30 days in New York City, Connecticut & Florida Itinerary
Created using Klarna Trips United States tour itinerary builder
Start: Rio de Janeiro
Fly
1
New York City
— 6 nights
Drive
2
New Haven
— 2 nights
Train to New York JFK, Fly to St. Augustine
3
St. Augustine
— 4 nights
Drive
4
Panama City Beach
— 3 nights
Drive
5
Pensacola
— 2 nights
Fly
6
Siesta Key
— 2 nights
Fly
7
Key West
— 5 nights
Drive
8
Marathon
— 2 nights
Drive
9
Islamorada
— 3 nights
Fly
End: Rio de Janeiro
Wed, May 17 - Thu, Jun 15
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View full calendar
New York City — 6 nights
©
Big Apple
Museum-lovers will appreciate The Metropolitan Museum of Art and New York Public Library. Shop till you drop at The Met Cloisters and Chelsea Market. There's still lots to do: explore the world behind art at The Museum of Modern Art (MoMA), get to know the fascinating history of Brooklyn Heights Promenade, visit Times Square, and examine the collection at Intrepid Sea, Air & Space Museum.
To find ratings, photos, maps, and tourist information, use the New York City visit planner.
Rio de Janeiro, Brazil to New York City is an approximately 13-hour flight. You'll gain 2 hours traveling from Rio de Janeiro to New York City due to the time zone difference. Traveling from Rio de Janeiro in May, expect New York City to be little chillier, temps between 24°C and 15°C. Finish your sightseeing early on the 23rd (Tue) so you can drive to New Haven.
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To find ratings, photos, maps, and tourist information, use the New York City visit planner.
Rio de Janeiro, Brazil to New York City is an approximately 13-hour flight. You'll gain 2 hours traveling from Rio de Janeiro to New York City due to the time zone difference. Traveling from Rio de Janeiro in May, expect New York City to be little chillier, temps between 24°C and 15°C. Finish your sightseeing early on the 23rd (Tue) so you can drive to New Haven.
Side Trip
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New Haven — 2 nights
©
Kick off your visit on the 24th (Wed): admire the masterpieces at New Britain Museum of American Art, then steep yourself in history at The Mark Twain House & Museum, and then see the interesting displays at Osborne Homestead Museum. Get ready for a full day of sightseeing on the next day: admire the masterpieces at Yale University Art Gallery and then identify plant and animal life at Ward Pound Ridge Reservation.
For where to stay, reviews, photos, and more tourist information, use the New Haven trip maker site.
You can drive from New York City to New Haven in 2 hours. Other options are to drive; or take a bus; or take a train. Traveling from New York City in May, you can expect nighttime temperatures to be slightly colder in New Haven, with lows of 11°C. Cap off your sightseeing on the 25th (Thu) early enough to travel to St. Augustine.
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For where to stay, reviews, photos, and more tourist information, use the New Haven trip maker site.
You can drive from New York City to New Haven in 2 hours. Other options are to drive; or take a bus; or take a train. Traveling from New York City in May, you can expect nighttime temperatures to be slightly colder in New Haven, with lows of 11°C. Cap off your sightseeing on the 25th (Thu) early enough to travel to St. Augustine.
Side Trips
Ward Pound Ridge Reservation, New Britain Museum of American Art, Osborne Homestead Museum, The Mark Twain House & Museum
Find places to stay May 23 — 25:
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St. Augustine — 4 nights
©
Escape the urban bustle at St. Augustine Alligator Farm Zoological Park and St. Augustine Beach. Let the collections at St. Augustine Lighthouse & Maritime Museum, Inc. and Lightner Museum capture your imagination. Change things up with these side-trips from St. Augustine: Fernandina Beach (Fort Clinch State Park & George's Jet Ski Adventures), Beach at Daytona Beach (in Daytona Beach) and Ormond Beach (in Ormond Beach).
For reviews, where to stay, maps, and more tourist information, refer to the St. Augustine trip planner.
Do a combination of train and flight from New Haven to St. Augustine in 6.5 hours. Alternatively, you can drive; or do a combination of train, bus, and taxi. Expect somewhat warmer temperatures when traveling from New Haven in May; daily highs in St. Augustine reach 33°C and lows reach 22°C. Wrap up your sightseeing on the 29th (Mon) to allow time to drive to Panama City Beach.
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For reviews, where to stay, maps, and more tourist information, refer to the St. Augustine trip planner.
Do a combination of train and flight from New Haven to St. Augustine in 6.5 hours. Alternatively, you can drive; or do a combination of train, bus, and taxi. Expect somewhat warmer temperatures when traveling from New Haven in May; daily highs in St. Augustine reach 33°C and lows reach 22°C. Wrap up your sightseeing on the 29th (Mon) to allow time to drive to Panama City Beach.
Side Trips
Find places to stay May 25 — 29:
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Panama City Beach — 3 nights
©
World's Most Beautiful Beaches
Visit Panama City Beach and Santa Rosa Beach for some beach relaxation. Escape the urban bustle at Scuba & Snorkeling and St. Andrews State Park. There's much more to do: do a tasting at Panama City Beach Winery, immerse yourself in nature at Henderson Beach State Park, take in the waterfront at The Village of Baytowne Wharf, and browse the different shops at Pier Park.
To find maps, where to stay, and more tourist information, you can read our Panama City Beach road trip planning site.
You can drive from St. Augustine to Panama City Beach in 5.5 hours. Alternatively, you can fly. Expect slightly colder evenings in Panama City Beach when traveling from St. Augustine in May, with lows around 19°C. Wrap up your sightseeing on the 1st (Thu) to allow time to drive to Pensacola.
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To find maps, where to stay, and more tourist information, you can read our Panama City Beach road trip planning site.
You can drive from St. Augustine to Panama City Beach in 5.5 hours. Alternatively, you can fly. Expect slightly colder evenings in Panama City Beach when traveling from St. Augustine in May, with lows around 19°C. Wrap up your sightseeing on the 1st (Thu) to allow time to drive to Pensacola.
Side Trips
Find places to stay May 29 — Jun 1:
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Pensacola — 2 nights
©
Western Gate to the Sunshine State
On the 2nd (Fri), stroll through Gulf Islands National Seashore, then stroll through Pensacola Beach, and then get up close to creatures of the deep with Chase-N-Fins. On the 3rd (Sat), you'll have a packed day of sightseeing: brush up on your military savvy at National Naval Aviation Museum and then kick back and relax at Navarre Beach.
For maps, photos, traveler tips, and tourist information, you can read our Pensacola attractions app.
Getting from Panama City Beach to Pensacola by car takes about 2.5 hours. Traveling from Panama City Beach to Pensacola, you'll gain 1 hour due to the time zone difference. In June in Pensacola, expect temperatures between 36°C during the day and 27°C at night. Finish your sightseeing early on the 3rd (Sat) to allow enough time to fly to Siesta Key.
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For maps, photos, traveler tips, and tourist information, you can read our Pensacola attractions app.
Getting from Panama City Beach to Pensacola by car takes about 2.5 hours. Traveling from Panama City Beach to Pensacola, you'll gain 1 hour due to the time zone difference. In June in Pensacola, expect temperatures between 36°C during the day and 27°C at night. Finish your sightseeing early on the 3rd (Sat) to allow enough time to fly to Siesta Key.
Side Trips
Find places to stay Jun 1 — 3:
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Siesta Key — 2 nights
©
On the 4th (Sun), stroll through Crescent Beach, then walk around Siesta Beach, and then glide peacefully along the water with some of the best stand-up paddleboarding in the area. Here are some ideas for day two: admire the masterpieces at The Ringling, kick back and relax at St. Pete Beach, and then take a stroll through Pass-a-Grille Beach, Florida.
Plan my Siesta Key trip by asking Klarna Trips to come up with tips and suggestions.
Traveling by flight from Pensacola to Siesta Key takes 3.5 hours. Alternatively, you can drive; or take a bus. Traveling from Pensacola to Siesta Key, you'll lose 1 hour due to the time zone difference. In June in Siesta Key, expect temperatures between 37°C during the day and 28°C at night. Finish up your sightseeing early on the 5th (Mon) so you can catch the flight to Key West.
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Plan my Siesta Key trip by asking Klarna Trips to come up with tips and suggestions.
Traveling by flight from Pensacola to Siesta Key takes 3.5 hours. Alternatively, you can drive; or take a bus. Traveling from Pensacola to Siesta Key, you'll lose 1 hour due to the time zone difference. In June in Siesta Key, expect temperatures between 37°C during the day and 28°C at night. Finish up your sightseeing early on the 5th (Mon) so you can catch the flight to Key West.
Side Trips
Find places to stay Jun 3 — 5:
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Key West — 5 nights
©
Conch Republic
Eschew the tourist crowds and head to Fort Zachary Taylor and Truman Little White House. Visiting Dry Tortugas National Park and Fishing Charters & Tours will get you outdoors. Next up on the itinerary: learn about all things military at U.S. Coast Guard Cutter Ingham Maritime Museum, go for a walk through Key West Garden Club, examine the collection at The Ernest Hemingway Home and Museum, and see the vivid underwater world at Vandenberg Wreck.
For ratings, maps, more things to do, and tourist information, read Key West day trip planning tool.
Traveling by flight from Siesta Key to Key West takes 3 hours. Alternatively, you can drive; or do a combination of bus, taxi, and ferry. In June in Key West, expect temperatures between 36°C during the day and 30°C at night. Finish your sightseeing early on the 10th (Sat) to allow enough time to drive to Marathon.
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For ratings, maps, more things to do, and tourist information, read Key West day trip planning tool.
Traveling by flight from Siesta Key to Key West takes 3 hours. Alternatively, you can drive; or do a combination of bus, taxi, and ferry. In June in Key West, expect temperatures between 36°C during the day and 30°C at night. Finish your sightseeing early on the 10th (Sat) to allow enough time to drive to Marathon.
Find places to stay Jun 5 — 10:
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Marathon — 2 nights
©
Heart of the Florida Keys
On the 11th (Sun), stroll through Bahia Honda State Park, then snap pictures at Seven Mile Bridge, and then enjoy the sand and surf at Sombrero Beach. On the next day, identify plant and animal life at Dolphin Research Center, look for all kinds of wild species at The Turtle Hospital, and then see what you can catch with a fishing tour.
To see photos, reviews, maps, and other tourist information, use the Marathon driving holiday planner.
Traveling by car from Key West to Marathon takes 1.5 hours. Alternatively, you can take a bus. In June, daytime highs in Marathon are 38°C, while nighttime lows are 30°C. Wrap up your sightseeing on the 12th (Mon) to allow time to drive to Islamorada.
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To see photos, reviews, maps, and other tourist information, use the Marathon driving holiday planner.
Traveling by car from Key West to Marathon takes 1.5 hours. Alternatively, you can take a bus. In June, daytime highs in Marathon are 38°C, while nighttime lows are 30°C. Wrap up your sightseeing on the 12th (Mon) to allow time to drive to Islamorada.
Side Trip
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Islamorada — 3 nights
©
The Village of Islands
Kick off your visit on the 13th (Tue): take a tour by water with Boat Tours & Water Sports, shop like a local with Lobster Trap Art Gift Shop and Gallery, then take an in-depth tour of History of Diving Museum, and finally enjoy the sand and surf at Anne's Beach. Get ready for a full day of sightseeing on the 14th (Wed): immerse yourself in nature at Lignumvitae Key Botanical State Park, then steep yourself in history at Pasta Pantaleo Signature Gallery, and then sample the tasty concoctions at Florida Keys Brewing Company.
To find photos, traveler tips, other places to visit, and more tourist information, read Islamorada attractions planner.
Getting from Marathon to Islamorada by car takes about an hour. Other options: take a bus. In June in Islamorada, expect temperatures between 38°C during the day and 30°C at night. On the 15th (Thu), you're off to home.
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To find photos, traveler tips, other places to visit, and more tourist information, read Islamorada attractions planner.
Getting from Marathon to Islamorada by car takes about an hour. Other options: take a bus. In June in Islamorada, expect temperatures between 38°C during the day and 30°C at night. On the 15th (Thu), you're off to home.
Find places to stay Jun 12 — 15:
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Connecticut travel guide
The Constitution State
Perhaps best known for its renowned private and public universities, Connecticut was once home to the country's first law school and still boasts one of the oldest secondary schools in America. More than just a small state packed with students, Connecticut offers visitors a chance to explore some of New England's finest tourist attractions while on vacation, including lighthouses, beaches, theaters, museums, galleries, and restaurants. Despite its small size, the state also boasts two large casino complexes, both located on Native American reservations. Rich in history and natural beauty, Connecticut draws newcomers from around the world, with large Polish, Chinese, and Hispanic communities.
Florida travel guide
The Sunshine State
The “Sunshine State,” Florida became a favorite winter destination for the affluent crowd over a century ago. Today, the state attracts visitors from around the world with its golden beaches and modern theme parks. You can spend your entire vacation enjoying the state's highly developed seaside areas, but remember that some of Florida's best-kept secrets are in secluded locations. Visit the big cities and their comfortable resorts offering top-notch dining and nightlife, but leave some time to see the peninsula's swampy landscape, filled with wild creatures and native plants. Farther away from the tourist-packed urban areas, the untamed wetlands of Florida offer a selection of things to do, such as kayaking, boat rides, and numerous other outdoor activities.
