Key West Day Trips

What's not to love about day trips during your vacation stays in beautiful and historic Key West? You're on vacation, so no one wants to lug around luggage, overstuffed bags, and all the other paraphernalia our overworked minds tell us we must have any time we venture outdoors. In the Conch Republic, just pack up your sense of wanderlust for walkabouts, half day adventures, and full day excursions.  These are some of our favorites. They're great ways to live like a local during your stay!

Our Walkable Neighborhoods

A great way for new visitors to experience Key West is with a guided tour around our city center. Just hop on and enjoy a trolley ride for a narrated tour around Old Town or Downtown Key West. 

There are 12 convenient stops for the trolley that take you by shopping, dining, attractions and sites. The trolleys visit each stop every 30 minutes. Is “see what you want when you want” more your style?  Your ticket to Hop-On Hop-Off is good all day. Experience the history and the lore and the legends of Key West at your own pace. 

Key West is very walkable from our luxury vacation rentals to hotspots along Duval Street and throughout our island paradise.

Kayak and Paddleboard Tours

When you experience the waterways of Key West, you’ll enter into a lush marine world of mangrove islands and patch reefs and sponge gardens. Kayak through our various ecosystems to meet a variety of tropical birds, rays, sport fish and the likes. Paddle across the Gulf of Mexico or explore our creeks and shallow water.  

Experienced eco guides will help introduce you to our wildlife in their tropical habitats and our unique coastal environment. Choose from morning or afternoon departures and various lengths, levels and amenities. 

You can also pack a backpack, grab your snorkel and head for Hurricane Hole on Stock Island. This two-hour guided tour takes you through the backcountry mangroves where you’ll delight in tropical fish, sea cucumbers, sponges sea stars and the like. 

Guided Water Activities 

From snorkeling and parasailing to jetting around on WaveRunners. Add a full-day catamaran excursion and make a day of it with full breakfast and buffet options as dolphins frolic alongside. 

Water activities guides also host several types of tours for groups. We recommend the double dip. It’s a tour that lasts about three hours and their catamarans take you to two different reefs. Guests love the boats that have a stairway to the sea for ease of entry and exit, freshwater showers on board and shaded lounge areas. They also provide complimentary snorkel gear, snacks and beverages.

 Spa Services

There are several luxury spas available right in Key West with full menus of luxury services from hair to nails to body treatments and soaks for men and women.  Perhaps you’d like to indulge in a destination spa experience You can have that, too. 

Accessible only by boat or seaplane, one fantasy castaway experience features their Madrugada Water Massage. When you arrive, you’ll be whisked away through the island’s Jamaican coconut palms and past the very important “no cell phone” sign.  Once you’re properly unplugged, immerse in their pleasurable menu of luxury services of Balinese and Thai massage. Those who really want to “get lost” can wade into the calming Caribbean waters for a customized massage by the ocean. Prepare to be serenaded by soft, lapping waves and native birds. 

You may also schedule a massage right at the edge of Casa Marina Beach which ends with you totally relaxed in a hammock. Or, take a short boat ride to Sunset Key. Couples delight in elegant treatment suites adorned with tropical flowers and French doors that lead to private patios. After, lovebirds don their special fluffy blue robes just steps away from a beautiful linen table serving champagne and tropical pleasures. 

Charter Fishing 

From a small group on a small boat to an all-day marine adventure, day or night, with a large group, Key West is where every angler wants to be. Choose from deep sea fishing, light tackle offshore fishing, flats fishing or backcountry fishing. 

Fishing in the flats and backcountry areas is best starting in March. It’s also when fishing charters are most popular. Tarpon gather near the harbors and channels in abundance through June and July. Bonefish are plentiful, too, as well as trout, red fish, barracudas, jacks, ladyfish, snook and snapper. 

Fishing the Wrecks Reef, you’ll find yellowtail snapper, mutton, jacs, barracudas, permit, sharks, kingfish, cobia, cero and spanish mackerel. Blue Water Deep Sea Fishing is where Sailfish can be caught year round with their peak arriving in March and April. 

Dry Tortugas and Fort Jefferson 

Named for the large population of sea turtles that live around the island, the Dry Tortugas are a group of islands located about 67 miles from the end of the Keys. Concierge Services are happy to help plan a day trip excursion by ferry, boat or sea plane and even an overnight glamping adventure, if you’d like. It’s a Bucket List paradise for secluded, exotic beaches, birding, snorkeling and more. 

Sunset Cruises 

Experience the magic of our sunsets without the crowds. What better way to get your island groove than out on the sea chasing the sun. Opt for a popular cruise that includes live music with lots of tropical food and drink. There are also small group sailings with wine and cheese pairings, champagne tastings and specialty cocktail menus. Romance the seas aboard a schooner, catamaran, a motor boat or a luxury yacht. 

Picnic lunch on a private island, snorkel with some of the most beautiful sea creatures and experience our beautiful coral reefs while waiting for the sunset. 

Concierge Services 

What’s the best way to pull it all together? Well, you’ve already got friends in Key West! Our Concierge Services are experienced, friendly and super knowledgeable specialists with a flair for elevating your Key West experiences. They’ll provide just the right personal touch to your experiences and assist you with your individual needs. 

 Ready for your Key West Day Trips? Concierge Services are available via phone at 305.296.1010, Option 5 or via email at concierge@historickw.com.