5 Quick Escapes from Miami Before the Holiday Rush
Travel by Stag & Stow Co.
Before the malls light up and the city hums with holiday chaos, there’s still time to breathe.
A few open roads, a short flight, and a small bag—that’s all it takes to reset. Whether it’s turquoise water, cobblestone streets, or a good café far from the grind, these five getaways give you space before the season hits full stride.
Above, you’ll find curated tours and experiences powered by GetYourGuide—handpicked to pair with each escape.
So grab your weekender, power down the inbox, and let the miles stretch
1. Islamorada, Florida Keys – Salt and Stillness
Why Go:
Just 90 minutes south of Miami, Islamorada feels like another country. The kind of quiet that only exists between the palms and the sea.
What to Do:
Ease into island time. Spend the morning out on the water with local captains who know every reef, or swing by Morada Bay Beach Café for sunset mojitos. When the light hits the horizon just right, you’ll understand why people never leave.
Where to Stay:
Check out stays like The Islander Resort or Cheeca Lodge & Spa through Expedia. Both capture that barefoot-luxury vibe—nothing fancy, just salt, sand, and peace.
What to Pack:
Bellroy Weekender — sleek, water-resistant, perfectly sized for two days of Keys living.
Peak Design Packing Cubes — to keep gear sorted after a beach morning.
Anker Zolo Magnetic Power Bank, 10,000mAh — because your phone shouldn’t die before the sunset does.
2. Naples, Florida – Gulfside Reset
Why Go:
Three hours west of Miami sits a different kind of coast—quiet, elegant, and calm. Naples trades city noise for Gulf breeze and golden evenings.
What to Do:
Explore Naples Pier or take a sunset sail through our [tour partner → “Naples Sailing Cruise” placeholder]. Stroll Fifth Avenue and stop for espresso at The Café on Fifth.
Where to Stay:
Find coastal stays like Edgewater Beach Hotel or The Inn on Fifth via Expedia → “Naples Hotels”.
What to Pack:
Filson 48-Hour Tin Cloth Duffle — built for durability.
Linen Button-Up Travel Shirt — breathable, stylish.
Leather Toiletry Bag for Men | Grooming Travel Kit | With Waterproof Lining | By Aaron Leather (Dark Brown)— to keep your essentials sharp.
3. St. Augustine, Florida – History with a View
Why Go:
Five hours north, St. Augustine blends Spanish charm with Atlantic salt. Cobblestone streets, balconies, and lanterns give it that lived-in beauty you can’t fake.
What to Do:
Book a historic walking tour or ghost tour via [tour partner → “Old Town Tours” placeholder]. End the night at Casa Reina Taqueria & Tequila.
Where to Stay:
Reserve your room at Casa Monica Resort & Spa or Marker 8 Hotel & Marina through Expedia→ “St. Augustine Hotels”.
What to Pack:
Sony α7 IV Mirrorless Camera — capture textures and light.
Lightweight Jacket — for evening strolls.
Anker Zolo Magnetic Power Bank, 10,000mAh — keeps your tech ready for night shots.
4. Nassau, Bahamas – Forty-Five Minutes to Paradise
Why Go:
In less than an hour, you can swap Miami traffic for Bahamian turquoise. Nassau isn’t just close—it’s a full reset.
What to Do:
Take a day trip to Exuma or Rose Island via [tour partner → “Bahamas Boat Adventure” placeholder]. Explore the Straw Market and hit Fish Fry at Arawak Cay.
Where to Stay:
Book premium stays like The Ocean Club or Baha Mar through Expedia→ “Nassau Hotels” placeholder.
What to Pack:
Bellroy Weekender — water-resistant and tough.
Quick-Dry Travel Shorts — perfect for salt and sun.
Waterproof Sandals — for coral trails and decks.
5. San Juan, Puerto Rico – Color, Café, and Cobblestones
Why Go:
No passport, no hassle—just rhythm, food, and sunlight. Old San Juan’s cobblestones pulse with music, espresso, and Caribbean color.
What to Do:
Book a culinary or rum distillery tour via [tour partner → “San Juan Food & Culture Experience” placeholder]. Take a side trip to El Yunque Rainforest for a quick hike.
Where to Stay:
Search O:LV Fifty Five or Hotel El Convento via Expedia → “San Juan Hotels”.
What to Pack:
Crossbody Sling Bag — lightweight and secure.
Anker Zolo Magnetic Power Bank, 10,000mAh — never lose a beat.
Linen Button-Up Travel Shirt — cool comfort for day or night.
Final Thoughts
There’s no better time to recharge than before the rush. Each of these escapes offers just enough distance to clear your head and bring back calm before the season hits full stride. Pack light, travel slow, and let every sunrise remind you why you left the noise behind.
Get inspired. Explore with Stag & Stow Co.
