Best 775 things to do in Big Pine Key, FL

Sail, kayak, and snorkel Key West's shallow waters on a private cruise

Sail Key West’s reefs, barrier islands, and mangroves

Tailor a private Caribbean sailing charter for your celebration or getaway

A clothing-optional all-male sailing trip with snorkeling, sandbar, or kayaking

Dolphin watch, snorkel, and visit a sandbar on a small-group Key West tour

Charter COWFISH for a Key West sandbar stop and guided snorkel, with snacks and water included

Private 4-hour kayak, snorkel, and sail trip for up to 6 in Key West

Paddle the mangroves and snorkel with a small group in the Key West National Wildlife Refuge

Snorkel the reef, visit a sandbar, and sail into sunset on a spacious catamaran

Ride a jet ski around Key West with 5–6 scenic stops and a free shuttle

Parasail from Smathers Beach with a 10–12 minute flight and up to 1 hour on the boat

Enjoy a high-flying 10–12 minute parasail ride with sweeping views of Key West

Snorkel Key West’s vibrant reef aboard a fast catamaran with breakfast and post-trip drinks.

Captain a two-person boat to secluded sandbars and mangrove islands.

Swim at a secluded sandbar and watch playful wild dolphins up close, with lunch and unlimited beer and wine included.

Paddle mangrove tunnels then relax on a secluded sandbar with lunch and unlimited drinks

Enjoy unlimited drinks, appetizers, and live music aboard a catamaran while you watch the famous Key West sunset.

Snorkel two reef sites, then cruise back at sunset with drinks after your swim

Spend 6 hours on the water with 11 activities, lunch, and draft beer on the cruise back

Parasail from Casa Marina with an 8–15 minute flight and up to 1 hour on the boat

Explore Key West’s remote backcountry with guided paddling and sandbar time

Snorkel Key West’s reef, then sip from the open well bar

6-hour Key West watersports combo with 10 activities plus lunch and drinks

Cruise to spot dolphins, snorkel a reef, then enjoy sunset drinks