Have you considered another Trans Atlantic Repositioning from Europe (UK) personally this sounds really relaxing for an itinerary and Celebrity Cruiseline's Celebrity Infinity is one of my favorites. Cruising in this manner you would only really have to fly one way back to the UK and you get to see Bermuda and stay overnight as well as Portugal and the Bahamas and the itinerary has lots of days at sea.
Mon Oct 13 London (Harwich), England 5:00pm
Tue Oct 14 At Sea
Wed Oct 15 At Sea
Thu Oct 16 Lisbon, Portugal 7:00am 4:00pm
Fri Oct 17 At Sea
Sat Oct 18 At Sea
Sun Oct 19 At Sea
Mon Oct 20 At Sea
Tue Oct 21 At Sea
Wed Oct 22 King's Wharf, Bermuda 3:00pm Exclusive Diving experience
Thu Oct 23 King's Wharf, Bermuda Depart next day 4:00pm
Fri Oct 24 At Sea
Sat Oct 25 At Sea
Sun Oct 26 Nassau, Bahamas 7:00am 5:00pm Exclusive Diving experience
Mon Oct 27 Fort Lauderdale, FL 6:00am
Alternatively, I would recommend a back to back Eastern and Western Caribbean or take the Norwegian Dawn and maximize your stated parameters by sailing from Boston to New Orleans (but I would want to stay over on Friday and Saturday night in New Orleans and fly back Sunday!
Fly Thursday and stay overnight in Boston and have Friday to explore before cruise
The greater Boston area is a wonderful blend of stylish sophistication and historic New England charm dine in one of our new restaurants (or dine in an old favorite), shop anywhere from upscale boutiques on Newbury Street to premium outlet malls a short distance from downtown Boston, take a tour. You’ll be in good company having breakfast at Parker’s. Since the late 1800’s, this venerable restaurant has built quite a prominent culinary legacy. From hiring the first celebrity French Chef in America, Chef Sanzian in 1855 to launching the culinary careers of Emeril Lagasse, Lydia Shire and Jasper White. Two cultural icons spent time on the Parker House staff: Vietnamese leader Ho Chi Minh served as a baker in the bakeshop from 1912-1913 and Malcolm X was a busboy in the early 1940’s during the Pearl Harbor invasion. Head over to Durgin Park, which, "established before you were born" features New England Specialties such as Prime Rib, delicious steaks and chops, a variety of fresh seafood and lobster. Other favorites include Pot Roast, scrod, Indian Pudding & Strawberry Shortcake. Enjoy the cozy Gaslight Pub or Blackhorse Tavern in a historical building in the shadow of Faneuil Hall. I have done this cruise personally from Boston and recommend staying pre-cruise either in Back Bay or out at the Seaport Take your time meandering down the Freedom Trail. It is sure to delight your historical senses, a 2.5-mile, brick-lined route that leads you to 16 historically significant sites — each one an authentic treasure.
After you’ve worked up an appetite on the Trail, enjoy a relaxing dinner at the historical Union omni-parker.jpgOyster House. It is the oldest restaurant in Boston
Fri Nov 7 Boston, MA 5:00pm
Sat Nov 8 At Sea
Sun Nov 9 At Sea
Mon Nov 10 At Sea
Tue Nov 11 San Juan, Puerto Rico 8:00am 5:00pm
Wed Nov 12 At Sea
Thu Nov 13 Curacao 8:00am 11:00pm
Fri Nov 14 Aruba 8:00am 6:00pm
Sat Nov 15 At Sea
Sun Nov 16 Ocho Rios, Jamaica 8:00am 5:00pm
Mon Nov 17 Grand Cayman, Cayman Islands 8:00am 4:00pm
Tue Nov 18 Cozumel, Mexico 10:00am 6:00pm
Wed Nov 19 At Sea
Thu Nov 20 At Sea
Fri Nov 21 New Orleans, LA 8:00am
Because the terminals are directly behind the New Orleans Convention Center, adjacent to the warehouse district and central business district, and within walking distance of the historic French Quarter, you don't need to worry about a shuttle service or taxis, although cabs are available. You can either walk 10 short blocks to Canal Street, the beginning of the French Quarter, or take the Riverfront Trolley line for $1.25 per person, with stops at Canal near Harrah's and Decatur, where the popular French Market is. Catch the trolley at the Convention Center, just steps from the terminal.
It may not be called Desire, but it's a thrill to take the St. Charles Streetcar into the leafy Garden District, with its many live oak trees and stately homes. Once home to new-money Yankee entrepreneurs shunned by the French Creoles in the Quarter, the Garden District is now a stately residential area with gorgeous architecture and fun shopping on Magazine Street, which features small, unique shops selling antiques, secondhand books, art, fashion and luxury items. The 13.2-mile crescent starts at Canal Street (at Carondelet) and heads uptown, around the riverbend, to Carrolton Avenue, past antebellum mansions, restaurants, hotels, Loyola and Tulane Universities, and the Audubon Zoo. Even if you don't get off, it's a great ride, a bargain at $1.25. (In case you were wondering, the Desire Line ran from 1920 to 1948, down Bourbon, through the French Quarter, to Desire Street in the Bywater neighborhood and back up to Canal.) Call the Regional Transit Authority (504-248-3900) for transit times and info.
Accommodations are at many extremes in New Orleans I personally like - the family-owned, 600-room Monteleone (214 Royal St., 504-523-3341) The vibe throughout is retro-European, from the guest rooms' rich fabrics and marble bathrooms to the liveried doormen and the 16-story building's distinctive Baroque facade. With its central location in the French Quarter -- a few blocks from the cruise terminal, Canal St., Jackson Square and the River Walk -- the Monteleone is an ideal home base for exploring the Crescent City in style. If getting around is a challenge then my daughter (lives there) says the best Location- A few steps from three streetcar lines, Harrah's and the cruise terminal, Loew's New Orleans (300 Poydras, 504-595-3300) transformed a former office building into a 21-story, four-star hotel, complete with the Brennan family-run Cafe Adelaide (named for colorful Ti Adelaide Martin, co-owner of Commander's Palace) and the Swizzle Stick Bar, named for Adelaide's favorite accoutrement. Rooms are huge and boast endless amenities, from city and river views and laptop-size safes to high-speed Internet access and local art.