Your Key West Weekend Dream Trip:
A Relaxed, Historic Escape on a Budget
Dreaming of turquoise waters, swaying palms, and a laid-back island vibe? Key West, Florida, offers solo travelers the perfect blend of relaxation, cultural discovery, and historical charm—all without blowing your budget. Here’s your ultimate guide to planning a Key West weekend getaway for around $1,000, with room for a few special splurges!
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Plan your escape for late August or September—a sweet spot for lower hotel rates as it’s off-peak season. A quick reminder: it’s hurricane season, so flexible dates and travel insurance are a smart move!
Estimated: Lodging $500 ~ Travel $450 ~ Food $150 ~ Activities $150 ~ Splurges/Buffer $125
Target Total $1,000–$1,275
Where to Stay
For a true Key West experience, skip the big chains and opt for a locally owned guesthouse or boutique inn. Think charming conch houses, tropical courtyards, and pools that invite you to unwind.
👉 Top picks:
- Seascape Tropical Inn
- NYAH (Not Your Average Hotel) — a social spot perfect for solo travelers
💡 Budget-friendly alternatives found in my search:
- Havana Cabana — $142/night (via Trivago)
- Fairfield Inn & Suites — $132/night (via Booking.com)
- Hilton Garden Inn — ~$500 total for 3 nights (via Booking.com)
How to Get There
- Fly Atlanta → Key West: Delta offers roundtrips from ~$259; United closer to ~$418
- Car rental: Once in Key West, grab a car (~$40/day) or go car-free—this tiny island is super walkable and bike-friendly
* I fly out of Atlanta which is where I came up with these prices.
Feeling adventurous? Fly into Miami (roundtrip ~$173) and drive the spectacular Overseas Highway. Imagine crossing 42 bridges, surrounded by endless blue water!
Pro tip: Book early and compare bundled deals that combine flight + hotel for extra savings.
🗺 Your 3-Day Itinerary: Relaxed, Cultural & Historic
🌅 Day 1: Arrival + Sunset Magic
- Check in and chill by the pool
- Wander Duval Street for shops, galleries, and island vibes
- Grab a Cuban coffee at Cuban Coffee Queen
- Catch the famous Mallory Square Sunset Celebration — free street performers + art, with the sea as your backdrop
- Splurge: Sip a Hemingway Daiquiri at Sloppy Joe’s Bar (~$10)
📜 Day 2: History + Hidden Corners
- Explore the Ernest Hemingway Home & Museum (~$19) — meet the six-toed cats!
- Climb the Key West Lighthouse for epic views (~$15.50)
- Snap a selfie at the Southernmost Point
- Visit the hauntingly beautiful Key West Cemetery (free)
- Lunch at El Siboney — hearty Cuban fare (~$15)
- Rent a bike (~$10-15) and discover Old Town’s quiet lanes
- Splurge: Feast on fresh seafood at Half Shell Raw Bar (~$30)
🌊 Day 3: Chill + Cultural Farewell
- Morning beach time at Fort Zachary Taylor State Park (~$2.50–$6) — swim, snorkel, explore a Civil War fort
- Visit the Custom House Museum (~$15.50-$17) for art + history
- Savor a slice of key lime pie at Blue Heaven (~$8)
- Stroll through colorful Bahama Village
🍽 Foodie Tip ~ Key West is full of happy hour bargains—think half-priced oysters, conch fritters, and mojitos!
🌤 Weather + Packing Tips ~ Expect it to be hot, humid, with the chance of afternoon rain.
✅ Light, breathable clothes
✅ Reef-safe sunscreen
✅ A poncho or travel umbrella
✅ Comfy sandals
✨ Final Thoughts ~ With a little planning and a spirit of adventure, Key West is a solo traveler’s paradise that blends culture, history, and island bliss—without breaking the bank. So pack your flip-flops, grab that travel insurance, and get ready to chase sunsets in one of Florida’s most magical corners!
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Soak up the sunshine and history of Key West with this gorgeous, done-for-you travel guide and editable trip planner bundle!
This 2-in-1 resource was designed for solo travelers, dream chasers, and planning lovers who want both inspiration and customization in one beautiful package.
📦 What’s Included:
PDF #1: Key West Travel Guide (18 pages)
✅ Pre-filled 3-day itinerary
✅ Lodging, food & activity recommendations
✅ Budget tracker & checklist pages
✅ Maps, photo spots, and insider tips
PDF #2: Editable Canva Trip Planner (33 pages)
✅ Fully blank version to customize your own trip
✅ Editable in free Canva account
✅ Reusable for future vacations
✅ Includes all trip sections: budget, bookings, restaurants, transportation, itinerary, etc.
💖 Why You’ll Love It:
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Combines done-for-you ease + custom planning power
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Professionally designed with a beachy, sophisticated vibe
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Fill in digitally or print and take it with you
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Perfect for bloggers, solo travelers, or thoughtful gifters
💬 How It Works:
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Click Add to Cart and complete checkout
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Receive an instant PDF download with:
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Your full 18-page Key West guide (non-editable, but includes fill-in sections)
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A clickable Canva link to access and edit your 33-page trip planner
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Open in Canva (free account OK!) and customize your own dream getaway
📌 Bonus Features:
✔️ Fill-in budgeting tables
✔️ Activity & attraction log
✔️ Photo inspiration prompts
✔️ Bucket list page
Licensing & Terms:
This is a digital product for personal use only. Redistribution, resale, or commercial use of the Canva template is prohibited. For collaborations or licensing inquiries, please email info@coastlineandcastles.com
💬 FAQs:
Q: Do I need Canva Pro to edit this?
Nope! A free Canva account is all you need.
Q: Can I reuse this planner for other trips?
Yes! The editable planner can be reused as many times as you like for personal use.
Q: Will I get a physical product?
No, this is a digital download only. Nothing will be shipped.