🦜 Tipsy’s Guide to Getting Off the Rock

Fishing, Sailing & Chasing Sunsets

Some of the best Key West adventures begin the moment you leave the dock. Whether you're chasing mahi offshore, hunting tarpon through the backcountry, sailing beneath a canvas of orange and pink, or dancing your way into sunset with a drink in your hand, this is where the island really starts to show off.

🌅 Sunset Party Cruises

Live Music • Drinks • Dancing • Good Times

For those who believe sunset should be celebrated rather than simply observed.

Sunset Watersports Key West offers sunset cruises with live music, drinks and food, including its popular dinner-cruise experiences.

Fury Water Adventures is another big Key West name for lively sunset cruises, including its music-oriented Commotion on the Ocean experience.

Sebago Watersports offers several sunset sailing experiences from the Historic Seaport, including catamaran and schooner options.

🦜 TIPSY SAYS: Cold drinks. Live music. Sunset. Frankly, we're running out of reasons to stay on land.

🥂 Sunset Sailing, But Make It Fancy

Champagne • Smaller Crowds • Couples • Date Night

A little less party boat, a little more “Would you care for another glass?”

Classic Harbor Line Key West sails the gorgeous 105-foot Schooner America 2.0, including its signature Champagne Sunset Sail.

Argo Navis Key West operates a 75-foot luxury sailing catamaran with a more curated experience featuring craft cocktails, wine and food.

Catamaran Echo offers a smaller-group Champagne Celebration Sunset Sail geared toward adults looking for a quieter experience.

🦜 TIPSY SAYS: Same sunset. Better glassware.

⛵ Old-School Key West Sailing

Schooners • Sails Up • Wind in Your Face

For guests who don't just want to go on a boat. They want to sail.

Schooner Appledore offers classic wooden-schooner sailing from the Historic Seaport with an emphasis on an authentic sailing experience.

Schooner Spirit of Independence offers an intimate two-hour sunset sail aboard a traditional schooner with a deliberately smaller passenger count.

Schooner Jolly II Rover brings some extra pirate flavor with its distinctive red sails and classic Key West sunset sailing experience.

🦜 TIPSY SAYS: Put the phone down for five minutes. The sunset knows what it's doing.

🎣 Let's Go Fishing

🐟 Deep Sea & Big Game

Mahi • Tuna • Wahoo • Sailfish • Serious Fishing

When someone says, “No, I actually came here to fish.”

Linda D Sportfishing is a long-running Key West operation offering private and shared fishing experiences from Charter Boat Row.

Cowboy Cowgirl SportFishing Charters offers private and shared offshore fishing and accommodates everyone from first-time anglers to experienced fishermen.

INXS Fishing Charters is the more luxurious sportfishing option aboard a 47-foot Viking, targeting species including mahi, wahoo, tuna and sailfish depending on season and conditions.

🦜 TIPSY SAYS: Go big or go back to the pool.

🌴 Backcountry & Flats

Tarpon • Permit • Bonefish • Calm Water • Wildlife

A completely different side of Key West. Shallow water, mangrove islands and sight fishing instead of running miles offshore.

ShadowCaster Flats Fishing specializes in private light-tackle trips through Key West's flats, channels, mangroves and backcountry.

🦜 TIPSY SAYS: Less boat. More hunt.

🐠 Reef, Wreck & Catch-Dinner Fishing

Snapper • Grouper • Action • Families

This is a great category for guests who simply tell you, “We want to go fishing, catch something and have fun.”

ALL IN Fishing Charters specializes in private trips with a strong emphasis on reef, wreck and bottom fishing for snapper, grouper and other Keys species.

Cora Beth Fishing runs limited-load reef fishing trips from the Historic Seaport and also offers the rather perfect-for-us Sunset Snapper Fishing trip.

Gulfstream Fishing offers a larger shared party-boat experience, making it an approachable option for families, first-timers and people who don't want to charter an entire boat.

🦜 TIPSY SAYS: Catch dinner. Find a restaurant that'll cook it. Pretend this was the plan all along.

👨‍👩‍👧‍👦 First-Timers & Easy Fishing

Families • Beginners • Shared Trips • No Experience Required

You don't need a Hemingway beard and 40 years of fishing stories to get on the water.

Captain Conch Charters offers private deep-sea charters, shared trips and lighter nearshore fishing options.

Cora Beth Fishing is another strong choice for beginners and families because of its limited-load shared trips.

Gulfstream Fishing specifically welcomes beginners, families, solo anglers and experienced fishermen aboard its shared trips.

🦜 TIPSY SAYS: Never held a fishing rod? Perfect. No bad habits to undo.

🌅🎣 Catch the Sunset AND a Fish

Because choosing is overrated.

This one deserves a special little Tipsy box on the site.

Cora Beth Sunset Snapper Fishing combines reef fishing with a Key West sunset. The operator currently lists it as a four-hour trip offered during Daylight Saving Time.

They also offer private sunset charters if guests want the boat to themselves.

🦜 TIPSY SAYS: Why choose between fishing and sunset when you can screw up both dinner reservations at once?

🧭 Build Your Own Adventure

Fish • Explore • Sandbars • Sightsee • Make It Up As You Go

Some people don't want an itinerary. I respect these people.

Good Times Key West offers customizable private boat trips that can incorporate fishing, sightseeing and longer adventures, including trips toward the Dry Tortugas.

🦜 TIPSY SAYS: Tell the captain what sounds fun. Figure out the rest somewhere between the dock and the horizon.