Best results for Water Activities in Sugarloaf Key, FL

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

Sail, snorkel, and toast with included drinks aboard a spacious catamaran

Sip bubbly and sail into the Key West sunset aboard a spacious catamaran

Private catamaran sailing with champagne, wines and a gourmet cheese buffet

Sail, snorkel, and seek sandbars aboard a private catamaran

Private Key West sailing with snorkeling, sandbars, and dolphin searches

Private sunset sailing with bubbly, wines and a gourmet cheese buffet

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

Fish Key West's shallow backcountry channels aboard a 36-foot boat

Charter Cowfish for a 4-hour private cruise with any two water activities

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

Sail, snorkel, and explore Key West waters on your private catamaran

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

Shape a private yacht charter around your celebration or vacation

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

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