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Miami and Cayman Islands by Air

6 to 9+ Nights from $1,469*
* Sample price: priced within the past 7 days for a 3/31/2025 arrival, departing New York City NYC (All Airports) (NY), US. Choose departure city, cabin and dates.

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Add Outbound & Return Flights

This 6 night sample itinerary includes:

  • Flight into Miami and out of Grand Cayman
  • Hotel for 3 nights in Miami
  • Flight from Miami and Cayman Islands
  • Hotel for 3 nights in Gran Cayman

Florida State and Cayman Islands are great options for an unforgettable holiday!. With this package, visit; Miami (Miami and South Beach, food, music and nightlife await you there) and in Grand Cayman (the largest of the three Cayman Islands, with its seven mile beach strip with clubs, restaurants/ bars, resorts, and hotels) you will spend fabulous days in the Caribbean. A flight connects these destinations.

What Makes Tripmasters Vacation Packages Different?
Unique, fully custom approach to vacation planning
Choose your preferred flight cabin class
Select up to 14 nights in each city during your stay
Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more)
Add transfers, activities and experiences, and more services to enhance your vacation
Live phone and chat support

Flexible Itinerary

  • Miami, FL

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  • Grand Cayman

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Cayman Islands
USA

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Trip Summary

  • Miami, FL
    Miami, FL

    Miami is the largest city in South Florida and one of the largest cultural, financial, and entertainment epicenters in the United States. Known for its eclectic energy, great nightlife, art galleries and museums, delicious cuisine, and a lively Latin and Caribbean community with particularly noteworthy Cuban and Haitian enclaves, Miami is a multitude of experiences rolled into one big magic city.

    Explore the Vizcaya Museum and Gardens, Bayside Marketplace, Miami Seaquarium, Jungle Island, Art Deco Historic District, PortMiami, Lincoln Road, Bayfront Park, Perez Art Museum, AmericanAirlines Arena, Venetian Pool, Lummus Park, Wynwood Art District, Freedom Tower, Calle Ocho Historic District, Key Biscayne, and so much more!

  • Grand Cayman
    Grand Cayman

    The exotic tropical Cayman Islands offer visitors sun-filled days, fantastic accommodations, and palm-fringed beaches for a memorable vacation experience. A charming island perfect for romantic strolls along the beach, sip cocktails at the world-famous Bar Jack Pina Colada and swim in the bluest of blue waters.

    Visit The National Museum of the Cayman Island, Rum Point, Pedro St. James, Bodden Town, The Turtle Center, The Mastic Trail, Seven Mile Beach, Starfish Point, and so much more!

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