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Your Perfect Cape Cod 3-day Getaway

Don’t struggle with tedious trip planning. Here’s your perfect Cape Cod 3-day getaway. We put together an itinerary filled with activities and great places to eat. Our carefully curated schedule makes your planning so simple; just pack your bags and come for a visit! The attention to all the details — outings, dining, and treats here at the inn — make for a fabulous stay. 

Peruse this itinerary and get ready for a simply lovely retreat!

Day 1

Check in to the Inn. We offer an early check-in beginning at 11 am. Take time to unload your bags, peek around the room, and have a snack on us. Complimentary drinks and a fruit and cheese board are provided. Enjoy this mini charcuterie in your room, in the dining room, or on the lawn (weather permitting). Double-check with the front desk for your dinner reservation for this evening at The Chatham Squire!

Shopping on Main Street
Head out for some shopping on Chatham’s world-renowned Main Street. You never know what treasures you’ll find! Retail therapy awaits in a plethora of unique shops with free parking areas to boot. Many of the shops are only about 1 to 1.5 miles away! Pick up some personal souvenirs, or find the perfect gift for that special person on your list. We like to look at the lighthouse and sea shell charms at Forest Beach Designer Goldsmiths. Find pieces for a sea-themed tablescape at Tale of a Cod. Enjoy the books and atmosphere at Where the Sidewalk Ends Bookstore.

Dinner at The Chatham Squire
Finish the first day here with dinner at our sister business: The Chatham Squire in downtown Chatham. As a guest of the Captain’s Inn, we will have a reservation for you with a 10% discount on your meal. Start dinner with a cocktail — the Cape Cod Margarita possibly (there’s cranberry in it!). Try the Berries & Fennel salad, and then try to pick (it’s all so tempting) from a scrumptious array of main dishes – lots of seafood and other choices too!

Day 2

Start with a gourmet made-to-order breakfast at the Inn. Have a tray in the quiet and coziness of your room, or join us in the dining room at tables set for two.

Today’s adventure is a bike ride on the Rail Trail. We provide a complimentary bike rental ($30 value), so no need to transport your own. The Rail Trail provides miles of paved pathways for a few hours or an all-day adventure. Regardless of how long you pedal, food is a must. Here are some eateries accessible from the Trail:

Other suggestions just off the bike path:

Come back to the room to get all gussied up for an elegant dinner. Connect with the front desk to make a reservation for one of these outstanding oceanfront restaurants. You know you are in for a true culinary experience with these lower Cape locations:

  • STARS at the Chatham Bars Inn. Mouthwatering menu items include pan-roasted monkfish, wagyu beef, roasted quail, and seared scallops.
  • Twenty-Eight Atlantic at Wequassett. Striped bass, Pennsylvania duck breast, or lentil dahl are sure to entice. The seven-course Coastal Tasting Menu gives a wow factor.
  • The Ocean House Restaurant on the coast of Dennis. Grilled oysters, wild rock shrimp ramen, and blackened swordfish are a few suggested culinary delights.

Day 3

Experience another gourmet made-to-order breakfast. The two-course meal features a fruit starter and a choice of the sweet or savory main dish. If the weather is nice, sit outside to dine!

Whale-watching Tour
Ready for a high seas adventure? Let us make your reservations for a whale-watching boat ride. Set sail from Provincetown aboard the Dolphin Fleet — one of the most renowned whale-watching experiences in the world. Whale sightings are guaranteed! Do remember to dress in layers, for temperatures on the water are a lot cooler than on land.

Shopping in Provincetown
Spend the rest of the day shopping along Provincetown’s legendary Commercial Street. This 3-mile stretch of boutiques and treats has something for everyone. Clothing at Soft as a Grape is just that — so, so soft. Provincetown Portuguese Bakery serves up custard cups (Pasteis de Nata) and almond cups (Torres Novas) along with other unique pastries. Get saltwater taffy at Cabot’s Candy; for sure try the cranberry taffy with local flavor!

For your last evening on the Cape make dinner reservations at one of our fantastic casual local spots:

  • Del Mar Bistro for bistro cuisine including local seafood and a variety of pizzas.
  • The Impudent Oyster where of course oysters are on the raw bar.
  • The Sacred Cod at Chatham Bars Inn where burrata and a classic lobster roll are available.

Day 4

Enjoy one last gourmet breakfast at the Inn. Take your time to enjoy, for a complimentary late checkout is 1 pm.

More Local Attractions
A leisurely meander on your way home will give you time to stop at a few attractions. Atwood House and Museum show how the houses used to be on Cape Cod. Marconi Radio Museum educates patrons on wireless radio technology through history. The museum building was once, “the largest ship-to-shore radiotelegraph station in the United States”! Then grab a bite to eat at Chatham Perk. A smoothie, chicken salad or roasted turkey sandwich, and a pastry to go will see you through the afternoon. Final stop is the Atlantic White Shark Conservancy. Learn about the sharks themselves, conservation efforts, and ways to continue helping sharks and humans coexist in peaceable ways.

As you head home from your Cape Cod 3-day getaway, with so many lovely memories! With shopping bags full of local wares and goodies, those memories will last and last. What fun it will be to recount the stories. Time’s a-wastin’ — check availability today!!


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