(Disclaimer: I’m trying to embed photos in this trip report – I hope it works!)

This trip consisted of my husband (Andy) and I and 3 friends (one couple + 1 guy). The one guy (Rick) we’ve known for a while and are good friends with. The couple (Chris & Olivia) we’d only met a few times, but they’re good friends with Rick. I was a little apprehensive about spending a week on a boat with a couple I didn’t know well, but it turned out great!

We originated from different airports, but all met up in ATL and were on the same flight to STT. We all gathered our checked luggage and met Kevin right inside next to baggage claim.


Hugs were exchanged and he got us into a cab and off to the ferry. (FYI, taxi cost with Kevin is $10 per person + $10 for all our bags + tip). Can’t recommend Kevin enough! We arrived at the ferry terminal an hour before departure so we bought our tickets ($35 per person + $3 per bag) and went upstairs to the Petite Pump room for a drink and to fill out our customs forms. An hour later, we’re on the ferry directly to Road Town where Andrew from TMM was waiting to pick us up.

We chartered a 2016 40’ catamaran Orion out of TMM. (The owner Mark is on this board and he was fantastic to work with!). TMM is a wonderful charter company. This was our 3rd with them and we love them. 4 cabins, 2 heads with electric toilets and separate showers, generator with AC, freezer, and super well equipped kitchen and interior. TMM must have just upgraded all the towels and linens because the towels & pillows were actually fluffy! We’re spoiled for future charters!

We sent 3 of the crew off to the big Riteway to provision some things while Andy and I familiarized ourselves with the boat and unpacked. We pre-ordered liquor & water from Caribbean Cellars, but that was nowhere to be found (it was after 5 pm) so we texted the grocery crew to be sure to pick up a bottle or two! After they returned, we walked over to Sharky’s for dinner. Everyone was starving and I think we all ordered fish & chips. It was good; not great, but good. We slept aboard that night. This is where the AC was great. There isn’t a breeze in the marina.

Day 1: We’re up early for a shower & coffee. Andy and I headed to the office to start the briefing and fill out last minute paperwork. In the office we found our Caribbean Cellars order – it was missing 20 gallons of water, 2 bottles of rum, and included an extra case of Red Stripe. This is the 2nd time we’ve provisioned with them and the 2nd time they’ve screwed up. The most critical of which was the water. Next time, we’re going with someone else. Suggestions are welcome! So we sent a few crew off to the small Riteway near TMM to get gallons of water. This is also the 2nd time that we realized that the small Riteway at TMM has everything (and then some) that the big Riteway does. Same prices. We won’t be making the trip to the big store next time.

Check out briefing done and we’re off to Cooper Island. No problem finding a ball – it wasn’t really crowded. We dinghied ashore for lunch and a bloody mary! Ceasar salad with shrimp was delicious. (note: they automatically add a 10% gratuity to all bills) We hit the rum bar which is small and cozy but Daniel behind the bar was friendly and enthusiastic about the rums and we sampled a few (including Sebastian’s where we would stay later in our trip). Back to the boat to gear up for some snorkeling at Cistern Point. We dinghied over there and tied up and in we went. The snorkeling was good. You gotta love it when a newbie gets in the water and immediately comes back up yelling “There’s FISH down there!” Ha ha ha! Back to the boat to float, relax and enjoy the view before heading back ashore for dinner.


Day 2: We’re off to Virgin Gorda! We made a stop at the Baths to swim in & hike the trail. We got to shore right after 2 big tour groups so it was slow going. Andy picked us up in the dinghy at Devils Bay and Rick & Chris snorkeled over there. They said it was really good snorkeling! We then headed to the North Sound and Leverick. The guys at the dock were great as usual. We filled with water and Andy backed us right into our slip. Went to the office to catch a taxi to (1) Hog Heaven for part of our crew and (2) a clinic & pharmacy for another part (Chris needed ear drops). Taxi driver is going to drop 3 of us at Hog Heaven while the other 2 head to Spanish Town for the clinic/pharmacy. As we’re heading up the hill out of Leverick, the van bottoms out over a speed bump and the spare tire drops from the underside of the back of the van. Chris is sitting in the back and is a somewhat large guy – hilarity ensued and we all busted out laughing about Chris breaking the van. His Instagram photo: #frontseatonly.


The guys were successful in getting ear drops & we were successful at holding down the fort at Hog Heaven.


We all headed back to Leverick for showers (great onshore showers!) and took the Saba Rock water taxi over to Saba for cocktails. Missed the Tarpon feeding, but the drinks & vibe over there were great. (Water taxi is free; just tip the driver)


We made it back to Leverick in time for the BBQ buffet and Jumbie party. This was awesome! Paula, our waitress, was wonderful. The food is great and the jumbie party is something you should definitely experience. Olivia and I danced our way around and under all the jumbie dancers and had a great time! We met Nick & Monica – two very sweet & kind people. Nick, we’ll be back next spring!


Day 3-4: We’re up early and off to Anegada! Took us about 2-3 hours sailing and it was a great day to sail. As we neared the channel we could see the salvage crew inflating large balloons to float the wreckage of the sunken barge.
After a brief rain shower (it seems to rain every time we’re at Anegada), we dinghied to shore to the Wonky Dog where we met Desne who took our dinner order for that night and she called Dean Whitley to pick us up for our rental car. Desne is an absolute sweetheart!! Got our rental jeep and headed to Loblolly where the boys snorkeled a bit. Then we all headed to Cow Wreck. This is by far my favorite beach bar of all time. It was so quiet and empty – only a few other people there. We visited with Ann and her son Branden and his new puppy Prince. The boys played darts while Olivia and I sat with our toes in the water. I could spend hours and hours here! But, we had dinner plans at Wonky Dog so we headed out.




Dinner at the Wonky Dog was absolutely amazing! Andy and I split a wedge salad and he had lobster Rockefeller while I had lobster thermidore. One of our crew remarked to Peter (when he reluctantly came out of the kitchen to accept a round of compliments and applause from everyone there) that our meal was Michelin star quality food. I can’t even find the right superlatives to describe this meal, but trust me. We provisioned more wine than we were drinking on board and Desne & Peter were kind enough to let us bring our own bottles for dinner. Thank you Peter! If you’re on Anegada you MUST eat there. It’ll be worth it. I promise.


After dinner, we met up with Sherwin Williams (yeah, no lie. That’s his name) He’s Ann’s (from Cow Wreck) cousin and he runs fishing charter trips. Chris & Olivia wanted to fish. $500 for the day of fishing and he “guaranteed” we’d catch fish – specifically mahi. This is where, in hindsight, we decided that in the islands after you’ve been drinking all day/evening you don’t necessarily need a designated driver. You need a DDM – a dedicated decision maker.

Next morning, we met Sherwin at his boat at the dock. It’s about 28-30’ and has no shade cover. We head out about 1-2 miles off shore. We were out there for 4-5 hours and caught a barracuda and 2 little orange fish. No mahi. By about hour 4 I’m starting to feel like Tom Hanks in the movie Castaway. We were all pretty miserable. Sherwin felt bad that we didn’t catch anything and he offered to bring us some lobster from his pots later that evening. Sure enough, a few hours later he shows up at our boat with 5 huge lobsters!! Chris cleaned them and Rick cooked them. That evening we had steaks, lobster tails, lobster mac & cheese, salad and roasted potatoes. It was a delicious meal and we were all stuffed and exhausted.
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The Anegada sunset that evening was simply breathtaking!
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Part two coming up!
Julie