Memorial Day Weekend is one of the biggest weekends of the year on Pensacola Beach, and the weather is shaping up for a perfect start to summer on the water.

From dolphin cruises and parasailing to sailing trips and kayaking around Pensacola Bay, there are plenty of ways to get out on the Gulf Coast this weekend.

Here are some of the best water activities happening around Pensacola and Pensacola Beach for Memorial Day Weekend 2026.

Dolphin Cruise on Pensacola Bay

One of the most popular Memorial Day Weekend activities in Pensacola is getting out on a dolphin cruise through Pensacola Bay and the Santa Rosa Sound.

These cruises regularly spot wild dolphins swimming near the boat while also giving visitors views of Pensacola Beach, local waterways, and waterfront landmarks. The vessel has both shaded seating and open deck space, making it an easy option for families and groups.

Book here:
Pensacola Dolphin Cruise

Guided Kayak Tour Around Pensacola Beach

This guided kayak tour launches from Little Sabine Bay and explores the calmer waters surrounding Pensacola Beach.

Along the route, guides often point out rays, fish, birds, jellyfish, and sometimes dolphins or sea turtles. The trip also includes a stop along the shoreline where guests can relax, swim, or snorkel before paddling back.

Book here:
Pensacola Beach Kayak Tour

Sunset Sailing Cruise

For a quieter experience on the water, sailing cruises around Pensacola Beach are one of the best ways to spend Memorial Day Weekend.

These smaller sailing trips explore the bay and Gulf waters around Pensacola Beach with room for only a few guests onboard, creating a much more relaxed atmosphere than larger tour boats. Dolphin sightings are common during the sails, especially during sunset hours.

Book here:
Pensacola Sailing Cruise

Parasailing Over Pensacola Beach

Parasailing remains one of the most popular adventure activities on Pensacola Beach during Memorial Day Weekend.

Flights rise hundreds of feet above the Gulf, offering views of Pensacola Beach, the Gulf waters, and Santa Rosa Island from above. Morning conditions are often calmer this time of year, helping create clear water views and smooth rides.

Book here:
Pensacola Beach Parasailing

Planning Memorial Day Weekend on Pensacola Beach

Memorial Day Weekend traditionally marks the unofficial start of summer across Pensacola Beach, with beaches, restaurants, bars, and water activities all seeing major crowds throughout the holiday weekend.

Booking tours and water activities ahead of time is highly recommended, especially for:

Many tours are expected to sell out during peak holiday hours.

More Pensacola Beach Guides

Looking for more things to do around Pensacola and Pensacola Beach this weekend?

See more local guides here:
https://www.mustdopensacola.com

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Things to Do on the Water in Pensacola for Memorial Day Weekend 2026