Luxury Gulf Coast Holidays

Florida’s Gulf Coast is one of the state’s most stunning regions — known for its calm, crystal-clear waters, golden sandy beaches, and close proximity to world-famous theme parks like Walt Disney World, Universal Orlando Resort, and Busch Gardens Tampa Bay. From the seaside charm of Anna Maria Island to the vibrant atmosphere of Clearwater Beach, the Gulf Coast offers something for every traveller. At Tailormadeflorida, we design luxury, tailor made Florida holidays that let you experience the very best of this remarkable coastline. Fly direct into Tampa with Virgin Atlantic or British Airways and let your dream Gulf Coast adventure begin.

Tampa Bay: The gateway to the Gulf Coast, Tampa offers something for everyone — from the thrills of Busch Gardens with its epic roller coasters and family-friendly Sesame Street attractions, to luxury shopping malls, the scenic Tampa Riverwalk, and world-class dining in historic Ybor City. Stay at top properties like the JW Marriott Tampa Water Street, the Tampa EDITION, or enjoy a beachfront retreat at The CURRENT Hotel. A tailor made Florida holiday allows you to combine Tampa’s vibrant city life with luxury coastal relaxation.

Clearwater Beach: Famous for its soft white sand and turquoise waters, Clearwater is a top choice for families and couples alike. Choose from luxury beachfront hotels such as the Opal Sands Resort or Hilton Clearwater Beach Resort & Spa. Families will love visiting the Clearwater Marine Aquarium, while nearby St. Petersburg offers culture, shopping, and its lively pier. A tailor made Gulf Coast holiday gives you the flexibility to enjoy both beachside relaxation and exciting day trips to Orlando’s theme parks just a short drive away.

Sarasota & Siesta Key: For those seeking a villa or condo stay, Sarasota is the perfect Gulf Coast destination. It offers stunning beaches, a relaxed lifestyle, and family-friendly accommodation options. Don’t miss Siesta Key, often named the most beautiful beach in Florida — perfect for a luxury tailor made villa holiday where you can enjoy space, privacy, and breathtaking sunsets.

Anna Maria Island: This charming island is the perfect escape for those wanting a slower pace and traditional Gulf Coast charm. Relax on stunning beaches like Manatee Beach, soak in breathtaking sunsets at Bean Point, and enjoy the feeling of being worlds away from Orlando’s bustle. A tailor made Gulf Coast holiday here combines tranquillity with authentic Florida beauty.

Orlando & Gulf Coast Twin Centre: Many of our clients choose to combine the excitement of Orlando’s theme parks with the laid-back luxury of the Gulf Coast. Spend a week exploring Walt Disney World and Universal Orlando before unwinding on the beaches of Clearwater, Sarasota, or Naples. This luxury tailor made twin-centre holiday truly gives you the best of both worlds.

Explore More of the Gulf Coast: Beyond these highlights, the Gulf Coast boasts even more stunning destinations including Naples, Fort Myers, and Henderson Beach State Park. Whether you’re seeking luxury beachfront resorts, private villas, or a tailor made itinerary that combines city, coast, and theme parks, Tailormadeflorida will design the perfect package for you.