnight mooring ball. With just a handful of NPS mooring balls here, enjoy the beautiful scenery in (relative) solitude. If it’s crowded, other options are Great and Little Lameshur Bays, just to the west.
Cruz Bay, St. John, base camp for the Virgin Islands National Park

Day 4: Cruz Bay for a night out

Before you leave, a great excursion is the short hike to Ram Head. On a clear day, you might be able to see all the way to St. Croix.

Sail around the south side of St. John to the moorings at Caneel Bay. We’re headed for Cruz Bay, but it’s off limits by some charter companies. From Caneel Bay, it’s a short(ish) dinghy ride into town.

If you’re into fishing, today is a great day to make a detour to the south drop for some chances at wahoo, mahi, or tuna. Check out my fishing guide for some tips!

Head ashore to Cruz Bay for an afternoon or evening of shopping, bar hopping, or dining. You can also find several grocery stores here where you can stalk up on provisions (it’s not cheap, so plan accordingly!).

If you’d like, the Visitor Center for the Virgin Islands National Park is located here.

Note: Caneel Bay can be exposed to northerly winds and swell, so if those conditions are present, you might want to consider this a day stop only. Continue on to Magens Bay or add another stop at a more protected St. John mooring field. Learn more about prevailing weather conditions in my weather and marine forecasting post.
Fantastic sunset while anchored at Magens Bay

Day 5: Onwards to St. Thomas US Virgin Islands

Raise your sails for an easy downwind passage around the north shore of St. Thomas. Consider checking out the uninhabited Hans Lollik Islands for a day stop on the way.

There are two possible anchorages, one inside the reef at Coconut Bay. Or head around the west side and enter the bay between the two Lolliks. Enjoy a beautiful beach at the former and some interesting snorkeling at the latter.
Exploring the bay between the Hans Lollik Islands
Enter Magens Bay at marvel at the spectacular setting. It really is special with a large crescent shaped beach and long peninsula which forms the bight. Drop the hook (no mooring balls here) in the areas marked on charts. We chose a deeper spot in about ~30 feet towards the NE corner.

The bay is huge, and you should have no trouble finding some room to spread out.

On weekends, there can be a party scene - expect some louder music from the beach bar ashore and the occasional jet ski 😖
Beach day at Magens Bay

Day 6: Beach day yacht charter optionality

I always like to plan a day where we don’t move the boat. Today’s that day!
Dinghy ashore to enjoy a relaxing day on this wonderful beach. Magen’s Point Beach Bar and Grill whips up some good pizza and serves up drinks from the bar.

Other options? You can rent kayaks and stand up paddleboards, or put on your shoes for a short hike up the hills in the area.

Magens Bay could also be a good jumping off point for excursions ashore (just make sure there are no cruise ships in town!). Phantasea Botanical Garden or Mountain Top are popular attractions, nearby. It’s easy to coordinate a taxi from Magens Bay. Grab a bite at Sib’s on your way back.

Day 7: Wrap up the USVI sailing itinerary at Water Island

Continue your downwind sail along the north shore of St. Thomas and enjoy the coastal scenery. Head for Honeymoon Bay at Water Island.

This anchorage can be crowded, and the mooring balls are private, so try and arrive early if you can.

You can’t go wrong just relaxing on Honeymoon Beach while liming away the afternoon. Dinghy’s Beach Bar is a popular spot, or you can walk up the road for a drink at Heidi’s Honeymoon Grill.

Unobstructed epic sunsets are almost guaranteed here - not a bad way to end your USVI sailing itinerary! You’re just a short 15 minute motor to return your charter yacht the next morning.

If you’d rather grab a mooring ball on your last night, continue on to Christmas Cove at Great St. James Island. The snorkeling is pretty good here (it’s a protected area) and Pizza Pi Vi is located here seasonally. Dinghy right up for a hot pie! Sunsets over Red Hook also won’t disappoint.

You will have to back track the next morning to Charlotte Amalie, but it’s only about an hour.


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