Written by Missy Johnston

Barnstable Harbor, cape Cod

Barnstable Harbor Channel

Cape Cod is a popular celebrity destination for good reason. The Cape and its surrounding areas offer a vacation like no other. Though there are several well-known attractions on Cape Cod that may hold appeal to land travelers, the ultimate experience in luxury and elegance is best accessed from the water.

Take a private yacht cruise to Cape Cod to enjoy a premier selection of activities and destinations not available to the average tourist. And, be sure to visit the nearby Elizabeth Islands. Even though they are private, yachts are allowed to anchor in lovely Hadley’s Harbor across from Wood’s Hole, a beautiful anchorage, only reachable by private yacht.

Create your own private whale watching tour

Humpback Whale

Between April and October, anyone on the water near Cape Cod will be treated to the majestic sight of whales occupying their summer feeding grounds on Stellwagen Bank. The peak migration months between June and September provide the best chance for awe-inspiring whale experiences.

Keep an eye out for Humpback, Finback, Pilot, Right, and Minke whales, which are the most likely types to breach in the area.

Visit Stellwagen Bank National Marine Sanctuary outside of chartered tour hours to enjoy glimpses of whales in peace and privacy. You can avoid the boat traffic of whale tours coming from Barnstable, Chatham, and Provincetown by staying out of the established tour routes in these areas.

Most commercial tour services book passengers in morning and afternoon groups, leaving the early morning and evening open for you to enjoy your off-hours personal time with these impressive mammals. Rest assured that whales are active at any time of the day you choose to visit.

Provincetown, Cape Cod

Sample vintages at the region’s eminent wineries and vineyards

No trip to Cape Cod would feel complete without a private wine tasting at one of the area’s best local wineries. Sample rare vintages unique to the region and dine on artisan cheeses carefully crafted for pairing with your personal wine selection.

Book a private tour or party at Truro Vineyards, Cape Cod Winery, or First Crush Winery on the Cape itself, and then close the evening out at Nantucket Winery, just a short cruise away.

Enjoy the variety of fine dining establishments

Sunset from Aquinnah (Gay Head), Martha's Vineyard

Sunset from Aquinnah (Gay Head), Martha’s Vineyard

Come ashore to Cape Cod for dinner at the Chatham Bars Inn, Old Yarmouth Inn, or The Glass Onion. Each are renowned for their elegance and unique charm and have received the “Best of Cape Cod” designation in recent years.

Alternatively, you have many choices on Martha’s Vineyard or Nantucket. Try The Terrace at The Charlotte Inn in Edgartown, Martha’s Vineyard, or The Chanticleer in Siasconset, Nantucket. Fresh caught seafood and classic American fare await you after a pleasant cruise on your yacht to visit any of these award-winning bistros and fine restaurants.