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Key West Rebecca

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Key West Rebecca

Key West Rebecca is a travel agency and a local concierge service. You can plan your whole vacation all in one place!
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09/05/2026

September can be a wonderful time to visit Key West, but dining plans require a little extra attention.

This is the time of year when many locally owned restaurants close temporarily for vacation, maintenance and a well earned break after a busy season.

Confirmed closures include:

• Blue Heaven: September 8 through October 15
• Louie’s Backyard: September 8, with dinner returning September 24
• Café Sole and Smoked BBQ: all of September
• DJ’s Clam Shack: September 7 through September 24
• Red Shoe Island Bistro: September 13 through September 30

Meanwhile, Smokin’ Tuna has returned in a new location at 313 Duval Street, bringing another food and live music option to the former Hard Rock Café building.

The restaurants listed in an old article or saved social media post may not be open during your vacation. Always check current schedules before planning your dinners!

08/24/2026

Reviews vs. Reality with Rebecca:
Havana Cabana 🌴

Did you know Havana Cabana is often described online as a waterfront resort, but there’s actually a road between the hotel and the water?

There is a seawall along the waterfront and no beach, so if you’re picturing yourself stepping out of the resort and walking straight onto the sand, this probably isn’t the right fit for you.

That doesn’t make Havana Cabana a bad choice. It's a great place to stay if you love a lively resort atmosphere, want a great pool, enjoy colorful tropical surroundings, and don’t mind that the beach is not right outside your door.

I’d recommend Havana Cabana to someone who cares more about the pool, atmosphere, and resort experience than having direct beach access. But if you told me that waking up and walking straight onto the sand was an important part of your Key West vacation, I’d probably have a better recommendation for you.

“Waterfront” may sound perfect, but the reality of what that actually means can change how you feel about your stay.

08/22/2026

Will I still have fun in Key West if I don’t drink?

Absolutely!

You do not have to build your Key West vacation around bars to have a great time here. There are so many other ways to experience the island. Maybe you start one morning on a guided kayak tour, paddling through the mangroves and shallow backcountry water. It’s quiet, beautiful, and completely different from the Key West most people picture first.

Another day, you could take a food tour and experience Key West through its flavors. You’ll try local dishes, hear some of the stories behind them, and probably discover a few places you never would have noticed on your own.

If you enjoy history, you have plenty to choose from too. You could visit the Ernest Hemingway Home & Museum, tour the Harry S. Truman Little White House, explore the Mel Fisher Maritime Museum, or climb the Key West Lighthouse.

And here’s one idea you might not expect from me: leave Key West for the day.

Rent a car, a jeep, or join a guided tour and take a road trip up the Keys. Stop at Bahia Honda State Park, visit The Turtle Hospital in Marathon, have lunch somewhere along the water, and take your time exploring the Overseas Highway. Sometimes one of the best Key West vacation days is actually the day you see a little more of the Florida Keys.

So if you don’t drink, please don’t assume Key West isn’t for you. Tell me what you do enjoy, whether that’s wildlife, food, history, being on the water, exploring new places, or simply slowing down, and I can help you find the Key West experiences that fit you.

Are you a non drinker that has visited Key West and ended up having a great time?

08/21/2026

“Everyone is excited about our Key West trip. I’m the one stressing about how we’re actually going to pull it off.”

I hear versions of this from group organizers all the time.

When you’re planning for several people, you’re not simply booking a vacation anymore. You’re trying to find accommodations that work for everyone, activities different personalities will enjoy, restaurants that can seat the group, transportation that makes sense, and a schedule that doesn’t leave everyone rushing from one reservation to another.

Meanwhile, everyone else gets to be excited about the trip except you.

There's a better way.

I help you build a Key West vacation around your group, including where to stay, what to do together, when it makes sense to split up, where to eat, how to get around, and how all those pieces fit into the days you actually have. A group vacation should give you memories with the people you’re traveling with, not months of stress trying to organize them.

Would you enjoy the trip more if you weren’t the one trying to organize everything?

08/20/2026

First trip to Key West?

I have one piece of advice: don’t let someone else’s “must-do” list plan your vacation. There are hundreds of ways to experience this island, and the best ones depend on the person coming here. Maybe your perfect Key West day means snorkeling over the reef. Maybe it means finding a fishing captain who knows where to give you the best chance at the fish you’ve always wanted to catch. Maybe you’d rather stay completely dry, explore the history, eat your way around Old Town, or spend an afternoon on a secluded sandbar. And maybe I tell you about something you’ve never heard of and your response is:

“Wait...we can DO that in Key West?” Those are some of my favorite conversations. Because Key West is a fantastic place to try something for the first time. So when you ask me, “What’s the one thing we absolutely shouldn’t miss?” I don’t want to give you everybody else’s Key West vacation.

I want to help you find yours.

Have you been to Key West before? What's your must do?

08/19/2026

Only one day in Key West? Let me give you two very different ways to make the most of your time here.

If you’re coming in on a cruise ship, you really don’t need to try to cram everything Key West has to offer into a few hours. I’d rather help you choose a day that fits you.

Want something quick, fun, and very Key West? Ask me about our jet ski tours. These tours are unique to Key West because they take you around the entire island. It's a great way to see the the whole island in about 2 hours. When you’re finished, stop for a slice of Key lime pie before heading back to the ship.

Want something more personalized? Ask me about a private Key West tour guide just for you. Tell me what you’re most interested in seeing. Maybe it’s the historic homes, famous landmarks, local neighborhoods, architecture, great photo spots, or the local favorite bars. Your guide can personalize the experience around what interests you most, and one of the biggest advantages is that your cruise schedule is part of the plan. You can enjoy Key West without constantly looking at your watch and wondering whether you’ll make it back to the ship on time.

Which one would you choose?
https://keywestrebecca.com/on-the-water/

08/18/2026

Have you ever thought about spending Christmas in Key West?

Picture your Christmas week with palm trees wrapped in lights, boats in the harbor, dinner outside, and warm evenings instead of coats and cold weather. You still get all those things that make Christmas feel like Christmas: the decorations, the lights, the festive atmosphere, and that little bit of holiday magic. It just happens to come with waterfront restaurants, sunsets, flip flops, and a whole lot more time outdoors. Maybe you spend the afternoon exploring Old Town. Maybe you take a sunset cruise before dinner. Maybe you spend a day out on the water. Or maybe the best part is simply being together somewhere beautiful without all the running around that can come with Christmas at home.

If you’re thinking about spending Christmas in Key West, now is when I’d start planning it. Starting early gives you more choices for where you stay and what you do, so you can put together the Christmas vacation you really want instead of choosing from whatever is still available later.

Could you see yourself spending Christmas here?

08/15/2026

A private charter can be the perfect choice when you want your boat day to feel less like a scheduled tour and more like your own day in the Florida Keys.

Instead of following a fixed route with a large group, a private charter gives you the freedom to explore at your own pace. Spend more time at a secluded sandbar, snorkel a shallow reef patch, look for tropical wildlife, or simply find a beautiful stretch of clear backcountry water and relax. Just a short boat ride from Key West can make you feel surprisingly far away from everything. It's also a wonderful option for couples, families, and groups who want more privacy and flexibility. Bring your favorite snacks and refreshments, settle into the plush seating beneath the shaded bimini, or stretch out on the loungers and soak up the sun with a 360 degree view of the water. The 26 foot custom Bennington tritoons are designed with comfort in mind, and the charter includes sanitized snorkel equipment, a large lily pad and floats, plus coolers stocked with ice and bottled water.

The biggest advantage is simple: the day belongs to you. You are not trying to fit your vacation into someone else’s schedule. You get to enjoy the Keys the way many locals do, out on the water, away from the crowds, with nowhere you have to be except wherever looks good next.
https://keywestrebecca.com/barefoot-private-charters/

08/11/2026

Trying to decide where to stay in Key West?

Before you start comparing hotels, I want you to think about something that can have an even bigger impact on your vacation:

What do you want your time in Key West to feel like?

Would you love stepping outside your hotel and wandering the colorful streets of Historic Old Town?

🎶 Do you want to be close to Duval Street, restaurants, live music and nightlife?

⛵ Would you rather stay near the Historic Seaport, where you can stroll along the harbor and watch the boats come and go?

🌊 Or are you picturing an oceanfront resort where relaxing by the water is part of the vacation itself?

Maybe you don't mind staying a little farther from Old Town if it means more space, easier parking or a quieter setting in New Town or Stock Island.

There really isn't one “best” place to stay in Key West. There is a best place for you and the kind of vacation you want to have.

That’s why when I help you plan your Key West vacation, I don't simply look for a nice hotel. I look at where you want to spend your time, what you want to do, how much you want to walk, whether you'll have a car, and the overall experience you're hoping for.

I wrote my latest blog to help you understand the different areas of Key West before you choose your accommodations.

🌴 Where Should You Stay in Key West? A Guide to Choosing the Right Location

👉 https://keywestrebecca.com/guide-to-choosing-the-right-location/

If you're thinking about a Key West vacation, what sounds more like you: being right in the middle of everything, or having a quieter place to retreat to at the end of the day?

08/08/2026

If you’re planning a trip to Key West, you may be wondering:
Which is better, the Conch Tour Train or the Old Town Trolley?

The truth is, I don’t think one is better than the other. It really depends on how you want to experience Key West.

If you’re thinking, “I want to sit back, hear the stories, learn some history, and get a good overview of Key West,” I’d probably point you toward the Conch Tour Train. It’s a fun way to see a lot without turning sightseeing into an all day event.

But if you’re thinking, "I want to explore. I want to get off, visit attractions, wander around, and then keep going,” the Old Town Trolley is probably going to suit you better. The hop-on, hop-off format gives you much more freedom to make a day of it.

I like to think of it this way:

Conch Tour Train: “Show me Key West.”
Old Town Trolley: “Help me explore Key West.”

https://keywestrebecca.com/train-trolley-tours/

Address

Key West, FL

Opening Hours

Monday	9am - 5pm
Tuesday	9am - 5pm
Wednesday	9am - 5pm
Thursday	9am - 5pm
Friday	9am - 5pm
Saturday	9am - 5pm
Sunday	9am - 5pm

Telephone

+13053048910

Website

https://www.keywestrebecca.com/

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