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We got married last February, but decided to defer our honeymoon for a year due to time & budget constraints (yo, weddings are EXPENSIVE!). To be honest, I think a lot of people just assumed we’d never actually go anywhere and that we were just talking about going SOMEDAY. Last fall we decided we needed to narrow down a location to visit so we could go in February, and settled on St. John. My requirements were somewhere warm with a nice beach or two, and JB’s were somewhere warm with stuff to do other than sit on a beach (spoiler alert: he sat on a lot of beaches ????). We’d never been to the US Virgin Islands but had heard so many good things about them that we were absolutely pumped.

St. John is a small island (about 13 miles long & 6 miles wide), but there are a bunch of different places to stay – most people stay in the Cruz Bay area which is where the ferry dock is & most of the bars/restaurants/shops. We opted to stay on the other side of the island in Coral Bay and couldn’t have been happier. It’s a much quieter area with stunning views and tons of animals. It was only about 20 minutes back to Cruz Bay and 10 to the beaches, so it was absolutely perfect. We rented a little one bedroom house off of VRBO on top of a hillside with views FOR DAYS. It was so nice to have a kitchen to cook breakfast in every morning & we loved not having to interact with other people like we would at a resort. One of my favorite parts other than the view was the outdoor shower at the house (except for the night that there was a frog in the shower and I fully panicked ????????‍♀️). We did cook one dinner at the house which helped us save some money and we ate PB&J sandwiches almost every day for lunch – I don’t even want to look at a PB&J for at least another month ????.

The weather was perfect when we were there – it averaged around 80 during the day and mid 70’s at night. We only ever ran the AC in the house when we slept, and otherwise left the windows and doors open with the fans on. A few mornings a rainstorm blew through and cooled it off and a few nights the same thing happened. The last full day we were there, a storm blew into Puerto Rico so it was HUMID on St. John and rained on & off all day. The sunsets were absolute perfection & I pretty much dream about going back every single day!


We flew from Boston to St. Thomas with a stop in Newark, although there are direct flights (I’d do that next time). Once you arrive at St. Thomas airport, you take a taxi to Red Hook where you catch a ferry to St. John. You CANNOT fly directly to St. John.

We rented a Jeep for the time that we were there and it was the BEST decision that we made. You do drive on the opposite side of the road even though the cars are all American cars meaning that the driver sits on the left side – it feels weird at first but we got used to it very quickly. Hot tip: don’t drive Route 10. It’s the worst – Route 20 is not only far prettier but better maintained since it’s part of the USVI National Park.

DAY 1: 

We came to St. John with a list of things we wanted to do and beaches we wanted to visit, but apart from that we had no daily plan (if you know me, you know how completely painful this was BECAUSE I REQUIRE A SCHEDULE!). We decided that our first official day would consist of driving around the island and getting our bearings since we got in much later in the afternoon the day before and were completely exhausted. We started off in Coral Bay and first drove to the Annaberg Ruins.

The Annaberg Sugar Plantation was one of 25 active sugar plantations on the island in the 18th century. It also produced molasses & rum, and is the only set of ruins on the island with a standing windmill. The ruins are scattered throughout the hills and include the windmill, factory, slave quarters & the great house. We made a last minute decision to stop here & were thrilled that we did since we were able to chat with a volunteer for the National Park. He told us how to hike to the great house & recommended some great hikes as well. When you look off to the right from the overlook at the plantation you can see Tortola, which is part of the British Virgin Islands.

We hit up a few beaches on our way to Cruz Bay to figure out what was closest and seemed less packed. Jumbie Bay was a beautiful beach that we stopped at, with a TINY parking lot and small protected beach – it was absolutely beautiful!

Since it was midday/afternoon when we passed through a lot of the beaches, we didn’t stop but headed to Cruz Bay to walk around the shops and grab an Irie Pop. Seriously the BEST popsicle I’ve ever eaten! They’re all freshly made every morning and SO good!! It’s also the cutest little shop by Mongoose Junction – for sure worth a stop!!

We felt confident after we figured out where everything was & what the parking situations were like that we could build a schedule for the rest of the week which was SO helpful for the rest of our time there.

DAY 2: 

We found out from the national park volunteer that there was a trail that accesses a beach called Salomon Beach which is right next to Honeymoon Beach. He said that we could park our car at the St. John visitors center in Cruz Bay and start at the trailhead access at the parking lot. It was a pretty easy hike that dropped us right at the beach. Salomon was SO quiet and calm & fully worth the hike in. You can also access Honeymoon Beach from the trail, so we walked down after lunch to see what it was like, but it was absolutely packed so we went back to Salomon and stayed for the rest of the afternoon ????. Honeymoon Beach is also accessible by the road – you enter through the old Caneel Bay Resort entrance and take a shuttle to the beach.

Caneel Bay Resort was hit really hard by the 2017 hurricanes and hasn’t been renovated because it’s tied up in litigation. You can pull off on Rt 20 at an overlook and see the whole thing spread out below you as the jungle is slowly taking it back. It’s beautiful and so sad.

The hike back to town is a little harder in the late afternoon because its SO much hotter, but we got a great view of Cruz Bay. We grabbed (our FAVORITE OF ALL TIME) sandwiches from a deli in town and took them back to our house for dinner – after our first full day being in the sun and water we were absolutely smoked ????.

Also YES, I did take approximately 7000 photos of this exact view because the light was so INCREDIBLE – especially on this particular night.


Also, directly across the harbor from us the the “downtown” of Coral Bay where there was a grocery store & a few restaurants.

DAY 3: 

We decided to hike to the ruins of the great house at the Annaberg Plantation that had been pointed out to us by the volunteer a few days prior. In order to get there, you have to hike into Waterlemon Bay and catch the trailhead there. It’s pretty rocky at the beach but was a pretty easy trail up.

There is a second set of ruins that you come up on first, but you have to keep going to reach the great house. It is 1000% worth the hike JUST for the view. It was my favorite view of the entire trip.

We had planned on hiking through to Brown Bay but as we were at the top, we realized there was a rainstorm heading quickly towards us just off of Tortola, so we chose to go back down to the beach and get completely soaked on the way ????????‍♀️. I would have stayed up there for so much longer if there was any place for us to get out of the rain just to stare at the ocean. We snorkeled a little at the beach but since it was so rocky it was a little annoying to get in and out (and I turned around in the water and was surprised by a lemon shark a few feet away so I was all set ????). We decided to drive over to Francis Bay which was about 2 minutes from Annaberg Plantation & so beautiful. It was calm, not too busy and a great place to chill out.

DAY 4:

I told you I took tons of photos of this view ????. Day 4 was the day I was most excited about – snorkeling at Maho Bay. They have sea turtles at Maho that you can snorkel with (if you’re early enough before anyone gets there). Not only was it AMAZING snorkeling, but the beach was beautiful. We got there around 9 and over the next half hour it filled up pretty quickly. I’d definitely get there a bit earlier next time!

That’s a turtle that popped up for air – it was the BIGGEST thing I’ve ever seen. The shell was around a 3 foot diameter and was so large that it had 2 lemon sharks attached to it. They’re absolutely beautiful and calm creatures and we were so excited to be able to have the opportunity to swim with them.

Maho Bay also has a food truck as well as a drink truck, paddle board rentals & bathrooms – it was definitely the nicest beach we went to in terms of amenities, but it was PACKED by the afternoon.

DAY 5:

We started off with great attitudes about the way that the day was going to go (famous last words ????). We planned on hiking Ram’s Head, which is essentially one of the easternmost points of the island. We knew that it was going to be a harder hike than it looked because it is super hot with no tree coverage and parts are fairly steep. We used a map that we got at the visitors center (which we HIGHLY recommend if you’re going to hike) and it had directions to each trailhead on the island as well as the varying degrees of difficulty for each hike. We knew that we had to start at Salt Pond Bay and find the trailhead (issue #1). Once we found the trailhead about 30 minutes after we should have ????????‍♀️, we ended up at what the map called a blue cobbled beach which was essentially a beach made up of blue tinted cobble stones.

It was really pretty and at this point you could tell that the vegetation was changing pretty significantly into more cacti and rocks rather than the lushness of the rest of the island. There’s no exact sign as to where the switchbacks up the trail start, but you can see part of it as you hike to the beach itself. Let’s just say…things went downhill from here. We started up what *appeared* to be the entrance to the trail which seemed rather steep and not entirely marked. I mentioned a few times that this couldn’t possibly be the trail because it was so densely packed and we should be on an exposed trail…and then it got steeper. And you had to find footholds and handholds, and have I mentioned that I am absolutely terrified of heights? About halfway up JB went ahead to see how much farther it was to the top while I literally clung to a tree on the side of the mountain and refused to look down because I was convinced I was going to fall. I’m sure that you can figure it out – we weren’t on the trail and in fact were climbing up a drainage gut cut through the mountain ????. The climb down was even worse and by the time we were halfway down I was contemplating divorce. It was a great hike.

Once we found the ACTUAL trailhead, it was a beautiful hike through the cacti. The view at the top is worth the hike but it was pretty steep at parts and VERY hot. After we were told that the best time to hike it is right around sunrise or sunset. I would definitely recommend it to anyone because I think its such a cool difference between the rest of the island and this little extension.

Salt Pond Bay has great snorkeling but we were pretty over it by the time we made it down so we ended up leaving early and heading to a late lunch at Miss Lucy’s which I HIGHLY recommend. It’s about 5 feet from the water and they have 1 waitress but it was probably one of the best meals we had – conch fritters and cornflake crusted grouper sandwiches. I still think about that meal ????.

We also hit up Colombo’s on the way home – it’s a roadside smoothie shop at the crossroads of Routes 10 & 20 and it was AMAZING. She adds a free shot of rum to every smoothie and they’re all freshly made. We were SO happy that we stopped there!!

DAY 6:

We decided that for our anniversary & JB’s birthday, we’d hit up Trunk Bay, which is one of the top 10 most beautiful beaches worldwide. I can see why – it had the clearest water of any beach we went to, and even though it was pretty busy (it was also a Saturday), it was stunning.

Trunk Bay also has an underwater snorkel trail with labels affixed to rocks with facts about the coral and sea life. It was so cool and we saw tons of fish & some really beautiful coral. 10/10 would recommend! It’s a little touristy because a lot of the cruise ship passengers head to Trunk Bay when they dock in St. Thomas, but it’s definitely worth it just to swim in that gorgeous water.

DAY 7:

We hit up Cinnamon Bay Beach on day 7 – first we started across the street at the Cinnamon Bay Plantation Ruins. It was an easy loop trail that walked through the ruins of the buildings which included the plantation house, servants quarters and factory buildings, as well as two cemeteries. It did have a few plaques scattered throughout that talked about the local trees & nature.

Cinnamon Bay Beach is the only beach on the island that has waves and we sorely underestimated a few of them ????. After a few hours, we decided to pack it in and head home. We randomly started talking to a woman sitting next to us who apparently lives about an hour from us (????????‍♀️) but she told us that she’d been snorkeling at a place out on the East End called Haulover Bay and it was perfect.

We were planning on heading out to drive to the East End anyways so we decided to stop at Haulover and it was the BEST snorkeling of the entire trip! We parked off the road and then cut through on a path that dumped us on the other side of the island (it’s one of the narrowest parts so its a 2 or 3 minute walk at most). The water was SO clear and there was a TON of sea life.

We chatted with a couple who walked through to the beach a few minutes after we got out and they told us that Haulover is rarely calm and usually incredibly wavy – so we got SUPER lucky on that day.

DAY 8:

Our last day ended up being a bit of a washout – like I mentioned before, a storm blew in overnight and settled around Puerto Rico (which is only a few hours away), and it caused a pretty big storm surge at the island. We planned to hike Peace Hill to Dennis Bay Beach and head into town later – but it didn’t exactly work out. Peace Hill was absolutely beautiful and we noticed a bunch of pretty big waves breaking farther out but didn’t think anything of it…until we hiked down to Dennis Bay. The waves were huge and we decided that we’d try another beach – all the while, clouds were building and moving around pretty quickly.

We tried to go to Jumbie Beach after that but the water was SO high that there was almost beach left…so we called it a day and went home ????. Seriously. We decided that we’d just switch our day around a little bit and go into town earlier than expected, and it was totally fine!! We were able to walk around to the shops and grab things that we wanted to get anyways as well as return our snorkeling equipment, so it all worked out.

This is the most perfect view of Coral Harbor that I could imagine – we stayed on the left hand side on the other side of that mountain. I was CONVINCED I was going to catch a sunset on a north shore beach so we headed to Maho with dinner…and it was totally cloudy ????. We stayed as long as we could because BUGS, and saw a bunch of turtles popping up and a lemon shark that kept swimming in front of us in the shallows. It was a beautiful way to say goodbye to St. John.

DAY 9:

For some reason when I booked everything, I decided that we should go from St. John to St. Thomas the day before our flight…I honestly have no idea why I thought that we needed to ????????‍♀️. Lesson learned.

We stayed in Frenchtown which is on the tip of Charlotte Amalie (where all the cruise ships dock), so we were slightly removed from the crowds of tourists, but it was no St. John. We wandered around a little but it was kind of a let down because it was SO touristy & kitschy. We won’t do that again ????. We did go to Fort Christian and we were able to walk around which was pretty cool. There’s so much history in the Virgin Islands (it’s pretty fascinating and we learned A LOT while we were on St. John). For instance, we had no idea that the fort was used as a jail until the mid 1970’s!

DAY 10:

We had been warned about the customs line at the airport, so when our checkout time came at the hotel, we just decided to go to the airport in case the line was insane. Our VRBO let us know that the day before the line was 3 hours (like WHAT). Luckily, it was only about 2 hours from arriving at the airport to getting into the terminal, but be prepared to wait for awhile. It’s a bit of a cluster.


Skinny Legs (Coral Bay): Our house was less than a mile from here and we went twice. It’s a small restaurant with outside seating (AND PEOPLE BRING THEIR DOGS ????), and the burgers are fantastic. It was definitely the cheapest place that we ate at and we both absolutely LOVED it. They have live music a few times a week and it’s worth checking out.

Rhumb Lines (Coral Bay): There’s also a Rhumb Lines in Cruz Bay, which means you can’t NOT check it out. It’s a beautiful place and we had the BEST Pad Thai of our lives there. It was pricey but we both had enough leftovers that we ate it for dinner again the next night. They also have a resident cat that hangs out as well as some chickens just roaming around.

Sam & Jack’s Deli (Cruz Bay): We went here twice as well and it was SO GOOD. I will never eat another sandwich without comparing it Sam & Jacks. They’re located in the marketplace and have a huge selection of massive sandwiches (and they have GF bread which was a huge win!).

The Longboard (Cruz Bay): We went here for our anniversary (honestly we went for happy hour and had plans to go to another restaurant) – their happy hour alone is worth going for. I love a craft cocktail and they don’t disappoint! Their menu was INCREDIBLE (I didn’t even plan to eat dinner there because I figured it was too bougie for JB ????) – we had homemade guacamole, fresh ceviche and the most amazing tacos ever. GO HERE.

Irie Pops (Cruz Bay): I mentioned them already but they’re worth another mention!

St. John Taproom (Cruz Bay): We stopped here for a mid afternoon snack and beer – JB had a shandy that was AMAZING. You can buy their beer all over the island.

High Tide (Cruz Bay): We ate brunch here the day that we caught the ferry back to St. Thomas. It was so yummy and their breakfast cocktails aren’t too expensive. #vacation

Colombo’s (Coral Bay): Rum in every smoothie. Enough said.

Miss Lucy’s (Coral Bay): It might be a little bit of a wait but it’s going to be the best meal that you eat! I’ve heard that their Sunday brunch is incredible as well.


Groceries are more costly here because it’s an island, so be prepared to pay a little bit more. Starfish Market in Cruz Bay is much pricier than Dolphin Market (there’s a Dolphin Market in Cruz Bay & Coral Bay), but they do have a better gluten free selection. Wine is pretty pricey but beer isn’t too bad. I brought all of my own GF bread and pasta (a loaf of GF bread was $14 ????) and we packed a lot of protein bars and nuts from home which helped us save some money. Restaurants are expensive here so we ate breakfast at the house and packed PB&J sandwiches for lunches.

There are gas stations ONLY in Cruz Bay, so beware of your gas consumption. It’s pretty hilly and that can eat up the gas pretty quickly. I also mentioned above that Route 20 is a far better road to take, and all of the North Shore beaches are off the road. It’s also part of the National Park which means the park maintains the roads.

Speaking of the roads, there are wild donkeys around the island (they’re the cutest!) and in Coral Bay there was a huge herd of sheep (so. many. babies.).

Parts of the island are still decimated/under construction from the hurricanes but for the most part it has bounced back tremendously.

You can rent snorkel gear at The Beach Bum – it’s right by the ferry and they’ll fit the masks to you. Worth every penny!!

I could honestly never recommend ENOUGH for people to travel here. It’s truly one of the most beautiful places I’ve ever been in my entire life.

I also can’t recommend enough for people to take their honeymoon a year after their wedding. It was SO stress free and we were so relaxed – after our wedding we were both exhausted and JB got super sick. It was so nice to just be able to get away with the two of us and not have to worry about a single thing.

We cannot WAIT to go back – we already have a list of things we want to do ????!!

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HI, I'M caitlin

New England based wedding and lifestyle photographer