My Florida Vacation: The Starting Itinerary
Below is a sample itinerary designed to inspire your journey. All elements — from accommodations to experiences — can be tailored to match your travel style and preferences.
Day 1: Arrival in Miami → Upper Florida Keys (Key Largo / Islamorada area)
Today is designed to be flexible depending on your arrival plans.
- Arriving in Miami today: pick up your rental SUV at the airport and begin driving south toward the Florida Keys, passing through the gateway town of Homestead before reaching the Upper Keys.
- Already in Miami: pick up your vehicle in the morning and head straight to the Keys for a more relaxed start.
We recommend spending part of the afternoon in the
Key Largo / Islamorada area—ideal for an easy first taste of island life. Optional add-ons can include a snorkeling excursion, a private or shared sunset cruise, or simply a slow-paced beach-and-dining evening.
Night: Upper Florida Keys (Key Largo / Islamorada area), 4-star superior coastal resort (preferred network), with an optional upgrade to a more exclusive boutique or luxury waterfront stay where available.
Day 2: Upper Keys → Key West
Drive south along the legendary
Overseas Highway, one of the most scenic routes in the U.S. The journey itself is part of the experience, with turquoise views, island-to-island bridges, and plenty of opportunities for photo stops and short breaks along the way.
Arrive in
Key West by early afternoon and enjoy the island at your own pace. Depending on your interests, you may explore the historic district, browse galleries and shops, or focus on the classic landmarks (Hemingway’s legacy, the lighthouse area, and Duval Street). Key West also offers a lively but relaxed evening atmosphere with local bars and live music.
Driving guide (approx.): ~2 hr 45 min / 128 miles (206 km), plus stops
Night: Key West, 4-star superior boutique hotel or resort (preferred network), with an optional upgrade to 5-star luxury.
Day 3: Key West → Everglades area → Marco Island (Gulf Coast)
Enjoy a relaxed morning in Key West to finish any sightseeing or simply take in the island rhythm. Then begin driving back north before turning west across Florida toward the Gulf Coast.
In the afternoon, plan time for the
Everglades—a dramatic change of scenery that adds a true nature-and-wildlife chapter to the trip. Optional experiences can include an airboat ride or a guided eco tour, depending on your preferred style (adventure-forward or comfort-forward).
Continue on to
Marco Island, where the Gulf Coast portion of the itinerary begins—known for calmer waters, sunset beaches, and a more resort-style pace.
Night: Marco Island area, 4-star superior beachfront resort (preferred network), with an optional upgrade to luxury.
Day 4: Marco Island → Sanibel area → Sarasota
Today is all about Florida’s
Gulf Coast—calmer waters, bright sand, and a completely different atmosphere from the Atlantic side. You’ll travel north from Marco Island toward the
Sanibel / Captiva area, then continue to
Sarasota, a stylish coastal town known for its walkable center, dining, and a more relaxed, refined pace.
We recommend choosing s
cenic coastal roads whenever possible, even if they take longer. The Gulf shoreline is best experienced slowly, with the freedom to stop for beach time, short walks, and spontaneous viewpoints.
Driving guide (approx.):
- Marco Island → Sanibel area: ~1 hr 30 min / 65 miles (105 km)
- Sanibel area → Sarasota: ~1 hr 50 min / 104 miles (167 km)
In the evening, enjoy Sarasota’s waterfront ambiance and a well-planned dinner (we can suggest areas based on your hotel location and preferred vibe).
Night: Sarasota area, 4-star superior coastal hotel or resort (preferred network) or boutique waterfront stay for added character.
Day 5: Sarasota → Longboat Key → St. Petersburg → Clearwater
Another day dedicated to the Gulf Coast, designed for a balance of
island scenery, culture, and beach time. From Sarasota, consider a coastal route via Longboat Key and, if you’d like, continue toward
Anna Maria Island for a classic Florida beach-town feel.
Later, head toward St. Petersburg for an arts-and-culture pause—many travelers enjoy dedicating time to the
Salvador Dalí Museum and a stroll through the downtown waterfront area. If you prefer nature and beaches,
Fort De Soto Park is a beautiful option before continuing on to Clearwater.
End the day with one of the most iconic simple pleasures of this itinerary: sunset on Clearwater Beach.
Driving guide (approx.): Sarasota → Clearwater ~1 hr 50 min / 76 miles (122 km), plus detours and stops
Night: Clearwater area, 4-star superior beachfront hotel or resort (preferred network)
Day 6: Clearwater → Crystal River → Orlando
Today you’ll make a short detour north before heading inland to Orlando. This route is ideal for travelers interested in the Crystal River area—one of Florida’s best-known places for
manatee encounters (seasonal), along with calm waterways and nature-focused excursions.
After your Crystal River experience, continue to
Orlando. The remainder of the drive is comfortable and keeps you well positioned for the next chapter of the itinerary—whether you’re focusing on theme parks, family-friendly attractions, shopping, dining, or simply using Orlando as a convenient base.
Driving guide (approx.):
- Clearwater → Crystal River: ~1 hr 40 min / 90 miles (145 km)
- Crystal River → Orlando: ~1 hr 40–2 hrs / ~90 miles (145 km)
Night: Orlando, 4-star superior resort (preferred network), with an optional upgrade to 5-star luxury. We recommend one of the luxury Disney Hotels for those looking for a Disney-themed stay with special perks.
Day 7–8: Orlando
Spend the next two days in Orlando, tailored around the theme parks and experiences that best match your travel style. You can focus on
Disney or
Universal, or combine both with a smart plan that balances park time with comfort and downtime—especially important for families traveling with children.
If you’d like a slower pace (or want to add water parks, shopping, or special experiences), we can easily extend the Orlando stay with additional nights.
Night: Orlando, 4-star superior resort (preferred network), with an optional upgrade to 5-star luxury. We recommend one of the luxury Disney Hotels for those looking for a Disney-themed stay with special perks.
Day 9: Orlando → Kennedy Space Center area → Merritt Island (Atlantic Coast)
Today you’ll return to Florida’s Atlantic side with a signature stop at the
Kennedy Space Center—a fascinating experience even for travelers who don’t consider themselves “space enthusiasts.” Plan for several hours here to enjoy the exhibits and the scale of the launch facilities.
In the afternoon, continue to the
Merritt Island area, known for its natural scenery and wildlife-rich landscapes. This adds a peaceful contrast to the energy of Orlando and sets up a relaxing coastal evening.
Night: Merritt Island / Melbourne area, 4-star superior hotel (preferred network). We can prioritize a coastal-style property with a more boutique feel.
Day 10: Melbourne → West Palm Beach → Miami (End of service)
Head south back to Miami. You can choose the faster inland route, or take a more scenic coastal drive and stop along the way whenever the mood strikes.
A refined mid-day stop option is
West Palm Beach, a polished coastal town known for its upscale ambiance, shopping, and palm-lined streets—ideal for a relaxed lunch and a short stroll before continuing to Miami.
Arrive in Miami by late afternoon, return the vehicle, and conclude services.
End of service.
Optional extension: add a
3-night Miami stay at the end of the itinerary (upscale beachside or lifestyle-luxury style, depending on your preference).
Route overview: My Florida Vacation at a glance
Let’s design your FLORIDA Journey
From the turquoise drives of the Florida Keys to the calm, sunset-facing beaches of the Gulf Coast, this itinerary is built to show you the Florida most travelers miss. Along the way, we blend iconic highlights with natural escapes—from Everglades landscapes and coastal island-hopping to a perfectly paced finish that can include Orlando and the Atlantic-side contrast of the Space Coast.
No two travelers experience Florida the same way, and that’s exactly how we plan it. We tailor the route, hotel style, and day-to-day rhythm to match your travel personality—whether you want an upscale, family-friendly road trip with easy logistics and smart pacing, or a more luxury, lifestyle-focused escape for couples with upgraded stays, dining, and curated experiences.
If Orlando is part of your plan, we can also assist with theme park tickets and planning support for Disney and Universal, including timing strategy and upgrade options depending on what kind of park days you want.
Ready to start planning? Share your preferred travel dates and style, and we’ll craft a personalized Florida road trip designed around your priorities.
