59 days in Florida, New York City & California Itinerary

59 days in Florida, New York City & California Itinerary

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59 days in Florida, New York City & California Itinerary

Helsinki
Fly + shuttle:  14​h 30​min
Key Largo
— 4 nights
Drive:  30​min
Islamorada
— 5 nights
Drive:  45​min
Marathon
— 5 nights
Drive:  1​h 15​min
Key West
— 6 nights
Fly + taxi:  2​h 45​min
Naples
— 5 nights
Drive:  1​h 15​min
Sanibel Island
— 5 nights
Drive:  2​h
Sarasota
— 6 nights
Drive:  3​h 15​min
Daytona Beach
— 5 nights
Drive:  1​h 15​min
St. Augustine
— 5 nights
Fly + train:  5​h 45​min
New York City
— 3 nights
bus + Fly + taxi:  10​h 30​min
Carmel
— 3 nights
Drive:  2​h 15​min
San Simeon
— 2 nights
+3
bus + Fly + tram + bus:  13​h 15​min
Miami Beach
— 3 nights
bus + tram + Fly:  14​h
Helsinki

4
days
Key Largo

The northernmost island of the Florida Keys, Key Largo provides stunning scenery, a number of watersports opportunities, and plenty of areas to relax on vacation.
Get outdoors at Florida Keys Wild Bird Rehabilitation Center and Nature & Wildlife Tours. You'll discover tucked-away gems like Swim with Dolphins and Robert Is Here Fruit Stand. Take a break from Key Largo with a short trip to Anhinga Trail in Everglades National Park, about 56 minutes away. The adventure continues: identify plant and animal life at Molasses Reef, stop by Shell World, admire all the interesting features of African Queen Canal Cruise, and discover the deep blue sea with a scuba or snorkeling tour.

To find where to stay, photos, maps, and more tourist information, you can read our Key Largo trip itinerary builder.

Helsinki, Finland to Key Largo is an approximately 14.5-hour flight. The time zone difference moving from Eastern European Time (EET) to Eastern Standard Time (EST) is minus 7 hours. In January, Key Largo is warmer than Helsinki - with highs of 27°C and lows of 17°C. Finish your sightseeing early on the 7th (Sun) so you can drive to Islamorada.

Things to do in Key Largo

Parks Wildlife Outdoors

Side Trips

Robert Is Here Fruit Stand, Anhinga Trail
Highlights from your plan
Anhinga Trail

5
days
Islamorada

Islamorada, long recognized as one of the world's top spots for sport fishing, encompasses six islands in the Florida Keys.
Get in touch with nature at Windley Key Fossil Reef Geological State Park and Parasailing & Paragliding. Get some cultural insight at History of Diving Museum and Michelle Nicole Lowe Art Gallery. The adventure continues: paddle through the water with a kayaking and canoeing tour, fulfill a lifelong dream with a swim-with-the-dolphins experience, get a new perspective on things with Robbie's of Islamorada, and tour the water at your own pace with Spray Watersports.

To find reviews, where to stay, other places to visit, and tourist information, read our Islamorada holiday planner.

Islamorada is just a short distance from Key Largo. Expect a bit warmer evenings in Islamorada when traveling from Key Largo in January, with lows around 20°C. Finish your sightseeing early on the 12th (Fri) so you can drive to Marathon.

Things to do in Islamorada

Outdoors Tours Wildlife
Highlights from your plan
A Lil' Tail Charters
History of Diving Museum

4
days
Marathon

A tiny city just 16 km (10 mi) long, Marathon is spread across several islands in the middle of the Florida Keys.
Relax by the water at Sombrero Beach and Bahia Honda State Park. Explore hidden gems such as Dolphin Research Center and Crane Point Museum & Nature Center. Go for a jaunt from Marathon to Big Pine Key to see National Key Deer Refuge about 34 minutes away. The adventure continues: snap pictures at Seven Mile Bridge, tour the water at your own pace with All Aboard Boat Rentals, tour the pleasant surroundings at Sunset Park Beach, and identify plant and animal life at The Turtle Hospital.

For photos, maps, reviews, and tourist information, read our Marathon custom trip planner.

You can drive from Islamorada to Marathon in an hour. Other options are to take a shuttle; or take a bus. In January, daily temperatures in Marathon can reach 28°C, while at night they dip to 21°C. Finish up your sightseeing early on the 17th (Wed) so you can go by car to Key West.

Things to do in Marathon

Parks Outdoors Wildlife

Side Trips

Big Pine Key, Sunset Park Beach
Highlights from your plan
Sombrero Beach
Dolphin Research Center
Scuba & Snorkeling

7
days
Key West

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.
Get a sense of the local culture at Key West Lighthouse and Keeper's Quarters Museum and Audubon House & Tropical Gardens. Eschew the tourist crowds and head to Stand-Up Paddleboarding and Waterskiing & Jetskiing. Spend the 18th (Thu) exploring nature at Dry Tortugas National Park. There's still lots to do: soothe aching muscles at some of the top local wellness centers, admire the majestic nature at Fort Zachary Taylor, stop by Rodriguez Cigar Factory, and take in the exciting artwork at Key West Pottery.

For traveler tips, more things to do, and other tourist information, use the Key West trip itinerary planner.

Getting from Marathon to Key West by car takes about 1.5 hours. Other options: take a bus. In January, daily temperatures in Key West can reach 28°C, while at night they dip to 22°C. Wrap up your sightseeing on the 23rd (Tue) early enough to travel to Naples.

Things to do in Key West

Outdoors Tours Adventure
Highlights from your plan
Fort Zachary Taylor
Waterskiing & Jetskiing
Stand-Up Paddleboarding

5
days
Naples

Naples is a city in Collier County, Florida, United States. Fifth Avenue South and Third Street South are good opportunities to explore the local culture. You'll discover tucked-away gems like Barefoot Beach Preserve and Lowdermilk Beach. You'll find plenty of places to visit near Naples: Miromar Outlets (in Estero) and Marco Island (Waterskiing & Jetskiing, South Marco Beach, & more). There's lots more to do: look for all kinds of wild species at Audubon Corkscrew Swamp Sanctuary, look for gifts at Waterside Shops, kick back and relax at Keewaydin Island, and take in the waterfront at Naples Pier.

To find where to stay, reviews, traveler tips, and other tourist information, you can read our Naples trip itinerary builder.

You can do a combination of flight and taxi from Key West to Naples in 3 hours. Alternatively, you can do a combination of ferry and taxi; or drive. Traveling from Key West in January, you can expect nighttime temperatures to be a bit cooler in Naples, with lows of 16°C. Finish your sightseeing early on the 28th (Sun) so you can drive to Sanibel Island.

Things to do in Naples

Parks Outdoors Beaches

Side Trips

Marco Island, Barefoot Beach Preserve, Miromar Outlets
Highlights from your plan
Barefoot Beach Preserve
Waterskiing & Jetskiing
Tigertail Beach

5
days
Sanibel Island

You'll explore the less-touristy side of things at Captiva Beach and Blind Pass Beach Park. For shopping fun, head to Sanibel Island Farmer's Market or B Unique Boutique. Change things up with these side-trips from Sanibel Island: Edison and Ford Winter Estates (in Fort Myers) and Fort Myers Beach (Fort Myers Beach & Lovers Key State Park).

To find photos, maps, ratings, and tourist information, use the Sanibel Island trip builder.

Getting from Naples to Sanibel Island by car takes about 1.5 hours. January in Sanibel Island sees daily highs of 28°C and lows of 15°C at night. Cap off your sightseeing on the 2nd (Fri) early enough to go by car to Sarasota.

Things to do in Sanibel Island

Parks Outdoors Beaches

Side Trips

Fort Myers Beach, Edison and Ford Winter Estates, Captiva Beach
Highlights from your plan
Bowman's Beach
Captiva Beach
Blind Pass Beach Park

6
days
Sarasota

Sarasota is a city located in Sarasota County on the southwestern coast of the U.S. Escape the urban bustle at Bean Point and Caspersen Beach. Do some cultural sightseeing at Marie Selby Botanical Gardens and The Ringling. Get out of town with these interesting Sarasota side-trips: Madeira Beach (My Sandbox & John's Pass Village and Boardwalk), The Dalí Museum (in St. Petersburg) and Saint Pete Beach (in St. Pete Beach). And it doesn't end there: immerse yourself in nature at Stump Pass Beach State Park, make a trip to St. Armands Circle Association, kick back and relax at Venice Beach, and tour the pleasant surroundings at Siesta Beach.

For traveler tips, where to stay, maps, and other tourist information, read our Sarasota travel itinerary planner.

You can drive from Sanibel Island to Sarasota in 2 hours. Another option is to do a combination of taxi and bus. In February in Sarasota, expect temperatures between 27°C during the day and 15°C at night. On the 8th (Thu), wrap the sightseeing up by early afternoon so you can drive to Daytona Beach.

Things to do in Sarasota

Parks Outdoors Beaches

Side Trips

Siesta Key, Madeira Beach, Venice, Bean Point, Stump Pass Beach State Park
Highlights from your plan
Siesta Beach
Bean Point
Caspersen Beach

4
days
Daytona Beach

The iconic seaside destination of Daytona Beach once supported sugar mill plantations, but now entertains up to 8 million visitors a year.
Step off the beaten path and head to Merritt Island National Wildlife Refuge and Mount Dora Olive Oil Company. For shopping fun, head to Angell & Phelps Chocolate Factory or Orlando International Premium Outlets. Explore the numerous day-trip ideas around Daytona Beach: Disney Springs (in Orlando), BOXELDER (in Sanford) and Stetson Mansion (in DeLand). The adventure continues: admire all the interesting features of Ponce de Leon Inlet Lighthouse & Museum and enjoy the sand and surf at Beach at Daytona Beach.

To see other places to visit, reviews, maps, and more tourist information, use the Daytona Beach sightseeing planner.

Traveling by car from Sarasota to Daytona Beach takes 3.5 hours. Alternatively, you can do a combination of bus and flight; or do a combination of bus and shuttle. Traveling from Sarasota in February, Daytona Beach is little chillier at night with lows of 11°C. Cap off your sightseeing on the 13th (Tue) early enough to go by car to St. Augustine.

Things to do in Daytona Beach

Shopping Parks Outdoors

Side Trips

Orlando, Ponce de Leon Inlet Lighthouse & Museum, Stetson Mansion, Merritt Island National Wildlife Refuge, BOXELDER
Highlights from your plan
Disney Springs
Stetson Mansion

5
days
St. Augustine

St. Get outdoors at Fort Matanzas National Monument and St. Augustine Beach. Give yourself a bit of retail therapy at Claude's Chocolate and Market To Market. There's still lots to do: see the interesting displays at Lightner Museum, learn about winemaking at San Sebastian Winery, enjoy the sea views from St. Augustine Lighthouse & Maritime Museum, and admire all the interesting features of Flagler College.

To find reviews, more things to do, traveler tips, and other tourist information, go to the St. Augustine tour planner.

Traveling by car from Daytona Beach to St. Augustine takes 1.5 hours. Alternatively, you can take a bus. Expect a daytime high around 22°C in February, and nighttime lows around 11°C. Finish your sightseeing early on the 18th (Sun) so you can travel to New York City.

Things to do in St. Augustine

Parks Historic Sites Nature
Highlights from your plan
Fort Matanzas National Monument
Lightner Museum

2
days
New York City

Writer Pearl Buck once called New York City “a place apart,” and this giant urban center remains unlike any other in the world.
On the next day, get a taste of the local shopping with Fifth Avenue and then revel in the low prices at Woodbury Common Premium Outlets.

To find reviews, ratings, where to stay, and other tourist information, go to the New York City custom trip planner.

You can do a combination of flight and train from St. Augustine to New York City in 6 hours. Other options are to drive; or do a combination of taxi and bus. In February, New York City is cooler than St. Augustine - with highs of 8°C and lows of -1°C. Finish up your sightseeing early on the 21st (Wed) so you can travel to Carmel.

Things to do in New York City

Shopping Museums Neighborhoods

Side Trip

Woodbury Common Premium Outlets
Highlights from your plan
Woodbury Common Premium Outlets
Fifth Avenue
St. Patrick's Cathedral

3
days
Carmel

Carmel-by-the-Sea, often simply referred to as Carmel, is a city in Monterey County, California, United States, founded in 1902 and incorporated on October 31, 1916. Ocean Avenue and Scheid Vineyards are good opportunities to explore the local culture. Discover out-of-the-way places like Julia Pfeiffer Burns State Park and McWay Falls. Get out of town with these interesting Carmel side-trips: Big Sur (Pfeiffer State Beach & Partington Cove). Next up on the itinerary: kick back and relax at Carmel City Beach/Carmel River Beach, look for all kinds of wild species at Point Lobos State Reserve, stop by The Cheese Shop, and stroll through Carmel River State Beach.

To find traveler tips, more things to do, other places to visit, and more tourist information, use the Carmel travel itinerary creator.

Getting from New York City to Carmel by combination of bus, flight, and taxi takes about 10.5 hours. Other options: drive; or do a combination of train and bus. The time zone changes from Eastern Standard Time (EST) to Pacific Standard Time (PST), which is usually a -3 hour difference. Expect a bit warmer temperatures when traveling from New York City in February; daily highs in Carmel reach 20°C and lows reach 8°C. Finish your sightseeing early on the 24th (Sat) to allow enough time to drive to San Simeon.

Things to do in Carmel

Parks Outdoors Beaches

Side Trip

Big Sur
Highlights from your plan
Point Lobos State Reserve
Pfeiffer State Beach

1
day
San Simeon

When you arrive in tiny San Simeon, which lies halfway between San Francisco and Los Angeles, you can see why William Randolph Hearst chose this coastal locale for his famous hilltop castle.
Kick off your visit on the 25th (Sun): stop by Red Moose Cookie Company, look for all kinds of wild species at Elephant Seal Rookery, then look for gifts at Sebastian General Store, and finally explore the historical opulence of Friends of Hearst Castle.

To see other places to visit, maps, more things to do, and other tourist information, you can read our San Simeon travel itinerary planner.

Drive from Carmel to San Simeon in 2.5 hours. Alternatively, you can take a bus. While traveling from Carmel, expect a bit cooler days and about the same nights in San Simeon, ranging from highs of 16°C to lows of 11°C. Wrap up your sightseeing on the 26th (Mon) early enough to travel to Miami Beach.

Things to do in San Simeon

Parks Wildlife Shopping

Side Trip

Red Moose Cookie Company
Highlights from your plan
Sebastian General Store
Friends of Hearst Castle
Red Moose Cookie Company

3
days
Miami Beach

Separated by water from the neighboring city of Miami, Miami Beach sits on a barrier island between Biscayne Bay and the Atlantic Ocean.
Get a sense of the local culture at Espanola Way and Collins Avenue. You'll get in some beach time at Hollywood Beach and Fort Lauderdale Beach. Explore the numerous day-trip ideas around Miami Beach: Dolphin Mall (in Miami) and Sawgrass Mills (in Sunrise). Next up on the itinerary: admire the landmark architecture of Art Deco Historic District, get a taste of the local shopping with Bayside Marketplace, and wander the streets of Ocean Drive.

To find traveler tips, ratings, other places to visit, and tourist information, go to the Miami Beach sightseeing planner.

Traveling by combination of bus, flight, and tram from San Simeon to Miami Beach takes 13.5 hours. Alternatively, you can drive. Due to the time zone difference, you'll lose 3 hours traveling from San Simeon to Miami Beach. Traveling from San Simeon in February, expect nights in Miami Beach to be a bit warmer, around 20°C, while days are warmer, around 30°C. Finish your sightseeing early on the 1st (Thu) so you can travel back home.

Things to do in Miami Beach

Shopping Parks Outdoors

Side Trips

Miami, Fort Lauderdale Beach, Sawgrass Mills, Hollywood Beach
Highlights from your plan
Ocean Drive
Hollywood Beach
Fort Lauderdale Beach

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