New Year’s advice

Question

We are coming to KW for 5 days for my 60th birthday. We will be there for NYE as my birthday is New Years Day. Any advice on must see and dos? There are 5 of us confirmed but could be 9.

Answer

Happy (early) 60th — celebrating your birthday in Key West over New Year’s is a wonderfully festive and memorable idea! Here are some detailed suggestions, tips, and must-dos to help you plan a truly special 5-day trip with the group (5 to 9 people) around NYE and New Year’s Day.

New Year’s Eve & NYE Tips

Join the Signature “Ball Drops” & Celebrations — Key West is known for its quirky New Year’s Eve traditions:
- The Conch Shell Drop happens from the roof of Sloppy Joe’s on Duval Street. It’s a classic Key West moment — loud, festive, with music, crowds, and a real island-party feel.
- The Red Shoe Drop at Bourbon Street Pub / New Orleans House features a drag queen in a giant red stiletto descending at midnight — colorful, vibrant, and very “Key West.”
- The Pirate Wench Drop at Schooner Wharf Bar is a nautical-themed show: a “wench” descends from a ship mast, cannons fire, there’s live music, and party favors.
- For a more relaxed waterfront vibe, consider celebrating from Sunset Pier at the Ocean Key Resort — they host a “Key Lime Drop” into a giant margarita glass at midnight, plus free champagne toasts.
Watch the Sunset Celebration at Mallory Square — Mallory Square is a must: its nightly sunset celebration of street performers, local artists, and food carts is magical, and on New Year’s Eve it’s extra festive.
Book Early & Pick Your Spot Wisely — For a group of your size, especially for NYE:
- Arrive early on Duval Street or to your chosen “drop” location to get a good spot. The area around Sloppy Joe’s and Schooner Wharf can get very crowded.
- If you want to avoid the densest crowds, consider watching from a rooftop bar, a waterfront venue, or even on a private or chartered boat. Boat charters on NYE are a unique way to celebrate while watching fireworks and city lights from the water.

Five-Day Itinerary & Must-Sees for Your Birthday Getaway

Historic & Cultural Highlights
- Visit the Ernest Hemingway Home & Museum — Walk through his house, learn about his time in Key West, and don’t forget the famous polydactyl (six-toed) cats.
- Stroll through Old Town — Explore charming streets, Duval Street’s shops and bars, and historical homes like the Fogarty Mansion.
- Visit The Armory — A small but historic site that gives a glimpse into Key West’s military past.
Get on the Water
- Take a sunset cruise — A catamaran cruise in the evening is romantic, relaxing, and perfect for a birthday. Many include drinks and live music.
- Go snorkeling or diving — The waters around Key West are beautiful and full of marine life. Even if some in your group don’t swim, you can arrange a family-friendly trip.
- Try a water adventure — On your birthday, consider jet-skiing (if you’re up for some fun), or hiring a small private boat for a half-day trip to hidden sandbars, mangroves, or nearby keys.
Local Flavors & Dining
- Plan at least one birthday dinner at a memorable restaurant — you could do something upscale with water views, or a laid-back but iconic island eatery.
- Eat your way through Old Town — sample Key lime pie, fresh seafood, and Cuban-inspired fare as you wander.
Relax & Celebrate
- Reserve a day for lounging — spend time on the beach, at a resort pool, or in a hammock, especially after a big NYE night.
- Consider a spa or wellness day — many Key West hotels have spas, and a birthday relaxing treatment is a great way to recharge.
- Take a historic or ghost tour — Key West has lots of quirky history and ghost stories, and a guided walking or trolley tour is fun for all ages. Reddit-users often recommend letting the “ghost train” or Conch Tour Train guide you through Old Town’s fascinating history.

New Year’s Day (Your Birthday) Ideas

Have a sunrise brunch — After NYE, a relaxed brunch is a sweet way to start your birthday; pick somewhere with a patio or ocean view.
Go for a private charter or small boat trip — Celebrate with your group (5–9 people) on the water: a morning boat ride, dolphin-watching, or exploring nearby Waters.
Visit the Key West Butterfly & Nature Conservatory — It’s peaceful and beautiful, and a calm spot to reflect and enjoy nature on your birthday.
Take some time to shop and stroll — Visit art galleries, local boutiques (on Duval and nearby streets), and pick up some keepsakes from your trip.

Logistics & Practical Tips

Book in Advance — For NYE especially, make reservations for dinner, cruises, and any private tours early. Venues fill up, and costs go up.
Plan for Crowds — Duval Street and the key celebration points will be crowded on NYE. Designate a meetup spot for your group in case people get separated. Reddit users often recommend picking a meeting spot ahead of time.
Pace Yourself — You’ve got 5 days, so mix party nights with downtime. Balance high-energy NYE with slower days of relaxation, reflection, and exploration.
Transportation — Get around on foot when you can: Key West is very walkable. For further trips (or for larger groups), consider hiring a golf cart, van, or boat for the day.
Bring Layers — Even though Key West is warm, evenings can be breezy, especially on the water. Pack a light sweater or wrap, especially for your birthday night or cruises.

Final Thought

This trip can be a perfect mix of celebration, relaxation, and Key West charm. On New Year’s Eve, lean into the island’s fun traditions (conch drop, pirate wench, maybe a rooftop toast), and for your birthday on January 1, make it memorable with a leisurely day, meaningful experiences, and time with your family. Whether you end up dancing amid the Duval crowds or watching a romantic sunset from a boat, the spirit of Key West will make your 60th birthday feel truly special.