Cruise Dreaming: A First-Timer’s Guide to Sailing Celebrity’s Key West & Bahamas
Curated By
Zandria Kajewski
Curator’s statement
I’ve never cruised, but I’ve spent a lot of time researching the best lines, itineraries, and onboard experiences throughout my training as a travel advisor. Celebrity’s Key West & Bahamas sailing keeps popping up as the perfect intro to cruising—accessible, beautiful, and full of thoughtful touches. While planning my dream cruise, I found myself drawn to Key West for its charm, color, and culture. Spots like the Tropic Cinema capture that retro whimsy I love.
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Where to stay in Key West & the Bahamas
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Things to do in Key West & the Bahamas
Explore Duval Street in Key West
Quirky shops, conch fritters, and key lime pie—this is the heart of Old Key West. I’d love to just wander and admire the southern-style architecture. I find beautifully designed buildings inspiring, whether I’m walking through Saskatoon or watching travel videos of the South online.
Visit Ernest Hemingway’s house
I first saw this house in a YouTube video and was instantly drawn to its old-world charm. Knowing it’s right there in Key West made this itinerary feel even more appealing. Between the tropical gardens and the cats, it seems like a magical literary landmark to step into.
Dolphin encounter in Bimini
Reading about this excursion brings back memories. When I lived in Victoria, BC, we’d go seal and whale-watching—though the whales were elusive! The ferry ride to the mainland is what finally delivered a surprise sighting. Seeing dolphins up close must feel just as magical.
Ride a glass-bottom boat in Nassau
I’ve done this a few times back in Victoria during the late ’90s and early 2000s, and it never stopped being amazing. You’re floating above a whole hidden world, watching the reef life unfold beneath you.
Relax at Serenity Bay Beach (Bimini)
Powdery sand, turquoise waters, and hammocks—everything a first cruise should include. This kind of setting would be perfect for journaling, sketching, or just reflecting.
Sunset walk at Mallory Square (Key West)
I’m a sunset person, and walking near the water as the day winds down is one of the simplest joys of travel. Whether I’m in another country or at home, I always notice how golden hour transforms the streets.
Places to eat & drink in Key West & the Bahamas
Blue Heaven (Key West): Iconic for brunch and live music, set under a canopy of trees.
Sloppy Joe’s Bar (Key West): Touristy, yes—but Hemingway drank here and the atmosphere is unbeatable.
The Fish Fry at Arawak Cay (Nassau): Try cracked conch and a local Kalik beer among the locals.
Sherry’s Beach Bar (Bimini): Beachfront, laid-back, and serves grilled lobster. Enough said.
Cafe Moka (onboard Celebrity): Perfect for a quiet morning with coffee and ocean views.
Need to know
This 3–4 night itinerary is great for first-time cruisers or anyone craving a quick, sunny escape.
Book early for the best rates, and look into Celebrity’s bundled airfare and hotel options for a smoother start and finish.
Shore excursions like dolphin safaris and glass-bottom boats can fill up fast—so pre-book if you can.
Travel Advisor
Zandria Kajewski
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