East Coast – Island Hopper | June 25 – July 1

June 25 | Welcome to Long Island

Arrive at your New York area airport, where your luxury motorcoach awaits. Sit back, relax, and enjoy the scenic journey to Long Island as your Island Hopper adventure begins. Upon arrival, check in to the Hyatt Place Riverhead for a delightful three-night stay. Take time to settle in and unwind before gathering this evening for a warm welcome dinner with your fellow travelers—the perfect introduction to your coastal getaway.

Overnight: Riverhead (D)

June 26 | Sag Harbor & North Fork Wine Experience

Start your morning with breakfast before setting out with your expert local guide for a day rich in history, seaside charm, and exceptional wine. Your first stop is the historic village of Sag Harbor, a once-thriving whal-ing port where sailors from around the world gathered during the 18th and 19th centuries. Today, this pictur-esque waterfront community welcomes visitors with beautifully preserved homes, inviting storefronts, and a timeless New England-style atmosphere. Visit the Sag Harbor Whaling Museum, housed in an elegant 19th-century mansion, and discover the fascinating maritime heritage that shaped this region. Explore exhibits featur-ing maritime artifacts, scrimshaw, and stories of the daring whalers who once sailed these waters. Afterward, enjoy free time to stroll along Main Street, browse charming boutiques and antique shops, and have lunch at your leisure in one of Sag Harbor’s delightful cafés or restaurants. This afternoon, travel to Long Island’s celebrated North Fork, a coastal wine region recognized for its fertile soils, maritime climate, and acclaimed vineyards. Here, visit one of the area’s award-winning wineries for a private tasting experience, sampling exceptional varietals while learning about the winemaking traditions that have made this region a favorite among wine lovers. This evening is at leisure to enjoy dinner on your own at one of the area’s many excellent restaurants. Whether you choose fresh local seafood, a cozy wine bar, or a farm-to-table bistro, the perfect ending to your day awaits.

Overnight: Riverhead                  (B)

June 27 | The Hamptons & Montauk Point Lighthouse

Enjoy breakfast before departing with your expert local guide for a glamorous day of coastal scenery, iconic villages, and maritime history. Today’s journey takes you through the Hamptons, the famed retreat of celebrities, business leaders, and discerning travelers, known for its pristine beaches, elegant estates, and unmistakable seaside sophistication. Arrive in Southampton, one of the Hamptons’ most exclusive villages, where you’ll have time to explore charming boutiques, art galleries, and inviting cafés. Stroll past historic homes and beautifully maintained gardens as you soak in the refined yet relaxed atmosphere of this beloved coastal destination. Continue with a scenic drive past the celebrated ocean-front estates along the Hamptons’ famed shoreline—often referred to as “Billionaire Lane”—where spectacular homes line the dunes with breathtaking Atlantic views. Along the way, enjoy a stop to take in the beauty of one of the area’s renowned beaches, a picture-perfect stretch of sand and surf. Travel onward to Montauk Point State Park, home to the iconic Montauk Point Lighthouse, New York’s oldest lighthouse, commissioned by George Washington in 1792. Here, you’ll have the opportunity to visit this historic landmark and enjoy sweeping coastal vistas where the Atlantic meets the horizon. Tonight, enjoy a planned dinner together as you reflect on a wonderful day exploring Long Island’s legendary East End.

Overnight: Riverhead                  (B,D)

June 28 | Block Island & Newport

After breakfast, cruise from Orient Point to iconic Block Island, located just off the coast of Rhode Island and long celebrated for its unspoiled beauty, relaxed pace, and timeless coastal character. Often described as one of the most naturally beautiful and well-preserved destinations in the region, Block Island offers a refreshing step back to a simpler era. Upon arrival, enjoy a special Grand Hotel luncheon at one of the island’s historic hotels—a delightful highlight of your visit. Then, set out on a guided island tour showcasing Block Island’s spectacular scenery, including rolling dunes, pristine beaches, dramatic bluffs, a historic lighthouse, and the charming Victorian village. Later this afternoon, board the ferry to Rhode Island and continue to Newport, where the evening is yours to enjoy at leisure. Dine on your own at one of Newport’s many excellent restaurants and soak in the vibrant coastal ambiance of this beloved seaside town.

Overnight: Newport area               (B,L)

June 29 | Martha’s Vineyard

Following breakfast, cruise to the enchanting island of Martha’s Vineyard, long cherished as a quintessential New England retreat. Upon arrival, enjoy a guided tour of the island’s distinctive towns. In Oak Bluffs, stroll through the historic Camp Meeting Grounds, home to the whimsical Gingerbread Cottages and the impressive Tabernacle. Continue to Edgartown, where stately Greek Revival homes reflect the island’s prosperous whaling past. Settle in for a two-night stay and enjoy time at leisure to embrace the island’s relaxed pace and coastal beauty.

Overnight: Martha’s Vineyard            (B)

June 30 | Nantucket day excursion & Farewell Dinner

This morning, ferry to the storybook island of Nantucket, known as “The Gray Lady.” Once the whaling capital of the world, Nantucket now charms visitors with its cobblestone streets, historic homes, and timeless maritime character. Enjoy time to explore its quaint village, browse local shops and galleries, or simply soak in the island’s unique ambiance. Later, enjoy a narrated island tour featuring scenic beaches, historic lighthouses, and picturesque villages. Return to Martha’s Vineyard in the afternoon. This evening, gather for a memorable farewell dinner at a local restaurant—celebrating the highlights of your Island Hopper journey.

Overnight: Martha’s Vineyard                  (B,D)

July 1 | Departure

After breakfast, board the ferry back to the mainland, where your motorcoach awaits for your transfer to the airport. As your journey comes to a close, take with you lasting memories of charming seaside villages, historic landmarks, and the timeless beauty of New England’s iconic islands.              (B)

Inclusions: 

• Round trip transportation to the XNA airport
• Air to New Your City and back from Providence or Boston (checked bag fees are not included)
• Seven days deluxe motor coach transportation
• Professional Tour Director
• Six nights accommodations
• Six breakfasts, One Lunch, and Three dinners, including a traditional lobster bake
• Sightseeing of Long Island South and North Folk, Block Island, Martha’s Vineyard, and Nantucket
• Admissions to Whaling Museum, Montauk Point Lighthouse & Museum
• Private Wine tasting
• Ferry tickets to all the Islands
• Luggage handling (one piece per person)
• Hotel taxes; meal taxes and gratuities
• All gratuities for drivers, guides, step-on guides