Top 5 VIP Experiences in Boston, Priced and Timed

1.Luxury Catamaran Sailing Charters in Maine

★★★★★★★★★★5.0 · 85 reviews · from $135Our pick

Set sail with Captain Nils and first mate Nick from Saco aboard a spacious catamaran, with a maximum of six travelers. The two-hour cruise passes Wood Island Lighthouse, Old Orchard, Biddeford Pool, and Cape Porpoise. Keep watch for seals, bald eagles, and whales, and bring your own food and drinks.

“The trip was relaxing and amazing and it was the perfect length. The boat was spotless, plenty of room to roam, and learned a lot about local wildlife and history. We had a small group but the boat could probably hold 25 comfortably.”

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2.Private Luxury Transportation to/from Boston Logan Airport (BOS)

★★★★★★★★★★4.5 · 26 reviews · 15 minutes to 1 hour (approx.)

Sleipnir Transportation provides a private, air-conditioned ride to or from Boston Logan for up to five people. Meet your driver in the airport’s designated limo pickup area, not inside the terminal. The ride includes bottled water, a phone charger, SiriusXM radio, flight tracking, and up to 60 minutes of airport waiting time.

“This is the best transfer that I booked. The driver picked us up at the hotel next to the airport and the car was luxurious. I wish I knew the difference because I was disappointed in the one I booked for going home which did not say luxury.”

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3.Marthas Vineyard Luxury Tour (2hrs)

★★★★★★★★★★5.0 · 26 reviews · 2 hours (approx.)

Laid Back Tours’ private, two-hour drive begins and ends at the Vineyard Haven Steamship Authority Terminal. Guide Craig takes your group past West Chop Lighthouse, Katama Beach, Edgartown, Jaws Bridge and Oak Bluffs’ Gingerbread Cottages, sharing island history along the way. Expect a clean luxury minivan, bottled water and a quick-paced route with brief stops.

“Craig was full of information that was interesting and we had not known before. Craig was funny and ready to answer any of our queztions. We truly enjoyed our time with Craig.”

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4.Best of Boston Combo: Harbor Cruise & VIP Freedom Trail

★★★★★★★★★★4.0 · 15 reviews · from $99Best value

This 4.5-hour Boston tour pairs a small-group walk through Beacon Hill, Granary Burying Ground, the North End and key Freedom Trail sites with entry to Old North Church and its bell chamber. Guides such as Alex, Cameron and Jessica have led lively, question-friendly outings. It ends with a narrated, one-hour harbor cruise.

“Our guide Will was amazing. Extremely knowledgeable and accurate. Answered any and all questions. He was a delightful.”

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5.3 Hour Luxury Van Tour With Breakers Admission

★★★★★★★★★★5.0 · 6 reviews · 3 hours (approx.)

You’ll take a private, narrated van tour around Newport, then get 90 minutes inside The Breakers Mansion with admission included. The full outing lasts about three hours and costs $850 for a group of up to 14. Guides Lydia and Todd have led the tour, though your guide may differ.

“The Breakers is something you should not miss when you’re in Newport. Driver was very friendly and knowledgeable about Newport.”

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