According to forum posts, some travelers recommend upscale hotels like The Pier House, The Reach, and Hyatt Centric, known for their quality but not necessarily matching Four Seasons luxury. Additionally, luxury boutique hotels such as The Marquesa, The Gardens, and H2O Suites are popular for their unique offerings and high standards.

For those considering different experiences, Sunset Key offers an upscale private island experience accessible by a ten-minute ferry ride from Old Town. Moreover, the Key West Harbor Inn, Angelina Guesthouse, and Casa 325 are mentioned for their quality and proximity to popular areas like Duval Street.

Travelers have noted that hotel prices in Key West can be high, especially during peak seasons. The Best Western Hibiscus is highlighted for providing reasonable rates and good amenities like a nice pool and convenient location near Old Town.

For a more unique or intimate lodging experience, the Orchid Key Inn offers an updated retro motel vibe with excellent service, while the Marquesa Hotel is described as an oasis in Old Town, highly recommended for over a decade by repeat visitors.

According to forum posts, popular happy hour spots in Key West include Martin’s, Boat House, White Tarpon, and Half Shell Raw Bar. These venues are repeatedly mentioned for their great deals and ambiance.

Some travelers have highlighted specific offerings like the Key Lime Margaritas at First Flight and the Key Lime Martini at Onlywood. Additionally, Alonzo’s is noted for its comprehensive happy hour menu.

For those looking for updated lists of happy hours, the Key West Florida Weekly and various apps recommended by users provide current information. These resources help visitors find the latest deals and specials around town.

Travelers recommend checking out places like Old Town Tavern for its extended happy hour times and Kaya Island Eats for discounted small plates. These spots are praised for good food and a pleasant atmosphere conducive to enjoying a relaxed evening in Key West.

According to forum posts, many travelers recommend a sunset cruise as a romantic celebration idea in Key West. Options like Fury’s sunset cruise have been highlighted for providing a memorable experience, which was still being talked about years later by one user.

Travelers have called out Louie’s Backyard, specifically the AfterDeck at Louie’s Backyard, as a great spot for a romantic meal. The combination of good food, excellent views, and the sound of waves provides a quintessential Key West atmosphere.

For those looking for a special dinner setting, posts suggest considering options like A&B Lobster House or Little Palm Island for a unique dining experience. These locations offer beautiful settings and are recommended for occasions like Christmas dinners, indicating a suitability for other celebrations as well.

Romantic leisure activities in Key West, as mentioned by some travelers, include enjoying live music at various local bars and engaging in water activities for active couples, such as sailing or jet skiing.

According to forum posts, Key West offers a variety of sunset cruises catering to different preferences. Some travelers prefer the more intimate and quieter experiences such as Danger Charters' Wind and Wine cruise, which is known for its good wines and fewer passengers. Others enjoy the livelier atmosphere of Fury's Commotion on the Ocean, which features live music and a larger crowd.

For families, the Jolly II Rover is frequently recommended due to its family-friendly environment. For adult-only outings, the Echo offers an adults-only sunset sail, which is appreciated for its more subdued atmosphere.

Travelers looking for luxury or small group settings have praised the Argo Navis for its top-notch service and beautiful vessel. Danger Charters is also favored for its upscale wine-focused trips with appetizers, providing a more refined sunset experience.

Travelers have called out the importance of considering the type of experience desired, whether it's a party atmosphere, a romantic setting, or a family-friendly voyage. Booking in advance is recommended, especially during peak times to secure a spot on preferred cruises.

According to forum posts, top recommended seafood restaurants in Key West include Azur, Little Pearl, and Half Shell Raw Bar. Azur and Little Pearl are praised for their excellently prepared seafood dishes, while Half Shell Raw Bar is noted for its casual setting and fresh catch specials.

For those interested in local shrimp, Key West Pinks and Royal Red Shrimp are highlighted as must-tries. Eateries such as Azur, Flaming Buoy, and Conch Republic Seafood prominently feature these local delicacies.

Some travelers mentioned Freshco as a new seafood restaurant with good prices and local fish options, although it's still establishing its reputation. Another recent favorite among forum users is Off the Hook Grill, known for its varied seafood offerings in a more casual ambiance.

Travelers have called out Salute on the Beach and Sunset Pier as good spots for seafood that also cater to families and provide a pleasant dining atmosphere. These locations offer a mix of excellent food, good cocktails, and scenic views, suitable for both high-end dining experiences and casual meals.

According to forum posts, one travel option to Dry Tortugas is by seaplane. Travelers have mentioned that the seaplane offers a standard trip of about 2.5 hours, suitable for exploring the fort, and an extended 6-hour version for those wishing to experience more, such as snorkeling or beach activities. However, it is noted as being more expensive than other options.

Some travelers mentioned the ferry as a cheaper alternative to the seaplane. The ferry provides a full 4-hour stay at Dry Tortugas, which is adequate for walking through the fort but might be restrictive for a complete experience. It's also highlighted that the ferry can be booked solid well in advance, indicating high demand and limited availability.

For those seeking a more exclusive or flexible travel option, private charters are available, as discussed by forum users. While significantly more expensive, private charters offer personalized trips, and some are licensed to offer overnight stays, fishing, and more comprehensive exploration of the area.

According to forum posts, Sunset Watersports and Fun in the Sun Charters are popular options for renting boats in Key West. Sunset Watersports offers rentals with a 10-mile radius restriction, while Fun in the Sun Charters, located on Stock Island, provides rentals that have been well-reviewed for quality and service.

For those interested in renting kayaks or paddle boards, Lazy Dog and Hurricane Hole on Stock Island are recommended by some travelers. Lazy Dog offers tours through the canals, and both locations are praised for their service and the quality of the equipment.

Although finding houseboat rentals in Key West is challenging, Back Country Boat Rentals offers options that can be picked up at Mellow Ventures, as mentioned by a forum user. This service allows for a more extensive exploration, though it's noted that navigating the waters around the Keys can be tricky and requires careful planning.

According to forum posts, popular spots for live music in Key West include Smokin Tuna, Hanks Hair of the Dog, Sloppy Joes, Ricks, Schooner Wharf Bar, Willie Ts, Salty Frog, Hogs Breath, and The Green Parrot. These venues are frequently mentioned by travelers as great places to enjoy live performances.

Some travelers have called out specific artists worth watching, such as Caffeine Carl, Cliff Cody, and Tony Baltimore. Caffeine Carl is noted for performing regularly at Smokin Tuna, often accompanied by other musicians like Zack Seemiller and George Chapman.

For those looking for unique music experiences, the Fury Commotion on the Ocean offers a sunset sail with live music. Additionally, the Green Parrot is recommended for a variety of music and is known for not being just a typical cover band venue.