Circumnavigate St. John

This trip is a great way to see the entire coastline of St. John! You’ll also get to stay in some of the island’s most loved campgrounds and cabins, and hike to places with some of the most amazing views.

Day 1: We meet at 8:00am at Arawak Expeditions’ shop and headquarters in Mongoose Junction in Cruz Bay.  After a brief introductory meeting, we’ll spend some time teaching you the fundamentals of how to kayak, then pack the kayaks and go!  Our first stop will be Henley Cay, where we will snorkel and have lunch before continuing on to our first night’s stop at Cinnamon Bay Campground.


Kayaks at Cinnamon Bay. Photo by Steve Simonsen.

Day 2:  This is our easy day.   We can sleep late, have breakfast and then paddle to Francis Bay where we will go on a bird-watching hike around the salt pond.  Next, we’ll have a picnic lunch at the beach here then paddle out to nearby Whistling Cay, where there is excellent snorkeling.   After our snorkel, we’ll head back to our campsite at Cinnamon Bay.

Kayaks at Mary Point. Photo by Steve Simonsen.

Day 3:  This will be our longest day of paddling.  We’ll get up early in order to take advantage of the calmer seas in the morning, then paddle our way upwind to Brown Bay where we’ll stop for a picnic lunch and snorkeling.  Next, we’ll continue up the north shore of St. John, and into Newfound Bay, where we will stay in a rustic campground.

Ram Head Trail

Day 4:  From Newfound Bay, we will head around the East End and then out to Flanagan Island where we will stop for some excellent snorkeling.  Next, we’ll paddle around Ram’s Head to Salt Pond Bay, where we will stop for more snorkeling and lunch before we check into our cabins at Estate Concordia.   After we get checked in to our cabin, we’ll have time for a sunset hike out to Ram Head.

Day 5:  On our last day, we’ll have a relatively easy, downwind paddle back to Cruz Bay.  Along the way, we’ll stop at Reef Bay, where we will visit the ruins of the sugar factory, then continue on to Ditliff Point where we will stop for a picnic lunch and a final snorkel.  We’ll finish in Cruz Bay, around 4 pm, say our goodbyes then head to our respective accommodations.

Remember, this is only a sample itinerary; your actual route can and will change due to wind, weather and sea conditions.  If, for example, the seas are too rough for paddling (i.e. there is a small craft warning) we may spend the day hiking or sightseeing rather than paddling.


  • length of trip: 5 days/ 4 nights
  • accommodations: tents, and cabins
  • included: all lodging, meals, equipment
  • departs from: St. John, USVI

Please click here for our schedule of Circumnavigation trip dates and prices.