It’s hard to believe just around a week ago we were on a boat sailing around the islands in the Caribbean… Time really does fly when you’re having fun! The trip was an absolute dream that we were so grateful to get to go on, especially with friends of ours who we love! We went with my friend Laura, her husband, and two children… I used to teach her daughter Olivia piano a few years back, and I’m still so grateful for the day she struck up a conversation about my top and we started talking about blogging! Sometimes of the best friendships are found in the oddest of places! It’s been years since Ross and I took an actual vacation (where we weren’t working to create content for hotels and/or a fashion week), and we came back so refreshed and reset!!
I got quite a few questions on what we did and where we went, so I wanted to do a post on the trip and the spots we hit!
We flew into St. Thomas, which is a US Virgin Island, then ferried to Tortola, which is British Virgin Island. We spent a fun night there, stocked up on groceries the next day, and proceeded to board the catamaran we chartered for the week from the company called The Moorings. We spent the week sailing around from island to island, snorkeling, dozing on beaches… it was amazing! We wrapped up back at Tortola and enjoyed a sunny day there before ferrying to St. Thomas and spending some time there before heading home. I’m going to share details on all of the spots we spent time at and what we loved, but first…
Boat life… Living on a boat for a week was a blast, but also challenging. It’s incredible to be able to sleep out on the water (and open your little window you sleep under so you can feel the ocean breeze and see the stars), sail to whatever island you want in just 1-2 hours, and just hop off the boat and swim to the beach you moored next to. Also, there’s nothing like watching the sunset right on the water and feeling the ocean breeze on your skin all day every day. I grew up boating during the summers on the Chesapeake, so it was so amazing to be back on a boat!
We hired a skipper/captain for the week who took over sailing the boat from island to island, charting our course & making sure it included the best spots, dingy-ing us from the islands to the beaches/restaurants when we didn’t want to swim/get wet, and just overall guiding and watching over us. I would highly recommend! It not only gave us so much peace of mind and allowed us to truly relax most of the time, but he also made us feel safe and made sure no one upcharged/took advantage of us. He was also so sweet… In the beginning he was very reserved and made it clear that he was there to help and not disturb us, but once we told him he was more than welcome to be with us and invited him to dinner, he opened up some, had dinner with us every night, and was a special part of our trip! We really enjoyed getting to know him and hear his story. His name is Chris, so if you end up booking through The Moorings, definitely request him!
There was enough room for the 6 of us, as there were 4 bedrooms and bathrooms, so we ended up with one bedroom left over for storage! The main challenges were that most of us got quite seasick on the journeys between islands and we were kind of ‘roughing it’ a bit as far as showers/cooking/bathrooms go (while there were 4 of each, they’re very tiny, water supply is limited, and it’s soooo hard to keep sand out of your bedrooms/beds because it’s so hard to keep your feet and the floors clean!). Obviously though, the challenges were nothing compared to the amazing time we had, and I feel like it’s good to get outside of your comfort zone every so often. We’d all 110% do it again!
Now for the fun part… the islands and spots we hit!
Our first night we spent at Maria’s by the Sea in Tortola. The hotel itself was not very nice and I don’t think I’d stay there again, but it was super close to everything which was nice! We walked there from the ferry post after making it through customs with our suitcases and it was less than 5 minutes. We had dinner at Pusser’s, which was an island Irish Pub, so funny, and it was EPIC. From the ‘chip tower’ to Olivia’s giant fried hot dog, it was so bad but soooo good! The only thing that wasn’t great were the drinks, but we found that they were pretty ‘meh’ when near ferry ports and super touristy spots in Tortola and St. Thomas as well. The charter company we got the catamaran from was on Tortola, and the hotel there was really lovely with a gorgeous pool, so possibly an option for next time! I’d recommend checking there first if you’re looking to stay on Tortola. We didn’t spend much time on Tortola, but the bit of touring we did was some shops at Pier Park. It was a cute spot checking out if you have some time on the island!
2) Normal Island
This was our first stop after setting sail and definitely a contestant for my favorite. The beach was very nice, the bar/restaurant had amazing food and drinks (not to mention giant jenga!), the view of the ocean and sunset was fantastic… The islands were obviously hit sooo hard from the 2 hurricanes last year, so some spots were really rough and not rebuilt, but this island was completely restored and so, so nice!
3) Jost Van Dyke
This island is known for the famous bar, The Soggy Dollar! So of course, we had to get a drink there. Ross’s mango cocktail was fabulous, but I opted for ‘The SoggyWhacker’ and I barely made it through 1/4 of it! It was basically all liquor on ice… So be careful, they make a lot of the drinks strongggg there… I’d opt for something fruity that says it has juice in it, but you guys know I’m usually a wine girl, so I like my mixed drinks fruit juice heavy and not crazy strong haha! That said, it was still a great beach to visit! There were a few others bars/restaurants, the sand was so soft and white, and water the purest aqua, and we got some super soft and cute tees/sweatshirts at the Soggy Dollar gift shop! We also stayed the night there… we did some paddle boarding while the sun set then made dinner on the boat and enjoyed the views and island breeze. It was quiet, and there was even a fairly well-known floating spa there if you felt like indulging in a massage!
4) Peter Island
Peter Island is home of the famous floating boat, the Willy T. So of course we had to have lunch there! The food was pretty good, and it was fun to boat up to a boat and eat there, but it’s kind of noisy and nothing extra special. We did it more because it’s one of those things you do to say you did it. The beach there was definitely my least favorite, as it was extremely rocky (like it hurt to walk around) and covered in trash. That said, it might be totally different in a year or so, as they were just beginning to rebuild the beach bars and clean up. We tried to help pick up as we actually found a whole trash can in the water… so sad. I should mention though, the snorkeling was not too bad here, and we saw some pretty huge tarapin and stingray around our boat after dinner on it that night, as they love the blue lights that come on under the catamarans at night!
5) Cooper Island
This was another contestant for my favorite island! The beach club was sooo nice on this island, it was basically a little resort, the food and drinks were excellent (save my shrimp at dinner, theyyy were gross, but the only thing that wasn’t great, and the mango margaritas totally made up for it, they were killer!), and the snorkeling was just insane!!! We went pretty far out (almost to the next island), and saw pretty much everything you could hope for save the turtles. We saw squid, stingrays, all sorts of beautifully colored fish, and I even found some sand dollars. Laura’s husband, Adam, rented scuba gear because he is certified and it is so cheap!!! Under $30 for a day’s worth of oxygen (2 tanks, I believe). The beach itself was really cute, with little tables in the water and palm trees all around. We spent the whole afternoon and evening there and were so sad to leave!
6) The Baths, Virgin Gorda
So this was actually just a boat by, since the day we were supposed to go ashore here the currents and wind were so strong that there were red flags out. I’ve actually been to the baths and got to explore/climb through the rocks about 8 years ago, and it was absolutely stunning! The sand is so white and aqua so white and water so aquamarine… I definitely hope to revisit one day and would definitely say it’s worth it!
7) Scrub Island and Co., Anguilla
I was pleasantly surprised by how incredible this area is (the ‘co.’ because there are some tiny next to it worth hitting!)! There is a tiny island that we spent the day at called Marina Cay, with lots of good snorkeling, an outdoor restaurant, and a boutique at the top of the island which has insane views! The boutique doesn’t have much to offer, but you can tell they used to have an outdoor bar/restaurant up there as well and I’m sure they’ll bring it back as soon as they can! We spent the day paddle boarding and snorkeling, then cleaned up on the boat and headed to a gorgeous Mariott resort on Scrub Island. It was beautiful, elegant, and the food and drinks were really good. I’d even stay there/recommend staying there a few nights if staying on that island/in that area was something we or you wanted to do!
8) St. Thomas
The joy being back here brought was incredible! I’d been with my family 8 years ago, and it was crazyyy getting De ja Vu and recognizing places from a trip that seems a lifetime ago! We stayed at a little resort called Point Pleasant… it was fine, nice enough with spacious rooms and gorgeous balcony views, but best of all was next door to where Laura and Co. were staying. They were at Margaritaville, which sadly sold out so quickly we couldn’t book there as well in time. Our place was nice, but theirs was really nice, so we just headed over there and hung out with them most of the time! We had dinner at the Margaritaville restaurant, and I have to say, the food and margaritas were AWESOME. The whole Jimmy Buffet obsession was a bit much, but the live band singing his songs and others was cool, plus the whole resort was really clean and posh.
The morning before we left, we headed to Charlotte Amalie to shop, as that’s where you can find crazy discounts on jewelry, decor and other neat finds, which is exactly what we did! I share quite a bit of all of what I’ve written about as well as what we bought in my vlog of the trip on my YouTube, so definitely check that out if you want to see what we bought! But I basically found some gorgeous handmade Moroccan dishes, jewelry, and coffee that I’m still adoring and using every day!
Going to wrap up here, since I’ve shared my main thoughts on everything, but definitely feel free to message me or check out my vlog if you want to see or learn more!!
Hope you enjoyed!