10 days in Hollywood, Islamorada & Key West Itinerary

10 days in Hollywood, Islamorada & Key West Itinerary

Created using Inspirock Florida tour itinerary planner

Plan created by another user. Make it yours
Fly
1
Hollywood
— 2 nights
Drive
2
Islamorada
— 2 nights
Drive
3
Key West
— 5 nights
Fly

S M T W T F S
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
1
2
3
4
5
6

2
nights
Hollywood

Diamond of the Gold Coast

The city of Hollywood is a classic Florida beach town and popular vacation spot, attracting visitors with its picturesque beaches, lively nightlife, and laid-back vibe.
Kick off your visit on the 22nd (Fri): enjoy the sand and surf at Fort Lauderdale Beach Park, then identify plant and animal life at Anne Kolb Nature Center, and then enjoy the sand and surf at Hollywood Beach. Keep things going the next day: examine the collection at Morikami Museum & Japanese Gardens, identify plant and animal life at Gumbo Limbo Nature Center, and then examine the collection at Lock & Load Museum.

For maps, reviews, ratings, and other tourist information, you can read our Hollywood trip builder tool.

New York City to Hollywood is an approximately 6-hour flight. You can also drive; or take a bus. Prepare for somewhat warmer weather when traveling from New York City in May: high temperatures in Hollywood hover around 86°F and lows are around 74°F. You will have some time to spend on the 24th (Sun) before leaving for Islamorada.

Things to do in Hollywood

Parks · Beaches · Outdoors · Wildlife

Side Trips

Find places to stay May 22 — 24:
Highlights from your trip

2
nights
Islamorada

The Village of Islands

Islamorada, long recognized as one of the world's top spots for sport fishing, encompasses six islands in the Florida Keys.
On the 24th (Sun), look for gifts at Bella Sol Fragrance Bar and Gifts and then identify plant and animal life at Alligator Reef Light House. Get ready for a full day of sightseeing on the 25th (Mon): zoom along the surf with a waterskiing or jet-skiing adventure, then take an in-depth tour of History of Diving Museum, and then get interesting insight from Tours.

To see reviews, photos, more things to do, and tourist information, refer to the Islamorada route planner.

Traveling by car from Hollywood to Islamorada takes 2.5 hours. Alternatively, you can do a combination of train and bus; or take a bus. In May, daily temperatures in Islamorada can reach 88°F, while at night they dip to 77°F. On the 26th (Tue), you'll have the morning to explore before heading off to Key West.

Things to do in Islamorada

Adventure · Outdoors · Tours · Museums
Find places to stay May 24 — 26:
Highlights from your trip

5
nights
Key West

Conch Republic

Located just 140 km (90 mi) from Cuba, Key West is an island only about 6.4 km (4 mi) long and 1.6 km (1 mi) wide.
Your cultural itinerary includes sights like The Ernest Hemingway Home and Museum and Key West Garden Club. Get some historical perspective at Saint Mary Star of the Sea and West Martello Tower. Go for a jaunt from Key West to Big Pine Key to see Bahia Honda State Park about 50 minutes away. And it doesn't end there: glide peacefully along the water with some of the best stand-up paddleboarding in the area, stroll the grounds of Key West Cemetery, see the vivid underwater world at Vandenberg Wreck, and fly like a bird with a parasailing or paragliding tour.

For photos, more things to do, traveler tips, and other tourist information, you can read our Key West journey planner.

Getting from Islamorada to Key West by car takes about 2 hours. Other options: take a bus. In May, daily temperatures in Key West can reach 85°F, while at night they dip to 77°F. You'll have a few hours on the 31st (Sun) to wrap things up before traveling home.

Things to do in Key West

Outdoors · Tours · Wildlife · Parks

Side Trip

Find places to stay May 26 — 31:
Highlights from your trip
Vandenberg Wreck ©
Must see
Vandenberg Wreck
4.8

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