Planning an epic road trip from the northern states down to the southernmost point of the continental U.S.? Key West and the Lower Keys are your tropical reward after a long haul down I-95 or U.S. Route 1. Once you’ve hit the Overseas Highway, you’ll find group tours that make the long drive worth every mile. Whether you’re driving down from New York, Pennsylvania, Ohio, or anywhere in between, these guided experiences are perfect for groups ready to explore paradise together.
1. Sunset Sails for the Whole Crew
After logging hundreds of miles, it’s time to unwind. Board a catamaran or schooner with your group for a picture-perfect sunset cruise. Many tours come with snacks, music, and drinks—exactly what you need to celebrate the journey south with your fellow road warriors.
2. Group Fishing Trips with Fish All In Charters
Want to turn your travel crew into a team of anglers? Fish All In Charters has what you need. Captain Garret Frey customizes your fishing trip for any skill level and provides all gear and bait. It’s a hands-on way to experience the water. Click to learn more.
3. Group Meals at Eaton Street Seafood Market
Every road trip needs a good feast. Pull up with your travel mates to Eaton Street Seafood Market and treat yourselves to fresh Florida stone crab, lobster rolls, and fish tacos. Outdoor seating makes it easy for the whole crew to dine together. More about what to order here.
4. Camping Adventures in Bahia Honda State Park
Looking for an overnight stay on the way to Key West? Bahia Honda offers campgrounds with ocean views and quick access to snorkeling and kayaking. It’s a great stop for road-tripping groups who like a side of nature with their adventure.
5. Group Snorkel & Dive Tours
If you’ve been cooped up in the car for days, diving into the warm waters of the Keys is the ultimate reset. Take your group on a guided snorkel or dive tour to see coral reefs and tropical sea life. It’s active, refreshing, and a total thrill.
6. Guided Drive Tours Along the Overseas Highway
Even if you’ve been driving for hours, don’t miss the chance to experience the legendary Overseas Highway with a local guide. These tours help you discover roadside gems you might’ve sped past—like secret beaches, old bridges, and tiny island towns.
7. Group Visits to the Southernmost Point and Historic Tours
You’ve made it to the end of the road! Commemorate the moment with a group photo at the Southernmost Point buoy, then dive into a walking or trolley tour of Key West’s colorful history. Great for groups who like stories as much as scenery.
8. Stock Island Art and Waterfront Tours
If your group is staying just before Key West, Stock Island is a treasure trove of waterfront charm. Take a guided tour that highlights local artists, working boatyards, and dockside eateries. It’s a quieter, artsier slice of the Keys.
9.Eco Kayak or Paddleboard Tours for Groups
Shake off the highway stiffness by paddling through the mangrove tunnels of the Lower Keys. Eco tours led by local naturalists are perfect for groups looking for a peaceful, eye-opening way to explore the area’s untouched beauty.
10. Fort Zachary Taylor Group Beach Day and History Tour
Finish your road trip strong with a group visit to Fort Zachary Taylor. Take a guided history tour of the Civil War-era fort, then hit the beach for a swim and group picnic. It’s history, beach vibes, and relaxation all in one scenic spot.
Driving to Key West from the northern U.S. is a journey worth celebrating—and these group tours make it even more special. Once you’ve made it down the Florida peninsula and across the bridges of the Keys, treat your group to unforgettable experiences that are as rewarding as the road trip itself. Just don’t forget your camera—there’s a lot to capture along the way.
