The first time I thought about creating a travel blog was at the end of this vacation. So, I found it fitting for this to be the first article on my site. This trip was so nontraditional, stressful (at times), and truly the biggest adventure I have ever taken. It changed me in a way once it was all over. In the end, it confirmed that I want to live on a yacht one day and cruise my days away.
What is Bareboating? Bareboat: (n) A boat, such as a yacht, that is chartered without a skipper or crew. That’s right, you rent the boat and head out to sea without any captain or crew….just yourself. I planned this trip with my husband in tow. We both have always loved boating, grew up owning a boat, and still own a boat today. It has always been a dream of ours to retire on a yacht, so I thought I would give bareboating a try to test the waters on our retirement dream.
When I say that we have always owned a boat, I am talking about a ski/wakeboarding boat that we take out on lakes while camping. This trip I planned was going to be for one week on a 38ft 2 bedroom/2bath power cat in the Carribean. We both had very little experience boating on the ocean. We had never anchored out at sea or used waypoints. However, I banked tens upon tens of hours researching this, and where would be the best place to bareboat for beginners. I came up with the Virgin Islands. The Virgin Islands are perfect because the islands are very close together so the seas are fairly calm. Plus, you can always see shore somewhere so that is very comforting as a newbie. Lastly, the route I chose had us driving the boat 1.5 hours (at the most) to get to our next stop. Bouncing around from island to island on calm water seemed like a perfect fit to get our feet wet.
We flew into St. Thomas, and took a ferry to Tortola which is where we were picking up the boat. We spent a couple of nights unwinding from our travels and also preparing for our ocean adventure. We hit the grocery store, got our fishing license/gear, and had a very nice dinner filled with nerves of excitement to board our boat. Our route was Tortola, Norman Island, Jost Van Dyke (including Sandy Caye), Virgin Gorda (two sides of this island), Cooper Island, and back to Tortola. We were shooting for six different islands in seven days.
I decided to rent our boat from Marine Max Vacations. For the main reasons that they were very fairly priced and had power cats. Most bareboating rentals in the BVI are sail boats. Sailing is really big in the BVI, but we opted for a power cat as we know nothing about sailing. I was very happy with Marine Max, and they actually rent boats for bareboating all over the world. I am secretly planning my next bareboat adventure while writing this Blog. Probably Greece or Croatia!
After a 2 hour orientation of our new home, we drove out of the marina into open waters with butterflies in our stomachs, and feeling totally in over our heads. Our first stop was Norman Island, which was a very short hop from the marina we were in. There were literally hundreds of boats anchored here, which definitely solidified the fact that the BVI is extremely popular for bareboating. We were the little guys on the block for sure. The boats around us were filthy gorgeous. I found yachters to be much like campers. All of our neighbors were so nice, and willing to help. Like that one time we woke up to find that our dingy was no longer tied to our boat…the dingy we had signed a $10,000 replacement cost on. Ya, that was a stressful moment! Our neighbors came and picked us up, and we found the dingy which had floated away. Yachters are good peeps! But back to Norman Island…We got our anchor secured (after about an hour of trial and error), bbqed some steaks and scallops, and took the dingy over to Willy T’s Floating Bar for some cocktails and dancing. This place was rowdy and fun! Everyone was getting straight up crazy!

I think we checked the anchor about 50 times that night, but we didn’t float away and woke up to a beautiful morning feeling confident to move to the next island.
Our second stop was Jost Van Dyke. We spent 2 nights here including NYE…Oh, did I mention the weather is perfect in the BVI’s at this time of year? I am always chasing that summer weather! We got to Jost Van Dyke early and scored a moor ball…no need to worry about our anchoring skills…winning! This island was a party. One of my favorite spots here was the Soggy Dollar where I consumed too many of their famous Pain Killers.

My other favorite spot was Foxy’s where I spent NYE dancing the night away in the sand. There had to be a thousand boats parked here for NYE. People travel from all over the Caribbean to come to the NYE party at Foxy’s. Our boat rental company strongly suggested that we stay away due to all the traffic on NYE. I was very happy we rolled the dice and went anyways because it was an absolute blast!

Before leaving the island we popped over to Sandy Caye on the dingy early in the AM. Not bad for New Years morning. We were literally the only two people on the island. It was gorgeous. We toasted a little champagne and enjoyed this little island to ourselves for a couple of hours. It was a great way to start the New Year!

On to the next stop! Virgin Gorda. This was our longest drive on the route at about an hour and a half. We trolled along the way but came up empty on catches. We went spent one night on one side of Virgin Gorda exploring and snorkeling the Baths. It is just a must if you ever visit BVI! The water was so pristine and the Baths lived up to their reputation. We got here pretty late and weren’t supposed to spend the night but oopsie…we had no choice because it got dark. No ticket in the morning. Yippee!
The other two nights were spent on the other side of the island at Bitters End. We were surrounded by multimillion dollar yachts, and caught fish right off the back of the boat. Pretty amazing! Saba Rock is also located here. It is such a small island they call it a big rock. We took the dingy here at night for lobster, cocktails, and dancing.

The last stop on the route back was Cooper Island. There were turtles everywhere and we had the most beautiful sunset of the entire trip. After all of the anxiety I started the trip with, I couldn’t have felt more relaxed at this island….and sad to return the boat the next day for that matter. I like to push myself to just a bit outside of the comfort zone when traveling. I always want to challenge myself with adventure. This trip ended up being the biggest adventure of my life (to date) and I am proud of how much I learned.

After being on a boat for a week, I was ready for a hot bath, some makeup, and high heels. We spent another four nights at the Frenchman’s Reef and Morning Star Marriot Beach Resort on St. Thomas before heading home to California. It was beautiful and luxurious, but I have to say….I preferred the boat!
Recommend this trip for: People that know more than the basics about boating. I really think anyone with a pulse would love this trip, but you do need to be able to handle the boat. If you can’t, hire a captain or invite a friend who is a boater. It’s great for families, couples, and friends.
Favorite restaurant in St. Thomas: Havanna Blue. Love me some Cuban food!
Favorite Bar in St. Thomas (Charlotte Amelie): Rum Island Pub, aka Husband Daycare.
Favorite Wine Bar in St. Thomas (Red Hook): XO Bistro
Favorite Place to shake my bon bon in St. Thomas (Red Hook): Duffy’s Love Shack
Bikinis on the trip: Beach Bunny and Victoria Secret.
Favorite bar/restauraunt on Tortola: Pussers I had chowder every time I went. So good!
Best place to stop for lunch on your way to Vigrin Gorda: The Dogs! The Dogs are a small group of five uninhabited Islands that sit just to the West of Virgin Gorda. They are named for the barking sound from the seal population that used to inhabit these islands (long ago). The Dogs are made up of Great Dog, George Dog, West Dog and Seal Dogs (east & little).
Tip for the trip: If you are prone to sea sickness or have a fear of becoming sea sick, get the prescription patch from your doctor. It works wonders! Slap that baby behind your ear, and come away with me.
Awesome experience!!
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Thank you so much! I can’t wait to do it again! 🙂
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