I’m so excited to share the highlights from my joint bachelor and bachelorette party with Jacob in Grand Cayman! When we started planning, we knew we wanted to celebrate together instead of separately—it just felt right for us. We love bringing our favorite people together, and this was the perfect opportunity to do that ahead of the wedding.
As for the destination, the Cayman Islands was the perfect backdrop for our celebrations. Between the breathtaking beaches, incredible food scene, local culture, and endless options for adventure, it had everything we needed for the ultimate getaway. Plus, we wanted a location where we could relax, explore, and create unforgettable memories with our friends and family. Grand Cayman - and the warmth, hospitality, and kindness of the people we met at every turn - exceeded all of our expectations! Let me tell you all about it, and share some tips for planning your own pre-wedding party in paradise.
Private Lodging at Cayman Islands Villas
For an exclusive experience, consider staying at one of the many Cayman Islands luxury villas. We stayed at Black Urchin, which features spacious rooms, an infinity pool, outdoor lounges, and more—the ideal setting for a large group. Black Urchin has an amazing concierge team who went above and beyond to make us feel right at home. They offer add-ons like beachside yoga, spa treatments, and snorkeling, making it the ultimate island retreat! Jacob and I had the most incredible time with both of our parties! I thought it was so unique that we were able to host a joint bachelor and bachelorette trip for all of us to celebrate together.
Indulge In Cayman Islands Restaurants
Great food and drinks are essential for any bachelorette party (did you know the Cayman Islands is known as the Culinary Capital of the Caribbean?!). We had the best food in Grand Cayman. Our party started with a private cocktail hour + welcome party at Black Urchin, featuring a rum tasting hosted by Cayman Spirits Co. A mixologist can even craft custom cocktails for your group (they made a custom cocktail called “Mei Mei Tai” – how special?!). This was truly the best way to start our weekend!
On our first night, we had a private catered dinner by Chef Jessica Moore of Fresca, known for her contemporary Caymanian cuisine. Chef Jess created a multi-course menu featuring fresh seafood, local produce, and island spices—from conch ceviche to traditional main courses. I’m still drooling over this meal!
Snorkel in Stingray City and Starfish Point
As an excursion, we went snorkeling in the Cayman Islands, and enjoyed a day on the water with a private boat charter by Cayman Luxury Charters. There are so many great Grand Cayman snorkel sites; we spent the day exploring Stingray City and Starfish Point. The water was beautiful, and I couldn’t believe the amount of stingrays we saw! Don’t forget to kiss one for seven years of good luck! Our whole group was able to relax on the boat and enjoy the day. We also went to Starfish Point, filled with beautiful starfish in clear, shallow waters. I’ll never forget being in paradise with my besties; singing, laughing, swimming - this day was a dream come true!
Explore Camana Bay
Camana Bay is such a chic spot – it combines Cayman Islands shopping, dining, and entertainment. We started our evening with a private experience at Island Jewellers, where we sipped champagne and browsed fine jewelry and watches. All of the boys shopped for their ladies at home, while Jacob and I knew just what to buy in Grand Cayman - our wedding jewelry!
We enjoyed a waterfront dinner on a private island (yes, it was just our group!) hosted by Agua, known for its seafood-centric menu blending Italian, Peruvian, and Caribbean flavors (the ceviche and roasted snapper were a few of my favs!). The view, the dinner set up, the company – 1000/10.
Experience the Cayman Islands’ Vibrant Nightlife
No bachelorette party is complete without a spontaneous night out! We went to the Full Moon Party at Sandbar for late night music and dancing. It’s an open-air beach venue with live music, beach bonfires, fire dancers, and more. It was a spur-of-the-moment decision to go out one night, and it was the cherry on top of an amazing day!
The Cayman Islands has something for everyone, whether you're an adventurer, a beach lover, a foodie, or a culture enthusiast – it truly stole our hearts! Having a joint bachelor and bachelorette party in the Cayman Islands was by far the best decision we have ever made – and we cannot wait to go back!
