I’ve taken 40+ weekend trips from Miami since 2019. Miami has the unique advantage of both Florida road trips AND short Caribbean flights within weekend range. Here’s the honest ranking.
The TL;DR
Best 2-hour drive: Florida Keys (Islamorada or Marathon). Calm Caribbean-style water, fresh seafood.
Best quick flight: Bahamas (Nassau or Exuma — 35 min flight). Cheaper than the Keys.
Best Florida nature: Naples + Everglades (2 hours). Wildlife + Gulf Coast beaches.
Best historic: St. Augustine (4 hours). Oldest continuously-inhabited European city in US.
Best for couples: Bahamas Out Islands (Exuma, Eleuthera).
The 12 trips ranked
1. Florida Keys (Islamorada + Marathon) — 90 min – 3 hours
Stay: Cheeca Lodge (Islamorada), Hawks Cay Resort (Marathon), Tranquility Bay
Do: Snorkel at John Pennekamp State Park, swim with dolphins at Theater of the Sea, eat fresh stone crab at Keys Fisheries, sunset at Robbie’s (feed tarpons)
Skip: Key West unless you want party vibe
2. Nassau, Bahamas — 35 min flight
Stay: Atlantis (kid-friendly), Sandals Royal Bahamian (couples)
Do: Paradise Island beaches, swim with pigs at Pig Beach (book ferry), conch salad at Potter’s Cay, stunning Junkanoo culture
3. Naples + Everglades — 2 hours
Stay: Naples Bay Resort, La Playa Beach Resort
Do: Everglades airboat tours, Naples Pier sunset, shopping on 5th Avenue South, Marco Island day trip, kayak the Ten Thousand Islands
4. Bimini, Bahamas — 30 min flight or 2 hour ferry
Stay: Resorts World Bimini
Do: Swim with stingrays + nurse sharks at Honeymoon Harbor, snorkel at Three Sisters Rocks, walk barefoot on white sand
5. St. Augustine — 4 hours
Stay: Casa Monica Hotel, The Collector Inn
Do: Castillo de San Marcos (oldest masonry fort in US), walk historic district, Lightner Museum, ghost tours, eat at Catch 27
6. Tampa + St. Petersburg — 4 hours
Stay: The Don CeSar (pink palace), Hotel Haya
Do: Salvador Dali Museum (largest collection outside Spain), Tampa Bay Lightning game, Ybor City Cuban food (Columbia Restaurant), St. Pete beaches
7. Orlando — 3.5 hours
Stay: Universal hotels (Hard Rock, Royal Pacific), Disney Springs hotels
Do: Theme parks (Universal, Disney World, Volcano Bay), eat at Disney Springs, escape rooms
Note: Best as 3-night minimum if doing parks
8. Tulum, Mexico — 90 min flight
Stay: Casa Malca, Be Tulum
Do: Tulum Ruins overlooking the ocean, cenote swimming (Gran Cenote, Cenote Calavera), beachfront yoga
Warning: Tulum has gotten expensive + sargassum problems. Consider Riviera Maya alternatives.
9. Exuma, Bahamas — 90 min flight
Stay: Grand Isle Resort, vacation rentals
Do: Swim with pigs (the actual famous Pig Beach), Thunderball Grotto snorkeling, exploring 365 cays
10. Sanibel + Captiva Islands — 3 hours
Stay: Sundial Beach Resort, South Seas Island Resort
Do: Famous shelling on Sanibel beaches, J.N. Ding Darling National Wildlife Refuge, bike Sanibel
Note: Hurricane Ian damaged some areas; check current conditions.
11. Eleuthera + Harbour Island, Bahamas — 90 min flight
Stay: The Cove Eleuthera, The Dunmore (Harbour Island)
Do: Pink Sands Beach (truly pink), Glass Window Bridge, Lighthouse Beach, golf cart explore
12. Havana, Cuba — 60 min flight (special travel rules apply)
Travel restrictions: US travelers must qualify under support-for-Cuban-people category and document compliance
Stay: Hotel Saratoga, casa particulares
Do: Old Havana walking tour, 1950s American car tour, Hemingway sites, mojitos at La Bodeguita del Medio
Trips not worth the drive from Miami
- Atlanta (10 hours): Fly
- New Orleans (13 hours): Fly
- Sarasota (4 hours): Doable but Naples is better same drive
FAQs
What’s the best weekend getaway from Miami?
Florida Keys (Islamorada or Marathon, 90 min – 3 hours) for Caribbean-style water without leaving the US. Bahamas Nassau (35 min flight) for actual Caribbean at similar cost. Naples + Everglades (2 hours) for Florida Gulf Coast + wildlife.
Can I fly to the Bahamas for a weekend from Miami?
Yes – flights to Nassau are 35 minutes, to Bimini 30 minutes, to Exuma 90 minutes. Many Bahamian destinations are easier to access for a weekend from Miami than driving down the Florida Keys.
Do I need a passport for weekend trips from Miami?
For Bahamas, Cuba, Mexico (Tulum) – yes. For Florida destinations (Keys, Naples, Orlando, St. Augustine, Tampa) – no. The Keys offer Caribbean vibes without passport requirements.
What’s the cheapest weekend trip from Miami?
Naples ($150-250/night, 2 hours), Florida Keys’ upper region like Key Largo ($180-300/night, 90 min), or Tampa ($150-250/night, 4 hours). For Caribbean: Bahamas all-inclusives often beat Florida Keys on cost.
When should I avoid Miami weekend trips?
Hurricane season (June-November, peak August-October) brings weather risk for both Florida and Caribbean destinations. December-April is peak season – expect crowds and 30-50% higher hotel rates.
Frequently Asked Questions
What’s the best weekend getaway from Miami?
Florida Keys (Islamorada or Marathon, 90 min – 3 hours) for Caribbean-style water without leaving the US. Bahamas Nassau (35 min flight) for actual Caribbean at similar cost. Naples + Everglades (2 hours) for Florida Gulf Coast + wildlife.
Can I fly to the Bahamas for a weekend from Miami?
Yes – flights to Nassau are 35 minutes, to Bimini 30 minutes, to Exuma 90 minutes. Many Bahamian destinations are easier to access for a weekend from Miami than driving down the Florida Keys.
Do I need a passport for weekend trips from Miami?
For Bahamas, Cuba, Mexico (Tulum) – yes. For Florida destinations (Keys, Naples, Orlando, St. Augustine, Tampa) – no. The Keys offer Caribbean vibes without passport requirements.
What’s the cheapest weekend trip from Miami?
Naples ($150-250/night, 2 hours), Florida Keys’ upper region like Key Largo ($180-300/night, 90 min), or Tampa ($150-250/night, 4 hours). For Caribbean: Bahamas all-inclusives often beat Florida Keys on cost.
When should I avoid Miami weekend trips?
Hurricane season (June-November, peak August-October) brings weather risk for both Florida and Caribbean destinations. December-April is peak season – expect crowds and 30-50% higher hotel rates.