Location: Bermuda
Sweater: Aritzia | Gingham Shorts: Crewcuts – Frankie short | Bandana: Levi’s (I also want this one and this one) | Sandals: Havaianas | Gingham Top: Whistles (I also like this gingham dress)  | White Shorts: Crewcuts (J.Crew version here) | Coral Dress: Zara (similar dress I want here and here) | Necklace: Amazon

My first boat experience was not a great one. Stephen’s family lived on a lake just outside of Portland, where we went to college, and on the first day of summer he took me to pick up his boat to drive it back to their house. Since he drives like a bit of an a-hole I went flying to the back of the boat and narrowly escaped serious head trauma, or worse, a broken tooth (this is one of my biggest fears). That summer, my friends and I basically lived on the lake, we went tandem inner tubing every weekend where I would get kicked in the face or catapulted into a face flop Every. Single. Time. Eventually I manned up and just admitted, “I hate inner tubing, I just want to lay out, tan, and talk.” No one protested this idea because, turns out, everyone felt like they were going to die inner tubing…you see how it only takes one person to speak up and make a change.
What’s the point of this long nostalgic rant you ask? On a semi-recent trip to San Francisco, apparently one of the top places to sail in the world, we decided to take a sunset sail under the Golden Gate Bridge; which brought my boat PTSD on hard. Turns out, sailing is awesome and boating is only horrible when Stephen is driving (or a 20-something college dude). I grew up in the Bay Area and have seen the Golden Gate Bridge so many times it has lost its appeal, but sailing underneath it was one of the coolest things I’ve done in San Francisco to date. Bermuda is also a great sailing destination, home to the 2017 America’s Cup and all, so we wanted to do a sunset sail around Castle Harbour on the east end of the island. We met the captain of Ocean Spirit at Somers Wharf in St. George’s, which is a tiny town that resembles an old English medieval village. The view from the boat was unparalleled, passing by the candy colored houses on the shore and St. Catherine’s Fort. The first mate was a singer, believe it or not, who serenaded us throughout the sail; he claims to have written the beat to ‘Tik Tok’ which was “stolen” by Ke$ha, but I don’t want to get sued so I’m staying neutral on this one. The first mate also happened to be a videographer so he took pictures of us in between songs, sort of lucked out on this one.  The boat captain was obsessed with spotting the “green flash” at sunset. You need optimal conditions and an unobstructed horizon (like over the ocean) to spot one. He claimed he saw this “rare phenomenon” occur, but I didn’t see it. I did however see a breathtaking sunset that lasted the majority of our sail. It was Lion King, Simba’s birth quality, with deep oranges and reds which muted to a gorgeous pastel sky at blue hour. I decided to just go fully themed out with my outfit, donning gingham linen shorts (they are from Crewcuts but J.Crew makes an adult version) and this Aritzia top that I’m obsessed with. I also added the bandana last minute which I actually purchased to wear under my helmet (I’m a germaphobe) while scootering, but after seeing the windy narrow roads on the island we decided to cab it and save our skin.   It was virtually impossible to get a cab back from St. George’s after the sail. The town had all but shutdown, except for a pub, and none of the dispatched drivers wanted to drive all the way back to Southampton. We waited for at least an hour before a cab drove through town to pick up two pub goers; luckily they were willing to share and the driver was willing to make the trip. The next day was spent sightseeing, which just so happened to be the hottest day of our trip. We hit up all of the “must see” spots including Crystal Caves, which was actually pretty beautiful, albeit we weren’t aware that you can only go through the cave with a guide in a large group. Apparently, two boys discovered the caves when their cricket ball fell into a hole that was the cave’s opening. Why two boys would lower themselves into a hole in the ground by candlelight is beyond me, but since they did, we can all enjoy the crystal caves for years to come. One place I really wanted to stop by but it was closed for repairs and restructuring, is the Unfinished Church. A gothic church that as the name suggests was never finished but looks remarkably beautiful in its incomplete state.
Our last day on the island we rented a boat from Rosewood Tucker’s Point, which is a gorgeous resort on the boring side of the island. There was far less to see in this area by boat and it was high tide, so the water was too high to pass under the bridge leading into St. George’s. The guys who set us up with our gear and introduced us to our boat seemed baked (it’s hard to tell with teenagers though) and they giggled through a vague description of the restricted boating areas. There is another shipwreck out on this side of the island so I asked where we could find it, to which we got some pointing and laughing. We thought we could see it poking out of the rough water and almost anchored our boat in the open ocean. Luckily, Stephen got a bad vibe so we went back to a shallower protected inlet by a sinking dock to try snorkeling there. Turns out the “rusty dock” we thought we were posted up next to was the Nonsuch shipwreck we had been trying to find. Here’s where things got interesting. It was cold, the water was rough, and since it was overcast there wasn’t a ton of visibility in the water. I swam ahead to check out the wreck when I saw a horrifying site. I swear to you it was a giant shark sized fish laying on the bottom of the ocean, I’m still not sure if it was dead or laying and waiting to attack. I must have popped up pretty quickly because I didn’t even finish saying anything before Stephen started frantically swimming back to the boat in sheer terror and then hopped back in leaving me behind. With the choppy waters I couldn’t get back in the boat and his reaction had thoroughly freaked me out, basically I felt like a sitting duck. I was also a little concerned that my husband would ditch me at the first sign of a shark attack (apparently my reaction said SHARK to him). He claims it was fight-or-flight taking over and since I was the better swimmer he needed a head start…
We sat in the boat till we calmed down and realized there were these large Betta looking fish that were jumping around the boat, so we fed them our complimentary cookies and watched as they jumped in the air to catch them. Eventually a park ranger came out to get in his nearby boat so I told him about my dead fish siting. He said there “shouldn’t” be any sharks “today” but we should watch out for barracuda which might take a test bite especially if we had on any shiny jewelry (of course we did). So moral of the story,
1. there are barracudas in the water on the east end
2. make sure you get a proper explanation before venturing out in any boats
3. there may or may not be a shark or large predator guarding the Nonsuch shipwreck

Stephen was not happy with my recollection of events so I am going to allow him to rebuttal below in pink in an attempt to further emasculate him:
In reality, my wife jumped half way out of the water screaming GOOOO, BACK TO THE BOAT!!! I swam right alongside her back to the boat and jumped over the side and immediately turned around to pull her in, to which she replied, “no, I don’t want to bruise my legs.” She then swam to the back of the boat and I helped her up the ladder. Apparently not getting bruised is more important than avoiding a shark attack.

We spent the rest of the day relaxing after our “near death” experience, we got burgers and berry coconut coolers (at least I did) and chilled at the resort before heading down to walk along Warwick Long Bay and Horseshoe Bay before dinner. I got a major 1990s Beverly Hills Beach Club vibe (à la the original 90210) from the clay tennis courts and bungalows which echoed the coral sand at both of the gorgeous beaches. Overall sentiments about Bermuda:
The island definitely runs on “island time” so be flexible, we had a number of our reservations and rentals rescheduled for various reasons, so don’t book anything too close together and have a backup plan. Transportation is the biggest issue on the island, rental cars are not allowed by law and there are no sidewalks. Cabs are pricey but your only other options are scooters (which is not recommended for beginners – a number of people at the airport were covered in head-to-toe bandages from road rash) or the intermittent buses. A few restaurant recommendations we continuously received from various cab drivers were Mickey’s, The Pickled Onion, and Waterlot Inn. The majority of food in Bermuda is very “Pubby” so if you’re a foodie this isn’t going to be your spot, but after a long day in the sun I was more than happy with a burger (actually I got the chicken avocado burger but this is just semantics), fries, and a float from Wickets. The Fairmont was a huge hotel, which had a great golf course (if you’re into that) complete with pink golf carts, newly renovated rooms, and some good restaurants. The hotel also has a free shuttle around the sprawling grounds and a ferry to their sister property, the Fairmont Princess which hosts an authentic High Tea. Sailing is something you don’t want to miss on the island and if you’re going to rent a motor boat, I recommend the west side of the island. I’d love to hear your recommendations of things to do and see on the island and if anyone has any insights on the creature I spotted at the Nonsuch shipwreck let me know.

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