72 Hours in Bermuda

A pink church in Saint Georges Island Bermuda. Jess Kirby's Bermuda travel diary

The first thing I said when we landed in Bermuda was, “how have I not been here before?” Working with JetBlue we were able to book the trip through their JetBlue Vacations. After looking through their different Bermuda packages we decided on the Princess Hamilton. After a very short (under 2 hour) flight from Boston, we landed on the beautiful island. When we landed we were greeted by a JetBlue employee who helped guide us through customs and grab a taxi to our hotel. One of my favorite things about visiting Bermuda was that you go through customs there. This made the return so much easier, when we landed in Boston we got off the plane and hopped right in our car to head home, no long lines waiting to go through customs (we sat in line for over 2 hours returning from our trip to Mexico a few months ago). Not only is Bermuda absolutely beautiful and easy to get to, but everyone is so nice. Not hard to see why when you get there, beautiful weather, stunning scenery and the most gorgeous turquoise ocean you’ve ever seen. The perfect place for a long weekend getaway. If you didn’t see it yet, make sure you watch our Bermuda vlog too.

Harbor Views from the Fairmont Princess Hamilton, Jess Ann Kirby's Bermuda travel diary.

Where to Stay

The only hard part about planning our trip to Bermuda was choosing which gorgeous property to stay. There were so many great options through JetBlue vacations, we ultimately settled on the Hamilton Princess. We chose the hotel for it’s central location, since we only had a few days, we wanted to be able to cover as much ground as possible. I’m so glad we chose the that location. We were greeted with yummy snacks and stunning harbor views in our room and the property was conveniently located for all of our activities. There’s also a scooter rental shop right next door. Luckily they rented two seaters because I was nervous about driving scooters around the winding, narrow roads (and they drive on the other side). If you’re up for it though, it’s really the best way to see the island.

Jess Ann Kirby in Bermuda wearing a Blush Midi Dress by Steele from Anthropologie
Jess Kirby wearing a Tavik Bikini from Anthropologie in Bermuda
Jess Kirby wearing a Coolchange Chloe tunic from Shopbop in Bermuda
A local woman in Saint George Bermuda

What to Pack

Everyone kept saying how hot it was going to be in Bermuda but it was actually the same if not a little cooler than Newport. The weather was perfect. It was hot during the day but not unbearable. We were out scootering and exploring all day. Night temps were perfect too. I basically wore a bathing, cut-offs and tees the entire time. At night I threw on this sweatshirt and for dinner I wore dresses. Definitely make sure you pack sunscreen and hats. It’s not unbearably hot but the sun is strong and you’ll get burned quickly if you don’t protect your skin.

Frame Denim Old School sweatshirt and levis cutoffs on Jess Kirby
Jess Ann Kirby goes Cliff Jumping at Admiralty Park in Bermuda

What to Do

We broke up our days by location. While Bermuda is not that big, it takes a little longer than you think to get places so plan accordingly. Our first day we went to the Hamilton Princess Beach Club. The hotel has their own private beach club which is really nice because they have tons of lounge chairs and umbrellas, and you order food and drinks. After the beach we really wanted to go cliff jumping so we found a place close to the hotel, Admiralty House Park, which is the most popular spot and easily accessible. On our second day we hopped onto the scooter and headed to Saint George’s Island early in the morning. It was a Sunday so none of the shops were open but we had the place to ourselves and spent a few hours walking around exploring the pretty cobblestone streets and admiring the architecture. We walked up to the unfinished church and then down along the harbor. If we had more time our third day would have been a trip to the Naval Dockyard, I definitely recommend doing that if you visit. We’ll just have to go back!

Exploring Downtown Saint George in Bermuda on JessAnnKirby.com
Jess Kirby wears AG Jean Shorts and a White Tee in Saint George Bermuda
Jess Kirby wearing a lace top and white cutoffs in Bermuda
A beautiful old church on Saint Georges Island in Bermuda
Jess Kirby wears a Tiare Hawaii Maxi Dress in Bermuda at Gibbs Lighthouse

Where to Eat

There’s no shortage of good food in Bermuda and we had some great meals. We were very pleasantly surprised by the food at our hotel too, and had several really good meals at their on-site restaurants. Here’s a few of our favorites:
Marcus’ – Nice for ore upscale dining, good dinner spot
1609 – We actually ate here twice, once for lunch and once for dinner. Great cocktail menu, live music and views of the harbor.
The Dining Room at Gibbs Hill Lighthouse – You can’t beat the views at this spot. Definitely ask to sit outside.
Swizzle Inn – Probably one of the most famous pubs in Bermuda. Nothing fancy but if you’re craving bar food and drinks this is your spot.
Rock Island Coffee Shop – If you’re a coffee lover, this is a must when you’re in Bermuda. Right in downtown Hamilton.
The Hog Penny – We didn’t make it here but it came very highly recommended.

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  1. Natali wrote:

    Beautiful photos, great beach time outfits and useful info in this post. I hope to someday visit Bermuda!


    7.26.17 | Reply
  2. Jenn Lake wrote:

    Looks like the most wonderful destination! Love how you captured it!

    7.26.17 | Reply
  3. Rach wrote:

    Omg it looks amazing there! Never been, but I definitely would love to go there!


    7.26.17 | Reply
  4. Kate wrote:

    Looks like you had a great time! Glad you made it to Admiralty House Park for some cliff jumping. Also, my sailboat made it into one of your photos 🙂 She’s moored right next to the HP!

    Hope you guys can come back again and see more of our beautiful island!

    7.27.17 | Reply
    • Jessica wrote:

      OMG so cool! Thanks for the rec. Such a beautiful place I definitely want to make a trip back. xx

      7.31.17 | Reply
  5. Sharon wrote:

    Wow! Bermuda looks beautiful and your photos are incredible. I especially love the shot of the pink boat and the all white outfit with the eyelet top that you wore. Thanks for the tips and sharing your amazing trip!

    7.27.17 | Reply
    • Jessica wrote:

      Oh thank you so much Sharon, so sweet. That pink boat was so cool!

      7.31.17 | Reply
  6. Mary wrote:

    This looks amazing! I cannot believe Bermuda is only a 2 hour flight from Boston! That is so surprising. Also, you could totally be an Anthro model! Everything you wore is awesome, but my faves are the blush dress, JOA ruffle shirt and the bathing suit. Totally fabulous!

    7.27.17 | Reply
    • Jessica wrote:

      I know crazy right?! It’s so close. You’re so sweet, thank you so much. xx

      7.31.17 | Reply
  7. You are so cute! What a fun trip!

    7.27.17 | Reply
    • Jessica wrote:

      Thanks girl! We had a blast. Such a beautiful place. xx

      7.31.17 | Reply
  8. Some really lovely pics of Bermuda, the island is perfect for fasion shoots as the colours and pastel shades naturally fit well with pics. Great work, love your site.

    1.10.19 | Reply

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