Orleans Vacation Planner

Hindsight Sportfishing

HINDSIGHT, is one of the largest and is the newest boat in our fleet. Full accommodations and very comfortable. Striped bass, bluefish and giant Bluefin tuna are our specialties. We also do whale watch trips as well as sight seeing tours of Cape Cod all the way to Provincetown. Sunset trips when available. We are located at Rock Harbor in Orleans.... show more HINDSIGHT, is one of the largest and is the newest boat in our fleet. Full accommodations and very comfortable. Striped bass, bluefish and giant Bluefin tuna are our specialties. We also do whale watch trips as well as sight seeing tours of Cape Cod all the way to Provincetown. Sunset trips when available. We are located at Rock Harbor in Orleans. Please visit our website at hindsightsportfishing.com. Or call us at 305.481.1291 hide

Categories: Fishing Charters

Rock Harbor, Orleans ~ (305) 481-1291 ~

The Rail

Grand opening in April 2021. Stop in for breakfast or lunch, sit out on the patio overlooking Main St., or grab n' go on your way to Nauset Beach. Open 7 days a week, 5am - 3pm.

Categories: Casual Dining

222 Main Street, Orleans ~ (774) 561-2161 ~

Award winning dining overlooking Town Cove - enjoy a lobster salad sandwich in the elegant O’Hagan’s Irish Pub or cocktails on the outdoor decks overlooking the Cove.

Categories: Waterfront Dining

3 Old County Road, Orleans ~ (800) 863-3039 ~

Rockin Robin Charters

Leaving from Rock Harbor, the Rockin' Robin, a 30' Boston Whaler, will take you fishing across Billingsgate Shoal, one of the most productive striped bass fishing spots on Cape Cod Bay. Please join us while you're staying on the Cape and enjoy the sun, fun, and the excitement that catching striper can only provide. Whether or not you're a seasoned... show more Leaving from Rock Harbor, the Rockin' Robin, a 30' Boston Whaler, will take you fishing across Billingsgate Shoal, one of the most productive striped bass fishing spots on Cape Cod Bay. Please join us while you're staying on the Cape and enjoy the sun, fun, and the excitement that catching striper can only provide. Whether or not you're a seasoned pro or have never fished before, you won't want to miss this! hide

Categories: Fishing Charters

Rock Harbor, Orleans ~ (774) 722-0974 ~

Pleasant Bay Trading Company

Featuring a wide variety of unique nautical and trade signs, Pleasant Bay Trading Company also carries a unique blend of primitive, reproduction home décor inspired by antiques. Come in and browse among our reproduction yellow ware pottery, canvas floor cloths, mirrors, pewter, table mats, custom tables, Period Windsor chairs, and many other... show more Featuring a wide variety of unique nautical and trade signs, Pleasant Bay Trading Company also carries a unique blend of primitive, reproduction home décor inspired by antiques. Come in and browse among our reproduction yellow ware pottery, canvas floor cloths, mirrors, pewter, table mats, custom tables, Period Windsor chairs, and many other unique items. hide

Categories: Other Shopping

80-82 Route 6A , Oracle Square, Orleans ~ (508) 255-5310 ~

Orleans Bowling Center

Open Monday - Thursday 9 am to 9 pm, Friday 9 am to 10 pm, Saturday 9 am to 11 pm, Sunday 12 noon to 9 pm.

Categories: Amusements

191 Rt 6A, Orleans ~ (508) 255-0636 ~

Emack & Bolio's

This ice cream parlor is the perfect way to cool off on a hot day. Try eclectic flavors such as 'Bye Bye Miss American Mud Pie. Candy, snacks and drinks are also available.

Categories: Ice Cream & Candy

82 Cranberry Highway, Orleans ~ (508) 255-5844 ~

Cape Escape

18 Holes of Mini Golf in a nautical setting with authentic Cape Cod fishing boats, a live Koi Fish Pond and beautiful waterfalls. Open 7 days a week (weather permitting) in June from 10 am until late, July - Oct 12 from 9 am until late.

Categories: Mini Golf

14 Canal Road, Orleans ~ (508) 240-1791 ~

Sea Howl Bookshop

Real live books sold here. We carry a thoughtfully curated selection of new & used books, along with greeting cards, notebooks, stickers, art prints, puzzles, and more unique, bookish finds.

Categories: Bookstores

46 Main St, Orleans ~ 508-255-3343 ~

Oceana

Oceana offers the finest in gifts, home accents and tabletop with an emphasis on the shore, and jewelry by designers such as Sealife by Kabana and Tom Kruskal. Oceana Kids has Cape Cod toys and books for children. Treat yourself at Oceana!

Categories: Jewelry

1 Main Street Square, Orleans ~ (877) 240-1414 ~