# Bermuda in May Is Built for a Father-Son Trip Worth Remembering *By James Hills, menwhoblog.com — Updated March 2026* Written by: [James Hills](https://menwhoblog.com/james-hills.html) Last Updated: 24 March 2026 New!Hits: 20Reading time: 05:15 Bermuda in May sits in that window where the weather is warm, the water is swimmable, and the island hasn't hit peak-season pricing yet. If you've been thinking about a trip with your dad - or taking your son somewhere that has more going on than a pool and a buffet - the island runs a stacked calendar in May that gives you built-in activities without having to plan every hour yourself. My parents went to Bermuda when I was in high school and came back talking about it for months. I've always thought about how fun it would be to go back with my dad and do a proper father-son trip there. May 2026 might be the year - SailGP racing, an exhibition celebrating the Bermudian behind Muppet Babies and Fraggle Rock, Bermuda Day celebrations, and [Harbour Nights](https://www.gotobermuda.com) every Wednesday in Hamilton. That's enough structure for a long weekend or a full week depending on how much beach time you want mixed in. ## SailGP Returns to Bermuda May 5-9 The [Apex Group Bermuda Sail Grand Prix](https://sailgp.com/races/bermuda/) brings wing-sailed foiling catamarans back to the island for two days of racing. These are the fastest sailboats in the world - the F50s hit speeds above 60 mph on hydrofoils and the racing happens close enough to shore that you can watch from land without binoculars. If your dad is a sailing guy, this is the trip hook. If he's not, the spectacle alone is worth it. The boats are loud, fast, and genuinely dramatic to watch. If you're planning a [guys trip](https://menwhoblog.com/blog/sports-themed-guys-getaway-in-phoenix-ideas-for-a-fun-guys-trip.html) with your dad and want something neither of you have done before, watching boats fly above the water at highway speed is not something you forget. ## The Michael Frith Exhibition: Muppet Babies, Fraggle Rock, and a Bermuda Childhood This is the one that sold me on the trip. Michael K. Frith grew up in Bermuda and built a career designing characters that Gen X grew up watching. He designed Dr. Teeth and Fozzie Bear for the Muppets, served as executive producer on Muppet Babies, co-created Fraggle Rock - which he based on his childhood growing up in Bermuda - and produced the PBS reading series Between the Lions. If you watched Muppet Babies on Saturday mornings, you spent years with this guy's work without knowing his name. Taking your dad to see the creative output behind those characters is a conversation that goes deeper than looking at art on a wall. And if you're bringing your own son, connecting the show he might know to the island you're standing on gives the trip a layer that most family vacations don't have. The exhibition runs throughout May in Hamilton. ## Harbour Nights and Bermuda Day ### Harbour Nights - Every Wednesday in Hamilton From April through early September, Wednesday nights in Hamilton turn into an open-air market and street festival along the harbor. Local artisans, food vendors covering the full range of Bermuda's mixed culinary heritage, and live performances. It runs late enough that you get the sunset over Hamilton Harbour as the backdrop, and it's free to walk through. For a father-son trip, Harbour Nights is the kind of low-key evening that works whether you're 25 and dating or 45 with kids at home. Grab food, walk through the vendor stalls, listen to whatever's playing, and just be somewhere together that isn't a restaurant table. If you're a new dad and your wife gave you the green light for a weekend away with your old man, this is the kind of night that makes the trip feel worth it without spending a fortune. ### Bermuda Day - May 22 Bermuda Day is the island's national celebration, and it reflects the blend of African, British, Caribbean, and Portuguese influences that make up Bermuda's culture. The morning starts with the Bermuda Day Half Marathon - a 13.1-mile course with locals lining the route. The afternoon shifts to the Bermuda Day Parade through Hamilton, which is the biggest cultural event on the island's calendar. Even if you're not running the half marathon, watching it gives you a feel for the island that resort grounds can't provide. The parade is loud, colorful, and genuinely community-driven. ## Between the Events: What to Do With a Free Morning ### Golf at Port Royal Bermuda has more golf courses per square mile than anywhere else in the world. [Port Royal Golf Course](https://bermudagolf.bm/port-royal/) is the public standout - a Robert Trent Jones Sr. design from 1970, refurbished in 2009 for $14.5 million ahead of the PGA Grand Slam of Golf. Green fees for visitors run $135-220 depending on the day, and the 16th hole is a par-3 over a cliff that shows up on every best-holes list for the Atlantic. ### Crystal Cave A subterranean [cave system](https://caves.bm/) with stalactites, crystal-clear underground pools, and a floating pontoon walkway through the main chamber. It was discovered in 1907 by two boys chasing a cricket ball and opened to visitors in 1908 - Mark Twain was the first tourist to descend into it. Takes about an hour and works especially well if you're traveling with a younger son who needs a break from beach days. ### Convex End to End Walk - May 2 If your dad is the active type, the Convex End-to-End is a charity walk across the entire island. The full route is 24.1 miles, but there's a Middle-to-End option at 14 miles. You walk through neighborhoods, along coastal paths, and through parts of Bermuda that most tourists never see. It's a solid shared experience and the kind of thing that becomes the trip story you tell at family dinners for years. ## A Trip Worth Planning Before the Kids Get Too Old Bermuda in May works for a 30-year-old taking his dad somewhere meaningful, and it works for a 40-year-old bringing his teenager somewhere that isn't another theme park. The events give the trip structure. The island's size - 21 miles end to end - means nothing is far and nothing requires a rental car. Scooters and buses cover everything. Flights from most East Coast cities run under three hours. May rates are lower than summer peak, and the water is warm enough to swim by mid-month. Book around [SailGP weekend](https://sailgp.com/races/bermuda/) (May 5-9) or Bermuda Day (May 22) to anchor the trip, and fill the rest with whatever combination of golf, caves, beaches, and Harbour Nights fits your crew. **Hey James Hills wants you to share this!**   --- {"html":""} --- ---   Written by: [James Hills](https://menwhoblog.com/james-hills.html) #MenWhoBlog MemberBlog MasterThought Leader James' passion for exploration and sense of duty to his community extends beyond himself. This means he is dedicated to providing a positive role model for other men and especially younger guys that need support so that they can thrive and be future positive contributors to society. This includes sharing wisdom, ideas, tips, and advice on subjects that all men should be familiar with, including: family travel, men's health, relationships, DIY advice for home and yard, car care, food, drinks, and technology. Additionally, he's a travel advisor and a leading men's travel influencer who has been featured in media ranging from New York Times to the Chicago Tribune, and LA Times. He's also been cited by LA Weekly "Top Travel Bloggers To Watch 2023" and featured by Muck Rack: "Top 10 Outdoor Journalists for 2022". He and his wife Heather live in St Joseph, Michigan - across the lake from Chicago. ### Cruises and Resorts Thinking about a cruise or all-inclusive resort vacation? We can help you plan your dream getaway ... 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