A Perfect Day in the Virgin Islands

Norman IslandSnorkeling, swimming and beach bars, oh my!  Who could ask for more from a day on the water in the Virgin Islands.  What a great day we had with Captain John from Palm Tree Charters exploring the US and British Virgin Islands.  On a trip to Caneel Bay on St. John, I really wanted to explore some of the smaller islands of the Virgin Islands and especially wanted to go to the Soggy Dollar Bar on Jost Van Dyke so we chartered a boat for the day.

We had been worried about rain, but woke up to a beautiful day.  We got to the Caneel Bay dock a little before 8:30am and wondered as each boat went by if it was the one for us.  Captain John was right on time and after a little paperwork for customs, we were on our way!

Palm Tree Charters

North Shore Beaches
We started with a tour of the north shore beaches and got to see Caneel’s beautiful beaches from the water.  Wow…I do think they are the best on the island.

Turtle Bay Beach Caneel Bay St. John

Scott Beach

Next was famous Trunk Bay, Cinnamon Bay and then on to the “high rent district” with one of the few beachfront houses on St. John.

St. John beach front house

St. John

Waterlemon Cay
Our first stop was at Waterlemon Cay to snorkel.  I admit, I freak out a bit when I have to jump off a boat the first time to snorkel.  I much prefer going in from the beach, but given this snorkel spot requires a hike and swim to get to from land, it was nice to have the boat drop us off.  The snorkeling was not that great though and I was getting uncomfortable in the current so we looked around for a while then went back to the boat to move on to our next snorkel spot.

The Indians

The Indians
As we approached the Indians, there were already a number of boats there.  The snorkeling here was much better than at Waterlemon, but the water was more crowded with people.  Somehow Chris and I lost each other and spent most of the time looking for each other.  I finally went back to the boat and Captain John knew exactly where Chris was snorkeling.

At this point, we were done snorkeling so now it was time for some drinks!!!

Pirates on Norman Island

Norman Island Pirates
Norman Island was the inspiration for the novel Treasure Island and home to the best bushwackers I had on this trip.  Chris was a fan of their rum punch.  I absolutely loved this place!  From the drinks to the beautiful scenery to the great conversation with Captain John, it was all perfect.

Pirates Norman Island

Pirates Norman IslandWe had to keep moving though to get to all of our stops so we did not have a chance to play the giant Jenga or Connect Four game.

Pirates Norman Island Jenga

Note that since we were there, Pirates did a major renovation, and then sadly burned to the ground in early October.  I believe there are plans to rebuild.

The Willy T

Willy T

I had seen The Willy T on the Travel Channel and Captain John picked this as our lunch stop.  I have a terrible problem with motion sickness though so the idea of being on a floating restaurant/bar made me nervous.  Unfortunately, I was right.  After about thirty seconds on The Willy T, I knew I needed to get off of it or I was going to feel sick for the rest of the day.  Captain John quickly got us back on his boat and came up with a new plan for lunch on land.

Pusser’s at Soper’s Hole on Tortola
Pusser’s was a hoot.  We sat at the large outdoor bar to eat lunch, have a couple more drinks and people watch.  Chris declared the burger the “best burger ever”, but I think that had more to do with the amount of alcohol consumed prior to eating said burger.

Soper’s Hole was really cute with Caribbean colored buildings, a steel drum band playing 80’s music and a few characters we will never forget.

Pussers Tortola

Steel Drum Band

Not long after we sat down, a gentleman sat next to us and put a paper bag on the bar.  We chatted with him and knew at some point this bag was going to get into the conversation.  After a couple of drinks, the man could not contain himself anymore and had to tell us what was in the bag.  I think all this time he wanted us to ask him, but we didn’t since it would be more fun to see how this played out.  It was a jar of some kind of strange spread that almost looked like Vegemite.  I am not sure what it was, but he was very proud of it and wanted us to stick our fingers in the jar to taste it.  No thank you sir.  Time to move on!

Smuggler’s Cove on Tortola
This beach was incredible!  We swam in from the boat and the water was as clear as a swimming pool.

Smugglers Cove Tortola

This beach also had Stephen who ran a little bar where he powered his blender by a car battery to make drinks.  We remember Stephen fondly and always refer to this beach as “Stephen’s beach”.  This trip was a while ago and I believe the bar was shut down, but this is still a beautiful spot that I would return to even without a bar.

Smuggler's Cove Tortola

By this point, I was feeling really good, but needed to slow down on the drinks so Chris drank most of my drink.  We did not have much time here since we still needed to get to our last stop.

Soggy Dollar Bar on Jost Van Dyke

Soggy Dollar Bar
Our final stop was what I was most excited about on this trip.  The beach bar on gorgeous White Bay famous for the Painkiller drink and paying with wet money (soggy dollars) since there is no dock and people have to swim in from their boats.

Jost Van Dyke


Soggy Dollar Bar Jost Van Dyke

I know this is not going to be popular, but…we didn’t like it.  The Soggy Dollar Bar has become too popular and it felt like a grown up frat party with everyone just standing around “seeing and being seen”.  There was a long line to get a drink, but I finally pushed my way through to get us two Painkillers.  There were so many boats and people that I think it ruined the beauty and charm of the beach and bar.

Soggy Dollar Bar

I think this place could be really special if there were fewer people, but it is a party place and that just was not what we were looking for on this trip.  Captain John said it was more crowded than usual because it was Sunday so I may give the Soggy Dollar Bar another try on a different day of the week and also earlier in the day.

Sadly, the day had to come to an end and we were dropped off back at Caneel Bay.

Caneel Bay

This was one of the most fun and memorable days I have had on a vacation….ever!

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  1. Great day! What day was this trip?
    We are going to STT this Sat 10/26 and are looking for a charter boat.

    • We went on a Sunday…I think it was Mother’s Day. I’d highly recommend you check with Palm Tree Charters. John’s wife (Sue) does all the bookings and is super helpful in planning your day.

  2. High Maintenance!

  3. We are going out with John in 2 weeks! Our first trip was back in 2011 with our kids and 2 of their friends. We can’t wait!

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