Best results for Water Activities in Summerland Key, FL

Rent a 23' center console and fish Key West your way

Charter a custom houseboat and relax on a remote Key West mooring

Build your own private Key West day on the water for up to 6 guests

Private sandbar and island-hopping charter with 4, 6, or 8-hour options

Choose a 4, 6, or 8-hour private charter to island hop local waters

Choose a 4, 6, or 8 hour sandbar and island-hopping charter from Sunset Key

Enjoy a customizable cruise through Florida Keys sandbars with snorkel gear and coolers included.

Spot playful dolphins and snorkel vibrant reefs on a small-group Key West cruise

Private Barefoot II charter for up to 6 to snorkel and relax in the Florida Keys

Adults-only Key West sunset sail with champagne and gourmet cheese

Private Key West sunset sail with your music and a flexible start time

Sail Key West waters on a private 4-hour charter for up to six guests

Spend a full day sailing from Key West with up to 6 guests

Charter The Coolwater for a Key West–style fishing trip for up to 6 people

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

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.

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