Project Description

Nantucket History & Wine Tour| Nantucket, Massachusetts

Mid-May, around the Nantucket Food and Wine Festival dates

Be immersed in island life: pristine beaches, picturesque villages, historic sites, swanky food, and world class wine during our tour centered around the Nantucket Wine Festival.

Join author of Discover Cape Cod, Shawnie Kelley for a few days of surf, seafood, and sipping our way around the around Nantucket.  After ferrying from Hyannisport to the island that was once the whaling capital of the world, take time wander the cobbled streets of colonial Nantucket with Shawnie’s guided commentary.  Over the course of three days, we’ll learn of Nantucket’s maritime heritage with an in-depth, private tour of the Whaling Museum; experience the island’s finest classic and contemporary dining, and experience the bustling harbor over waterfront cocktails.

Built-in free time allows you to join us for an optional whale watching excursion or go off-the-beaten-path for a beer tasting and to meet the owners of Cisco Brewery, known for making “nice beer, if you can get it.” Venture off on a rental bike for an easy cruise around the windswept island to sweeps of dunes and beaches or shop for traditional scrimshaw and Nantucket baskets.

Wine lovers and foodies rejoice as our visit takes place during the Nantucket Wine Festival.  We’ll attend wine and food tastings held along the waterfront at the White Elephant Hotel where we’re wooed with prestigious world wines, fabulous artisan food, and live entertainment.  Add on extra wine classes, culinary seminars or demonstrations.  We’ll sip our way around the world without ever having to leave the Island. Whether you come for the whales or wine, seafood or surf, romance or revelry, you’ll find Nantucket a magical retreat in the springtime.

Call us for pricing

Single Supplement: Call us for pricing, Airfare not included, Attractions, Meals and some Wine included

Features & Attractions

  • Level 1 Accommodations $$: Centrally located Inn
  • Level 2 Accommodations $$$: The Summer House Family of Hotels
  • Level 3 Accommodations $$$$: White Elephant Hotel
  • Airfare is not included, but we are happy to help coordinate flights and shuttles to our ferry point at Hyannisport.
  • Private guided walking tour of historic Nantucket Town
  • Tour of the Whaling Museum
  • Nantucket Wine Festival VIP Grand Tasting
  • Optional Extra: Whale watching boat excursion*
  • Optional Extra Bike ride and beer tasting*
  • Pre-travel consulting services with one of our Travel Consultants
  • Full-time services of two travel guides
  • First-class accommodations of cultural or historical interest
  • All meals noted in itinerary
  • Limited wine with meals
  • Food or drink tastings
  • Tour guide book and reading list
  • Itinerary with an emphasis on history, culture, and regional cuisine
  • Luggage transfer between destinations
  • All ground transportation as noted in itinerary (taxis, private vans, trains, etc.)
  • All taxes and gratuities at hotels and restaurants


All aboard a late morning, high-speed ferry from Hyannisport to Nantucket Island. During the hour long ferry ride enjoy a welcome cocktail and local pastries. Guided walking tour and historical overview with Discover Cape Cod author, Shawnie Kelley. Free time to explore, imbibe, or attend wine festival seminars before our group dinner.

Breakfast in your hotel is at your leisure each morning.  Start the day with a private guided tour of the Whaling Museum. Join us for an optional whale-watching excursion or bike ride to Cisco Brewery for a beer tasting.  Or just strike off on your own to rent bikes, shop, or beach hop.  This evening we share an exquisite dinner in a historic Nantucket building.

Morning and breakfast at your leisure.  We will fortify with an early lunch before attending the Nantucket Wine Festival held along the waterfront and harbor at the exquisite White Elephant- Nantucket’s classic five-star hotel.  We will sample wines from prestigious wineries from around the world; taste an array of cuisine from the regions best chefs; and enjoy live entertainment.  A late dinner can arranged upon request.

Your final morning on the island is spent with breakfast at your leisure, free time to shop, relax at the beach, or walk out to Nantucket’s Oldest House with Shawnie.  Our ferry from Nantucket to Hyannisport departs mid-afternoon.  We can help arrange return transportation from Hyannisport to your respective airports or car parks.