Between the Walt Disney World Resort theme parks and world class beaches, it's no surprise that Florida is one of the most visited states in America. The Sunshine State, as it has become known due to its wonderful year-long weather, is home to some of the most beautiful scenery and exciting attractions in all of North America, and no visit to Florida can be complete without a trip down to Key West. CDC information for travelers. Hours/availability may have changed.


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Located in Monroe County in the southern part of Florida, this city is situated at the very end of US Route 1. It's the southernmost city in the contiguous United States and is an unmissable part of any Florida vacation. A beautiful city with a vibrant Old Town area and several key landmarks like the Winter White House of Harry S. Truman, the Southernmost Point Marker, the Ernest Hemingway House, and the Tenessee Williams House, Key West is a lot of fun for people of all ages to explore.

One of the best ways to explore Key West is via trolley, and one of America’s favorite trolley companies, Old Town Trolley Tours, operates in the area. In fact, Old Town Trolley Tours actually got started in Key West way back in the 1970s. The company knows Key West better than anyone else and features high quality trolleys, lots of stops, discounted entry into various attractions, and more to make your Key West trolley tours as memorable and enjoyable as possible.

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2.Trolley Tours

Trolley Tours
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Old Town Trolley Tours of Key West

Old Town Trolley Tours runs several different trolley tour services in the beautiful city of Key West. Read on to learn all about each one of these options and choose the right tour for you. All tickets can be purchased either on-site in Key West or online for discounted prices, and these trolley tours are open to people of all ages.

Hop On Hop Off Old Town Trolley Tours

The Hop On Hop Off Old Town Trolley Tours are the classic option for taking a trolley tour of Key West. As the name indicates, these tours feature a hop on and hop off system in which riders can choose to get off at any of the stops and hop back on board later on without needing to buy an extra ticket or pay any additional fees. These tours therefore give you total freedom to explore the city and enjoy the magic and history of Key West like never before.

These Key West trolley tours run on a daily basis and begin at 9 am each day, with the final tour leaving at 4.30 pm. Tours run every thirty minutes on average and are fully narrated by expert, friendly guides who can teach you so much about the city in a fun, entertaining way. Old Town Trolley Tours hop on and hop off tours of Key West are one of the best ways to see the city, with a 100% satisfaction guarantee. If you're not happy with the service, you can get your money back, and the cost of a ticket also comes with a special offer to get a second day of trolley tour fun for a discounted price of just $15.

The Hop On Hop Off Old Town Trolley Tours feature 13 unique stops and also come with free admission to Papa's Hemingway Pilar Rum Distillery, as well as passing by more than 100 individual points of interest. All ticket purchases also come with a full color map of the city and a coupon book to help you cut down the costs of your stay in the local area.

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3.More Trolley Tours

More Trolley Tours
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Ghosts and Gravestones Night Tour

The Ghosts and Gravestones Night Tour only operates in the evening and shows off the spooky side of Key West. These tours leave at 7 pm, 8 pm, 9 pm, and 10 pm on a daily basis, but the schedule can vary depending on the time of year, with limited service during certain months, so be sure to check in advance and be sure of your dates before planning your ride on the Ghosts and Gravestones Night Tour of Key West.

As you might imagine, these tours are all about the scarier side of Key West, visiting various allegedly haunted locations around the Old Town area and learning more about why Key West has consistently been classed in lists of the top ten most haunted American cities. Your tour will come with free entry into the East Martello Fort, which is said to be haunted by silhouettes and ghostly orbs. You'll also be able to listen to all kinds of spooky stories from your ghost host guides.

Holiday Trolley Tours of Key West

The Holiday Trolley Tours of Key West only run in December and are all about celebrating the festive season. These tours typically run in the evenings after the sun has set, so everyone can really appreciate the sights of the many lights and decorations that have been put up all around Key West to honor the festive season. For a fun Christmas experience in America’s southernmost town, don’t miss out on these holiday trolley tours.

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3 Best Key West Trolley Tours

More Ideas: Casa Marina in Key West

Key West heritage meets contemporary sophistication in the Waldorf Astoria’s luxurious Casa Marina, a Waldorf Astoria Resort in Key West, Florida. Opened on New Year’s Eve in 1920, Casa Marina has been a landmark of grace, charm, and tranquility for nearly 100 years. Exuding the elegance and opulence of Old Key West, the resort presents an exquisite seaside retreat with beautifully-appointed accommodations, award-winning fine and casual dining, an array of facilities, amenities and activities for all desires, and impeccable service.

Established by American railroad tycoon Henry Flagler to offer wealthy customers of Flagler's Overseas Railroad a glamorous destination to stay, Casa Marina was designed by architects Thomas Hastings and John M. Carrere of New York's Metropolitan Opera House and New York’s Public Library fame. Built as a monument to Flagler, who died before construction began, the luxurious resort honored every detail of Flagler's original vision, and today, it is one of Key West’s most celebrated and beautiful resorts.

Surrounded by more than 1,100 feet of pristine sandy beaches lined with swaying palm trees, gin-clear waters, and manicured green lawns, this Casa Marina, fondly known as “the house by the sea,” offers an unforgettable seaside escape. The resort is also just steps away from the famous Duval Street with its vibrant boutiques and stores, bustling restaurants and buzzing bars, and numerous attractions. Listed on the National Register for Historic Places and ideal for romantic escapes, corporate getaways, or family vacations, this landmark Key West resort is ideally situated to do everything or nothing at all.

Casa Marina offers a range of exclusive and well-appointed guest accommodations in the form of 311 rooms and suites. Reflecting the Old Key West that gained a reputation for attracting and inspiring artists, writers, and political luminaries, the resort promises guest rooms and suites that fuse luxury, comfort, and style with contemporary flair.

All guest rooms and suites are non-smoking and feature modern amenities, including flat-screen televisions with premium channels, telephones with direct dial and messaging services, and deluxe bath products.

Standard Guest Rooms are spacious and bright with two double beds or a single king-sized bed and en-suite bathrooms with showers and/baths. The rooms can be connected for larger space requirements.

Ocean View Guest Rooms are located on the upper floors of the resort's historic Flagler building and are airy and light with nine-foot-high ceilings and large picture windows overlooking the swimming pool, gardens, and ocean beyond. These distinctive rooms are tastefully decorated and feature two double beds or one king-size bed, en-suite bathrooms with baths and/showers, and private balconies with breathtaking views. Ocean View Rooms with Lanais have the additional luxury of exclusive, fully furnished lanais just steps away from the beach, while Grand Ocean View Rooms with Terrace boast sweeping resort and ocean views from a large, private terrace.

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One- and Two-Bedroom Suites with Balconies are ideal for families, as they come with a separate bedroom and living area. Located in the exclusive suite building, these spacious, family-friendly suites feature a king-size bed in the bedroom, a pull-out sofa bed in the living room, a dining table for four to six people, and a furnished balcony overlooking the quiet neighborhood of Key West. The two-bedroomed suites feature an upstairs loft with one king-size bed and a downstairs master bedroom with either one king or two double bed, and two full bathrooms.

Ocean View Suites with Lanai Patios or Balconies can accommodate up to four guests with a private king-size bedroom, a separate living room with pull-out sofa bed for two guests, and a spacious dining area. Located in the separate suite building, suites feature a furnished, walk-out lanai and enjoy easy access to the resort swimming pools and the private sandy beach just a few steps from the suite.

Next read: Best Time to Visit Key West, Florida & Other Travel Tips

Guests at Casa Marina Resort can relish in a range of dining options, from informal and casual fare to award-winning fine dining against a backdrop of spectacular oceanfront views. From freshly caught seafood and tropical salads at Sun Sun to juicy steaks and crispy chicken at Spencer's by the Sea, there is a healthy option for every culinary occasion.

Boasting an exotic, “toes-in-the-sand” style setting and laid-back tropical island ambiance, Sun Sun fuses a refined menu of classic Key West cuisine with magnificent ocean views to bring diners one of the best spots to eat in Key West. The menu features fresh seafood, grilled meats, unique salads, and other locally grown produce and is accompanied by signature cocktails from the Sun Sun Bar such as the famous Southernmost Mojito, Casa Key Lime Colada, and Sunrunner. Tuck into a delicious breakfast buffet each morning on Flagler’s Terrace as you overlook the beach and sea.

Offering diners an unforgettable Key West dining experience with breathtaking views of the Atlantic Ocean, Spencer's by the Sea serves breakfast, lunch, or dinner in a casual, airy ambiance. Lunches include sandwiches, wraps, fish and chips, and salads, while signature dinner dishes include fresh seafood, prime steaks, and short ribs.

Named after the famous private railcar of resort founder Henry Flagler, Rambler's is a comfortable, casual eatery and coffee house that serves an array of home comfort food such as breakfast pastries and bagels, sandwiches and snacks, grab-and-go salads, homemade gelato, and freshly brewed Lavazza coffee.

Relax with friends or sip cocktails before heading out on the town at the elegant Lobby Bar, which has an extensive bar menu of specialty beers and ales, local and international wines, imported spirits, and custom-blended cocktails, including the infamous absinthe-infused Green Fairy. The Lobby Bar also offers a small menu of tapas-style sharing plates and bar snacks. An in-room menu is available for those who want a night in and is on hand for breakfast, lunch, dinner, and in-between snacks.

Whether you want to relax on a lounger on the beach or by the swimming pool with a tall cocktail, explore the area on bicycles, or while away the hours under water as you snorkel or scuba-dive, Casa Marina has an array of facilities to suit every need.

Two beautiful ocean facing swimming pools are the perfect place to cool off or relax with a drink on one of the poolside loungers, while a state-of-the-art fitness center will keep fitness levels up with a fully-equipped gym with treadmills, stationary bikes, stretching area, and free weights section. Yoga classes are held every morning on the pier in front of the resort overlooking the Atlantic Ocean. The resort’s private exclusive-use beach promises an escape from the crowds and boasts loungers, sunbeds, and umbrellas.

Home to the largest private beach on Key West, Casa Marina is the go-to spot for recreation and water sports with a variety of activities to enjoy, including deep-sea fishing, kayaking, sailing, scuba-diving, parasailing, snorkeling, or swimming in the crystal clear waters.

Additional resort amenities include 24-hour concierge and front desk services, two business workstations with computers, printer and fax access, laundry and dry cleaning services, and onsite equipment rentals, including bicycles, mopeds, and sports gear. For guests traveling with children, babysitting services, cribs, and high chairs are available, as well as special activity programs for kids.

The resort’s exclusive Spa la Mare is a tranquil oasis where guests can escape to relax and rejuvenate. Inspired by the surrounding marine environment, the spa celebrates the healing powers of the sea, offering an array of spa services that focus on refreshing, revitalizing, and re-energizing the mind, body, and soul. The full-service spa has beautifully appointed treatment rooms that offer havens of tranquility with stunning ocean views, as well as secluded spots in which to relax.

Certified, professional therapists apply a variety of skills and techniques to ensure maximum satisfaction across a range of body therapies and treatments, massages, skin care treatments, facials, manicures, pedicures, and enhancements. In-Room Spa services are also available should guests wish to enjoy treatments in the comfort of their rooms, and customized spa packages are offered for both individuals and groups.

Casa Marina features 22,600 square feet of meeting and event space featuring flexible indoor and outdoor venues, including newly transformed ballrooms, cutting-edge technology and functionality, and impeccable services for all occasions.

The resort offers a range of venues for all types of events and functions from board meetings and corporate events to weddings, receptions, birthday parties, and balls. The resort features the luxurious Flagler's Ballroom and vast Keys Ballroom along with the Grand Ballroom, which can accommodate up to 274 guests.

Seven outdoor receptions areas are available and can accommodate up to 200 people, with five indoor room options on offer. Professional events planning, wedding planning, and catering teams are on hand to take care of all the details to ensure a fruitful and stress-free event.

1500 Reynolds Street, Key West, FL 33040, Phone: 888-303-5719 or 305-296-3535

Back to: Florida Weekend Getaways.

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