Islamorada day trip itinerary, planned by mile marker

Islamorada is a strip of islands along US 1, so the easiest day trip runs in one direction and never doubles back. The Village says it stretches from Mile Marker 90.0 to Mile Marker 72.6. Below is a north-to-south plan using hours and fees the operators posted when we checked on October 21, 2026, and a planner that puts any stops you choose in mile-marker order. We give no drive times because we have not sourced any.

• The Village says Islamorada sits in the middle of the Florida Keys, between Mile Marker 90.0 and Mile Marker 72.6 on U.S. Highway 1. Islamorada, Village of Islands: Why Islamorada Matters

Build your own day

Decision tool · day planner

Plan your day in Islamorada

Pick how long you have and what you like. The planner chooses sourced stops along US 1 in Islamorada and puts them in order from the Hurricane Monument at MM 81.5, so you are not driving back and forth between the keys.

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Or start from one of three ready-made plans:

A morning on the water

Breakfast, the tarpon at Robbie's, then Anne's Beach and lunch on the dock.

1. Midway Cafe (80499 Overseas Hwy): An espresso bar with breakfast, pastries and lunch, open 7 a.m. to 2 p.m.
2. Robbie's of Islamorada (77522 Overseas Hwy): Hand-feed tarpon from the dock at MM 77.5 on Lower Matecumbe Key, with kayak and paddleboard rentals on site.
3. Anne's Beach (MM 73.5, Oceanside, Islamorada): The Village's oceanside beach at MM 73.5, open sunrise to sunset, with 300 feet of boardwalk and six pavilions.
4. Hungry Tarpon Restaurant (at Robbie's) (77522 Overseas Hwy Islamorada, FL 33036): The waterfront restaurant at Robbie's, MM 77.5, open 6:30 a.m. to 9 p.m.

The islands' story on land

The 1935 memorial, the diving museum, the fossil reef quarry and the discovery center.

1. Hurricane Monument (Florida Keys Memorial) (US 1 at Mile Marker 81.5): The 1937 Florida Keys Memorial at MM 81.5, listed on the National Register of Historic Places, for the people lost in the 1935 Labor Day hurricane.
2. History of Diving Museum (82990 Overseas Hwy): A non-profit museum of the history of diving on Upper Matecumbe Key; its site lists it open 10 to 5 daily.
3. Florida Keys History & Discovery Center (82100 Overseas Hwy): Aquariums, fishing and historical exhibits on the Islander Resort property, open Tuesday to Sunday, 10 a.m. to 5 p.m.
4. Windley Key Fossil Reef Geological State Park (84900 Overseas Highway): A former Flagler railroad quarry where you walk beside 8-foot quarry walls cut through ancient coral; open Thursday to Monday, 8 a.m. to 5 p.m.

Paddle, then a bayside evening

A mangrove-tunnel paddle, a small beach on the creek, then dinner by the bay.

1. Green Turtle Hammock Nature Preserve (MM 81.2, Bayside, Islamorada): Flat nature trails and a floating kayak launch through a mangrove tunnel at MM 81.2; open 8 a.m. to 5 p.m., free.
2. Library Beach Park (MM 81.5, Bayside, Islamorada): A small beach on a mangrove-lined creek at MM 81.5, open 8 a.m. to sunset.
3. Lorelei Restaurant and Cabana Bar (Mile Marker 82, Bayside): Look for the mermaid at MM 82, bayside: breakfast, lunch and dinner daily with views of Florida Bay, in its own words.

Every stop comes from our sourced list of places in Islamorada (checked October 21, 2026). Distances are straight-line estimates from OpenStreetMap coordinates, not driving routes along US 1. Time per stop is your chosen time split evenly, not an official duration. Check each place's hours before you go; Indian Key is left out while its dock is rebuilt.

Planning your next trip before this one ends? See what living in Islamorada is like.

Living in Islamorada

Check the day of the week first

• Tuesday and Wednesday close both Windley Key Fossil Reef Geological State Park and Lignumvitae Key Botanical State Park, which open Thursday through Monday only. Islamorada Fish Company is closed those days too.
• Monday the Florida Keys History & Discovery Center is closed (it opens Tuesday to Sunday, 10 a.m. to 5 p.m.).
• Friday to Sunday are the only days of the Lignumvitae Key ferry from Robbie’s Marina, 1 to 4 p.m.
• Third Wednesday of the month, the History of Diving Museum stays open late for its free 7 p.m. talk. On the third Thursday, the Morada Way Art Walk runs from 6 to 9 p.m.

• Florida State Parks says Windley Key Fossil Reef Geological State Park is open 8 a.m. to 5 p.m., Thursday through Monday, and closed Tuesday and Wednesday. Florida State Parks: Windley Key Fossil Reef Geological State Park, Hours & Fees
• Florida State Parks says Lignumvitae Key Botanical State Park is open 8 a.m. to 4 p.m., Thursday through Monday, and closed Tuesday and Wednesday. Florida State Parks: Lignumvitae Key Botanical State Park, Hours & Fees
• Florida State Parks says Florida Keys Boat Rentals at Robbie's Marina runs a ferry to Lignumvitae Key on Fridays, Saturdays and Sundays, 1 to 4 p.m., 305-664-5533. Florida State Parks: Lignumvitae Key Botanical State Park
• The museum hosts its free "Immerse Yourself!" presentation the 3rd Wednesday of every month at 7 pm, in person and on Zoom, with extended hours and last admission sold at 6:45 pm. History of Diving Museum: home page
• The Morada Way Arts & Cultural District says its Art Walk is every third Thursday of the month, 6 to 9pm, on Morada Way in Islamorada, and has run since 2011. Morada Way Arts & Cultural District: Art Walk Information

A north-to-south day

MM 87: Founders Park and the visitor center

The Islamorada Chamber of Commerce & Visitors Center is at 87100 Overseas Hwy, Mile Marker 87 bayside (305-664-4503). Founders Park, at 87000 Overseas Highway, is open from sunrise to sunset. It is free for Village residents and their guests, and its page lists non-resident entry at $10.00 for adults and $7.00 for ages 3 to 17 ($15.00 and $10.00 on summer weekends and holidays). Rain Barrel Village, a cluster of artisan studios and shops at 86700 Overseas Hwy, opens daily from 9 a.m. to 5 p.m., and it says its Betsy the Lobster is “believed to be the World’s Largest Lobster.”

• The Islamorada Chamber of Commerce & Visitors Center is at 87100 Overseas Hwy, Mile Marker 87 bayside, phone 305-664-4503 or 800-FAB-KEYS. Islamorada Chamber of Commerce: Holiday Fest 2026
• The Village describes Founders Park as 45 acres, open sunrise to sunset, the center of the Village park system. Islamorada, Village of Islands: Founders Park
• The Village says Village residents and their guests get free admission to Founders Park; park fees apply to non-Islamorada residents. Islamorada, Village of Islands: Founders Park Rules

MM 84.9 and MM 84.5: Windley Key

Windley Key Fossil Reef Geological State Park, at 84900 Overseas Highway, is open from 8 a.m. to 5 p.m., Thursday through Monday. Admission is $2.50 per person. Visitors walk along 8-foot-high walls in an old quarry that supplied Flagler’s Overseas Railroad. Theater of the Sea, at 84721 Overseas Hwy, is open from 9:15 a.m. to 5:00 p.m. Its general admission is $49.95 for ages 11 and up and $32.95 for ages 3 to 10. The last set of shows starts at 2:00, and parking is free.

• Windley Key Fossil Reef Geological State Park is at 84900 Overseas Highway, Islamorada FL 33036 (Mile Marker 84.9), phone 305-664-2540. Florida State Parks: Windley Key Fossil Reef Geological State Park
• Admission to Windley Key Fossil Reef Geological State Park is $2.50 per person. Florida State Parks: Windley Key Fossil Reef Geological State Park, Hours & Fees
• Florida State Parks says the Key Largo limestone here was sold to the Florida East Coast Railroad to build Flagler's Overseas Railroad, and the quarry produced decorative Keystone until the 1960s. Visitors walk along 8-foot-high quarry walls. Florida State Parks: Windley Key Fossil Reef Geological State Park
• Theater of the Sea lists park hours of 9:15 a.m. to 5:00 p.m.; the last set of shows starts at 2:00 and the last program at 4:25. Parking is free. Theater of the Sea: Show Schedule & Map
• Theater of the Sea lists general admission at $49.95 ages 11+, $32.95 ages 3 to 10, and free for ages 2 and under. Theater of the Sea: home page

MM 83 to MM 81.5: the museums and the Hurricane Monument

The History of Diving Museum, at 82990 Overseas Hwy, is open daily from 10 a.m. to 5 p.m. and charges $15 for adults. The Florida Keys History & Discovery Center, at 82100 on the Islander Resort property, lists $15.00 general admission. The Hurricane Monument stands at US 1 at MM 81.5, according to the National Park Service, which lists it in the National Register of Historic Places. We found no official page with visiting hours or parking for it. Library Beach Park, at MM 81.5 bayside, is open from 8 a.m. to sunset, with a small beach and a playground. The history page tells the story of the 1935 storm.

• The museum and store are open daily 10 am to 5 pm, except Thanksgiving, Christmas Day and New Year's Day. History of Diving Museum: Location & Hours
• The museum lists admission at $15 adults, $13 seniors 62+, $7 children 6 to 11, free for children 5 and under, $12 US veterans and $11 college students with ID; US active military are free. History of Diving Museum: Ticket Information
• The National Park Service lists the Florida Keys Memorial in the National Register of Historic Places under reference number 95000238, located at US 1 at Mile Marker 81.5 in Islamorada. National Park Service NPGallery: Florida Keys Memorial (NRIS 95000238)
• The National Park Service record for the Florida Keys Memorial gives its location and National Register details, but we did not find an official page with visiting hours or parking for the monument when we checked on October 21, 2026. National Park Service NPGallery: Florida Keys Memorial (NRIS 95000238)
• The Village lists Library Beach Park at MM 81.5 bayside, open 8 am to sunset, with a small beach, playground and pavilion; no dogs, no motor boats or PWC, no fishing. Islamorada, Village of Islands: Parks & Beaches

MM 81.2: a paddle from Green Turtle Hammock

Green Turtle Hammock Nature Preserve, at MM 81.2 bayside, is open 8 a.m. to 5 p.m. and is free. The Village says it has an ADA-accessible floating kayak launch that leads through a mangrove tunnel to Little Basin, plus a flat 0.4 mile loop trail. Leashed dogs are welcome. Details: the Village preserve page.

MM 77.5: Robbie’s

Robbie’s of Islamorada, at 77522 Overseas Hwy, Mile Marker 77.5 bayside, is open from 7 a.m. to 9 p.m. daily. Tarpon feeding costs $2.50 per person, plus $5 for each bucket of fish. Robbie’s also runs kayak and paddleboard rentals and boat rentals, and the Lignumvitae Key ferry leaves from Robbie’s Marina.

• Robbie's of Islamorada lists its address as 77522 Overseas Hwy, Islamorada, FL 33036, at Mile Marker 77.5 bayside. Robbie's of Islamorada: home page
• Robbie's posts tarpon feeding admission at $2.50 per person and $5 per bucket of fish; the tarpon dock is open daily 7 am to 9 pm. Robbie's of Islamorada: Feed the Tarpon
• Robbie's lists its hours as 7:00 am to 9:00 pm daily, with the Hungry Tarpon restaurant open 6:30 am to 9:00 pm. Robbie's of Islamorada: home page

MM 73.5: end at Anne’s Beach

Anne’s Beach, at MM 73.5 oceanside, is open from sunrise to sunset. It has 300 feet of boardwalk, six pavilions, a shallow swimming area with little to no wave action, and leashed dogs are allowed. The Village says no fishing and no open flame or grill. No lifeguards are mentioned, so you swim at your own risk.

• The Village lists Anne's Beach at MM 73.5 oceanside, open sunrise to sunset, with 300 feet of boardwalk and six pavilions; it reopened August 23, 2019 after Hurricane Irma. Leashed dogs are allowed. Islamorada, Village of Islands: Parks & Beaches
• The Village says Anne's Beach has little to no wave action and a shallow swimming area; no open flame or grill and no fishing. Islamorada, Village of Islands: Parks & Beaches

Indian Key is closed

Florida State Parks posts that, effective April 2026, Indian Key Historic State Park is completely closed to the public while contractors rebuild its dock, a project “slated to take up to six months.” When we checked, no reopening date had been posted. FWC also lists the Indian Key Fill ramp as temporarily closed for repairs. For the paddle out, see the Indian Key and Lignumvitae page.

• Florida State Parks posts: "Effective April 2026: Indian Key Historic State Park is completely closed to the public while contractors rebuild the Park's dock. The project is slated to take up to six months." Florida State Parks: Indian Key Historic State Park
• Florida State Parks said in April 2026 that Indian Key would be fully closed for up to six months while its dock is rebuilt; no reopening date was posted when we checked on October 21, 2026. Florida State Parks: Indian Key Historic State Park

Costs to budget, as the sources post them

• State parks: Windley Key $2.50 per person. Lignumvitae Key $2.50 per person plus a $2 tour fee. San Pedro preserve, no fee.
• Museums: History of Diving Museum $15 for adults. Florida Keys History & Discovery Center $15.00 general admission.
• Theater of the Sea: $49.95 for ages 11 and up, $32.95 for ages 3 to 10.
• Robbie’s: $2.50 per person at the tarpon dock, plus $5 a bucket.
• Getting around: Freebee costs $2 per rider (since July 2026).
• Fishing: an FWC non-resident saltwater license is $17 for 3 days, $30 for 7 days or $47 for a year. Anglers on a licensed charter are exempt, and so are anglers under 16.
• Staying over: Monroe County’s 5% Tourist Development Tax applies to stays of 6 months or less.

• Lignumvitae Key charges a $2.50 per person visitor fee and a $2 per person tour fee. Florida State Parks: Lignumvitae Key Botanical State Park, Hours & Fees
• San Pedro Underwater Archaeological Preserve State Park is open 8 a.m. to sunset, 365 days a year, with no fee. Florida State Parks: San Pedro Underwater Archaeological Preserve State Park
• The Village says Freebee is an on-demand electric rideshare across Islamorada at $2 per rider; the $2 fare was implemented in July 2026. Islamorada, Village of Islands: Ridesharing Services (Freebee)
• FWC lists non-resident saltwater fishing licenses at $47.00 annual, $17.00 for 3 days and $30.00 for 7 days. FWC: Recreational Saltwater Licenses & Permits
• FWC exempts anglers saltwater fishing from a for-hire vessel (guide, charter, party boat) with a valid charter license. FWC: Do I need a license or permit?
• FWC exempts youth under 16 from recreational fishing licenses and snook and lobster permits. FWC: Do I need a license or permit?
• The Monroe County Tax Collector says the Tourist Development Tax is 5% of the total rental amount for stays of 6 months or less in hotels, motels, condominiums, RV parks and similar lodging. Monroe County Tax Collector: Tourist Development Tax

Fishing from shore? FWC says you need a license if you cast a line, even for catch and release, and the Village bans fishing at Library Beach Park, Anne’s Beach and Founders Park. Fishing rules change, so check FWC before you go. Seasons are on the fishing page.

• FWC says that if you cast a line or catch and release, you need a fishing license. FWC: Do I need a license or permit?

Season and weather

The Atlantic hurricane season runs from June 1 to November 30, according to the National Hurricane Center. To see what is on and what is open on a given date, use the season and date checker. Places to eat and sleep are on the restaurants and where to stay pages.

• For the Keys, the season to plan around is the Atlantic hurricane season: June 1 through November 30 every year, as NOAA's National Hurricane Center defines it. NOAA National Hurricane Center: Tropical Cyclone Climatology

Islamorada day trip FAQ

Dates, rules and hours can change. The organisers have the final word: Village of Islamorada (official site)