Updated April 28, 2026
May is one of the best months to get on the water, and 2026 is packed with standout boating and travel events across the U.S., Bahamas, and Caribbean. From the global celebration of World Boating Day to Maine’s license-free fishing weekend and immersive culinary festivals in Antigua and Barbuda, this month offers something for every kind of boater and traveler. Whether you’re planning a dock-and-dine outing in Florida, a sportfishing escape in New England, or a luxury island adventure in the Bahamas, these top May 2026 events highlight the season’s best experiences on and off the water.
- Miami Swimwear Brand Carasoles Designs
- World Boating Day 2026
- Maine Free Fishing Weekend 2026
Explore Harbour Island Like a Local
- Antigua & Barbuda Culinary Month 2026
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Southeast Boating Events Across Florida and Beyond
Celebrate World Boating Day 2026 with Events Across Florida and Beyond
World Boating Day 2026 brings a global week of events, offering behind-the-scenes access, boating education, and waterfront celebrations from Florida to international destinations.
Set a course for merriment on World Boating Day—May 23, 2026—with events taking place May 18-24 at shipyards and boating businesses around the world. Founded by The Superyacht Life Foundation, World Boating Day shines a spotlight on the global leisure boating industry, offering exclusive behind-the-scenes access while bringing enthusiasts together to celebrate life on the water. On May 23, MarineMax Fort Myers invites clients and the southwest Florida boating community to drop anchor at Redfish Pass for a day of mingling, music, grilling, and giveaways. Boats will depart MarineMax Fort Myers at around 9:30 a.m. At Pier Sixty-Six Marina in Fort Lauderdale, they’ll teach boating basics, water safety, and focusing on environmental awareness for families and young people. There will also be hands-on activities and interactive demonstrations. For more events, visit worldboatingday.com.
Miami Swimwear Brand Carasoles Designs Boating-Ready Swimsuits for Active Women
Miami sister duo Valery Rocha and Victoria Loguidice of the lifestyle brand Carasoles create swimsuits made for boaters’ active lifestyle. Their swimwear is designed to move with you, from tying lines and diving in to being dock-and-dine-ready. Their muses? Travel and culture. carasoles.com
Boaters aren’t just sunbathing on board; they’re snorkeling, fishing, swimming. How do your swimsuits hold up to active lifestyles?
Victoria: The coverage stays in place, and the fit still feels flattering. We make everything in Colombia with a premium knit fabric that’s super soft, quick-drying and colorfast, so the colors won’t fade after a season of salt and sun. We also double line our pieces with the same fabric, which means they’re not see-through and they hold their shape better. I like to say our suits are for women who actually get in the water.
What pieces move from boat to dock in style?
Victoria: Versatility is really at the heart of our design process. We want women to be able to dive in, sunbathe, and then step off the boat looking effortlessly put together. Our sarongs are a favorite for that reason, as they’re lightweight, elegant, and made to mix and match with any suit in the collection. We recently introduced a pair of flowy beach pants that drape beautifully, offer just the right amount of coverage and instantly make you “dock-ready.”
Tell us about your inspiration for the latest collection.
Valery: When creating our latest Goddess Collection, I was deeply inspired by the vibrance and magical moments I experienced throughout Greece. I’m longing for every future destination we visit to have that same positive impact on our designs. Looking ahead, we’ll likely head somewhere with great wine, food, and people for our next major drop, but we’re also dreaming of a local Miami capsule.
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Northeast: May in Maine
Maine Free Fishing Weekend 2026: Fish Without a License This May
Maine’s Free Fishing Weekend 2026 invites anglers of all levels to fish license-free while exploring the state’s lakes, rivers, and coastal waters.
With its world-class saltwater fishing, more than 32,000 miles of rivers and streams, and 6,000 lakes and ponds, Maine is an anglers’ playground. Top catches include striped bass, Atlantic cod, native brook trout and the leaping landlocked salmon known for their acrobatic jumps. Don’t have a fishing license? No worries. The main event in May for Maine is Free Fishing Weekend, held May 30 and 31, 2026. Anyone in the state without a fishing license can cast a line and hope to snag the “big one” on those dates. The occasion is meant to spark a love for fishing in those who haven’t experienced it or who are considering getting a license. Other fishing laws, including size and bag limits, still apply. maine.gov
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Bahamas Islands Adventures
Explore Harbour Island Like a Local with Conch & Coconut Luxury Experiences
Conch & Coconut delivers bespoke Bahamas adventures, from Harbour Island pink golf cart rentals to private boat excursions across Eleuthera.
If you’re traveling to the island of Eleuthera—one of the Bahamas’ Out Islands—consider Conch & Coconut for bespoke island adventures, from zipping around in a buggy to curated excursions on land and sea. The locally owned luxury concierge and experiential services company is based on Harbour Island, so if you’re docked at one of the marinas there, such as Valentines Resort & Marina or Briland Club Marina, they can arrange one of their signature pink golf carts so you can explore like a local. They also offer land-based adventure tours around Harbour Island and North Eleuthera as well as private boat excursions to secret spots for swimming with turtles and rays, and even to an island where pigs roam free. If you’re bringing your own boat, they’ll connect you with fishing guides, private chefs, and more. conchandcoconutbahamas.com
Caribbean Culinary Month
Best Food Festivals in the Caribbean: Antigua & Barbuda Culinary Month
Antigua & Barbuda Culinary Month 2026 showcases Caribbean cuisine, top chefs, and Restaurant Week experiences across the islands.
There’s more to Antigua and Barbuda than secluded beaches with pristine turquoise waters. The sister islands recently won the Caribbean’s “Best Emerging Culinary City Destination 2025” from the World Culinary Awards—and this month, you can experience the best of their culinary creativity and rich culture. Antigua and Barbuda Culinary Month shines a spotlight on the islands’ beloved dishes along with homegrown and visiting chefs with Caribbean heritage. Plan your visit around Antigua and Barbuda Restaurant Week (May 3-17), when more than 50 local restaurants offer prix fixe menus at three price points. Guest chefs will cook at special events throughout the month, including St. Lucian native Nina Compton of Compère Lapin in New Orleans, British chef and TV personality of Antiguan heritage Andi Oliver, first-generation Antiguan and Barbudan chef and Chopped champion Claude Lewis, and Trinidadian chef Tristen Epps-Long, winner of Top Chef Season 22.
The “Eat Like a Local” experience highlights a curated list of casual island cookshops run by Antiguan and Barbudan restaurant owners and cooks. So, what should you try? Start with national dishes like pepperpot and fungee, then move on to goat water, ducana, and saltfish. antiguabarbudaculinarymonth.com
By Angela Caraway-Carlton
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