Memorial Day – Things to Do in Key West [2026]
Memorial Day in Key West marks the unofficial start of summer, bringing warm tropical weather, turquoise water, sandbars, boat rentals, and outdoor adventures. Visitors can expect sunshine, calm seas, and some of the best boating conditions of the year.
Memorial Day is not just about barbecues; it’s a day to honor and remember those who have died in military service to the United States.
Key West Cemetery at the USS Maine Memorial
The Navy League hosts a ceremony at the USS Maine Memorial in the Key West Cemetery.
Annual Schooner Wharf Minimal Regatta
To compete in the wacky challenge, each six-member team must construct a craft out of the most minimal supplies: a single sheet of 4-by-8-foot plywood, two 8-foot-long 2-by-4s, a pound of fasteners and a trusty roll of duct tape. Regatta rules even forbid the use of caulking or adhesives, though epoxy paint is permitted. The “sink or swim” challenge is a Memorial Day Weekend tradition in the Florida Keys, with Sunday’s fun scheduled to begin at 11 a.m. when teams can register at the Schooner Wharf Bar, 202 William St.
Live Music at the Green Parrot
The Resolvers Reggae
The Resolvers draw influences from classic Jamaican Reggae, Rocksteady, and Ska along with American Rock, Jazz, Funk, and Soul. Their live show has been described as explosive with up to 10 musicians on stage, including a full horn section, and led by the powerful brother & sister duo of Ojay & Sahara Smith on lead vocal roles.
Get Out to a Sandbar!
Spend your vacation like a local, at the sandbar!
Skip the beach as Summer winds bring in sargassum and head out to a sandbar that’s sargassum free.
Be your own captain with a boat rental or let us do the driving and take one of our sandbar charters.
Animal Farm Open House
Visit the family-friendly Monroe County Sheriff’s Animal Farm, open the second and fourth Sundays of each month from 1 to 3 p.m. Visits are free of charge, but donations are always welcomed. Stock Island Detention Center, 5501 College Rd.
Tour Key West in Style
Enjoy the open-air and refreshing sea breeze of Key West with a Golf Cart, Scooter, or Electric Cart rentals.
Drive through the tight streets of Old Town with ease as our nimble and roadworthy rentals offer the perfect way to explore paradise, island-style.
FAQs for Memorial Day in Key West
What is the weather like in Key West during Memorial Day weekend?
Memorial Day weekend in Key West is warm, sunny, and tropical, with daytime temperatures typically in the mid-80s to low-90s and warm ocean water ideal for swimming and boating.
Is Memorial Day a good time to visit Key West for outdoor activities?
Yes. Late May offers calm mornings, clear water, and ideal conditions for sandbars, boat rentals, snorkeling, and sunset cruises. See our Guide to the Best Key West Boat Tours.
Does it rain in Key West during Memorial Day weekend?
Brief tropical showers are possible, but they are usually short and followed by sunshine. Rain rarely disrupts full-day boating plans.
Is the ocean warm enough for swimming in May?
Yes. Water temperatures are typically in the upper 70s to low 80s, making it comfortable for swimming, snorkeling, and sandbar trips.
Does sargassum affect Key West beaches in summer?
Summer winds can bring sargassum seaweed to some beaches. Many visitors choose offshore sandbars, which are typically clearer and seaweed-free. Sandbars are free of sargassum.
What should I pack for Memorial Day weather in Key West?
Lightweight clothing, sunscreen, polarized sunglasses, swimsuits, sandals, and a light rain layer are recommended. See our Boat Day Packing Guide for Key West.
Is Key West family-friendly during Memorial Day weekend?
Yes. Key West offers family-friendly activities including sandbar trips, eco tours, snorkeling, golf cart rentals, and educational Memorial Day ceremonies.
What are the best family activities in Key West?
Popular options include sandbar charters, pontoon boat rentals, the Monroe County Sheriff’s Animal Farm open house, and exploring Old Town by golf cart.
Are sandbars safe for kids?
Most Key West sandbars are shallow, calm, and waist-deep, making them ideal for supervised family outings. Our captains will find the best spot for your family and weather.
Can families rent boats in Key West?
Yes. Families can rent deck boats, pontoons, or center consoles, or book a captained sandbar charter for a relaxed experience.
What is the easiest way for families to explore Key West?
Golf cart rentals and captained boat charters are convenient, flexible, and family-friendly ways to explore.
What boat rental is best for families?
Pontoon boats and deck boats are ideal because they provide stability, shade options, and comfortable seating. See our Guide to Key West Boat Rental Boats or contact us, we’re happy to help you decide.
Why choose a sandbar instead of a beach?
Sandbars offer clearer water, fewer crowds, and less seaweed compared to shoreline beaches during summer months.
How do you get to a Key West sandbar?
You can reach a sandbar by renting a boat, booking a captained sandbar charter, or joining a guided eco-tour.
Are sandbars busy on Memorial Day weekend?
Memorial Day is popular, but experienced captains can navigate to multiple sandbar locations to find open space.
What should you bring to a sandbar?
Sunscreen, drinks, snacks, towels, waterproof speakers, floats, and plenty of water are recommended. See our Sandbar Packing Guide.
Do you need a boating license to rent a boat in Key West?
Florida requires a temporary boating safety certificate for operators born after January 1, 1988. We can send you a link.
Can you rent a boat with a captain in Key West?
Yes. Captained charters are available for sandbar trips, sunset cruises, snorkeling tours, and eco adventures.
Is Memorial Day a busy weekend for boat rentals?
Yes. Memorial Day is one of the highest-demand weekends for boat rentals in Key West.
How far in advance should you book a boat rental for Memorial Day?
Booking at least one to two weeks in advance is strongly recommended. If not right when you book your vacation. Boats and Charters can sell out.
