things to do in Summerland Key, FL

Chase seasonal offshore species with live bait and light tackle

Relax as a private guide reveals Key West’s history, culture, and architecture

Explore Key West's supernatural stories from a cozy pedicab

Walk Key West’s landmarks with local insight from Kino Sandals to the Southernmost Point

Explore Key West’s history, culture, and early industries on a small-group walk

Walk Key West’s historic streets and uncover the stories behind its landmark buildings

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 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

Tailor a luxury vessel day with fishing, swimming and waterfront fun

Create your own fragrance in a guided Key West perfume class

Relax on a captain-led deck boat escape to a local Florida Keys sandbar

Relax on a private deck boat with a captain and enjoy Key West’s local sandbars

A private, captain-led evening on the water as the Florida Keys sunset unfolds

Learn to snorkel with an experienced captain in the Florida Keys

See Key West sights and local history from the water without getting wet

Reach Key West sandbars for soft white sand and clear water

Watch Key West’s sunset from your private boat

Search Key West waters for dolphins on a private boat ride

Choose a Key West charter that pairs snorkeling with a sandbar stop and dolphin viewing