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Sag Harbor 5-Day Adventure Itinerary

Last updated: 2024 Jun 27

Exploring Sag Harbor's Charm

Morning

Start your day with a visit to the iconic Sag Harbor Whaling & Historical Museum. This museum offers a deep dive into the maritime history of the area and is a must-see for anyone interested in the rich cultural heritage of Sag Harbor. Afterward, enjoy a leisurely stroll through the historic district, taking in the charming architecture and quaint streets.

Afternoon

In the afternoon, embark on From Mattituck: North Fork Area Bike Tour with Food Tasting. This guided tour will take you through scenic routes while offering delicious food tastings along the way. It's a perfect blend of adventure and culinary delight.

Evening

Conclude your day with dinner at The American Hotel, a highly-rated restaurant known for its elegant ambiance and exquisite cuisine. After dinner, unwind at Baron's Cove, where you can enjoy a drink while overlooking the harbor.

Bedtime

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From Mattituck: North Fork Area Bike Tour with Food Tasting
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Cycling Through Vineyards and Breweries

Morning

Begin your morning with breakfast at SagTown Coffee, a cozy coffee shop that offers excellent coffee and pastries. Then head to Havens Beach for some relaxation by the water or take a short walk along its serene shores.

Afternoon

In the afternoon, join From Mattituck: Guided Brewery and Vineyard Tour by Bicycle. This tour will take you through some of Long Island's best breweries and vineyards, offering tastings of local brews and wines. It's an excellent way to experience the local flavors while enjoying beautiful landscapes.

Evening

For dinner, visit Bay Burger, known for its delicious burgers made from locally sourced ingredients. Afterward, head to The Corner Bar for some evening drinks in a lively atmosphere.

Bedtime

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From Mattituck: Guided Brewery and Vineyard Tour by Bicycle
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Wine Tasting Adventures

Morning

Kick off your day with breakfast at Jack's Stir Brew Coffee, where you can enjoy organic coffee and freshly baked goods. Then visit Mashashimuet Park for a morning walk or some recreational activities like tennis or basketball.

Afternoon

Spend your afternoon on Mattituck: Long Island Wine Region Bike Tour and Tastings. This tour offers an immersive experience into Long Island's wine country, complete with tastings at various wineries along picturesque bike routes.

Evening

End your day with dinner at The Beacon, which offers stunning views of Sag Harbor Bay along with delectable seafood dishes. For post-dinner drinks, stop by Wolffer Kitchen to enjoy their extensive wine list in a chic setting.

Bedtime

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Mattituck: Long Island Wine Region Bike Tour and Tastings
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Exploring Greenport's Hidden Gems

Morning

Start your day with a delightful breakfast at Blue Duck Bakery Cafe, known for its freshly baked pastries and artisanal bread. Afterward, take a leisurely stroll through Mitchell Park, where you can enjoy the beautiful waterfront views and perhaps even take a ride on the antique carousel.

Afternoon

In the afternoon, embark on Greenport Village Rides: Your Full-Day Driver Service. This tour offers a personalized experience, allowing you to explore Greenport's charming village, local shops, and hidden gems at your own pace with the convenience of a dedicated driver.

Evening

For dinner, head to The Frisky Oyster, a highly-rated restaurant known for its innovative seafood dishes and vibrant atmosphere. After dinner, unwind at Brix & Rye, where you can enjoy craft cocktails in a cozy setting.

Bedtime

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Greenport Village Rides: Your Full-Day Driver Service
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Self-Guided Adventures in Mattituck

Morning

Begin your morning with breakfast at Love Lane Kitchen, a popular spot known for its hearty breakfast options and friendly service. Afterward, take some time to explore Love Lane's quaint shops and boutiques.

Afternoon

In the afternoon, set off on Mattituck: Self-Guided Bike Tour. This tour allows you to explore Mattituck's scenic routes and attractions at your own pace. Enjoy the freedom to stop at local wineries, farms, or scenic spots along the way.

Evening

Conclude your trip with dinner at Amano Restaurant, which offers delicious Italian cuisine made from locally sourced ingredients. For a final toast to your adventure-filled trip, visit Roanoak Vineyards for some wine tasting in a beautiful vineyard setting.

Bedtime

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