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Ultimate 5-Day Thousand Islands Adventure with Culinary Delights

Ultimate 5-Day Thousand Islands Adventure with Culinary Delights Itinerary

Last updated: 2024 Jun 14

Island Hopping and Historic Sites

Morning
Start your Thousand Islands adventure with a hearty breakfast at Thousand Islands Club, a historic and picturesque spot. Afterward, embark on a scenic cruise to explore the beautiful islands and catch a glimpse of the famous Boldt Castle (Heart Island) and the charming Singer Castle (Dark Island).
Afternoon
For lunch, head to Riverwatch Dining for a delightful meal with river views. Post-lunch, visit the Alexandria Bay for some leisurely shopping and a walk along the waterfront. Then, enjoy the rest of the afternoon at the family-friendly Aquatarium to learn about the local aquatic life and history of the region.
Evening
Dine at Windows on the Bay and savor the flavors of the region. After dinner, take a relaxing evening stroll at the Thousand Islands Bridge and enjoy the illuminated views of the islands and the shimmering waters.
Bedtime
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Nature's Wonders and Cultural Delights

Morning
Begin with breakfast at Seaway Grille before heading to the enchanting Singer Castle (Dark Island) for a guided tour. Afterward, take a scenic drive to the Thousand Islands Tower for panoramic views of the region.
Afternoon
Enjoy a picnic lunch at the serene Wellesley Island State Park and spend the afternoon exploring the park's trails and nature. Later, visit the Antique Boat Museum to admire the impressive collection of vintage boats and maritime exhibits.
Evening
Dine at The Channelside and indulge in their fresh seafood offerings. Cap off the evening with a sunset cruise, taking in the breathtaking views of the islands as the sun dips below the horizon.
Bedtime
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Historic Mansions and Island Leisure

Morning
Enjoy a delicious breakfast at Bonnie Castle Resort & Marina before embarking on a visit to the opulent Boldt Castle (Heart Island). Explore the grand rooms and the beautiful gardens, learning about the fascinating history of the castle.
Afternoon
Have a leisurely lunch at Mavericks, known for its casual elegance and waterfront dining. Post-lunch, take a guided tour of the historic Singer Castle (Dark Island) and immerse yourself in the Gilded Age ambiance.
Evening
For dinner, head to Riley's by the River and enjoy the warm and inviting atmosphere. Afterward, take a moonlit kayak tour, gliding through the calm waters and under the starry skies, experiencing the magic of the Thousand Islands at night.
Bedtime
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Island Exploration and Scenic Drives

Morning
Start your day with breakfast at Coyote Moon Vineyards on the River, where you can enjoy a delicious meal with vineyard views. After breakfast, take a self-guided tour of the Thousand Islands Winery and sample some of the region's finest wines.
Afternoon
Pack a gourmet picnic from the winery and head to Wellesley Island State Park for a relaxing afternoon by the water. After lunch, take a scenic drive along the Thousand Islands Seaway Trail, stopping at the various lookout points and charming towns along the way.
Evening
Dine at The Ivy Restaurant, known for its elegant ambiance and exquisite cuisine. After dinner, enjoy a live performance at the Clayton Opera House, immersing yourself in the local arts and culture.
Bedtime
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Final Island Gems and Farewell

Morning
Have a delightful breakfast at The Ivy Restaurant to start your last day in the Thousand Islands. Then, visit the Antique Boat Museum to explore the rich maritime history of the region and admire the beautifully preserved boats.
Afternoon
Enjoy a leisurely lunch at Wellesley Hotel & Restaurant, savoring the flavors of the islands. Afterward, take a final cruise to soak in the scenic beauty and bid farewell to the enchanting Thousand Islands.
Evening
Conclude your trip with a sumptuous dinner at Bonnie Castle Resort & Marina, reminiscing about the wonderful experiences and the natural splendor of the Thousand Islands.
Bedtime
Find amazing hotels in Thousand Islands, New York, USA.

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